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The Transcript

How One Successful Digital Entrepreneur Stays Entertained by Her Business

Voiceover: Rainmaker FM.

You are listening to The Digital Entrepreneur, the show for folks who want to discover smarter ways to create and sell profitable digital goods and services. This podcast is a production of Digital Commerce Institute, the place to be for digital entrepreneurs. DCI features an in-depth, on-going instructional academy, plus a live education and networking summit where entrepreneurs from across the globe meet in person. For more information, go to Rainmaker.FM/DigitalCommerce. That s Rainmaker.FM/DigitalCommerce.

Jerod Morris: Welcome back to The Digital Entrepreneur, the show where digital entrepreneurs share their stories and the lessons they ve learned so that we can all build better digital businesses. I am your host, Jerod Morris, the VP of Marketing for Rainmaker Digital, and this is episode number 32.

This episode of The Digital Entrepreneur is brought to you by the Rainmaker Platform. I will tell you more about this complete solution for digital marketing and sales a little bit later, but you can check it out and take a free spin for yourself at Rainmaker.FM/Platform. That s Rainmaker.FM/Platform.

On this week s episode, I am joined by someone who four years ago was working a corporate job that she didn t love anymore. She began growing her blog, building her email list, and expanding her social media following. After nine months of serious hustling, she made her escape and literally ran away with the circus. We re going to have to ask her about that.

Now she spends her days teaching other bloggers, freelancers, and solo business owners how to create a kickass online presence through ebooks, workbooks, and courses so that they can conquer their goals too. She is Sarah Morgan, and she is a digital entrepreneur.

Sarah, welcome to The Digital Entrepreneur. How are you?

Sarah Morgan: Thank you for having me. I m good. How are you?

Jerod Morris: I m very good. Very good. Very excited for this chance to talk. Looking forward to it.

Sarah Morgan: Thank you.

Jerod Morris: I have to start out with this. When I was doing some research ahead of time, I read on your website a little bit about your history. I want you to, obviously, get into telling us more about that, but there was one line that I found particularly interesting, and we have to start here. You said, After nine months of serious hustling, she made her escape and literally ran away with the circus. Can you ?

Sarah Morgan: Yeah. My fans were excited about that.

Jerod Morris: Can you unpack that sentence for us a little bit?

Sarah Morgan: Yeah. I guess I can tell you my whole journey and how that fits in, because I did also have a real job as well.

Jerod Morris: Yeah, let s do it.

How She Went from Corporate Job and Circus Performer to Thriving Digital Entrepreneur

Sarah Morgan: I m a blog strategist. I started blogging when I was a teenager. I used that to learn web design and development, and then after college I got a corporate job doing web design at a TV station in Detroit. I m originally from Michigan. At some point in there, like most people that end up self-employed, I was not loving my job anymore. Not loving getting up and going to work, the projects, or anything that I was working on. I started a side hustle doing freelance web design. Around the same time, I had a — I call it my side, side hustle. That was as a circus performer. I was performing Cirque du Soleil aerial silks and trapeze, that kind of stuff.

Jerod Morris: Wow.

Sarah Morgan: Yeah. So I was performing a lot and I was teaching. I was blogging in the morning and then going to work and blogging. Getting my work done really fast. I was very efficient. Then, editing photos, coding, and doing all of that stuff any time I had a minute at work. And then, after work, I would go and train, or teach, or perform, or go and do more web design client work.

Jerod Morris: Wow. How did you have time for all of this?

Sarah Morgan: Yeah. It was more like, How did you have time for anything else? because I pretty much It was like a year, nine months where I was doing everything all at once, and I didn t do anything else. I wasn t partying. That was in my late 20 s. How long have I been doing this, four years?

I should ve been going to the bar and going out to dinner, doing all kinds of stuff. I was working like a crazy person. I always say I was working 25/8. I was working from the second I got up until the second I went to sleep, and I loved it … 95 percent of the time. The rest of the time, I was super stressed out.

Jerod Morris: Yeah. I don t want to dwell on this too long because it s obviously a show about digital entrepreneurship, but I am interested about the performing part of it, because that seems like this outlier detail about your whole story. Is that something that you had grown up doing, and what are you Are you still doing any of that now?

Sarah Morgan: Yeah, I moved to San Diego a little over two years ago. I still teach. I don t really perform anymore because it takes a really high level of training. I would have to be in the studio training six, seven days a week, and at the moment I m feeling lazy about that. I m really focused on building my online courses. So I m still teaching and I still go in and train every once in a while.

But when I was back home in Detroit before I moved here, I was performing a few times a month. I did outdoor festivals, fairs, and corporate events. I did, actually, a couple of NBA halftime shows. I got to perform with Salt-N-Pepa, which was crazy.

Jerod Morris: Wow. Hey.

Sarah Morgan: Yeah. They re like, Do you want to come and do this show? I was like, Yes. Yeah, whatever you want me to do, no problem.

Jerod Morris: Of course. Yeah. When you do your online courses, are you doing a lot of video stuff? Are you on camera for the courses?

Sarah Morgan: Some of them I am. I have one course, my main blogging course about growing blog traffic and your email list.

Jerod Morris: Yeah.

Sarah Morgan: I am on camera doing video for every single module.

Jerod Morris: This performance history that you have, does that come out at all in your videos? Are you able to use any of that, or is it more just like sitting in a desk straight into the camera?

Sarah Morgan: I m not sitting at a desk. I m more of a work-on-the-couch kind of person, so it s a little more relaxed probably than most people that make online courses.

Jerod Morris: Yeah.

Sarah Morgan: Yeah, I m not upside-down or anything, or wearing the clown makeup.

Jerod Morris: Not yet, but for future courses.

Sarah Morgan: Not yet. Yes.

Jerod Morris: Sarah, I ve always believed that the number one benefit of digital entrepreneurship is freedom.

Sarah Morgan: Yes.

Jerod Morris: The freedom to choose your projects. The freedom to chart your course. Ultimately, the freedom to change your life and your family s life for the better. What is the biggest benefit that you have derived from being a digital entrepreneur?

Sarah Morgan: I m going to go with freedom as well. I really am bossy, so I like being in charge and I like deciding what project I work on, who I m working with, who I m collaborating with. I like being able to structure my own days. I like being able to like fly home to see my family whenever I want. Michigan is cold so I don t really do it that often, but I can if I want to. Also, that I can experiment. I can try something, and if doesn t work then it doesn t work and I can try something else. There s nobody going to come down and with a hammer on me or something like that.

Jerod Morris: Yeah.

Sarah Morgan: I m able to move a little bit quicker than I would if I was doing this same type of work under someone else at a corporate job or something.

Jerod Morris: Sure, so you described what you were doing before you got to the point where you re at now. When was that moment when you said, Okay, I m pivoting and I m going online. I m doing this full-time with ebooks and with courses, and this is how I m going to make money. What was that decision like?

Sarah Morgan: It started a couple years in. Maybe three years in to the seven years at my corporate job, I had a moment of feeling like I didn t enjoy designing websites anymore, and that was something I had been doing since I was like 13.

I always say I had a mid-20 s crisis. I was like, If I don t design websites anymore, what am I supposed to do? I didn t have any other interests, hobbies, or career path. That was my thing. So I panicked. That s when I started blogging again. I had stopped for a couple of years because I was doing a lot of design work and writing news stories, which is super boring. I was doing that all day at my corporate job, so I stopped blogging.

At that point, I started blogging again. I started getting a little bit more into creative design and blog design, and I realized that I had people coming to me and asking for blog headers or asking questions about how to format their own website. I ended up starting a little bit, and then nine months before I left my job I got very serious. I was really unhappy. I really didn t want to go to work in the morning.

I decided, “In a year, I m leaving my job. Next September, I m leaving. That s it. I think my boyfriend at the time and my parents were a little bit concerned for my mental state of being. I was like, I m leaving my job. I can t do this anymore. This is 40 hours out of my week that I m unhappy.

Jerod Morris: Yeah.

Sarah Morgan: Yeah. I decided, and from that point on, I worked like a crazy person to make it happen.

Jerod Morris: Sometimes you got to put your own back against the wall and you find out what you re capable of.

Sarah Morgan: Yeah, absolutely.

Why She Won’t Apologize for Cursing, Naps, or Walking Her Dear Old Dog

Jerod Morris: I m looking at your website, and you ve got your tagline on here, The no bullsh*t blog strategy for the daring and driven. I m curious, as you went about developing your brand and putting this all together, did you just follow your own personality, or were you very intentional about adding a little bit of an edge to how you were going to present yourself?

Sarah Morgan: That s my personality. If you talk to me in person I will probably swear at you. I get people that email I used to be on MailChimp, so people could write a comment when they unsubscribe. All the time people would say, You swear too much. I can t take the cursing, and I m like

Jerod Morris: You swear in your emails?

Sarah Morgan: Oh, yeah.

Jerod Morris: Yeah?

Sarah Morgan: I try to not drop the f-bomb too much anymore. I’ve pulled back a teeny-tiny bit, but yeah. I say all the other four-letter words. That s the way I sound.

Jerod Morris: Yeah, I think that s interesting. I think some people shy away a little bit even if that is their natural way. Have you found that it has helped you to attract the kind of people that are going to be your best kind of customers and repel the people who won t?

Sarah Morgan: Yup, absolutely. That s one of the reasons that I ve never been shy about swearing or writing in the way that I speak, or creating videos and not being in a blazer at a desk. I m always sitting on my couch or I m sitting at my kitchen table, and I m dressed the way that I always dress. I think that does attract the right people to me. Because I do a lot of I run online communities for all my courses. I do weekly hangouts for some of my courses, and I don t want to be hanging out with people that aren t on the same vibe that I m on.

Jerod Morris: Yeah, just a very authentic way of doing business.

Sarah Morgan: Yeah, it brings in the right students and I always have fun when I m doing the consulting and coaching.

Jerod Morris: Yeah. Tell me about the milestone or moment in your career as a digital entrepreneur so far that you are the most proud of.

The Joy She Felt in That Moment When She Realized That She Was Making More as a Digital Entrepreneur than She Had at Her Corporate Job

Sarah Morgan: Ooh, that s a big one. Okay. It was when I realized I was making more money being self-employed than I had been making at my corporate job.

Jerod Morris: Wow. Yeah.

Sarah Morgan: That was about two and a half, three years in. I just remember standing in my kitchen and being like, Holy sh*t. I make more money doing all of this stuff by myself than I did working for somebody else. It s crazy. I didn t think — I really assumed, “I m going to be making $30,000 a year, and that s fine if I can work from home and build my own business. That s fine. I ll be a starving artist or whatever.

Jerod Morris: Yeah.

Sarah Morgan: I did not expect that to happen at all. When it did, I was really shocked and really proud of myself.

Jerod Morris: Was it a steady progression to that point, or were there some pretty big jumps that got you there?

Sarah Morgan: It was definitely a whole year of doing webinars and finally growing my email list. Finally taking all of the advice in creating an email list. The couple years before I d been making $25,000 to $30,000 a year, and then yeah, that one year I more than doubled my income.

Jerod Morris: Wow. Congratulations on that, by the way. That s fantastic.

Sarah Morgan: Thank you.

Jerod Morris: Alrighty. Let s take a quick break. When we come back, I m going to ask Sarah about her most humbling moment as a digital entrepreneur.

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Now, back to my discussion with Sarah Morgan.

Alrighty. Sarah, you told us about your proudest moment as a digital entrepreneur. Now tell us about the most humbling moment in your career as a digital entrepreneur thus far, and most importantly, what you ve learned from it.

Her Failed Photoshop Course and What She Learned From the Experience

Sarah Morgan: Okay. I definitely have had a course that was a failure. I did a Photoshop course, but I didn t really take into account that people would have to purchase Photoshop in order to take my course. It was like, Spend $500, or $200, or whatever on Photoshop, and then also spend $300 on my course. It didn t really work. That was a bummer because I put a lot of time into it and it was a really good course, but the people that were buying it were the ones that were already in my audience and already had Photoshop, and that was not enough for it to be sustainable.

Jerod Morris: Yeah, so what have you done with that course? Is that still out there just for folks who can use it, or did you shutter that one?

Sarah Morgan: Yeah. It was online for maybe a year after. I just left it in my shop. A few people purchased it, but eventually I really wanted to drill down on blogging and create a progression of courses, so I took it offline.

Jerod Morris: Is there anything that you would do differently with that course if you were going to re-launch it? Obviously there s an inherent challenge there with needing people to buy Photoshop, but how would you approach something like that where you have a useful skill to teach but you ve got this barrier there where people need to buy X product? Is there anything that you would do differently in a similar situation? Maybe it s just not do the course, but is there anything else?

Sarah Morgan: I think I would have focused more on design, and then included tutorials for Photoshop and a couple of the online free design platforms so that it was accessible to anyone. But for me, I really When I learned Photoshop, I felt like I learned maybe like 10 percent of it, so that was my intention with the course, is that you really miss all of these tools that are really helpful. But it didn t really work. It definitely needed to be more accessible by having a free platform that people could try all of the tech tutorials for.

Jerod Morris: Yeah. Thank you for sharing that with us. I appreciate it.

Sarah Morgan: Yeah.

Jerod Morris: Let s fast-forward to now. What is the one word that you would use to sum up the status of your business as it stands today? One word.

Sarah Morgan: You re getting me with all these questions.

Jerod Morris: And it can t be a curse word.

Sarah Morgan: I m feeling very entertained by my business right now. I m just trying lots of stuff.

Jerod Morris: Oh, that s a good one. We haven t had anybody use that word before.

Sarah Morgan: Yeah. It s always been entertaining, but the more I get interesting opportunities — I had the opportunity to go to New Orleans and speak at a conference which was like, Okay, sure.”

Jerod Morris: Yeah.

Sarah Morgan: “I would love to go to New Orleans for free. If I have to get on stage and speak, I can probably do that.” Yeah, it s been entertaining to see what s happening, interact with my audience, and build communities. I m just having fun over here.

Jerod Morris: Is that something that you want to do more of, speaking?

Sarah Morgan: I think it is. I would panic in high school, and middle school, and college when they would call on me or where you had to write a presentation and you had note cards and stand up in front of class. That was my worst nightmare.

Jerod Morris: Yeah.

Sarah Morgan: Somehow, I think through teaching and doing webinars, I ve become a lot more comfortable talking to people and having people all stare at me all at once. So it was a really good experience to go and speak at the conference, and I think I would do it again.

Jerod Morris: What is your biggest recurring pain point as a digital entrepreneur?

The Work Habits and Discipline That Help Her Get Her Work Done and Keep Moving Forward

Sarah Morgan: Oh, probably getting enough done. I can have 15 tasks every single day. I m always adjusting and adding. I just adjusted the end of some of my email sequences, but now I want to go back through and do it to all of them. I could literally work non-stop and not sleep and not eat.

So really staying focused and organized. I ve been using Asana, which is very helpful in order to get specific things done and put off adjusting all of those email sequences to next week or next month, or something like that.

Jerod Morris: That is a pretty common recurring pain point, I think. That s the one. It s the double-edged sword of freedom. You have this freedom, but then there are so many different things that can fill up the time. How do you, a) keep your priorities in order and make your choices for what you re going to do, and b) try to keep some barrier around your professional life so that you can have a personal life as well?

Sarah Morgan: Yeah. So I said Asana, that really helps. I generally try and put like three tasks per day, three big things. And I plan a quarter in advance. So I know for November and December, while I haven t gone through and added daily tasks, I know I m going to be reworking one of my courses in that month. I have my end goal for those two months, and then I can go in and say, This week I need to do the sales page. This week I need to do emails. This week I m going to go through lessons or videos.

Having those larger goals and then breaking it down into months or weeks, and then breaking it down into days and not putting too much into each day. One of the nice things about Asana is that I can go back through and see, Really, what did I accomplish every day? Can I do 10 things? No. Okay. I can only do 5 things every day. If I m doing video, that s probably going to take my whole day. If I m writing a blog post, I can probably add in another two things.

Jerod Morris: Cool. What element of your work gives you the most satisfaction on a daily basis?

Why Hanging out in Her Communities (on Her Couch) Fuels Her Why

Sarah Morgan: Hanging out with my communities, for sure.

Jerod Morris: Yeah?

Sarah Morgan: I love talking to people. It s two things. It fuels my why, my purpose and motivation for creating courses and doing what I do — blogging and writing emails. But it also is really great research. Any time I build a course, do a webinar, or send an email, it s generally because one of my students or community members has had a question or is trying to figure something out that they re stuck on. Then I can take that and turn it into something that works for my entire audience. So that s been really nice, to do daily, really easy research.

Jerod Morris: Yeah. You mentioned before how much Asana has helped you. I want to open your toolbox a little bit and figure out what tools you re using. In addition to Asana, what s another technology tool that contributes the most to your success?

Sarah Morgan: I ve got three that I ll tell you. I love ConvertKit for doing emails, sending emails to my list. Their tagging tools are amazing. I was on MailChimp. This blows MailChimp out of the water. It s so easy to segment my list and send emails just to people related to the specific things they’re interested in so that I don t have to send thousands and thousands of people every email. That never works.

I really loved Tailwind for scheduling blog posts to Pinterest. I get 90 percent of my social media traffic from Pinterest, so I always have that scheduled in advance.

Jerod Morris: Oh, wow.

Sarah Morgan: Yeah. It works. It s not just for recipes and makeup tips.

Jerod Morris: Yeah. How do you do that then, with Pinterest? Do you have to have a pretty defined visual style? Do you create specific blog post images that go with your posts? What s your strategy with Pinterest?

Sarah Morgan: Yeah. My blog post images are Pinterest-sized. They re giant, big, tall images. Then I pin those into my boards and group boards. I use Tailwind because I can pin 1 pin to like 20 boards in literally 2 seconds. It s two clicks and then they re all in there, they re all scheduled. So I can pin a ton of content, which Pinterest really likes. I can pin a lot of content all day long, and I only am working maybe 5 or 10 minutes, depending on how lazy I m feeling.

Jerod Morris: Yeah. Wow, very cool. That sounds like a really neat program.

Sarah Morgan: Yeah, and then I also use Buffer. For Twitter and Facebook I use Buffer.

Jerod Morris: Yeah. What about the non-technology tool that contributes the most?

Sarah Morgan: Can I say my couch? Taking a nap?

Jerod Morris: Sure, whatever works.

Sarah Morgan: That s what I do when I need a break. I just pass out.

Jerod Morris: Okay. How important is that, though? I think a lot of people are scared to take a nap or take breaks, always feeling they have to fill every moment with work. Is that a big part of what keeps you fresh and keeps you going?

Sarah Morgan: Yeah. Oh, yeah. I am very serious about sleeping. If I need a nap, I know that I m going to produce crap work if I try and push through when I m falling asleep. So I m all about taking a nap. Especially if I do the circus training in the morning, I need a nap and then I can wake up and actually work. Yeah, that and taking my dog for a walk. I know a lot of people — people get mad at me. I have a blog post where I detail how my day runs, and that is the only post on my website that I get hate comments.

Jerod Morris: Really?

Sarah Morgan: They re very mad that I can walk my dog during the day and take a nap.

Jerod Morris: By hate comments, do you mean like jealousy-driven like, I wish I could do that. Or like, You should be in the community paying your attention to us?

Sarah Morgan: No, it s like, How dare you say you re productive when you take a nap during the day.

Jerod Morris: Oh.

Sarah Morgan: I m like, I don t know. That s how I work. Sorry.

Jerod Morris: Yeah. It all goes to quality over quantity.

Sarah Morgan: Yeah.

Jerod Morris: If you re able to get more better work done in a shorter amount of time because you re fresher, then it all works out.

Sarah Morgan: Yeah, or else you just end up burning out.

Jerod Morris: Yes.

Sarah Morgan: That s not worth it.

Jerod Morris: Earlier I asked you for the one word that you would use to sum up the status of your business as it stands today. You said, Entertained, which is a great answer. If we talk again in a year, what word would you want that to be?

Sarah Morgan: Oh, man.

Jerod Morris: It has to be different.

Sarah Morgan: I probably still will be entertained. Something to do with expanding.

Jerod Morris: Okay.

Sarah Morgan: I have a free beginner blogging course, and I would like to really expand the number of students that are in that course. That s my main goal for next year is to like 10x that so that I can get a lot more people online blogging. I have tons of middle-aged, 50-something women who are coming into my courses, which is not My branding is not really geared toward that person, but they re showing up in droves and I love it. Yeah, I want to expand. I want things to be bigger.

Jerod Morris: What s your current attraction strategy? How are these people finding you and how are you targeting the people that you –not that you don t want those people — the people that you are targeting. How are you going about doing that?

Sarah Morgan: Through social media. Sharing my own blog content on Twitter, I get a lot of traffic. And Pinterest — like I said. Then I run Facebook ads every once in a while. I m about to run one in the next day or two for my list-building course, so that will bring in a whole new audience. I try and target outside of the people that I already have.

Jerod Morris: Yeah.

Sarah Morgan: Yeah, so that will help bring in lots more people.

Jerod Morris: Cool. Good luck as you work towards continuing to expand.

Sarah Morgan: Thank you.

Jerod Morris: I ve got a few rapid-fire questions here to end with. I will let you know, most people I send these questions to ahead of time and I forgot to do it in this case. But you seem ready, like you don t need them ahead of time, so I think we ll be okay. I think you ll do a perfectly fine job answering these. Are you ready?

Sarah Morgan: Yes.

Jerod Morris: Okay. If you could have every person who will ever work with you or for you read one book, what would it be?

Sarah Morgan: It s Start with Why by Simon Sinek.

Jerod Morris: Good one.

Sarah Morgan: Yeah, I love I just saw him speak and it blew my mind.

Jerod Morris: Did you? Where did you see him speak?

Sarah Morgan: He came to San Diego and did Creative Mornings.

Jerod Morris: Very nice. Yeah. I have not yet seen him speak other than, obviously, his TED Talks and online, but I imagine that had to be pretty great.

Sarah Morgan: He s super funny. It was awesome.

Jerod Morris: If you could have a 30-minute Skype call to discuss your business with anyone tomorrow, who would it be?

Sarah Morgan: Oh, man. You might laugh at me for this. I want to talk to Bethenny Frankel from

Jerod Morris: Yeah.

Sarah Morgan: The Real Housewives are my guilty pleasure. But I think she is a badass, so that s who I want to talk to.

Jerod Morris: Yeah. Hey, there s no judgment with these questions. Whoever you think will help. What is the one email newsletter that you can t do without?

Sarah Morgan: I don t really subscribe to anything.

Jerod Morris: Really?

Sarah Morgan: Honestly. I like a real clean inbox. Yeah. I don t subscribe to anything.

Jerod Morris: Is that because you want to keep it clean or because you don t find value in an email newsletter subscription?

Sarah Morgan: I don t take the time to read emails when I m subscribed to them because there’s so much other stuff in my inbox. I m like, Oh, there s 30 unread messages here. I m going to wait to read this. I would start putting them into a To Read folder and then I would never read them. I just unsubscribed from everything so I can focus on the most important stuff that s showing up.

Jerod Morris: Interesting. What non-book piece of art has had the biggest influence on you as a digital entrepreneur?

Sarah Morgan: Oh my gosh.

Jerod Morris: This is the one that always seems to get people.

Sarah Morgan: I am a big reader. I ll read like a hundred books in a year, so that is my thing.

Jerod Morris: Yeah.

Sarah Morgan: Okay. I really like going to the opera. Does that count?

Jerod Morris: Of course. Absolutely.

Sarah Morgan: Yeah.

Jerod Morris: Just as an escape, or have you Is there anything that you ve taken from that experience that has helped you in what you do?

Sarah Morgan: Mostly, as an escape. It s so different than the world we re in today.

Jerod Morris: Yeah.

Sarah Morgan: Yeah.

Jerod Morris: Okay.

Sarah Morgan: I love it.

Jerod Morris: Hey, that works. What productivity hack has had the biggest impact on your ability to get more meaningful work done?

Sarah Morgan: Definitely tracking my tasks in Asana. It doesn t work to have that never-ending to-do list. Once I put everything in there and started really keeping track of what things were getting done, I can look back and see like, Oh. Well, that week, I got nothing done. High five to myself. It really helps to keep me accountable and see what s getting done and what s not getting done, and how long things realistically take. Because I do have days when I put 15 things into it and 2 of them get done. Yeah. It keeps me in check.

Jerod Morris: That s because you re always walking your dog and napping.

Sarah Morgan: Of course.

Jerod Morris: Okay, so what —

Sarah Morgan: My dog is old. Those walks only take about 10 minutes.

Jerod Morris: Yeah. My final question for you. What is the single best way for someone inspired by today s discussion to get in touch with you?

Sarah Morgan: Come over and hang out with me on XOSarah.com or find me on social media, @xosarahmorgan.

Jerod Morris: That is XOSarah.com?

Sarah Morgan: Yup.

Jerod Morris: Perfect. Sarah, thank you so much for coming on The Digital Entrepreneur and lending your insight.

Sarah Morgan: Thank you for having me.

Jerod Morris: This was great. Absolutely, and good luck expanding your business in the new year.

Sarah Morgan: Thank you.

Jerod Morris: Thank you very much for listening to this episode of The Digital Entrepreneur. Always appreciate those of you who listen all the way to the end. You are the true Digital Entrepreneur diehards. Of course, my thanks to Sarah Morgan for joining us, and my thanks to our production team here at Rainmaker.FM: Will DeWitt, Caroline Early, Toby Lyles and his team. The show would not be possible without you all, so thank you very much.

And a reminder: go to Rainmaker.FM/Platform to take the Rainmaker Platform for a free test-drive. See if it s for you. It is the all-in-one solution for digital marketing and sales. I think you will find that you like it and you will find it useful. If you have any questions, comments, anything, hit me up on Twitter, @jerodmorris. That s @jerodmorris. I will look forward to speaking with you next week on another brand new episode of The Digital Entrepreneur. Talk to you then.

The Transcript

How to Create Impact That Endures (Instead of Ending Up in a Landfill)

Voiceover: Rainmaker.FM. You are listening to The Digital Entrepreneur, the show for folks who want to discover smarter ways to create and sell profitable digital goods and services. This podcast is a production of Digital Commerce Institute, the place to be for digital entrepreneurs. DCI features an in-depth, ongoing instructional academy, plus a live education and networking summit where entrepreneurs from across the globe meet in person. For more information, go to Rainmaker.FM/DigitalCommerce.

Jerod Morris: Welcome back to The Digital Entrepreneur, the show where digital entrepreneurs share their stories and the lessons they’ve learned so that we can all build better digital businesses. I am your host Jerod Morris, the VP of marketing for Rainmaker Digital, and this episode No. 31. This episode of The Digital Entrepreneur is brought to you by the Rainmaker Platform. I will tell you more about this complete solution for digital marketing and sales later. You can check it out and take a free spin for yourself at Rainmaker.FM/Platform.

On this week’s episode, I am joined by someone who has built her professional life around teaching savvy business owners how to boost their marketing skills. My guest is an award-winning graphic designer and marketing consultant who has helped small businesses and large organizations create big brands since 1987, hint, hint.

In 2010, she founded Big Brand System to show small business owners how a system of strategic marketing and great design makes them look professional, cohesive, and successful. She believes that your business may be small, but your brand can be big. If you’re a regular listener of Rainmaker.FM shows and a reader of Copyblogger.com, then you’ll be very familiar with her and her work.

She’s currently the executive vice president of educational content at Copyblogger Media, where she helps people like you build a strong presence on the web. She is about to become a published author because her book, Master Content Marketing, will be officially released tomorrow. That is Friday, the day after this episode goes live, Friday, October 21st. You can get more information at MasterContentMarketing.com. She is Pamela Wilson, and she is a digital entrepreneur.

Pamela, welcome to The Digital Entrepreneur. How are you?

Pamela Wilson: I am great. I’m thrilled to be here.

Jerod Morris: You’re just back from Digital Commerce Summit, yes? As I am as well.

Pamela Wilson: Yes, have not finished unpacking my bags, but I’m back.

Jerod Morris: I barely finished unpacking my suitcase over the weekend. Man, it was really a great event. You gave a great presentation on developing an interactive community. Was there any one single takeaway for you from the event, from the experience overall?

Pamela Wilson: Overall — and I think we’ll probably talk some more about it — what I loved the most was just interacting face to face with people whose names I knew, whose avatars I had seen. Just to see them face to face, talk, get to know a little bit more about their businesses, and hear their questions — that element of it I just love. It’s my favorite part.

Jerod Morris: That is always the best part of the events, no question — to be able to meet people that we’ve interacted with via email or over Twitter, and being able to put faces with names. Yeah, just to hear everybody’s stories, talk about their individual businesses and projects, that’s by far my favorite part, too.

Pamela Wilson: You have that moment over and over where people are going, “That’s really you,” and you’re going, “That’s really you in the flesh. Yes, you’re a real person.”

Jerod Morris: Yes. Something else exciting happened while we were at Digital Commerce Summit. That is that I got to hold a physical copy of your new book, which I believe is the first physical copy out in the wild, if I’m not mistaken.

Pamela Wilson: It’s funny. This is a new thing for me. This is the first book I’ve ever written. I’m still learning the ropes, obviously. I had set this release date for later this week, but I still am not completely clear on how this happened. The company that’s doing the print-on-demand work started shipping them, despite the fact that, in my file, it says they’re not supposed to ship them until later.

Leslie Staller, who’s one of our long-time customers, showed up at the Summit with a copy of my book. She said, “I have your book. Have you seen it?” I said, “No.” She showed it to me. It was fantastic. It was such a good feeling to see it in real life. Again, it’s that feeling of seeing something in real life, right? Something that’s been virtual.

Jerod Morris: Absolutely, and it looked great. You sent me the proof of what the cover will look like, and it looked great in person. For Leslie, she’ll have a collector’s item forever, the first copy of this book.

Pamela Wilson: She will, and it’s the first book I ever signed as an author. That was kind of cool. Somebody took a photo, and we have photo evidence of the first book I ever signed.

Jerod Morris: Isn’t that cool?

Pamela Wilson: It was very cool. The other piece of it that was neat is that my background is as a publication designer. I did that for decades. Magazines, books, brochures, newsletters — anything in print that was basically taking words, putting them into print, and making them look good — that was what I did for decades, in English and in Spanish.

I did it for a really long time, and I haven’t created a physical product in a really long time. That piece of it was fantastic, too — just to see pages that I had designed all bound together into this object that you could hold. That was such a good feeling.

Jerod Morris: Yeah, now people may be wondering listening to this, why are we talking about a physical book when the show is called The Digital Entrepreneur?

The Motivation Behind Pamela’s New Book, Master Content Marketing

Pamela Wilson: Yeah.

Jerod Morris: The reason why is because a lot of what you talk about in this book, it’s lessons that you have learned along the way as a digital entrepreneur. Plus, you kind of walked through the process of creating this book on the show that you had. It was called Zero to Launch, was that the …

Pamela Wilson: Zero to Book with Jeff Goins.

Jerod Morris: Zero to Book, yeah.

Pamela Wilson: Yes.

Jerod Morris: Zero to Book on Rainmaker.FM, and you are actually doing an episode with us on The Showrunner talking about that experience as well. For folks who are interested in learning more about that experience, you can go to Showunner.FM and learn more about that.

Obviously, for the rest of this episode, we want to dive into the background that gave you a lot of the experience that you talk about in this book, your background as a digital entrepreneur. Let’s dive into that, if you’re good with that. Are you ready?

Pamela Wilson: Yeah, let’s do it.

Jerod Morris: Let’s start out with the question that I always ask our guests to start out. I’m always interested to hear the many varying responses that we get. I’ve always believed that the number one benefit of digital entrepreneurship is freedom — the freedom to choose your projects, the freedom to chart your course, and ultimately, the freedom to change your life and your family’s life for the better. What is the biggest benefit that you have derived from being a digital entrepreneur?

Pamela’s ‘Contrarian’ Answer About the Biggest Benefit She Derives From Being a Digital Entrepreneur

Pamela Wilson: Well, you know me well enough, Jerod, you know I’m kind of a contrarian, right? My answer is going to sound a little bit contrarian, but it’s because I had my own business for almost 25 years at this point. From the beginning, my office was always in my home. That was because, when I started my business, I was a brand-new mom, and I basically just wanted to be where my children were.

Twenty-five years is a long time ago, and back in those days, people kind of looked at you side-eyed if you worked from home. It was like, “Oh, you don’t actually have an office? You work from home” — which is laughable nowadays because the tables have completely turned. I think in a way people are like, “Oh, you have to go into an office? You can’t do your work from home?” Right?

Jerod Morris: We’re the ones laughing now.

Pamela Wilson: I know, seriously. I have seen that whole change happen over the years. I was on the other side of that continuum. Now I’m over here where it’s totally accepted, and it’s almost expected that you work from home, especially in certain fields.

This is the contrarian part — as far as my working environment, I actually have had a lot of freedom and flexibility from the very beginning because I set it up that way. The difference that I have seen since I’ve become a digital entrepreneur and had an online business — which I started in 2010, Big Brand System –for me, it’s been about reach.

Back in the day when my business was offline, I had local clients, I had regional clients, and I had a handful of national and even international-level clients. But the national and international clients were all based regionally. They were people who I could drive to their offices and have a meeting with in person.

One of my clients was the United States Golf Association, which is a pretty big organization nationally. They oversee the US Open. They write the rule book for golf in the US. They were like a 45-minute drive away. I used to go over to their offices, and I produced a publication for them. I had another kind of international client that, again, was based locally. They were a 30-minute drive away.

That’s the difference that I see is I was able to get some reach, but really the clients were all local. The difference now is that I’m helping people from all around the globe. In Authority for example, we have people from all over the place, and we meet with them virtually and help them. I just love that aspect of it.

Jerod Morris: Well, and you kind of started to answer my second question here, which is, I’d love for you to take us back before you became a digital entrepreneur and explain what you were doing, which you did. Really, what was missing that led you to want to make a change and led you to want to start Big Brand System?

The Epiphany About the Eventual Destination of Pamela’s Print Work That Led to Her Desire to Shift Gears

Pamela Wilson: Well, I started my career as a designer, but I was always a designer who was interested in marketing. I ended up offering both things, kind of marketing consulting, and then design work. If there was print work involved, I could help to make that happen as well.

For part of my career, I actually was living in South America. I did my work in Spanish. I had my business down there. I just got to this point after almost two decades of doing that where I felt like I had designed everything that there was to design — from business cards to billboards, to magazines, to books, in English and in Spanish. You know what I mean?

Jerod Morris: Mm-hmm (affirmative).

Pamela Wilson: I was just like, “I feel like I’ve done it all three times over in two languages.” It just did not have the same kind of challenge for me that it had in the early days. Then I also had this major crisis, and I’ve never told you the story. At one point in the late ’90s, it hit me that all the marketing materials that I was working to help create and bring to life ended up in a landfill. It just hit me like a ton of bricks. All this stuff that I’m helping people to create to promote their businesses, it all gets thrown away eventually.

Jerod Morris: Yeah.

Pamela Wilson: Nobody hangs onto it, right? That realization hit me in the late ’90s, and honestly, it wasn’t until later in the 2000s that I was able to figure out how to change that. That was where online business, online marketing, and content marketing really came into play. That’s one of the reasons I wanted to write Master Content Marketing. I feel like it’s a much better way to market your business. It just feels a lot more like you’re serving the people you want to reach, rather than just pushing messages out at them — which is what the first decades of my career were all about.

The marketing can be so valuable that people actually save it instead of throwing it away. I literally created marketing that would arrive in your mailbox, and you would stand over the garbage and just throw it out. That’s what I was doing for many, many years. They were beautiful pieces. Except for maybe the magazines and maybe some annual reports and books, there were really just a very small percentage of what I was bringing to life was saved and valued.

Now you can even see through social sharing, you can see the online content that people are valuing. People all the time come up to me and say, “You know, I save every email newsletter that you send.”

Jerod Morris: Wow.

Pamela Wilson: That’s unbelievable to me. It’s such a change. I love that element of online marketing and content marketing — that it’s starting from a position of really helping people.

Jerod Morris: Was there a particular eureka or flash-bulb moment when you had that realization about, as you said, all your marketing materials ending up in a landfill? Or was it something that you came to gradually?

Pamela Wilson: No, there was a eureka moment. The thing is, it was in the late ’90s when that realization hit me. It wasn’t, like I said, until almost 10 years later, like 2009, that I figured out what to do about that realization. I basically spent almost 10 years feeling like, “I’m creating future landfill material right here. The best-looking future landfill material that I can possibly create, but that’s definitely where it’s all ending up.”

It just dawned on me. One thing that designers do, and it probably doesn’t happen as much anymore, but when you were a print designer, you had a physical portfolio with samples of all your pieces. I think that’s where it hit me. I was like, “I have a portfolio full of what other people consider to be garbage, and that’s what I’m showing as my work. Here’s this brochure. This is the last remaining copy because everybody else threw it out after they got it.”

Jerod Morris: Yeah, wow. Tell me about the milestone or moment in your career since you’ve become a digital entrepreneur, since you’ve moved online, that you are the most proud of.

The Humbling (and Exciting!) Honor of Being Published on Copyblogger

Pamela Wilson: Yeah, well, I’ll tell you, Big Brand System actually started out that it was going to be a book. I wanted to write a book. I felt like I had learned a lot about how small businesses can create a recognizable brand that helps to position their businesses, and I was going to write a book. Right around that time, I found Copyblogger. That was how Big Brand System became a blog instead of a book. I’m very happy that it worked out that way. That was really the best way to do things.

What I did after I found Copyblogger is I signed up for Teaching Sells, which was launching right around the time that I found Copyblogger. I got to know the team a little bit, and I submitted a first guest post in early 2010. This is literally like only a few months after I started to write online content. That was unbelievable that was accepted by them, you know?

Jerod Morris: Wow, yeah.

Pamela Wilson: Sonia was managing the blog at the time, and I was just thrilled to my core that she wanted to publish this guest post. It’s this post called The Bobby McFerrin Plan for Creating a Remarkable Business. I had been to a Bobby McFerrin concert, and I saw all sorts of connections between what he was doing from the stage and what we were trying to do with our online businesses. I wrote this post. She published it. As soon as she published it, I sent another post to replace it. I’m like, “Okay, you like that? Here, I have another.”

She published the second one, so I sent another. This went on for a few months. She would publish something. I would send another to replace it. Finally, in June of that year — so a few months after I submitted that first post — she asked me to write for Copyblogger once a month. This, by far, is the digital entrepreneur moment that I’m most proud of.

At the time, it felt like I was being invited to perform at Carnegie Hall once a month. It was just unbelievable that a site like Copyblogger wanted to publish my writing, and I didn’t feel like I was a writer. It just felt like major validation for something new that I was doing and was very exciting. I think I walked around a couple of feet off the ground for a couple of days. It was very exciting.

Jerod Morris: Hey, it’s obviously led to many opportunities since, so that’s great.

Pamela Wilson: I know, I’m still pinching myself. I can’t believe it.

Jerod Morris: On the flip side of that then, tell me about the most humbling moment in your career as a digital entrepreneur and, more importantly, what you learned from it.

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Now, back to my discussion with Pamela Wilson.

Why Pamela’s First Online Course and Community Struggled, and What She Learned From the Experience

Pamela Wilson: Well, I spoke about this at the Summit just a little bit because I did speak about membership sites, like you said. I took Teaching Sells. The whole point of Teaching Sells at that time was to teach you how to put together an interactive membership site. I took the course. I went through every single module, took notes on everything, and I put my head down and started creating my membership site.

Well, what I ended up doing, and I mentioned this at the conference, is trying to pour the entirety of my professional knowledge into this one course. It was just way too much information. I since have seen a lot of other people make this mistake, and I recognize it because I did it myself.

What I realize now is that people actually want less information, but they want that information to be more digestible. You can’t just drown them in facts and figures. It’s not fair. People are busy, and they need you to break it down and make it easy for them to understand. The other thing is that you burn out. As an information creator, you end up burning yourself out when you pour way too much into it.

Now what I do is make sure that everything I teach has some kind of structure that helps the people who are receiving the teaching to understand it and digest it. It also helps me to deliver that information in a format that’s just easier to produce.

Jerod Morris: Yeah, well, and that has shown in the work that you’ve been doing at Copyblogger in charge of the educational content, for instance with Authority, which just has so much information. That’s been some feedback early on was, “There’s almost too much here.” You’ve really gone about putting that information into little mini courses, grouping stuff together, and making it much more digestible for folks. You’ve really put this into action everywhere you’ve been.

Pamela Wilson: Right, yeah. We’ve been working on those mini courses for months. You just gave people a little preview because they have not been released. They’re in the middle of quality insurance checks right now, so it’s coming up very soon. Yeah, that was part of what I wanted to do was just to organize some of the sessions inside Authority so that they made sense together to teach specific concepts. That’s coming soon. I’m excited about that.

Jerod Morris: Let’s fast forward to now. What is the one word that you would use to sum up the status of your business as it stands today?

The Incredible Feeling of Being ‘Published’

Pamela Wilson: The one word that I would use is ‘published.’

Jerod Morris: Published, nice.

Pamela Wilson: Yes. It took a long time to get there, but like you said at the top of the podcast, it’s just this incredible feeling to hold this book in your own hands that you’ve been working on. It’s almost been a year that I’ve been working on that, talking about it on my podcast with Jeff, just putting in the hours to get it done, then learning the ropes of how to get it produced, and all of that. It’s been a huge, huge project. But when you finally have that published piece in your hand, it’s just an incredible feeling. I enjoyed it so much that I’m working on book two now.

Jerod Morris: Already?

Pamela Wilson: Oh yeah. This one I’m going to be co-writing with this person you know well, Sonia Simone.

Jerod Morris: Oh yes, I’ve met her.

Pamela Wilson: Yes, doesn’t that name ring a bell to you?

Jerod Morris: It sure does.

Pamela Wilson: Yeah, we’re really excited. We’re going to be working on a book together. We’re still nailing down a topic, but it’s basically online business the Rainmaker Digital way and the Copyblogger way, which is a little bit different than maybe some people teach it. I’m excited about that.

Jerod Morris: Yeah. Hey, I should have asked you this earlier. For folks who are interested in getting your current book, where’s the best place to go to order it, or to get information about it?

Where to Find Pamela’s Book

Pamela Wilson: What I did is I created a landing page with links to all the different places where people can get it because people have their preferred places to find books. Because of the way I have it produced, it took a little extra effort to make this happen. I had it produced by a company that basically distributes anywhere.

If you have a bookstore down the street where you would like to order it, you may have to order it, but you could get it from your local bookstore. It’s basically available wherever books are sold, but if you want to find a convenient page with a little more information on the book and then some links that you can click on, you can go to MasterContentMarketing.com.

Jerod Morris: That’s a great domain.

Pamela Wilson: How about it?

Jerod Morris: Yeah.

Pamela Wilson: That was one of those things that I checked to make sure the domain was available before I nailed down the name of the book.

Jerod Morris: By the way, you know you’re a content marketing nerd when you get excited about someone’s domain when they tell you and you’re like, “Oh, that’s so great.”

Pamela Wilson: Totally.

Jerod Morris: “And you got that in the .com, too. That’s awesome!”

Pamela Wilson: Yeah, definitely.

Pamela’s Biggest Recurring Pain Point (It’s Personal), and How She Hopes to Overcome It

Jerod Morris: What is your biggest recurring pain point as a digital entrepreneur?

Pamela Wilson: It’s interesting because it was highlighted in a good way last week at the Digital Commerce Summit. What I am finding is that I miss that personal touch that I had in my offline business. I used to have a lot of personal contact with clients. We would have meetings, go to coffee, or have lunch. I would make presentations to them, even phone calls.

Nowadays, when you have a purely online business, even a phone call seems weird in a way, you know? Everything is so online, email, virtual, and social media. That still seems a little bit weird to me. I am a person who, really, I like people, and I miss being around them. When I say it was highlighted in a good way it’s because I got to have that contact with people last week, and I loved it.

I think the pain point now for me is to try to figure out how we can combine the virtual delivery of our education with some kind of personal contact. Even if it’s not in real life, but it’s over video or on the phone. I think there’s a way to do that. I’m excited to pursue that and see if there’s a way to personalize our education a little bit more than maybe what we’ve been doing.

Sonia and I have already talked about it and talked about ideas that we might be able to implement. I have a feeling that’s going to fuel what we do going forward.

Jerod Morris: Well, and it’s going to be interesting to see where this goes. There is likely to be a coming revolution in this area with virtual reality as well, as Brian talked about in his keynote at Digital Commerce Summit. It’s going to be really interesting to see how that affects how we teach, how we interact with folks online.

Pamela Wilson: Yeah, I would embrace that honestly. Anything that makes it feel a little more personal and like you’re really dealing with people, and there’s a little more two-way conversation going on, I would really embrace that. I think it’s missing. I miss it. That’s all I know. I think the students miss it, too.

I tried to introduce some things in Authority, just some sessions and things that highlight our community members, and I think people have enjoyed that.

Why Pamela Relishes Being the Captain of Her Own Ship (Even If It’s a Little Row Boat)

Jerod Morris: Yep. Okay, so other than participating in conference calls with Robert Bruce, what element of your work gives you the most satisfaction on a daily basis?

Pamela Wilson: You picked the biggest highlight, so what am I going to talk about now?

Jerod Morris: Right.

Pamela Wilson: I’m sure you feel the same way. I have a really amazing job situation right now. I have had my own business for almost a quarter century at this point. I had absolutely no intention of going to work for someone else. That was not even on my radar. When I was asked to join the team a couple of years ago, my thought was kind of like, “Well, I wouldn’t even entertain the notion if it was any other company.”

But like I said to Brian at the time, “I like the work that this company is doing in the world, so yes, I’d like to be a part of it.” But I still have enough time for my own projects, and I really value that. It’s just important to me personally to remain the captain of my own ship, even if that ship is just a little row boat compared to the company that I work for.

It’s important to me. I think it might be part of my identity at this point. I wouldn’t say that I’m unemployable exactly, but I’m someone who highly values entrepreneurship. It’s just an important part of who I am.

To sum it up, what gives me satisfaction is the fact that I can have both of those things. I can work for this company that’s doing this amazing work in the world, but I can still captain my little row boat. I’m happy about that.

How One Little Tool Manages All Pamela’s Important Information

Jerod Morris: Yeah, absolutely. Let’s open up your toolbox real quick here. What is the one technology tool that contributes the most to your success as a digital entrepreneur?

Pamela Wilson: I would say Evernote, honestly.

Jerod Morris: Ooh.

Pamela Wilson: Yeah, I know. I was using Evernote before I joined the team, but after I joined the team a couple of years ago, the volume of information that I had to manage just exploded. There was just so many more meetings and projects that I needed to track. Evernote is an extension of my brain. I cracked it open the first week and started using it pretty aggressively, the first week I started working as a member of the team, and I’ve never looked back. It’s completely searchable. I don’t lose things in there. When in doubt, I dump it in Evernote basically.

Jerod Morris: Yeah, that’s not a bad philosophy. It’s one that a lot of people follow, I’m starting to learn. What is the non-technology tool that contributes the most to your success?

The Unique (and Surprising) Strategy Pamela Has for Keeping Her Many To-Dos Straight, so She Can Get Meaningful Work Done

Pamela Wilson: I would say that would have to be pencil and paper.

Jerod Morris: Hmm, old school.

Pamela Wilson: Yeah, I know. I write out my to-do list every morning. It’s like a piece of lined paper, and it’s got one of those red lines and a narrow column along the left side. I write the hours of the day — 7:00, 8:00, 9:00, 10:00, 11:00, 12:00, 1:00, 2:00, 3:00, 4:00, 5:00 — however many hours I’m blocking off to get work done. Then next to those hours, I basically write in what I want to accomplish in those different blocks of time. That has been tremendously helpful, just to have a map of my day. It doesn’t always play out that way because stuff happens. Just to kind of have a map of what I’m aiming for first thing in the morning, that has been super helpful.

Jerod Morris: And you go pencil and paper. Do you have a tool that you use to track your to-dos, calendar, and all of that?

Pamela Wilson: Yeah, I’m just laughing because it’s so low tech it’s kind of ridiculous. I have an ongoing to-do list in ByWord. It’s just a document where I have everything dumped that I need to get done. Like we’re recording on a Monday — so I have everything I wanted to get done on Monday, but it’s not in any kind of order. I pull it from there and put it onto my pencil and paper to-do list next to hours of the day.

That’s how I know they’ll actually get done. It’s like, “From 9:00 to 11:00, I’m going to do this thing,” and I have this chunk blocked out for that one thing. It’s like a centralized list where all the to-dos live, and I put them into blocks of time with pencil and paper. Very low tech.

Jerod Morris: But very effective.

Pamela Wilson: Yeah, I’ve tried lots of other tools, and this seems to work better than anything else.

Jerod Morris: Earlier I asked you for the one word you would use to sum up the status of your business as it stands today. You said ‘published.’ If we talk again in a year, what would that one word be? You’re not allowed to say published again with your book with Sonia.

The Possibilities That Keep Pamela Excited, Along with Being ‘Published Again,’ That Is

Pamela Wilson: Jerod, are you serious? I was going to say ‘published’ again. Now what am I supposed to say?

Jerod Morris: Were you really?

Pamela Wilson: Yeah.

Jerod Morris: Did I really steal it? Okay, you can use it.

Pamela Wilson: Well, I am hoping that by this time next year, the book that I’m writing with Sonia will be out, and we’ll be talking about it. I’m hoping it will be out before then. We’ll have to see how it all plays out. I have that second book. I’m starting to get really excited about it.

I think some changes will be coming for the education inside Copyblogger. It was something that Sonia and I met about at the conference last week, but at this point, I’m not really sure what those are going to look like. I’m excited about all the possibilities, but I don’t know what they’re going to look like. I don’t have a word for them because I don’t know what they’re going to look like yet.

Jerod Morris: Okay, but ‘published again,’ that’ll work. That is a big, ambitious goal to get a book out this year, do it again.

Pamela Wilson: ‘Published again,’ and it’s two words. I don’t know, published again, maybe we’ll hyphenate them and make them a compound word or something.

Jerod Morris: Yes.

Pamela Wilson: Published again, that’s a big goal.

Jerod Morris: Okay, are you ready for some rapid-fire questions here to close this out?

Pamela Wilson: Oh yeah, bring it on.

The One Book Pamela Would Insist You Read

Jerod Morris: All righty. If you could have every person who will ever work with you or for you read one book, what would it be?

Pamela Wilson: It would definitely be Predictable Success By Les McKeown, and I’ll send you a link to it. It is a fantastic book about the way businesses grow. It could be an online business. It could be an offline business. But it just explains the stages of growth in a way that’s different than anything else I’ve ever read. It’s super helpful to give you some kind of a map to follow, with some goals to aim for.

Jerod Morris: Hmm, okay.

Pamela’s Ideal 30-Minute Skype Call to Discuss Her Business

Jerod Morris: If you could have a 30-minute Skype call to discuss your business with anyone tomorrow, who would it be?

Pamela Wilson: The funny thing is, it would be Joanna Penn, who I ended up sitting next to at our conference one of the days last week.

Jerod Morris: Oh wow.

Pamela Wilson: She asked me to sit next to her, and of course, I didn’t want to fangirl out too much. I’m like, “I’m sitting next to Joanna Penn!” But she has built a business around books, so I would love to have 30 minutes to ask her. I was too embarrassed to do it during the conference because it’s hard if somebody’s sitting there peppering you with questions. I didn’t want to be that person, you know?

Jerod Morris: Yeah.

Pamela Wilson: I’m very lucky that because of the Zero to Book podcast, I had many, many calls, I mean way more than 30 minutes, with Jeff Goins, who has been through that book-publishing process as well. He’s a successful author, so I got a lot out of my conversations with Jeff. We obviously recorded them all so that other people could benefit from them, too.

Joanna has a slightly different take. She does things differently. She’s a lot about volume of books and building up collections of books that you can then maybe group together and sell. I love that approach, and it’s worked really well for her. Joanna Penn of the CreativePenn.com.

Jerod Morris: Yeah, she really focuses on creating intellectual property assets. By the way, for anybody who is interested, we have a case study with her inside of Digital Commerce Academy. I know from when this episode comes out, we’re actually closing the doors to Digital Commerce Academy for a while, probably until early 2017. If you’re interested in learning from Joanna, you can get in and watch that case study. It was fascinating just to see her life story — where she was, where she is now, and just the whole strategy that she has.

Pamela Wilson: She really approaches it as a business, which I think is fascinating.

Jerod Morris: She does.

Pamela Wilson: I think a lot of people think that writing a book is all about it being a passion project. That is super helpful. It’s helpful to have that passion, but she’s very strategic about it. I love that. I get a lot out of her materials.

Jerod Morris: Yeah, and when you meet someone for the first time at these conferences, you don’t always know, obviously, how they’ll be in person. But she proved to be about as nice, kind, down to earth, and friendly as anybody could be. She was phenomenal.

Pamela Wilson: Absolutely, yeah.

The One Email Newsletter Pamela Can’t Do Without

Jerod Morris: Next question, what is the one email newsletter that you can’t do without?

Pamela Wilson: I am really liking what CoSchedule is putting out these days.

Jerod Morris: Ooh, yeah.

Pamela Wilson: Yeah — they just have very well-researched, well-written, and nicely presented content. I find it very useful. They talk a lot about social media. I come from old-school marketing, so social media is still something I’m learning more about. And it’s always changing. They just have really good, solid information. I enjoy it.

Jerod Morris: Yep.

The Non-Book Piece of Art That’s Had the Biggest Influence on Pamela as a Digital Entrepreneur

Jerod Morris: Next question, what non-book piece of art has had the biggest influence on you as a digital entrepreneur?

Pamela Wilson: This is like the world’s most awesome question, I have to tell you. Nobody’s ever asked me that. I am very inspired by Pablo Picasso’s volume of work, and I talked about it in my book. He just created a lot of work. He just did a lot of work. It’s one of the things that I recommend to people when it comes to content marketing is to just write a lot.

When you create a lot of work — first of all, you’re practicing, so you get better at it — but you just have more of a chance of creating a handful of pieces that become masterpieces the way his work became. Not all of it. He created a lot of work, and I’ve seen a lot of it in museums because he’s one of my favorite artists. What I said in the book is that not everything that he created was a masterpiece. Some of it, it just looks like he was trying to work out an idea, and the idea didn’t quite work, you know?

Jerod Morris: Mm-hmm (affirmative).

Pamela Wilson: But you can see that he just kept at it, kept at it, and then he created a few pieces, they just take your breath away when you see them.

Jerod Morris: Hmm, great one.

Pamela’s Biggest Productivity Hack for Doing Meaningful Work

Jerod Morris: You may have spilled the beans on this one already when we opened up your toolbox, but I will ask you anyway. What productivity hack has had the biggest impact on your ability to get more meaningful work done?

Pamela Wilson: Yeah, well I have a different answer than what we talked about.

Jerod Morris: Oh good.

Pamela Wilson: Yeah, my productivity hack really is breaking down a piece of content into its component parts and then understanding what each part of the content needs to accomplish. That’s actually the premise of my book. Really the guts of Master Content Marketing is this seven-chapter section basically, right in the middle of it, that talks about your headline, your first sentence, your introduction, your subheads, your main copy, your summary, and your call to action.

Once I understood that good content marketing was made up of those pieces, and then I understood what each piece needed to accomplish, it became so much easier. That’s why I wrote the book that way. It’s like, “If you want to write a good first sentence, this is how you do it,” and I devoted a whole chapter to it.

Jerod Morris: Wow.

How to Get in Touch with Pamela

Jerod Morris: Finally, what is the single best way for someone inspired by today’s discussion to get in touch with you?

Pamela Wilson: Well, I’m on Copyblogger every week because I’m now managing the editorial team, as you know. The best place to find me really is on Copyblogger, but they can also find me on Big Brand System. That’s two ways, so it’s double for your money. There you go.

Jerod Morris: Yep, and that is BigBrandSystem.com, yes?

Pamela Wilson: Right, that’s it.

Jerod Morris: Excellent. Well, Pamela, it was fantastic to see you last week at Digital Commerce Summit. It is always great talking with you. Thank you for joining us on The Digital Entrepreneur.

Pamela Wilson: Thank you, and thanks to everyone who listened.

Jerod Morris: All righty, well thank you for tuning into this episode of The Digital Entrepreneur. My thanks, of course, to Pamela Wilson, my guest on this week’s episode. My thanks also to Will DeWitt and Caroline Early, who helped me produce this, and to the great Toby Lyles, who edited this episode for you.

Just a quick reminder, go to MasterContentMarketing.com to check out the details on Pamela’s book. Don’t forget, as I mentioned, Digital Commerce Academy, we’re closing the doors next week. Not closing the doors forever, we’re just kind of shutting the doors for now. We’re going to re-open them in early 2017.

If you want to get in and get access to all of the great education that is in there, including that case study with Joanna Penn that I talked about and Brian Clark’s course on how to build your online training business the smart way, go to DigitalCommerce.com/Academy, get the details, and get in. When we re-open it in 2017, the price will be higher. Don’t forget about that as well.

Don’t forget to join us next week for another brand-new episode of The Digital Entrepreneur. We will be here. We will have another great guest, another great discussion for you. As always. you can find me on Twitter, @JerodMorris. I always appreciate your feedback on the show, so Tweet me anytime. With that said, have a great rest of your week, and I will talk to you next week on another brand-new episode of The Digital Entrepreneur. Take care.

The Transcript

How Will Falconer Stopped Trading Dollars for Hours and Found His Calling

Voiceover: Rainmaker.FM.

You’re listening to The Digital Entrepreneur, the show for folks who want to discover smarter ways to create and sell profitable digital goods and services. This podcast is a production of Digital Commerce Institute, the place to be for digital entrepreneurs. DCI features an in-depth, ongoing instructional academy, plus a live education and networking summit where entrepreneurs from across the globe meet in person. For more information, go to Rainmaker.FM/DigitalCommerce. That’s Rainmaker.FM/DigitalCommerce.

Jerod Morris: Welcome back to The Digital Entrepreneur, the show where digital entrepreneurs share their stories and the lessons they’ve learned so that we can all build better digital businesses. I am your host, Jerod Morris, the VP of Marketing for Rainmaker Digital. This is episode number 30. This episode of The Digital Entrepreneur is brought to you by the Rainmaker Platform. I will tell you more about this complete solution for digital marketing and sales later, but you can check it out and take a free spin for yourself at Rainmaker.FM/Platform. That’s Rainmaker.FM/Platform.

On this week’s episode of The Digital Entrepreneur, I am joined by someone who is passionate about the health and vitality of your animals. He was a conventional veterinarian for seven years, but felt a calling from within that made him move on. Even though he knew that drugs and surgeries for animals worked for the most part, he felt that something was off, that animals needed a new way to be healed.

Today, he hosts a number of vital animals courses, as he wants to share his knowledge of what practices prevent illness effectively, naturally, and sensibly in order to help people who want the best for their animals. He is Will Falconer, and he is a digital entrepreneur.

Alrighty, Mr. Falconer, welcome to The Digital Entrepreneur.

Will Falconer: Hey! Glad to be here, Jerod.

Jerod Morris: Yeah, it’s awesome to have you here. I’m very excited about this conversation. To get started, I’ve always believed that the number one benefit of digital entrepreneurship is freedom. The freedom to choose your projects. The freedom to chart your course. Ultimately, the freedom to change your life and your family’s life for the better. For you, outside of freedom, what is the biggest benefit that you have derived from being a digital entrepreneur?

Will Falconer: I’d have to say my biggest is reach. I’ve been a homeopathic vet for 25 years now out of my 37 or 38 as a vet. I found myself trying to fix broken animals one at a time who’ve been damaged by conventional medicine, mostly. All man-made disease. In the last five or eight years, I really realized that I’ve got to get out in front of that prevention that’s damaging them and teach on a much wider scale.

Having a digital teaching ability has been huge. Now I’m able to get in front of — instead of one-on-one — 100 people. I’m on the cusp of bringing that up to a much bigger audience.

Jerod Morris: What’s so fascinating about what you’re doing … We hear so much about us as humans how much we’ve been impacted by over-prescription of medication and poor diet, all of these different things. It’s interesting to see you applying that to animals. Are you on the cutting edge of that? Of getting this message out there?

Will Falconer: I am. I think I really stand alone in being — I guess radical is the right word. I’m literally realizing that we’re causing the damage that these animals are then coming back to the vet for. We’re over-vaccinating them. We’re sending them out the door with devitalized food. We’re recommending — “we” meaning my conventional colleagues, I don’t do this anymore — sending them out the door with poisons that kill flees that you were supposed to just drop on their shoulders. That say on the label, “Oh, by the way, don’t get this on your skin. Don’t eat. Don’t drink. Don’t smoke while you apply this to your dog.”

All these things are adding up. It’s been a complete correlation line in my graphing of this situation where the more an animal visits a vet, the sicker they end up being because of all these interventions. There’s a huge parallel.

Jerod Morris: That’s a vicious unfortunate cycle. My goodness.

Will Falconer: Yeah.

Jerod Morris: What’s the response been? Have you found that these messages are met with some skepticism, or do you think that because we’re all starting to see this in our own lives as humans that people are receptive to it with their animals too, like it makes sense?

Will’s Audience Comes to His Defense

Will Falconer: Yeah, it goes both ways. I have a lot of following on my blog. I’ve been blogging now for about five years at VitalAnimal.com. A lot of people are resonating with the message. They’re saying, “This guy’s honest and he’s shooting straight, and he gives us all sorts of free information. We trust him. We really like what he’s saying and we trust him.”

I wrote a blog post that spoke about a client who wrote me and said, “I get shakes when I go to my veterinarian because she does this and she does that. If I miss a vaccination by a month, she makes me go through two more.” I wrote a blog post called something like: “Have You Been Abused by Your Veterinarian?” She was, basically, and it was her story.

Conventional colleagues piled in and said, ” It’s a bad thing he’s doing,” and yet they didn’t have anything substantive to add to the conversation. I had a pile of people on Facebook who were giving me negative reviews. And then, lo and behold, the magic happened, which was my community jumped to my defense. I was busy making a course. My latest course is out now, and I was busy building it, and I didn’t have time or, really, inclination to keep up with all the chatter on Facebook.

My community came to my defense and said, “Tell us what you’ve got that says we should be vaccinating — every year — our dogs.” They had nothing except screams and protests that, “He’s saying bad things,” and yada-yada-yada. They took the high road, my people did. They ended up forcing the hand of these people, and these people withdrew their negative reviews. It was really brilliant.

Jerod Morris: Wow! The power of content and authority. That is when you know that you have a great audience, when they come to your defense like that. That’s phenomenal.

Will Falconer: Yeah, it really was. I looked late at night one night before falling asleep and I said, “Just let me see how this is going.” All the negative reviews were replaced with positive reviews. It was just like, “Wow, that’s amazing!”

Why Will Decided to Stop “Trading Dollars for Hours”

Jerod Morris: Wow. That is awesome. Let’s go back. I want you to take us back to before you became a digital entrepreneur. What were you doing and what was missing that led you to want to make a change?

Will Falconer: As I mentioned, really just working one-on-one. I’ve been a specialist in this field. There’s just a relatively small handful of us who are certified veterinary homeopaths. Like everybody in a busy veterinary practice, we’re busy with patients. That’s where I was buried. I consult with people both long distance on the phone and I consult with people here in Austin where I live.

If I was out of the office — I like to travel to India and spend a few weeks or a month — my income would go to zero because I was there trading hours for dollars. That’s life before digital entrepreneurship. Afterwards has been totally different. One of the test cases was a few years ago when some affiliate income and some ebook sales pretty much replaced my month away with a darn near amount of income. I went, “Okay, this is doable.”

Jerod Morris: Wow. Very cool. Now, there’s a story that also helped lead to an epiphany. I think I was reading it on your website. Could you share this story of how your own cat Cali led to your “aha” moment?

Will Falconer: Oh, yeah. This is when I was really just a budding homeopath. I was probably in the middle of round two of studies that went five segments in a year. My own cat came struggling back home. A teenage bride who’d had her kitties die within her womb. She came in dragging herself and skinny. We hadn’t seen her for a few days, and this foul-smelling discharge was coming out of her womb. Boy, in the old days I would have hammered her with all these antibiotics. I just said, “No. I know that homeopaths of old have cured things worse than this with nothing but homeopathic remedies. Let’s give this a run.”

I found a particular remedy that read really well for her symptoms and I gave it to her. It’s a remedy made especially for things that happen during the puerperal period, meaning around the birth period. Lo and behold, she just turned around, on a dime almost. These things don’t go away in an hour, but it seemed like literally within hours she was perking up. The discharge slowed and started to smell more normal.

Within just a couple of days, she was back up eating full-on and acting totally normal. I went, “Okay. That’s the power of this medicine? There’s no way I’m going back to the old style of drugs and harmful things.”

Will’s Journey to Digital Entrepreneurship

Jerod Morris: How important do you think that personal story of yours — that personal connection that you have — has been in telling your own story and then attracting people? Getting people to be attracted to you and trust what you say.

Will Falconer: I think it’s huge. They know I’ve been over that road, and I have so many cases in my history now that I can pull from. People who I’ve never met who write me and say, “I went through this and I found a homeopathic vet, a colleague of yours, and they pulled my dog out of the fire. He got so much better.”

Or, a common one is, “We changed my dog who was struggling and struggling with the veterinary treatments of the day, and we finally just said, ‘Enough. We’re not going to anymore.’ We took him off a cereal food — a kibble they call it — and we put him on a raw food diet that’s balanced and more like what a wolf would eat. Slowly but surely he climbed out of the trenches and he got better. He’s never looked back, and we haven’t had any more drugs since. We didn’t need any.” I get stories like that to pull from all the time.

Jerod Morris: Tell me about the milestone or moment in your career as digital entrepreneur that you’re the most proud of.

Will Falconer: Probably it would be this very last course that launched. I set my price at a higher price point. It scared me a little bit because I’d had a nice turnout. I think my first course was only $197, and then my second one doubled that and it went up to $497. I had a few tiers. This one, I said, “I’m really going deep on this. I want to teach people how to raise their puppy from even preconception — which homeopathy can affect — all the way up to the first year, which is where all the decisions are made that could affect the trajectory for the life. I’m going to charge $997 and see how we do, because I think it’s really worth a lot, especially when you contrast it with what could be spent from chronic illness that results from prevention done wrongly.”

I had not as much as I figured would come in, but the people that came in — there’s 54 students — they were enthralled to be in and to be learning from Dr. Falconer. “We’ve heard so much about him.” Several of them had taken courses. I gave my past alumni a nice hefty discount. Probably one of the funniest things was a golden moment. Once the cart closed, I still had a day to release the course to everybody. I said, “Now, it’s coming out tomorrow, so hang in there. We’ll all get together. You can chat on Facebook and introduce yourself.” Someone got on Facebook and said, “Now I know what an iPhone launch is like when I’m waiting in line for the latest iPhone. I’m so excited to be here.”

Jerod Morris: That’s awesome.

Will Falconer: It’s continued. We did our first live webinar over the weekend and we’re on week two now, and everybody is just enthused and really happy to learn the stuff. There’s no mention of, “it’s too high-priced.” We’re getting value transmitted here. It’s real obvious. That’s probably the pinnacle of my digital entrepreneurship so far.

Jerod Morris: How important was it for you as you were making the case for this higher price to really contrast it against what people might have to pay at a vet? That seems like it would be a really important case to make, especially as you’re trying to go up to that higher price point. Is that something that you tried to do?

Will Falconer: Yeah. It was definitely a part of my sales page. In my pre-launch videos, the last one of … I did three in Jeff Walker’s style. In the last one, I interviewed an old client from 20 years ago who Skyped with me from Mexico where she was with her pack of dogs. She basically told the story about how what I taught her 20 years ago has served her through three generations of Akitas, these big dogs that are just fury love balls. She said, “You know, we really don’t have any veterinary expenses.” I said, “How has that affected your budget?” She said, “It’s big. It’s huge.”

“We originally came to Dr. Falconer, because we had this dog who was going down the tubes and conventional medicine seemed to be making things worse. He used homeopathy and it turned the tables and everything got well. But what we learned about raising animals stayed with us, and we were determined to do a differently for the next couple of generations.”

That story alone was really a golden opportunity. I brought it out again in the sales video and in the sales copy to say, “The commonest disease of our time is now allergies. Allergies are a chronic disease. It means your dog is going to be scratching and chewing and making holes in her hide and losing hair. Between allergy testing and allergy treatments and years and years of really no cure, you are going to quickly spend thousands of dollars.”

The other part of the equation was I had many people who had come to me after trying conventional medicine to cure these chronic cases and they’d say, “I’m really sorry to be finding you so late, but we’ve already spent multiple thousands of dollars and our dog is still not well.” It was easy to bring that forward and say, “That’s what you’re looking at if you do this prevention wrong.”

Jerod Morris: Wow. Those are some great testimonials to have.

Will Falconer: Yeah. They really were.

Jerod Morris: On the flip side of that, tell me about the most humbling moment in your career as a digital entrepreneur. And most importantly, what you learned from it.

The Moment that Led to Will’s Realization That He Could Make a Difference

Will Falconer: It was humbling to see that I had a message that was resonating with people. I started out blogging to the ethos. I didn’t really have any list. There was almost nobody reading my stuff, and yet I just kept plugging away. I was following Copyblogger at that time and I was just saying, “I’m going to give free content and valuable content and I’m going to keep at this, and something’s going to come of it.”

For the first nine months or a year, year and a half, it was pretty much crickets. I’d have a few comments here and there. Then it finally got going like a steamroller. It was humbling to know that I was touching so many people in such profound ways. I would have these heartfelt emails coming in after a blog post and a lot of real engaged comments after a while when I reached that tipping point.

I really saw that I could affect a lot of change. It helped me realize that I couldn’t just keep my game small. I had to bring it to a larger audience. In fact, I’ve had an ebook that’s dribbled along for a long time about how to prevent heartworm without drugs. While it’s had great responses, I brought it out in this past spring when I invested heavily in my digital career and said to my people, “I want to bring this out to a much larger audience. I invested more in how to do this than I have in vet school for four years. I’m going to offer a 50% discount for anyone who wants to buy this ebook and audiobook combination.”

I launched it for just four days, a very quick launch. People stepped up and bought that book even if they already owned it, because they really love the message that “I’m going to get out in front of this prevention that’s causing damage.” That was humbling and inspiring, to know that I had these people really behind me. That they saw I was honest and solid, and I was offering something of value and I wanted to reach a wider audience. They were going to help me do that.

Jerod Morris: Gosh. I’m sure there’s somebody who is listening to this right now who have been at this for a while who can really relate with you start out and you’re blogging to the ethos and it’s crickets. Eventually, it does turn into a steamroller if you keep at it, if you have that stick-to-itiveness. I have to assume that part of what kept driving you to keep going even when it was crickets was your passion for this project, for this topic. If you weren’t so personally invested, do you think is something that you would have kept going at and that you would be doing right now what you are doing?

Will Falconer: No, I’m totally invested in it. I tell it to the reader. I say, “I think these vital animals can change the world one shiny, bright, healthy animal at a time, because they’ll be an example.” They become magnetic. They draw people to them. They go, “Oh my gosh! How did he get so healthy? He feels so soft. His eyes and his teeth gleam and he’s well balanced in his behavior.” They come up to an animal owner at a dog park and ask these questions. Then a conversation begins, “Oh! You don’t vaccinate him anymore. Interesting. You feed him a raw diet. You’re preventing heartworm — this supposedly killer disease — without any drugs. That’s amazing! Tell me more.” Yeah, it’s the passion that I have that keeps me in it for sure, and that’s kept me just plugging away.

Jerod Morris: All right. We’re going to take a short break. We’ll be right back with Dr. Will Falconer to find out his one word. Stick around.

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Now, back to my interview with Will Falconer.

All right. We’re back. Let’s fast forward to now. What is the one word that you would use to sum up the status of your business as it stands today?

Will Falconer: It is growing at rocket-speed. I’ve combined what I learned from Copyblogger and my experience blogging with Launch Learning from Jeff Walker. Between the two, it’s been like this rocket ship ride upward now. I’m reaching way more people and growth is just … Finally, my list has gone from hovering around 5,000 to well over 10,000 in this last launch. It’s just up and up from here.

Jerod Morris: We will officially file the one word as “rocket ship.” I like that. Very descriptive. Things are going great, which is phenomenal. It’s great to hear. What is your biggest pain point though as a digital entrepreneur right now?

Why Will Is Striving for More Balance in the Next Year

Will Falconer: I think it’s still probably finding the balance to get everything accomplished that I want to. I don’t want to completely let go of practice, because that’s fulfilling in itself. Yet I’ve dialed it back. I’ve raised my fees. I’ve discouraged new clients for a while, especially while I was launching this course.

It’s keeping a hand in that while growing a digital presence ever bigger. Wanting to reach that point where I’m not spending seven days a week, which I have been for quite some time. Not necessarily all eight hour days or anything. I’ll sneak away. Just getting to that point where I’m more automated, less involved on a day-to-day, hour-to-hour basis.

Jerod Morris: How are you trying to do that? What are some ways that you’re trying to become more automated?

Will Falconer: Now that I’ve got some courses in the can, I’m exploring a membership site idea. I’ve had a free membership that’s been very popular for a long time, but I’m exploring how to take that — again, without tying a ball and chain around my leg — to bring people in at a regular income level so I’ve got some stability. It’s great having a course to launch. Now that I’ve got a couple in the can I can re-launch them, of course. But that’s a real episodic income. I want to explore more about how to get a membership site rolling and keep it stocked with useful content. But not to where I’m having to feel pressured about creating forever.

Jerod Morris: Trying to find some recurring revenue model to go with the launch model that you have with the courses.

Will Falconer: Yes.

Jerod Morris: Is it just you, or do you have a team or virtual assistants that you work with?

Will Falconer: For the last two courses, I’ve hired a tech helper to be behind the scenes in Rainmaker to make sure that I don’t have to think about that because I’m so busy with so many other plates on sticks spinning in the air. I’ve found a tech person now who’s really in with both feet on Rainmaker who has helped me.

I’ve just, this time, hired a couple coaches in exchange for my course. They’re right up at the top level of all my students, so they’re in there fielding questions in my Facebook forum, my private group that people are discussing this course on. I’m going to keep them on board, one way or another. They’re just extremely valuable. I’ve had a transcription person. Just odd jobs here and there, not a steady employment. I’m not sure I want to change that model too much. I’m really happy with it right now.

Jerod Morris: When you say coaches, not coaches for you, but people who are really good students and they’re now helping you coach the other students who are in there in exchange for free membership in the course?

Will Falconer: Exactly.

Jerod Morris: Got you. I want to talk about the courses a little bit. I think you said that your courses for 2016 have closed. Your launch just ended, so the doors have closed for 2016. I’m curious what lessons you’ve learned from this year’s courses and from your latest launches in addition to what you talked about with the pricing, and how you intend on applying those lessons to the future.

The Important Lesson Will Learned from His Latest Online Course

Will Falconer: I think I learned that I probably started out a little too low. I didn’t really have a feel for a price point when I began. I’m an expert. I’ve got authority coming out of my ears. I’ve been doing vet work for 36 years and I’ve been on both sides of the fence.

It was a little bit of a sticker shock when I finally went to $997 on this last course. But what that’s done, I think, is it’s laid a really good groundwork for future courses. A suggestion was made from an expert I listen to, to come with a piece of this larger course and do a deep dive with it, probably early next year. I’ll give a specialized smaller chunk of a course and I’ll likely market it down around $297, $397, something like that. It will likely bring in all those people who said, “I really wanted to learn from you this time, but it was just out of my range.”

This one deep dive is a pain point that many pet owners write me about. I’ll be able to offer that at a more affordable level. My vision is — we’ll see if the hallucination comes true — that they’ll pile in at this lower price point, appreciate the knowledge they’ve gotten for it — a relatively small chunk of important knowledge that helps them through a pain point — and then be ready to step up to a higher-priced course when it comes back out again because they’ll see the value of my teaching.

Jerod Morris: Very smart. Let’s open up your toolbox, if you don’t mind. What is the one technology tool that contributes the most to your success as a digital entrepreneur right now?

The Tools Will Finds Contribute the Most to His Success as a Digital Entrepreneur

Will Falconer: If the Rainmaker Platform counts as a tool, although it’s a multi-armed tool, I think that’s the one.

Jerod Morris: We’ll count it. It’s all-in-one. We’ll count it.

Will Falconer: Yeah. The ability to blog. I have yet to jump in on RainMail, but that’s coming real soon. The ability to send these courses out to people easily and have them get in and log-in and get all their free membership stuff. That’s been the most powerful thing.

Jerod Morris: What is the non-technology tool that contributes the most?

Will Falconer: A book that made a huge difference that I got for next to nothing, or maybe it was free, was Jeff Walker’s Launch paperback book. That’s set the trajectory for me to say, “Okay, I’ve got Rainmaker in place. I can teach. How about getting a launch that attracts people, turns it into an event, gets all these triggers like reciprocity and scarcity in play, and helps people get off the fence and make a decision. ‘Yes, I’m going to jump in and buy this.’”

That was huge. I’m not a big reader of things that aren’t online, but I got this in paperback form and I dove in and I went, “This is going to make a huge difference,” and it’s proved to do so.

Jerod Morris: You had Rainmaker first and then found the Jeff Walker book to help you then maximize Rainmaker, or was it the other way around that you found the book and then needed the tool to help you make it happen?

Will Falconer: No, I was an early adopter with Rainmaker. I got in right at the get go. Launch came along probably a year in.

Jerod Morris: Got you. Okay. Earlier, I asked you for the one word that you would use to sum up the status of your business as it stands today. You said, “rocket ship.” “Growing at rocket speed,” I believe was the exact phrase. If we talk again in a year, what do you want that one word to be?

Will Falconer: Balance. I want to have that steadier, less-intense time commitment, and yet still be serving a large amount of people and having more time to pursue things that are non-work related.

Jerod Morris: Alrighty. Are you ready for some rapid fire questions here to close this episode out?

Will Falconer: Sure.

Jerod Morris: Alrighty. If you could have every person who will ever work with you or for you — or in this case, really, let’s say any person who will be a student at one of your courses as well, we can look at it that way. If you could have those people read one book, what would it be?

Will Falconer: Quite different between the two groups.

Jerod Morris: Yeah, I’d be interested in both answers, actually.

Will Falconer: Okay. My students … one book. It’s hard to narrow it down to one. There’s a lot of good things out there. Although it’s come out in probably third or fourth edition, the students can learn a lot from my teacher in homeopathy, Dr. Richard Pitcairn. He’s got a book called The Complete Guide to Natural Health for Dogs and Cats. He’s had since I got my start in holistic medicine 20, 25 years ago. Something like that. For the people who are in the digital world as entrepreneurs, I think that paperback book called Launch was a game changer for me.

Jerod Morris: Launch by Jeff Walker.

Will Falconer: Yeah.

Jerod Morris: Cool. All right, second question. If you could have a 30-minute Skype call to discuss your business with anyone tomorrow, who would it be?

Will Falconer: Brian Clark. I’d get on the horn with him in a minute.

Jerod Morris: I think since I’ve started asking this question, he’s gotten about half of the responses. I’m just going to start booking appointments for him on his calendar. He’ll wonder where they’re coming from.

Will Falconer: Yeah.

Jerod Morris: What’s the first question you’d ask him?

Will Falconer: I think what I’ve got is a whole lot of valuable content that I haven’t really gotten focused into driving income. So how to take that valuable content and turn it into funnels that bring people step-by-step through what I’d like them to know and to come out on the other end with a steady income.

Jerod Morris: That is a great question. Wow! I’d like to hear his answer to that too. What is one email newsletter that you can’t do without?

Will Falconer: I pretty much read everyday Seth Godin’s newsletter. The smaller they are, the more pithy they are, the more I appreciate them.

Jerod Morris: Yeah. That’s a great one. What productivity hack has had the biggest impact on your ability to get more meaningful work done?

Will Falconer: I think a big one for me has been, because I write so much, it’s been using Scrivener to have lots of pieces that I can juggle and play with. When I’m writing something I love to have that broken down into subheads and content pieces under those subheads. If I decide the order is wrong, I can easily just drag one up or drag one down. It’s such a great tool for such an inexpensive price, that it’s changed the way I write.

Jerod Morris: I’ve heard a lot of good things about Scrivener. I think I’m going to need to use it too, for a couple of my projects. Finally, what is the single best way for someone inspired by today’s discussion to get in touch with you and to learn more about how to take better care of their animals?

Will Falconer: They would just go to VitalAnimal.com and dig in. There’s a contact page there, of course, to reach me directly. It takes you right through a whole lot of good content about things that you can do right from the get go about feeding, about thinking about vaccines. I’ve got a Begin Here page, for instance, that’s got some of my top content in it.

Jerod Morris: Yeah. I recommend that people check this out. Not just to learn more about how to take better care of their animals, but also from a meta perspective. How you’ve set this up with your content that leads people to the courses — obviously you’ve been very successful with it. I think your site is a good example for how to do that and how to set that up properly. Another good reason to go there. That’s VitalAnimal.com.

Will, thank you so much for being here. This was a pleasure. I really appreciate you sharing your stories and your lessons with us here on The Digital Entrepreneur.

Will Falconer: Thanks for having me Jerod. My pleasure.

Jerod Morris: Sure. We’ll talk soon.

My thanks to Will Falconer for taking the time to join us on this episode of The Digital Entrepreneur. My thanks also to Caroline Early and Will Dewitt for helping me out on the production side. Of course, Toby Lyles and his great team at 24 Sound for editing it, putting it all together, and making it sound good.

Of course, my thanks to you for being here and listening to this episode of The Digital Entrepreneur. I always greatly appreciate your support and you lending me your ear for the half hour, 35 minutes, 40 minutes — however long we’re here talking.

One last reminder, go to Rainmaker.FM/Platform. Check out the Rainmaker Platform. Take it for a free test drive. You will like it. But don’t take it from me, go check it out for yourself. Rainmaker.FM/platform.

All right. I will talk to you next week on another brand new episode of The Digital Entrepreneur. Take care.

The Transcript

Are One-on-One Connections the Key to Jump-Starting Your Online Business?

Jerod Morris: Hey, Jerod Morris here. If you know anything about Rainmaker Digital and Copyblogger, you may know that we produce incredible live events. Some would say that we produce incredible lives event as an excuse to throw great parties, but that’s another story. We’ve got another one coming up this October in Denver. It’s called Digital Commerce Summit, and it is entirely focused on giving you the smartest ways to create and sell digital products and services. You can find out more at Rainmaker.FM/Summit.

We’ll be talking about Digital Commerce Summit in more detail as it gets closer. For now, I’d like to let a few attendees from our past events speak for us.

Attendee 1: For me, it’s just hearing from the experts. This is my first industry event. It’s awesome to learn new stuff and also get confirmation that we’re not doing it completely wrong where I work.

Attendee 2: The best part of the conference for me is being able to mingle with people and realize that you have connections with everyone here. It feels like LinkedIn Live. I also love the parties after each day, being able to talk to the speakers, talk to other people who are here for the first time, people who have been here before.

Attendee 3: I think the best part of the conference for me is understanding how I can service my customers a little more easily. Seeing all the different facets and components of various enterprises that helps me pick the best tools.

Jerod Morris: Hey, we agree. One of the biggest reasons we host a conference every year is so that we can learn how to service our customers, people like you, more easily. Here are just a few more words from folks who have come to our past live events.

Attendee 4: It’s really fun. I think it’s a great mix of beginner information and advanced information. I’m really learning a lot and having a lot of fun.

Attendee 5: The conference is great, especially because it’s a single-track conference, where you don’t get distracted by, Which sessions should I go to? and, Am I missing something?

Attendee 6: The training and everything, the speakers have been awesome. I think the coolest aspect for me has been connecting with both people who are putting it on and then other attendees.

Jerod Morris: That’s it for now. There’s a lot more to come on Digital Commerce Summit, and I really hope to see you there in October. Again, to get all the details and the very best deal on tickets, head over to Rainmaker.FM/summit.

Welcome back to The Digital Entrepreneur, the show where digital entrepreneurs share their stories and the lessons they’ve learned so that we can all build better digital businesses. I’m your host Jerod Morris, the VP of marketing for Rainmaker Digital. And this is episode No. 28.

On this week’s episode, I am joined by someone who is passionate about community building, branding, collaboration, and connection. She is a community and brand coach who can assist people from launchpad to take off. She believes that her middle name should be adventure. Oh, and she also believes in Oxford commas and exclamation points too. She is a short-form poet and haiku enthusiast, and she recently self-published her first poetry collection called Brave Little Bones just last year.

She actually got her start by hosting the first-ever Twitter chat for creative bloggers and business owners at #CreateLounge. She is now bringing her extensive background and online community building to help others build a community that supports their brand vision. She is Kayla Hollatz, and she is a digital entrepreneur.

Real quick, before I bring you my discussion with Kayla, I want to let you know a little bit about the Rainmaker Platform. Obviously the Rainmaker Platform powers The Digital Entrepreneur. It powers all of our shows at Rainmaker.FM. It is the complete solution for digital marketing and sales. What Rainmaker does is it empowers you to build your audience with articles, audio, and video. It empowers you to grow your email list faster. To earn more with marketing automation. To craft killer landing pages, start profitable membership programs, sell online courses and digital products, and much more.

It does it all — all in one integrated, simple platform. There is virtually nothing that you cannot do with Rainmaker. Even better, you never waste valuable time searching for plug-ins, worrying about themes, or trying to understand complicated code. Forget about hosting maintenance and security updates — Rainmaker covers all of that for you, so that you can focus on your business and less on your technology. To take the tour, to check it out, to see everything that Rainmaker has to offer, go to RainmakerPlatform.com. You can do a 14-day free trial. So you can really get in, kick the tires, see what Rainmaker is all about. Try it out for yourself.

All righty, let’s go. Let’s talk with Kayla. This is a great discussion. I think you will really enjoy it. A lot of energy, a lot of insight. She gives two really interesting answers to the questions I ask about the one word that she would use to describe her business now and a year from now. I haven’t heard these words before. I think you’ll find them interesting. All righty, here is my interview with digital entrepreneur Kayla Hollatz.

Ms. Hollatz, welcome to The Digital Entrepreneur.

Kayla Hollatz: Thank you so much for having me, Jerod. I have been following along with Rainmaker and Copyblogger for so many years now. It is so amazing to be on the podcast today. Thanks so much for having me.

Jerod Morris: Oh, for sure. It’s our pleasure. You and I have interacted a lot on Twitter. That’s one of the things I love about hosting different podcasts, is a lot of times there will be people I have interacted on social media, and then eventually we have reason to jump on a podcast together and actually talk. It’s a great way to take those relationships from social media to the next step. Not like we’re meeting in person, but at least our voices are together.

Kayla Hollatz: Absolutely, yeah. It almost comes full circle in that way.

Jerod Morris: Yes, yes it does. All right, so let’s jump in. Are you ready to answer some questions about digital entrepreneurship?

Kayla Hollatz: Oh, I am so ready. Let’s go.

Jerod Morris: Excellent. Okay, so let’s start from the top. Kayla, I’ve always believed that the number-one benefit of digital entrepreneurship is freedom. Most people agree — the freedom to choose your projects, the freedom to chart the course, and ultimately the freedom to change your life and your family’s life for the better. Besides freedom, what benefit of digital entrepreneurship do you appreciate the most?

What Kayla Considers the No. 1 Benefit of Digital Entrepreneurship

Kayla Hollatz: I think the freedom definitely is huge, like you said. I think a lot of it is being able to utilize my skills in a way where it’s going to transfer over not only to my business, but also to all of the other passion projects that I actually work on outside of my business too.

I know once I had a day job, it was difficult for me to be able to find that time in order to dedicate it to all the different projects that I had. Now that I have dove into digital entrepreneurship, it allows me to have that more flexible schedule, which I’m sure goes along with freedom. Yeah, that flexibility and being able to choose your own path is huge.

Jerod Morris: Yeah, it’s funny. Almost everybody’s answers to that question — it’s some subset of freedom. You’re so right. For me personally, obviously I do what I do for Rainmaker Digital, and hosting the show is one of those things. Then the side projects, and being able to do a show like I do with The Assembly Call — that is obviously not something I do for work, but takes what I do for work. And then I can take that to the next level and develop it, and even use it as case studies. It’s a really nice benefit. That’s a good one.

Kayla Hollatz: Yeah. I really love what you said about that too. Because I was always that kid who grew up, and everybody was telling me that I had to pick one thing that I was going to be forever. And I just couldn’t do it. Even into college, I had a hard time with that. I transferred universities, I changed my major.

I think a lot of people can also relate to that, because it is hard sometimes when we hear that we have to choose one thing. Yeah, I love being able to feel like I can be multi-passionate and have multifaceted brands and still be successful in the digital entrepreneurship space.

Kayla s Journey to Digital Entrepreneurship, Which Started in College

Jerod Morris: Yeah. Take me back to before you became a digital entrepreneur. What were you doing, and what was missing that lead you to want to make a change?

Kayla Hollatz: Sure. I really started my blogging journey back when I was a junior in college. When I graduated from college, I got a PR agency job right away here in the cities in Minneapolis, Minnesota. I did like the work that I was doing there. I felt like the people who I wanted to talk to and get out of bed in the morning for were those creative bloggers and entrepreneurs.

I had been connecting with them for quite a while through my blog and also through a Twitter chat that I run, which is #CreateLounge. Really after doing a lot of that and seeing that there’s so much potential there, and starting to test out a few different monetization streams, I saw that this would be my chance to try and take the leap from that day job and run the business that I had always wanted to run back when I was in college. I went for it. It’s been incredible ever since.

Jerod Morris: How long ago was that?

Kayla Hollatz: That was in April of this year. It has been about four or five months now.

Jerod Morris: Okay, you’re fresh into this?

Kayla Hollatz: Yeah. I’m a newbie, but I’m loving it.

How Kayla s Background in Public Relations Has Helped Her Grow Her Online Business

Jerod Morris: Okay, you talked about the hashtag, the Twitter chat. Can you find that a little bit, how you got going with that, and maybe some of the benefits that you’ve seen from it?

Kayla Hollatz: Yeah, absolutely. My background is really in public relations. That’s what I went to school for and got my degree in. When I was in college, I wanted to try and put myself out there and be in front of different agencies and other companies that were in town. I would participate in quite a few different Twitter chats. I did that for about a year and a half before I decided to start my own.

The huge reason why I decided to start my own was because I saw that there was this huge gap in the creative blogging and entrepreneurship industry at the time. Nobody was really talking to a lot of the bloggers that I was talking to in that specific kind of platform. I thought, Hey, why not try and host a Twitter chat? It was the month after I graduated that I launched it. I’ve been running it now for over a year and a half. It’s been crazy to see the growth that’s happened because of it.

Jerod Morris: Basically the way a Twitter chat works is you pick a hashtag, and then there’s a specific time when you’re going to talk about this topic. Then you have maybe some questions set up at the beginning that leads the conversation. Then people from all over chime in on that hashtag, right?

Kayla Hollatz: Yeah, you’ve got it.

Kayla s Advice on How You Can Utilize Twitter Chats to Help Reach Your Audience

Jerod Morris: Of our listeners, who do you think would benefit from doing something like that? Someone’s trying to get a conversation going with their audience — who might benefit from a Twitter chat?

Kayla Hollatz: I see that Twitter chats, again, are a great space for people that are in the blogging space specifically. The entrepreneur space as well. Also, I see a lot of freelancers popping up into chats as well. I think why that is, and especially for a lot of us who are starting businesses on our own and in the solopreneur space — it can be a little bit lonely and even isolating at times.

I think being able to gather around other people who are like you, even if you can’t necessarily gather in the same physical space — being able to be together live on a platform like Twitter, and having those conversations and having a dedicated space every week in order to do so, is really powerful. Not only for me, but I see it a lot for the participants as well.

How Kayla’s “Milestone Moment” Inspired Her to Grow Her Online Community

Jerod Morris: Tell me about a milestone or moment in your career as a digital entrepreneur. And I know it hasn’t been a long one so far. Tell me about a milestone or moment that you have been the most proud of.

Kayla Hollatz: Honestly, I would say my milestone moment was when I saw that the #CreateLounge Twitter chat that I had grown for quite a few months, when I started to get so much feedback from participants saying: We want more. We want more of this community. We want it to reach other sorts of different platforms.

That’s when I started to have some fun thinking about all of the different ways that I could grow this online community. Which would make sense for my business, but would also make sense for the community that had been so dedicated to what we were doing.

I decided that I wanted to bring it to a platform like a podcast, which has been so fun to run. I have different people from the community that I interview, of course. It’s been really cool to be able to allow people to have a platform to tell their story in more than just a 140 characters. I’m sure all of us on Twitter know that it’s a little bit difficult to shorten what we want to say in that little of a space. It s been really cool to have different evolutions, I guess, of your community and your brand. And being able to look back and see that all of those little wins make up the huge wins all in the process.

Jerod Morris: Your podcast, most of the guests have come from that Twitter chat?

Kayla Hollatz: Oh, absolutely.

Jerod Morris: That’s interesting. I just recorded a new episode of The Showrunner with Jonny Nastor yesterday. Our topic was how to identify guests for your podcast. This one would have been a great way to add: Start a Twitter chat, get conversations going, and find people there. There we go. Need to record an addendum to that episode.

Okay, on the flipside from that question, you told us what your proudest moment was. Tell me about the most humbling moment that you’ve had so far as a digital entrepreneur, and more importantly what you’ve learned from it.

Why It’s Imperative to Extend an Olive Branch to Find Out Exactly What Your Customers Really Want

Kayla Hollatz: That’s a really good question. I would say the first one that comes to mind is when I was first thinking about monetizing, and at that point I was thinking about doing an ebook, since writing is my first love. When I was thinking an ebook topic, I was thinking about maybe doing something about rebranding, since I had been known for rebranding quite a bit in my early stages, until I fell into this niche of online community building. When I was thinking about doing that, I said: I want to make sure that it’s something that my audience wants.

I reached out to my audience through a quick photo on Twitter and a few different other places and asked them, Hey, option A, option B. Do you guys want me to talk about rebranding? I picked a random topic out of the sky to compare it to content strategy, since that made sense for where my brand was headed. And 72 of the 75 people that reached out to me said that they would rather have that content strategy instead of the rebranding ebook.

That was a huge reminder to me that even though I’m talking with my audience weekly, and I may think sometimes I know exactly what they need, it’s always so important for us to extend that olive branch to start that conversation and ask them what they really want.

Jerod Morris: Great lesson — instead of assuming, actually ask and find out. That’s great. Let’s fast-forward to now. What is one word that you would use to sum up the status of your business as it stands today?

The One Word Kayla Would Use for the Status of Her Business Today

Kayla Hollatz: Ooh, I love that. I would say the word that I’m focused on the most right now is actually rhythm.

Jerod Morris: Oh, rhythm.

Kayla Hollatz: Yes. I’m somebody where I’m a little bit more on the scattered creative side when it comes to my creative process and the way that I work on my projects. I read this book that’s called Manage Your Day-to-Day by the 99U contributors. It was amazing to hear how so many different bloggers and writers and entrepreneurs manage their day and try to fit into a routine.

For the longest time, routine was a dirty word to me, since I do like to be a little bit more spontaneous. The more that I’ve tried to look at my time and my distractions, and even some things that I was doing that were acting as red flags, it’s really helped me in trying to find a little bit more of a rhythm. Rhythm feels a little bit better to me than routine anyway. But that’s basically what it is. That’s what I’ve been focusing on in this season of my business.

Jerod Morris: I like it. You’re rebranding your need for routine for a need for rhythm. Okay, what objective then is at the top of your priority list right now, and what specifically are you doing to achieve it?

The Objective That s at the Top of Kayla s Priority List

Kayla Hollatz: Sure, that’s an awesome question. I would say the top priority right now is trying to build up my core shop that I have for my website. I’m sure that’s something that a lot of entrepreneurs are also doing, since courses have become such a huge platform for being able to teach and connect with your audience. It’s something that I have been creating behind the scenes and launching a few here and there too.

It’s been really cool to see how so many more people can really learn, because I’ve done a lot of coaching with my clients. It’s also nice to be able to give them that alternative of something where they can do something that’s a little bit more affordable and also at their own pace. That’s specifically what I’m doing behind the scenes right now. I, of course, have all other kinds of ideas. I’m really trying to focus on this one right now for that rhythm.

Jerod Morris: You haven’t launched any of the courses yet, but you’re building them in the background right now, getting ready for launch?

Kayla Hollatz: I actually do have one course that I launched, which is called #ChatBoss, which is of course about hosting your own Twitter chat. I have been creating some other ones that are a little bit more about the whole community-building process, and goes a little bit more into the exercises that I go through with my own coaching clients.

Jerod Morris: Okay. That’s interesting, because in preparation for this, I was looking at your website. Maybe you can give folks a little bit more insight into how people work with you currently. If you look at your Work with Me page, you’ve got some different coaching packages — The Leap and The Plunge, and the prices are there, and what people get.

That’s what I was thinking as I was going to looking at what you’re describing is, this is ripe for a course. Obviously you may want to keep these packages, these premium packages for people who work one-on-one. Maybe for people who don’t want to make that big of an investment or have the time for a course to be able to give it to them that way — that’s really exciting to hear that that’s the direction you’re going in.

Kayla Hollatz: Yes, absolutely. It wasn’t until I had a few people who weren’t quite able to financially take that leap into one of the coaching packages that said, “Man, I just wish that I could use your brain for a little bit.” Maybe it wouldn’t necessarily be the one-on-one intention. That’s really why I decided to do this.

Like you said, it was one of those light bulb moments, where you’re like, Wow, I should have thought of that before. It’s a great way to go about it for anybody who is doing services and is maybe having some potential clients that are wanting to access them, but in different ways.

Jerod Morris: Yeah, it allows you to work with more people, it allows you to multiply your efforts in a sense without doing anything more. I think the way that you’re going about it is smart, because you’re able to hone your message and your teachings through the services. Now you’re probably more ready to teach a good course than if you had jumped into it before you had that experience. I think it’s a great path to follow.

Kayla Hollatz: Oh, absolutely.

Jerod Morris: With that then, tell me about the biggest challenge that you’re facing as you’re trying to take what you’ve been teaching and turn it into courses.

Kayla Hollatz: Sure. You know, I think it’s probably the same challenge of a lot of people who are in their first year of business, which is sustainability. Trying to find a business model with those different streams of income, as well as having different tiers, like we were just talking about, in a way that all works together — it flows together, and it gives you some of that sustainable income. You’re able to work on more of those passion projects and other things that you’re doing, while still having something that’s going to keep clients as well as students coming in too.

The Tool That Kayla Finds Contributes Most to Her Success as a Digital Entrepreneur

Jerod Morris: Yeah. Let’s open up your toolbox a little bit. What is one technology tool that contributes the most to your success as a digital entrepreneur?

Kayla Hollatz: I feel like Google Drive in such a tough one to put out there, because almost everybody uses Google Drive.

Jerod Morris: Hey, but if it works.

Kayla Hollatz: Right? I totally love Google Drive. I hardly actually have any folders on my own computer, because I keep everything there, since it’s accessible from anywhere. I would say Google Drive is definitely where I am constantly the most.

Jerod Morris: I’m glad that you said that, because I think a lot of people just take it for granted. I’ve asked this question many times and I’ve always thought about what my answer would be. I’ve never thought about Google Drive, but yet I use it all the time. I take it for granted. It’s there in the background, but it works. That’s a good one.

Kayla Hollatz: Yes, it’s great.

Jerod Morris: What is the non-technology tool that contributes the most?

Kayla Hollatz: Oh, definitely my journal. Without a doubt, my journal. I have about five different journals going on right now. I am an avid journaler.

I’m one of those people where I don’t really know what I’m thinking unless I have it on the page right in front of me. I love being able to write, especially in a way where I can keep it private and it’s only for me to be able to work through whatever my mindset is, and whatever I’m going through in my business. Or even just my personal life too, so journaling for sure.

Jerod Morris: Journaling, okay. I really like that one. All right, moving forward. Earlier I asked you what the one word was that you would use to sum up the status of your business as it stands today, and you said rhythm. If we talk again in a year, what would you want that one word to be?

The One Word Kayla Hopes Sums Up Her Business One Year from Now

Kayla Hollatz: Oh, definitely ease.

Jerod Morris: Ease?

Kayla Hollatz: Yes. I think with rhythm comes a feeling of ease. To me that word feels like an exhale. I think so much, when you’re starting your business, everything feels like you’re inhaling everything. And you’re trying to take in as much as you possibly can. I think in a year I really want to feel like I’m at an exhale point in business.

Jerod Morris: Very nice, rhythm and ease. I like that. I want to go back to your podcast again real quick. How do you plan on using your podcast, and how do you think it will help you as you grow your business, as you go from rhythm to ease? How do you think the podcast plays into it?

Kayla Hollatz: I think especially with what I’m doing with podcast right now is, I actually have the rest of the podcast episodes all recorded up until the end of this year of 2016. That to me helped me feel like I was a little bit more at ease, because I’m doing everything in the background right now.

It helps me too, because all of the podcast episodes — how I’ve structured it is that the podcast episodes go out on Thursday, and then every following Wednesday is when I have the podcast guests as the guest host then for the Twitter chat, and we talk about the topic. It’s nice to have everything scheduled out, not only the podcast but also the Twitter chat. I’m able to get everything done at one time, so then I can focus on some other projects too.

Jerod Morris: That’s smart to use the podcast in conjunction with the Twitter chat, I like that. When you’re working with folks, you typically work with folks and help them to grow and build their communities, right?

Kayla Hollatz: Yes, absolutely.

Why One-on-One Connections Are Crucial During the Early Stages of Launching Your Online Business

Jerod Morris: As you work with people on building their communities, growing their communities, what have you found tend to be the one or two things that aren’t necessarily missing, but tend to be the things that when people really focus on them, it gives them the biggest bang for their buck or the most bang for their energy when they turn it around or make some changes?

Kayla Hollatz: I absolutely love this question, because I hear it quite a bit. The thing that I think a lot of people overlook is the importance of those one-on-one connections. That’s really how I built up my personal brand and why I was even able to take that leap into my business.

When I launched my services, within that first month I told myself, if I could book my services out for about four to five months, I could start to think about possibly leaving my agency job. I was able to do that within that first month of launching.

The only reason that I think I was able to do that was because I for two years had built up this really dedicated tribe of people through the one-on-one connections. With not having connections just start on Twitter and stay there — really taking it to phone calls and video calls and even sometimes meeting in person. I think it’s something that is so important for us to do, especially in the early stages of business. Because those connections are going to end up following you into all the different evolutions of your business.

Jerod Morris: What tends to make that click for folks? Do you think that people are afraid that that won’t scale? Are they afraid of making the connection? Do they think it’s not that impactful? What tends to be the thing that gets that to click?

Kayla Hollatz: I think some of it is what you just said about worrying how in the world that’s going to scale, what’s that ROI that everybody talks about. I think the main thing too is that a lot of people feel a little bit timid about trying to go into somebody’s inbox and introduce themselves. I know all of us probably have pretty full inboxes right now.

I think the important thing is to remember that it all depends on the personality and what you put into your email. It’s not going to feel like just another email in somebody’s inbox if you personalize it and make it something really special. And also show that you know the person well already, that you’ve already invested some time and energy into figuring out what they’re all about and trying to take that connection further through another kind of medium.

Jerod Morris: Kayla, are you ready for some rapid-fire questions to close this out?

Kayla Hollatz: Beyond ready. Let’s do it.

Jerod Morris: Let’s do this. Okay. If you could have every single person who will ever work with you or for you read one book, what would it be?

The One Book Kayla Would Insist You Read

Kayla Hollatz: You know, I feel like in this season right now, I have to pick Big Magic. I know that’s a huge book right now, especially in the creative world. It’s by Elizabeth Gilbert, who wrote Eat, Pray, Love. That’s what she’s most known for.

I love the book because it talks about creative living beyond fear, and I think it’s a practical way to start thinking about your creativity, how ideas come to you, and fostering your own sense of creativity. Also for a lot of people who are listening, who may not necessarily feel like they’re a creative person. This book is going to debunk a lot of those myths that you’ve been told.

Jerod Morris: If you could have a 30-minute Skype call to discuss your business with anyone tomorrow, who would it be?

Kayla s Ideal 30-Minutes Skype Call to Discuss Her Business

Kayla Hollatz: I think I would have to pick — and this is a hard question for me too, because I have so many people that run through my mind. I think I would have to pick Sophia Amoruso, who is the founder of Nasty Gal who also wrote the book #GIRLBOSS. She has created a huge movement for female entrepreneurs.

What I love most about her is she has built her business in such a unique and Sophia-only kind of way. I think I would want to meet with her specifically, because she not only knows business, but she also knows how to do it in a way that’s authentic to her, which I admire.

Jerod Morris: What would your first question be to her?

Kayla Hollatz: You know, I would probably say, What is the thing that you learned from one of your employees that you think was the — something about, What did you learn from one of your employees that completely changed the way that you run your own business?

The One Email Newsletter Kayla Can t Do Without

Jerod Morris: Good one. Very good. Okay, what is the one email newsletter that you cannot do without?

Kayla Hollatz: I would have to say, right now I am all about Caroline’s newsletters from Made Vibrant. I think that she creates some of the most beautiful art prints. I have a few that are actually hanging up in my office right now. What I love most about her is she talks about business, but also creativity and what it’s like to live a creative life out loud. I always honor her transparency and her vulnerability in all of her newsletters.

The Non-Book Piece of Art That s Had the Biggest Influence on Kayla as a Digital Entrepreneur

Jerod Morris: That leads us right into this question. What non-book piece of art had the biggest influence on you as a digital entrepreneur?

Kayla Hollatz: It’s so hard for me to pick a non-book one. I don’t know if anybody else

Jerod Morris: That’s why I asked the question this way.

Kayla Hollatz: When I was actually thinking about this question before too, I was like, Oh, shoot, all the things I’m coming up with are books. I would have to say that the biggest non-book piece of art would be Magic Lessons. It’s a little bit of a cheat, because Magic Lessons is actually a podcast that is based off of the book Big Magic that I talked about earlier in the episode.

I’m going to say that I can give myself a little bit of that loophole, because I totally love the podcast and what Elizabeth Gilbert has done with interviewing so many different creatives from all paths of life, who are really struggling and figuring out exactly what their path is going to be, and then bringing on experts who can share a little bit more of their story. It gives you access to meeting a whole lot of people you would probably never meet, as well as, of course, the experts that are always fun to hear from.

Jerod Morris: I’m going to have to check with the judges on that to see if we can allow that. Judges? Yes, okay, all right good. We’re going to allow that. It counts.

Kayla s Biggest Productivity Hack for Doing Meaningful Work

Jerod Morris: What productivity hack has had the biggest impact on your ability to get more meaningful work done?

Kayla Hollatz: I think it relates to what I was talking about before, about batch scheduling. With the podcast episodes and the Twitter chats, like I was talking before, batch scheduling has been my number-one best friend. It’s helped with that rhythm that I was talking about before too, of feeling like instead of having to fit writing and editing podcast episodes, and creating blog visuals and all of those different things that can be hard to shift between, it allows me to be able to dedicate a full day to writing, and then the next day is maybe all about podcast episode taping and editing. It makes it really nice, because you don’t have to shift when you’re already in the zone in a specific kind of task.

Jerod Morris: It helps you get into a flow state much more easily. When you’re a digital entrepreneur, you have the freedom to do that, if you choose to do so.

How to Get in Touch with Kayla

Jerod Morris: Final question for you Kayla, what is the single best way for someone inspired by today’s discussion to get in touch with you?

Kayla Hollatz: It’s probably no surprise after this episode, but it would definitely be Twitter. Everybody jokes that I live on Twitter, and they aren’t wrong. On Twitter I am @Kayla_Hollatz. It’s pretty easy to find me. You can also jump in, of course, with the Twitter chats at #CreateLounge on Wednesdays at 7 p.m. Central. Yeah, thank you so much.

Jerod Morris: Wednesdays at 7 p.m. Central — always the same time?

Kayla Hollatz: Oh, yes.

Jerod Morris: Very nice. Helps people know where to find you.

Kayla Hollatz: Absolutely.

Jerod Morris: It’s @Kayla_Hollatz, right?

Kayla Hollatz: You’ve got it.

Jerod Morris: Excellent. Kayla, this was a lot of fun, really appreciate you coming on.

Kayla Hollatz: Thank you so much for having me, Jerod. This was a total blast.

Jerod Morris: Yeah, great to talk to you. Have a good one.

Thanks to Kayla Hollatz for taking some time to join us here on The Digital Entrepreneur. My thanks as well to my production team here on The Digital Entrepreneur: Caroline Early, Will Dewitt, and also our great editing team led by Toby Lyles. The Digital Entrepreneur would not be possible without you guys. Thank you. Of course, thank you, the listener, for being here. Without you there would be no reason to have these Digital Entrepreneur episodes.

I do want to give you one more quick reminder. Go to RainmakerPlatform.com. Check it out. If you want to get more power with less pain and higher profit with your website, then you need the complete solution for digital marketing and sales. That’s what the Rainmaker Platform is. That’s why I’m telling you about it here. That’s why I use it for all of my personal sites. Go check it out. Take the 14-day free trial and see if it is the right platform for you.

All right, Everybody. Have a great week, and we will talk to you next week on another brand-new episode of The Digital Entrepreneur. We have a great guest planned for you. This is a guy who you probably know. It’s a face you know, a voice you know, and he is here to lend his insight on The Digital Entrepreneur. So tune in next week for that. Talk to you then.

The Transcript

How Jay Baer Is Navigating New Waters With His Latest Digital Product

Voiceover: You are listening to The Digital Entrepreneur, the show for folks who want to discover smarter ways to create and sell profitable digital goods and services. This podcast is a production of Digital Commerce Institute, the place to be for digital entrepreneurs.

DCI features an in-depth, ongoing instructional academy, plus a live education and networking summit where entrepreneurs from across the globe meet in person. For more information, go to Rainmaker.FM/DigitalCommerce.

Jerod Morris: Welcome back to The Digital Entrepreneur. I am your host, Jerod Morris, the VP of marketing for Rainmaker Digital. This is episode No. 29, and on this week’s episode, I am joined by the world’s most inspirational marketing and customer service keynote speaker. And that’s just a very small portion of what this hardworking, seemingly ubiquitous guy does.

But real quick, before I reveal this week’s guest, I want to let you know that this episode of The Digital Entrepreneur is brought to you by the Rainmaker Platform. I’ll tell you a little more about this complete solution for digital marketing sales later, but you can check it out and take a free spin for yourself at Rainmaker.FM/Platform.

All right, so on to my guest this week. He’s the founder of ConvinceAndConvert.com, one of the world’s most popular online resources for marketers and business owners. He is the co-host of the SocialPros podcast, one of the most influential social media and marketing podcasts out there. He is also the author of several great books, including Youtility and his latest, Hug Your Haters: How to Embrace Complaints and Keep Your Customers.

He is also perhaps the most impeccable enunciator I have ever heard. I bet you already figured it out, but he is Jay Baer — and he is a digital entrepreneur. He’s also a birthday boy, at least on the date this episode goes live, September 29th. If you’re listening on the 29th, send Jay a Tweet, @JayBaer, and wish him a happy birthday. Tell him Jerod sent you.

All right. Here now is my interview with digital entrepreneur Jay Baer. Mr. Baer, welcome to The Digital Entrepreneur. It’s great to have you here.

Jay Baer: I am delighted to be here, Jerod. I’m ready to digitalize some entrepreneurship.

Jerod Morris: Let’s do it. Your book, Hug Your Haters, that came out in March of this year, right?

Jay Baer: That is correct.

Jerod Morris: March of 2016.

Jay Baer: Yup, that’s right.

Jerod Morris: How’s the response been so far?

Jay Baer: It’s been amazing. It’s been a lot of fun, too, talking about customer service and how customer service is the new marketing instead of what I’ve been doing for the last couple of years, which is just talking about marketing. So it’s a little bit of a different approach with different audiences and different themes. It’s been amazing.

It’s a concept in a book that wakes people up. Look, customer service is being disrupted, but we don’t talk about it. We talk a lot about marketing disruption — I mean a lot — and write lots of books about it, have lots of conversations about it, lots of podcast. But we don’t really have a lot of chatter about customer service disruption, and it’s really, really important. It’s been fun.

Jerod Morris: And I believe the website for that, if you go to JayBaer.com/hug-your-haters let me know if there’s an easier URL to say.

Jay Baer: Just go to HugYourHaters.com.

Jerod Morris: HugYourHaters.com, even better. One thing that I was really interested in, I noticed that you have a course there.

Jay Baer: Built on Rainmaker, I should say.

Jerod Morris: Very nice, very nice. Built on Rainmaker, and you have a course there, the Keep Your Customers course, and I’m curious, just to begin before we get into the normal questions that we ask, what’s the impact been of the online course in conjunction with the book?

How Jay’s Course and New Book Helped Him Identify the Three Buckets of Challenges to Creating a Digital Course

Jay Baer: Well, somewhat foolish, I did not launch the course contemporaneously with the book. I wanted to, but it’s my first online course. It took me longer than I thought it would take me to do it at the level of quality that I want to do things. The course has only been out maybe four to six weeks, and people who have been through it love it because it’s really comprehensive. I’ve got 55 videos, 120-page workbook, and all kinds of exercises.

I worked with Dr. Carrie Rose, who is brilliant, and she was my curriculum consultant on it and took the principles of the book and turned it into a serious course that I’m really, really proud of. It’s been a hard road. I won’t lie about that. Having never done a course before, I’ve learned a lot of things I didn’t know already, but it’s been really gratifying. It’s a different way to get what I know out there into the world.

Jerod Morris: I found it interesting that — and let me know if I’m just not going through the right process — you click on the course, and instead of just being able to go and buy or sign up for the course, you have a video there and then a survey that folks have to take before they can even get to it. What was the thinking there behind that strategy?

Jay Baer: What we’re trying to do is get a handle on what each potential course enrollee’s key customer service problems are so that we can then focus subsequent email nurture campaigns around that pain point.

Certainly, there are circumstances when somebody is just like, “Take me to an order form,” but I don’t want to be quite that presumptuous. If we can identify what is your primary consideration, then we have multiple email sequences behind that so that, if they’re not ready to buy right now, we can send you some more customized email approaches on what you would typically do, which is, “Hey, how come you haven’t bought the course yet?” We can do that of course, but also do it in the context of what we believe to be their biggest problem.

Jerod Morris: Very nice. You can really adapt the experience to the person based on what their actions have shown and what their answers have shown that they’re interested in.

Jay Baer: Yeah, because what we discovered in the research for the book is there’s only a few different reasons why somebody isn’t as good at customer service as they could be. It’s almost always fear, time, or confusion. There’s three buckets of problems there, and we are able to identify that pretty easily through the quick survey that we have at the top of that funnel. Then once we identify it, then we can send you messages that are more relevant to that particular pain point.

Jerod Morris: Yeah. Well, for anybody who wants to dive in more on this topic of customer service, definitely recommend that you go to HugYourHaters.com. We could spend this entire episode talking about that.

Jay Baer: You could buy a book. You could listen to a book. You could listen to me read you the book into your head, which is a lot of fun.

Jerod Morris: Oh very nice, very nice. Let’s switch gears a little bit, Jay, and get into the questions that we normally ask here on The Digital Entrepreneur. I want to start where we always start. I’ve always believed that the number one benefit of digital entrepreneurship is freedom — the freedom to choose your projects, the freedom to chart your course, and ultimately, the freedom to change your life and your family’s life for the better.

Besides freedom, what benefit of digital entrepreneurship do you appreciate the most?

How the Real Estate Market Crash in 2008 Lead Jay (Eventually) to Where He Is Today

Jay Baer: Besides freedom, I would say just the ability to get paid. Let me tell you a story. I’ve been a digital entrepreneur for a long time. When I sold my last business 10 years ago or so, something like that, I did my earn out, and the plan was to go teach at a university. I was going to be a marketing professor. I always wanted to that. I always wanted to be a teacher. My mom was teacher. My stepdad’s a teacher. My aunt’s a corporate trainer. It’s kind of always been my thing, so I was going to go do that.

Then, right after my earn out was up, we had the simultaneous stock market and real estate market collapse. I looked around and said, “You know, I don’t know that I have as much cash as I would want to have to go teach,” so I decided to start this company, Convince & Convert, and ended up doing lots of consulting, writing books, blogs, podcasts, emails, and all the things that I’ve subsequently done.

I turned around one day and realized, “Oh, I actually am a teacher. I’m doing the exact same thing I want to do. Just now I’m doing it in front of larger audiences and for way better money.” If you are good at digital entrepreneurship, you can monetize that disproportionate to the way you can monetize it offline, I believe.

Jerod Morris: What was the business that you were in before you made the shift?

Jay Baer: I’ve always been in similar businesses. I’ve always been in professional services — for the very longest time, marketing consulting, digital consulting, and things like that. Way back, when I first started out, I was in traditional marketing. I was a spokesman for a state government agency for a while, and I started my career in politics. I was a political campaign consultant.

Jerod Morris: I bet you have some good stories from that time.

Jay Baer: I do have some good stories from that time. I also have some good stories from my time as a spokesman. I was the spokesperson for the Arizona Department of Juvenile Corrections, so I’ve lots of harrowing tales of kid prison if you want to hear some of those sometime.

Jerod Morris: Oh my. You took us back there to what you were doing before you became a digital entrepreneur. In addition to this, being able to control your ability to get paid and that freedom, is there anything else that you felt was missing that led you to want to make the change and what you’d been doing to what you’re doing now?

Jay Baer: My previous company, the one that I sold, we did a lot of the same services that we offer now at Convince & Convert, but we did it in a more classical sense where we had employees. We had an office. We had chairs, a break room, and a HR department. Now, having gone fully digital, we’ve also gone fully virtual. When I started this company and decided that I was going to really do it, I said look, “What are all the things that I didn’t like about a non-digital environment, and how can we take all that away?”

For example, everybody at Convince & Convert is a contractor. Nobody is an employee. Everybody on my team has their own clients and their own hustle on the side. We have one meeting a year, one actual meeting a year. We have approximately four to six phone calls a year. We almost never visit clients in person. We almost do it all via Skype and tools like that. We have stripped away the things that get in the way of good work and kept what remains.

Jerod Morris: Ah, I like that. I love how intentional you were — “What are the things about the non-digital environment I don’t like?” and just strip them one by one and make it something that works for you.

Jay Baer: The other thing that we do that’s somewhat different from my previous firm is that, in this organization, we only do strategy. Convince & Convert only does strategic planning. We do not do tactics. We do not do execution. We are not an agency, although some people think that we are. We only do social media strategy, content marketing strategy, customer service strategy, and influencer strategy. That’s it. That’s the list of the things that we do. People asked us all the time, “Can you make us an ebook? Can you make us a video? Can you make us a podcast?” and no, we don’t do that.

Because we only do strategy, we only have senior people. We only have people who have got a ton of time in digital and are very, very, very high level. There’s no layers. There’s me. There’s our head of our consulting, and then there’s everybody else. We don’t have any junior team. That’s one of the other things that is very intentional about how we set this business up.

When I was in my previous firm and running a 60, 70 person agency, you spend all your time dealing with HR issues, with who gets promoted and her, she doesn’t like this person, and how do we switch account teams. You’re constantly hiring. We had zero percent turnover in this company for six years in a row.

Jerod Morris: Wow.

Jay Baer: I just very intentionally said, “What are all the things that get in the way?” and don’t do those anymore.

Jerod Morris: Wow. Jay, tell me about maybe a milestone or a moment in your career as a digital entrepreneur that you’re the most proud of.

The Accomplishment, Pride, and Relief Jay Felt When Youtility Grew Popular

Jay Baer: A milestone or a moment that I’m the most proud of — there’s a number of things that I could point to, but I’d have to say, even though it’s not really an entrepreneurial mission, it’s just one that is a milestone. When my book Youtility came out as a New York Times Best Seller, and you can actually go on down to the CVS, get a copy of The New York Times, flip to the book section, and there’s your book, that’s one that I’m not going to forget anytime soon. That’s a pretty cool thing.

Jerod Morris: Yeah. How did that make you feel when you saw that?

Jay Baer: It was certainly a sense of accomplishment and pride, but also a real sense of relief just because you have to work really, really hard to make that happen, at least in my category and for somebody like me. I know other people probably have an easier time of making a list like that. We put an awful lot of time and effort into marketing that book and all of our subsequent books. To say, “Yeah, we actually did it. It actually paid off,” that was gratifying for sure.

Jerod Morris: When people say you have to put in a lot of time and you think about writing a book and how much time it takes to write a book, do you think the general person underestimates how much time it takes after the book is actually done?

Jay Baer: Oh well, of course, yeah. It depends. This a famous saying — it’s not mine. “It’s called The New York Times Best Selling List, not The New York Times Best Writing List.” There’s a reason for that. There’s lots of books out there that sell a ton that aren’t very good and vice versa, of course. We probably spend, on average, three hours marketing a book for every hour creating a book in general.

Jerod Morris: Wow. Okay, so on the flip side of that then, tell me about the most humbling moment in your career as a digital entrepreneur and, then, more importantly what you learned from it.

Jay’s Most Humbling Moment as a Digital Entrepreneur, Which He Is Currently Going Through as He Develops His First Online Course

Jay Baer: I definitely made some mistakes on this course, so I would say the most humbling moment may actually be unfolding as we’re having this conversation, which is a little bit unfortunate. I didn’t follow everybody’s advice, including people that we all know and love, who said, “Hey, it’s your first course. You just start really small.” That’s not what I do.

I am very much in the school of, if I’m in for a penny, I’m in for a pound. I go all in on everything, which is typically a good approach for me. For something like this, we’ve never done it before, it may be not a good approach. Time will tell. Probably my most noteworthy, fully baked failure is actually along the same lines. You may know the story.

About three years ago, my team and I created a website called MarketingPodcasts.com. The idea there was that podcast discovery is terrible, and it still is. It’s ridiculous. If you want to go find a show like this show or any of the six shows that I produce, it’s hard to do that. iTunes is a hot mess. There really is no Google for podcasts. Lots of people have written a blog post here or there about, “I like this show,” or, “I like that show,” but it’s not linear in any way, shape, or form.

We decided to fix that, so we built this site called MarketingPodcasts.com. We created our own proprietary ranking algorithm, lots of custom database work, built it on WordPress. It was slick, man. It’s still there. It still works. We launched it — really proud of it, really proud of the technology — but I had built that project because I was mad that it didn’t exist.

I didn’t actually have a business model for it, so we created it without really understanding what we were going to do with it or how we’re going to monetize it. As a result, we had to set it aside because we have other things that we work on where I can actually get paid and make money. That ended up not being one of them. That was a mistake and humbling because I realized, “Look, just because it’s a good idea doesn’t mean you should do it.”

Jerod Morris: When you have things like that, that happen, do you regret doing that, or do you appreciate the lessons that you learned and what you got out of it even though it didn’t end up fulfilling what you wanted to?

Jay Baer: Yeah, both. I mean I always financially regret it, but from a, “Hey, you know what, we learn things when we fail.” Everything even that we fail at, there’s pieces of it that succeed every time. There’s no such thing as a total failure. That’s a misnomer. We use that phrase a lot, “That’s a total failure,” but there’s no such thing. It doesn’t exist. We learned a lot about marketing, about WordPress dev, about the ins and outs of the iTunes algorithm. We learned a lot of things on that project. Just making money out of it was not one of them.

Jerod Morris: You mentioned earlier, with this course, that a lot of people had told you, “Don’t go so big. It’s your first course.” That conflicted with this with your natural inclination to go big or go home, do it big.

Personally, how do you balance that when advice that you’re getting and maybe this best practice that you’re seeing goes against your core, your gut, how you want to approach something? How do you try to balance taking this advice that other people are saying but still doing it the way that it works for you?

Jay’s Guidance on How to Balance Taking Advice with Your Own Ideas for How to Do Things When They Conflict

Jay Baer: It’s really hard because I’ve had the opposite happen, too. I’ve had people give me advice, and I didn’t follow it — and I was right, and they were wrong. In this case, they may have been right, and I may have been wrong. When you don’t have a consistent pattern there, it is hard. You start to second guess yourself, which is not my MO. I’m not a second guesser. It’s point the ship in that direction to head for the horizon line.

But I also realize that, as digital entrepreneurship expands, changes, and morphs, and consumer behavior changes, and technology changes, nobody knows it all. Only a fool thinks that he does. Anybody who tells you they know everything, either by definition doesn’t know everything or is a liar, at least to themselves. As I get older, and as the tentacles of my business get more numerous and elongated as well, I find it becomes more worthwhile to seek the counsel of others.

I’ll give you an example from a different part of my business. I spend a lot of my time now speaking and doing keynotes and those kinds of things all around the world. I’m pretty good at it I would say, and other people might agree, but I spent a bunch of money on speaker coaching. The bigger I get, the more I spend because I feel like you’ve got to continue to level it up. At some point, leveling up that next step on the ladder gets farther and farther apart. I need to start following that same advise in other parts of my business evidently.

Jerod Morris: Hey, real quick. Excuse me for butting in here, but I just wanted to say a few quick words about our sponsor for this episode, the Rainmaker Platform. When we get back to the interview in just a few seconds, I asked Jay for the one word he’d use to describe his business right now, and he cheats with his answers. You can decide if I go too easy on him.

Anyway, as you probably know stitching together a website that truly gives you everything you need to connect with your audience on the modern-day web is no easy task. Finding good hosting plus security and support you can trust, that’s a headache. That patchwork of plugins that you rely on can prove to be a nightmare at the worst possible time.

You need the ability to create content types, ranging from blog posts to podcasts, to possibly even online courses. And what about integrated landing pages, email marketing, and marketing automation? These aren’t nice-to-have features for the smart digital entrepreneur who is building a modern marketing website. These are necessities.

Well, you have two choices. One, you can piecemeal it all together, pay more in total, and then cross your fingers and hope everything plays nicely together — or you can use the Rainmaker Platform.

Rainmaker is a fully hosted online marketing and sales solution that gives you everything out of the box in one dashboard. Write simple blog posts. Host paid membership areas. Sell in-depth module-based online courses. You can even use RainMail to host all of your email list and send broadcast emails instead of autoresponder sequences right there in your Rainmaker Dashboard. No more third-party email service. Oh, and rather than having to choose from one of 100 different places for support when you have a question, with Rainmaker, it’s just one support team ready and excited to help you out.

All of these reasons and more are why Rainmaker.FM runs on Rainmaker and why all of my personal sites do, too. Don’t just take my word for it, check out the Rainmaker Platform for yourself. Go to Rainmaker.FM/Platform and start your free 14-day trial today. All right, now back to my interview with Jay Baer.

Okay, so let’s fast-forward to now. What is one word that you would use to sum up the status of your business as it stands today?

The One (or Two) Word(s) Jay Would Use for the Status of His Business Today

Jay Baer: ‘Growing’ and ‘transitioning.’ That’s actually three words.

Jerod Morris: We’ll take it. ‘And’ doesn’t really count, so two words growing and transitioning. What objective right now is at the top of your priority list, and what are you doing specifically to achieve it?

Why Jay’s Adding Proactivity and Wisdom to the Business Development Process

Jay Baer: Well, that’s one of my challenges. I’m not very good at having one priority like most people. I would say, categorically, we are adding proactivity and wisdom to the business development process. We’ve been able to succeed in a tremendous way and been on the Inc list a million times and all that kind of jazz without ever trying to get a client.

Everything we’ve done has been inbound and have been able to grow a very nice business. But at some point, you have to be more specific and proactive about who you’re working with, so that is a major piece of what we’re doing now — retooling the sales process, the lead-gen process, and all those kind of things.

Jerod Morris: What have been the biggest challenges in that shift in mindset for you guys?

Jay Baer: We haven’t had people associated with that work. Obviously, we know how to do it. We do that kind of consulting for clients all the time, but we’ve never done it ourselves. We’ve never said, Hey, let’s create content that has, as its only purpose, lead gen. Then let’s do paid promotion to make sure people see that content, and let’s do follow-up emails sequences to make sure the people are interested get nurtured” — like all the things that, of course, people know how to do, especially in digital entrepreneurship, we’ve never done because we’ve never had to.

And we don’t have to now, but I want to because I want to make sure that we have a richer top of the funnel and a more linear path to revenue. As we get bigger, we’ve got more mouths to feed, so at some point, you can just assume that, “Well, we’re going to get a bunch of inbound leads this month because we always have every other month.”

Jerod Morris: Yeah. Okay, let’s open up your toolbox a little bit. What is one technology tool that contributes the most to your success as a digital entrepreneur?

The One Technology Tool That Contributes the Most to Jay’s Success As a Digital Entrepreneur

Jay Baer: Especially because we’re so virtual and I’ve got people in Costa Rica, Dominican Republic, like all over, we use Sococo as our virtual office environments. It includes chat. It includes voice calls. It includes video calls, and it includes screen sharing. One of the things that we really like about Sococo is it has a virtual office environment.

If you log in to our Sococo instance, each of us has an office. You can see right in your screen. I’ve got an office. Everybody has an actual office and then, almost like The Sims, people can walk into each other’s office, sit down, have a conversation, turn on the video cameras. Even though the whole thing is just a fake layer, that adding a little bit of geospatial relationship to a virtual company adds a richness and depth to the interactions that’s proven very effective for us.

Jerod Morris: That’s really interesting. Do you think that that cuts down maybe on some of the random IM interruptions that might happen?

Jay Baer: Totally. Absolutely because you know where somebody is. You can see if they’re in somebody else’s office having a conversation. It’s not just ‘do not disturb’ the way you might find on Slack. You really have a little bit more of a sense of what the other person is doing, or if two people are talking and you think you might need to be in the conversation, you just pop in there and say hey. It’s nice. I like it.

Jerod Morris: That’s really interesting. Do you think that kind of thing is the wave of the future as we go toward more virtual and augmented reality.

Jay Baer: I don’t know. You would think, but you see so many organizations using Slack or similar that don’t have that layer. They seem be getting along just fine without it, so I’m not sure. You raised an interesting point, though, about VR and AR. I can absolutely see what Sococo does taken to the next level, almost a Pokemon Go sort of a sense where, on your smartphone, have more of a three-dimensional representation of the office environment.

Certainly, if we get to the point where we’ve got VR goggles on and can still get work done as opposed to look at roller coasters or whatever — obviously, we’re fast-forwarding a few years — that could be really interesting. You talk about digital entrepreneurs laying on their couch, wearing their goggles, and they’re walking through the office and interacting with their coworkers around the world. That’s going to get real exciting.

Jerod Morris: Yeah, it is. On the flip side of that thing, what is the non-technology tool that contributes the most to your success?

Long Live the Written To-Do List

Jay Baer: The non-technology tool, hmm. We have 57 software licenses, so the non-technology list is short. Look, I still write down a to-do list every day on paper, partially because I’m old, but that’s just how I remember things. That process of writing it down actually makes it sink into my head and stick into my head quite a bit.

That’s actually one of the things that we do, but I’ll tell you, probably the real answer from the company is that we do have that one meeting every year. We get the whole company together with spouses or significant others or plus ones, and we all stay in a giant house together and spend multiple days thinking through what we’re going to do for the next year, building relationships, and those kind of things. That one little thing every year has been a huge driver of our success.

Jerod Morris: Has there been any talk to installing cameras and making it a reality show?

Jay Baer: There’s been talk. There has been late night drunken talk, but that talk gets vetoed by me.

Jerod Morris: Nothing beyond that. Hey, as for the to-do list, I’ve heard a lot of people say that, about riding down the to-do list, do you have a master to-do list that you work from, or do you wake up fresh every day, one, two, three on the paper and write it down?

Jay Baer: Master, so I have two. I’ve got a digital one. I use Wunderlist. I use Wunderlist, which works cross-functional, of course phone, tablet, desktop, and then I’ve got a paper to-do list. They are somewhat similar. The Wunderlist one that’s digital that I have on my phone all the time is more what am I doing over the next, say, 15 days. I’m always moving things around based on reprioritization. Then the written list is more, “What are doing over the next 15 to 90 days?” It’s more of a chunky list.

Jerod Morris: Got it, okay. Earlier I asked you what the one word would be that you would use to sum up your business today, and you said growing and transitioning. If we were to talk again in a year and I hope we will, what would you want that one word to be?

The One Word Jay Hopes Sums Up His Company One Year from Now (and the Challenges to Making That a Reality

Jay Baer: I would want that one word to be, a year from now, ‘systematized.’

Jerod Morris: Hmm. In what specific ways, where would you specifically …

Jay Baer: All ways.

Jerod Morris: In all ways?

Jay Baer: Yeah, we are at that point — and this is my fifth company that I’ve started, so it’s not like I don’t know what’s happening or what’s coming — we’re at that point where it’s not just Jay and some people and we’re going to manage it via Post-it note. It’s a real company with millions and millions of dollars of revenue. We have to set up systems and policies and procedures where we can do the same thing over and over again. Whereas, historically, we’ve been doing a lot of things kind of one off or two off, which just leaks efficiency. We just have to make it a company more so than a collective, and that’s hard.

Jerod Morris: What’s the biggest challenge in making that a reality?

Jay Baer: I think partially that most of the people who are on our team came to the organization before we were of a size where those things were required. So it’s a little bit of, “Hey, we used to be one way. Now we got to be another way.” That starts and ends with me. I would prefer to not do that, but it has to be done. That’s certainly part of it.

Then also, because we’re virtual and because everybody’s super busy and traveling a lot and all that, it’s very difficult to do what you would typically do at a classic environment, which is to say, “Okay, here’s the plan. We’re going to have a two-hour meeting every day for two weeks to make all this stuff happen.” We don’t really have that opportunity. We just can’t. Sometimes the virtual thing’s amazing until you need to get everybody on the same page quickly, and then it gets harder.

Jerod Morris: We’ve gone through some of the same challenges at Rainmaker Digital, too. You do run the real risk of different departments getting siloed, there not being enough communication, and things slipping through the cracks. Or like you said, losing efficiency and not systematizing things that you could. I think that’s a common challenge, especially for virtual companies as they get bigger and more mature.

Jay Baer: And there’s not that many virtual companies that are that big. It’s a little bit unproven. You look at what Buffer’s doing and what you guys are doing, or some other people, there’s not that many bigger companies or midsize companies that are purely virtual. We’ll see how well it works at scale.

Jerod Morris: Yeah. I’ve got some rapid fire questions to end this if you’re up for the challenge.

Jay Baer: Okay. I’m ready. I’m up for the challenge. Otherwise, we’d have close up the show: “He’s not up for the challenge. Thank you.”

Jerod Morris: Yeah. I figured you would be.

The One Book Jay Would Insist You Read

Jerod Morris: Okay. If you could have every person who will ever work with or for you with one book, what would it be?

Jay Baer: I’m going to give you two. I would say Utility just because I wrote it and it’s the fundamental premise that we do consulting about. It’s tricky to work with us or for us if you don’t know what that book says. Not that I’m like, “My book’s so great.” I’m not saying that. It’s just that you have to know that principle in order to do stuff with us, so that one.

Probably the one that I would recommend that’s not from me would be Procrastinate on Purpose from my good friend Rory Vaden, which is the best book ever written on time management.

Jerod Morris: Very nice. Procrastinate on Purpose, okay.

Jay’s Ideal 30-Minute Skype Call to Discuss His Business

Jerod Morris: If you could have a 30-minute Skype call to discuss your business with anyone tomorrow, who would it be?

Jay Baer: And I should probably do this. Probably Brian Clark from Rainmaker because I need to talk about this course thing and where we head next, so I may just call him up and do that.

Jerod Morris: He’s a good person to talk to about courses.

Jay Baer: Yeah, among other things.

Jerod Morris: Yes. You’re not the first person who said him in the answer to the question.

Jay Baer: Is that right? Everyone’s a suck up.

The One Email Newsletter Jay Can’t Do Without

Jerod Morris: Okay, what is the one email newsletter that you can’t do without?

Jay Baer: You know which one I love right now is Scott Monty’s weekly newsletter, The Full Monty. Scott puts a ton of time and effort into it, and every week, he publishes an email newsletter that has links and short commentary to kind of all of the big digital marketing trends, especially on the brand side, that have happened in that week. It’s really well done and a big time saver.

The Non-Book Piece of Art That’s Had the Biggest Influence on Jay as a Digital Entrepreneur

Jerod Morris: Okay, what non-book piece of art had the biggest influence on you as a digital entrepreneur?

Jay Baer: Piece of art.

Jerod Morris: This is always the one that people take the longest with to answer.

Jay Baer: Okay, when I was first starting out, this is 1994, I was vice president of marketing at an Internet company called Internet Direct, first Internet company in Arizona. We were primarily a dial-up provider, and then my partner in that company invented virtual hosting.

Before then, if you wanted to have a website, you had to have your own server. It was domain to one server. He invented the partitioning algorithm, which made virtual hosting possible, which of course has then made Rackspace possible, and Bluehost, your company, and lots of other things.

I didn’t really realize what the magnitude of that was, nor did any of us, but we grew the company really fast as a result because we were the only ones in the world who could do it. That was the first time that, that sort of code piece of art, if you will, was the first time that I realized like, “Oh, this Internet thing could be not just my current job but what I do for the rest of my life.” Fast-forward 22 and a half years, and I’m still doing it.

Jerod Morris: Great answer.

Jay Baer: Thanks.

Jay’s Biggest Productivity Hack for Doing Meaningful Work

Jerod Morris: What productivity hack has had the biggest impact on your ability to get more meaningful work done?

Jay Baer: I mentioned that we have the annual meeting of Convince & Convert. One of the things we try and do with that meeting every year is we audit how I spend my time: “How does Jay spend his time day to day, week to week, month to month?” Then we try to take away 15 percent of that every year. We say, what are the things that I’m doing that I don’t have to do, that I’m not uniquely qualified to do, and who else in the organization or who else could we have as a third party take those tasks on.

When you do that, year after year after year after year, what you’re left with is a concentrate. If you try to make a sauce, you put it on the stove, and you’re like, “Man, this is way too much liquid. This is like a gallon jug of sauce,” but then when you keep putting it over the burner, it evaporates and thickens, and evaporates and thickens, and evaporates and thickens until you have a nice, dense, concentrated sauce. That’s how I look at my time.

The best possible scenario is that I spend every minute of every day doing things that only I can do. That nobody else in my company could do this podcast with you Jerod. Nobody else in my company could go on stage and do what I do on stage. Nobody else in my company could write the books that I write, and the more that I can set it up so I’m spending my time doing the things that nobody else can do, the better off I am and the better off they are.

Jerod Morris: And the more that your people are going to grow by taking on those responsibilities as well.

What Jay Believes Holds Every Digital Entrepreneur Back

Jay Baer: That’s right. One of the worst habits that entrepreneurs have is they believe that they can do it better. They say, “Well, sure I could delegate that, but you know what, I do it better than they do.” Of course, you do but you don’t do it enough better to make it a difference maker. Could you do this task 7 percent better than anybody else in your team? Yeah, probably, but who cares. That’s what holds entrepreneurs back. Ego is what holds them back, that they know it better than everybody else.

How to Get in Touch with Jay

Jerod Morris: What is the single best way for someone inspired by today’s discussion to get in touch with you?

Jay Baer: There’s a lot of ways to find our staff, ConvinceAndConvert.com is probably the best because we’ve got, as I mentioned, six podcasts of our own, 12 blog posts a week, four emails a week, all kinds of goodness there, ConvinceAndConvert.com.

Jerod Morris: Then HugYourHaters.com for the book as well.

Jay Baer: For the book, yep. Absolutely.

Jerod Morris: My final question, a bonus question, will you be making it to any Indiana basketball games this year?

Jay Baer: I am, of course, going to make some games. I gave up my season tickets this year unfortunately, which is a bummer because the Hoosiers should be pretty good this year. The challenge is with my travel schedule, it’s just crazy. Basketball tickets in Indiana are expensive because the football team is anything to write home about.

Obviously, a legendarily good program so tickets are really pricey, and I can never go. I’m investing all this money in tickets, and I got to give them away or try and sell them. This year, I did not actually get season tickets for the first time, but I’m just going to go to a few games when I can go, which I think will be a wiser decision.

The other thing is my son is in high school now and is on the high school hockey team. They play a ton of games, and they play essentially three games every weekend for five months. That schedule lays on top of basketball season. I could probably go to even fewer games than typical, but I’ll go to something for sure.

Jerod Morris: Very nice. Well, enjoy the newly renovated Assembly Hall.

Jay Baer: Yeah, this year’s only half renovated. They’re only half done this year. It’s a total mess. Front entrance is still closed. This season’s going to be a real challenge just from a fan standpoint because it’s under construction, and they’re going to have to funnel everybody through a couple of doors and all that. And parking’s messed up. Next season for 2017-2018, it’s going to be dope. It’s going to be really, really cool.

Jerod Morris: Well, hopefully this year can make it worthwhile even it’s a little more challenging to get in there.

Jay Baer: They’re going to be strong. They got a good team and really deep. They’re strong down low. I think the only question is, do they have a point guard? I guess we’ll find out pretty quickly.

Jerod Morris: Well, Jay, thank you so much for being here on The Digital Entrepreneur.

Jay Baer: Hey, my pleasure. Anytime, you let me know. I’ll be back.

Jerod Morris: Yeah, great to have you.

Jay Baer: See you, man.

Jerod Morris: All right, thanks.

Hey, hey, all right. Well, thank you for listening all the way through here to this latest episode of The Digital Entrepreneur. Always appreciate you being here. My thanks of course to Jay Baer, a great guest as I knew he would be, really appreciate Jay coming on and sharing his insights. Go check out Jay’s books. Hug Your Haters. The latest one, good read — you’ll enjoy and learn a lot.

My thanks is always to our production crew at Rainmaker.FM. Toby, who’s at the controls, Caroline, who helps me with scheduling, and Will, of course, who helps with all the production. Thank you all. The Digital Entrepreneur would not be what it is without you.

And hey, just a reminder, go to Rainmaker.FM/Platform for our sponsor for this episode, the Rainmaker Platform, and more importantly, check it out for yourself. See if you like it. I love using Rainmaker for my personal sites. I’ve built The Assembly Call on Rainmaker. Rainmaker.FM is built on Rainmaker. I think when you try it out, you’ll like it, too. So go to Rainmaker.FM/Platform. Start your 14-day free trial.

Now, if you are still listening, you are a Digital Entrepreneur diehard because you listened all the way to the end of the episode. You got through all this stuff at the end. I want you to do me a favor. Send me a Tweet @JerodMorris. Declare yourself a Digital Entrepreneur diehard.

Seriously, I’d love the opportunity to thank you personally for being a Digital Entrepreneur listener. I really appreciate you being part of the audience, so declare yourself a diehard. Send me a Tweet. Let me know that you listened all the way through. I look forward to it.

All right. We’ll be back next week with another brand-new episode. Until then, take care. Talk to you soon.

The Transcript

The Upside of Setting Outrageous Goals

Jerod Morris: Hey, Jerod Morris here. If you know anything about Rainmaker Digital and Copyblogger, you may know that we produce incredible live events. Well, some would say that we produce incredible live events as an excuse to throw great parties, but that’s another story. We’ve got another one coming up this October in Denver. It’s called Digital Commerce Summit, and it is entirely focused on giving you the smartest ways to create and sell digital products and services. You can find out more at Rainmaker.FM/Summit.

We’ll be talking about Digital Commerce Summit in more detail as it gets closer, but for now, I’d like to let a few attendees from our past events speak for us.

Attendee 1: For me, it’s just hearing from the experts. This is my first industry event, so it’s awesome to learn new stuff and also get confirmation that we’re not doing it completely wrong where I work.

Attendee 2: The best part of the conference for me is being able to mingle with people and realize that you have connections with everyone here. It feels like LinkedIn Live. I also love the parties after each day, being able to talk to the speakers, talk to other people who are here for the first time, people who have been here before.

Attendee 3: I think the best part of the conference for me is understanding how I can service my customers a little more easily. Seeing all the different facets and components of various enterprises then helps me pick the best tools.

Jerod Morris: Hey, we agree — one of the biggest reasons we host a conference every year is so that we can learn how to service our customers, people like you, more easily. Here are just a few more words from folks who have come to our past live events.

Attendee 4: It’s really fun. I think it’s a great mix of beginner information and advanced information. I’m really learning a lot and having a lot of fun.

Attendee 5: The conference is great, especially because it’s a single-track conference where you don’t get distracted by, “Which session should I go to? and, “Am I missing something?”

Attendee 6: The training and everything, the speakers have been awesome, but I think the coolest aspect for me has been connecting with both people who are putting it on and then the other attendees.

Jerod Morris: That’s it for now. There’s a lot more to come on Digital Commerce Summit, and I really hope to see you there in October. Again, to get all the details and the very best deal on tickets, head over to Rainmaker.FM/Summit.

All righty. Hey there, everybody. Welcome back to The Digital Entrepreneur. I am your host, Jerod Morris, the VP of marketing for Rainmaker Digital, and you are listening to episode No. 27.

On this week’s episode, I am joined by a man who says that hard work and helping people was instilled in his DNA. Sounds like our kind of guy. This man started two businesses at the age of 21 and two more after that, and currently, he is a digital marketing consultant for purposeful companies and the host of the podcast, Sell More, a show for entrepreneurs, solopreneurs, marketers, and aspiring entrepreneurs who want to sell more online.

And get this, he says that his goal for the next five years is to help five billion people — that’s billion with a B — with their efforts to grow a business. Whoa, right? Clearly, this is not someone who needs help setting bold goals.

Who is this man helping people by the billions? He is Brandon Lewin, and he is a digital entrepreneur and our guest on this week’s episode.

Get the Inside Scoop on RainMail — The Rainmaker Platform s Integrated Email

Jerod Morris: Now, real quick before I bring you my discussion with Brandon, I want to let you know about a webinar that I hosted recently with Brian Clark and Chris Garrett. It was about the Rainmaker Platform. Specifically, it was about RainMail, the new email marketing feature built right into the Rainmaker Platform.

You’ve heard us talk on the show before about how much having email marketing baked right into the Rainmaker Platform would be a game changer. Now it’s here — with plenty of updates and new RainMail features on the way, too.

I actually just switched my site, AssemblyCall.com, over to RainMail, and I’ve already seen a big difference in the growth of both my email subscribers and my site members, as well as their engagement once they subscribe or sign up, which is really the goal, right? I’ve gotten this increased engagement by having my email marketing, my landing pages, my content pages, my marketing automation all able to work together in a fully integrated way.

We took some time a few weeks back with Rainmaker Platform customers to answer some frequently asked questions and provide some use-case examples of the difference that RainMail can make. The live event, when we held it, was just for customers because we really wanted to hone in on the questions that customers had who had used RainMail, get some of their experience so that we could talk about it.

But we’re happy to share the replay with you so that you can learn more about what RainMail is, what it could do, and why it takes the Rainmaker Platform to the next level as a true all-in-one solution for digital marketing and sales. In other words, the perfect solution built by digital entrepreneurs for digital entrepreneurs.

If you want to watch the webinar replay, totally free. You don’t have to sign up for anything. Just go to Rainmaker.FM/RainMail, and you’ll be redirected to the replay page. I just posted it a little while ago on the Rainmaker Platform blog, but go to Rainmaker.FM/RainMail. That URL will redirect you there. If you have questions, just know, as I hope you do already, that you can always reach me on Twitter at @JerodMorris. I will be happy to answer. Once again, that URL is Rainmaker.FM/RainMail.

Jerod Morris: All righty. Now let’s get to this week’s discussion with the man who won’t stop working until he’s impacted five billion people, Brandon Lewin. Here it is right now on The Digital Entrepreneur.

All righty, Mr. Lewin, welcome to The Digital Entrepreneur. It’s a pleasure to have you on the show.

Brandon Lewin: It’s a pleasure to be here. Thanks for having me. I’m super excited. I can’t wait to share a little bit about my story and see if we can help some people, inspire them, and do all that good stuff as entrepreneurs as we do.

Jerod Morris: If only we were in person sharing a Community Mosaic right now. That would make this even better.

Brandon Lewin: Especially at 10:00 in the morning.

Jerod Morris: Exactly.

Brandon Lewin: Nothing better than a good cold brew at 10:00 in the morning.

Jerod Morris: That’s right.

Brandon Lewin: It makes for a sane rest of the day, let me tell you.

Jerod Morris: Brandon, I’ve got to start off by asking you this because I found this quote on your LinkedIn profile, and it kind of blew my hair back. Here’s the quote. You say, “My goal for the next five years is to help five billion people with their efforts to grow a business.” That is one heck of a goal.

Brandon Lewin: Yes.

Jerod Morris: How are you going to do that?

Why Brandon Finds It Imperative to ‘Give Away’ All the Information He Possibly Can

Brandon Lewin: How am I going to do that? That’s a very good question. I haven’t quite figured that out. No, I’m just joking. There’s a lot of things that I’m doing in a concerted effort to do that. One is, just for the last year, I have been doing as much as I possibly can from sharing content.

When I say five billion, it doesn’t mean I’m necessarily getting paid by five billion people to help them out, but it’s just about sharing content. I think that comes down to some of this you can actually track some of the numbers. Some of it is not trackable. Really simply, what I do is I share as much content as I possibly can. I’ve always been a big believer of just giving away the farm. There are some people who share that mentality. A lot of people do, but there’s still a lot of people that want to keep stuff close to their chest and want to make people pay for it.

My thing is just really, first and foremost, sharing as much content as I possibly can, getting on platforms that have large audiences to be able to share that. I track those numbers. Not everything is trackable, but I track as much as I possibly can.

In the last year, I have hit over 10,000 plus people. I don’t have the specific numbers, but we’re moving in that direction. Obviously, those numbers need to jump if I’m really going to five billion, but it’s sharing content, doing it through podcasts, videos, anything I possibly can. Then I also am doing online training programs. I’m speaking in various cities. Like I said, I’m trying to hit the numbers as much as I possibly can. Yeah, and just the services that I provide.

That’s right now the efforts. I do have bigger plans as far as creating services and products that are going to hit the millions. That’s where it comes down to even getting into other aspects of service-based businesses. I shouldn’t say service-based business because that’s what I’m doing right now. It’s SaaS businesses because that number can really jump once you start providing those type of services. Those are all in the works, but from the basic stuff right now, it’s just sharing content, man.

Jerod Morris: Yeah, I love it. I love the big, bold goal. It’s one of those, even if you don’t reach the five billion, say you reach one billion or two, that’s still pretty impressive.

Brandon Lewin: Absolutely. I don’t know if you read the book Bold, but that’s where it came from. It said if you can help one billion — and I hear this all the time now — but if you can reach one billion people, you’re going to be very, very wealthy in a lot of different fronts. I want to be wealthy.

That’s always been a huge goal of mine, not just so much about having materialistic-type things, but as you get a little bit older and wiser and you start having kids and a family and all that stuff, you start to realize how much wealth and money really can affect the world.

It’s always been something that’s been close to me, giving back to charity, but I’ve been getting more and more involved in it as of recently. There are just so many people that want to really, and are currently really doing big things in the world. By me being able to hit that billion, five billion people, and create a wealth of money, but also just connections and everything that comes with that, I can do so much more for the world. That’s always been a huge goal of mine.

Jerod Morris: Well, being able to reach a lot of people, being able to chart your own course, those are all really great benefits of digital entrepreneurship. I’ve always felt that the number one benefit of digital entrepreneurship is freedom — the freedom to choose your projects, the freedom to chart your course, and ultimately, the freedom to change your life and your family’s life for the better. Besides freedom, what benefit of digital entrepreneurship do you appreciate the most?

The Biggest Benefit Brandon Derives From Being a Digital Entrepreneur

Brandon Lewin: Freedom comes down to everything really. My big thing is teaching people, giving away stuff. Besides the freedom, just having the flexibility to give away and do what I want to do. I guess that still comes back to freedom. I have a hard time thinking of anything outside of that, but it’s the flexibility. What really sparked me to go back on my own … my story goes up and down. There are a lot of different twists and turns, but I started off as an entrepreneur in college. Then I ventured off and was doing my own businesses.

Then I actually started my family and went to work for some people. I quickly learned that working for somebody else doesn’t work well when you’re an entrepreneur at heart. When I went back on my own, it was really about … something that I learned working for other people, and it was still in the agency world of doing digital marketing, was that those people didn’t see the value in giving away information.

Like I said, there’s still a lot of people that carry that kind of philosophy of not giving away and want to hold stuff close. To me, it’s never worked. I always give things away. My philosophy is, you give things away, and if people are going to take it, they’re going to run with it, and they’re not going to pay you for your services, that’s fine — because they never were in the first place.

Then being able to just give it away and having that flexibility and saying, “I can wake up today, and if I feel like I want to give away my secrets to how to do this, I can do that.” I guess that really does come back down to freedom. That’s really, to me, what’s sparked getting back in the world of digital entrepreneurship.

Jerod Morris: On that thought — you kind of started to do this — but take me back to before you became a digital entrepreneur. Tell us what you were doing and what was missing that led you to want to make a change.

Brandon’s Story on How He Got the Taste for Entrepreneurship at a Young Age

Brandon Lewin: Do you want to go all the way back? Do we have enough time with all that?

Jerod Morris: Yeah, go all the way back. You can shorten it if you need to, but go all the way back.

Brandon Lewin: All right. I’ll try to keep it as abbreviated as possible because it can get kind of lengthy. In college, I went to school in DePaul in Chicago, and it was at that time that I really just always had an entrepreneurial mind. When I was younger, my dad made me it was the first taste I got as an entrepreneur. He told that if I wanted a toy — I forgot what it was, I think it was like a Transformer or something like that — he was like, “Yeah, right, you’re 10 years old. If you want this, you need to earn it.”

I went out. It was the dead of winter in Chicago. I got a buddy of mine. We got a shovel. We went around the houses. We charged people $5 for a driveway and sidewalk, and we started shoveling driveways. I think in the first couple days we made about $200 apiece.

Jerod Morris: Wow.

Brandon Lewin: That’s really where I got the taste for entrepreneurship. It was great because I liked just helping people. That’s something that I got right away, that sense. My dad’s an entrepreneur. My mom’s an entrepreneur. It’s just something that runs in our blood line.

Then I went off to college. My dad always told me this. He said, “All right. If you’re not playing sports and you’re not in school, you’re going to be working.” Actually, there was a summer when I was 13 years old, and at the time, legally, you weren’t supposed to work. You couldn’t get your permit until you were 14. He got me to work for one of his clients in a warehouse. I did that, and I had to travel about an hour each way just to get there.

At that moment on, every time I wasn’t playing a sport, I had a job. I worked my way through high school, through college, up until this year. My hard work came from my dad, who taught me all of that. Not only did he teach me and made me do it, but he also showed me how it worked because he’s an accountant. Especially during tax season, he’s working 16-hour days. That really just instilled it in me.

What Led Brandon to the Realization That He Never Wanted to Work for Anybody Else

Brandon Lewin: When I went into college, I have always been a social person and very outgoing. I had a really large network, and I even would talk with my dad and his friends and his clients. I always reached out to them. I might have been far younger than them, but we had a relationship. I developed this online ticket brokerage with a friend of mine back in 2003, I believe it was, and it didn’t last very long. It only lasted eight months, but it was my first taste of starting an online business. We created a website. I had a templated kind of website that actually allowed you to bring in tickets from other ticket brokers and stuff like that.

Jerod Morris: Wow.

Brandon Lewin: This was in the era where StubHub was just starting. I put all this together, and I was reaching out and building networks. I was selling it, and I was delivering tickets. I was doing everything. It was amazing. I got my first taste of networking and speaking in front of people during that period of time. I just fell in love with that whole process. I was like, “I never want to work for anybody else. This is what I want to do.”

I continued to develop from that point on. Although it didn’t work out, I actually really liked the sales part of it. I made a concerted effort at that point to say, “All right. I understand that sales works in everything. It doesn’t matter what you’re doing in business.” To have the skillset of being able to sell, even if you’re not in that sales role, is extremely important. I had focused on actually developing that skillset.

I went to work as an outside sales rep for a construction company. I was horrible at it the first three months I did it. I almost got fired a bunch of times because I was just not producing the numbers, but something clicked. I was reading books. I was doing as much as I could, and it clicked. I did really well, exceeded. I was the top four, top five producer for two years straight within the company, and then transitioned and went back on my own.

That’s when I went into the world of financial services because my dad’s an accountant, so it was an easy transition. That’s where I got the taste of social media. This was back in 2009 when Facebook opened up. I started actually putting friends and people that I hadn’t talked to in a while from high school and stuff into a group on Facebook.

Then I started giving them information about what’s going on in the market, why they should save up, all this stuff that I was helping people do. It was just informational articles. It was a gray area at the time. We weren’t really regulated, although I got a few warnings from my higher-ups. I was just using social media, and I was just using LinkedIn to connect with people that had networks to potential clients. I developed this process that really worked well and business boomed.

I was making so much money at the age of 24, I didn’t even know what to do with it. I put it aside, and I actually started investing in another company, which was supposed to be an online business. It was going to compete with LinkedIn because I saw some holes at the time — and luckily, I didn’t do that — but it transitioned into an actual digital marketing shop. We actually were just a small agency. We helped other businesses do the social media stuff.

This is where I got really involved in email marketing. I was sending out newsletters all the time. I was doing webinars. I remember, now that you see everybody doing webinars, that was a big part of my business back then. It just shows sometimes when you do things before everyone catches up, you just got to keep with it, and I did. It did really well for me, and it still does. It was something that I used a lot.

Fast forward, I grew that business into a small little agency. I had about six people working underneath me, and then that’s when I transitioned to going to work for somebody else. I did that for three years, learned a lot, and then I went back on my own. That’s been about actually two years was my anniversary a couple of days ago.

Jerod Morris: Wow. Congratulations.

Brandon Lewin: Thank you. It’s been an amazing journey. I’ve learned a lot. There’s been a lot of ups and downs. I think, as any entrepreneur, you learn a ton as you go through this. That’s the best thing. I can’t say that I feel like I’ve been super successful, although a lot of people have given me praises for that, but I just feel like there’s so much more to be accomplished. I’m looking forward to what the future holds.

Jerod Morris: All right. Tell me about a milestone or a moment in your career as a digital entrepreneur, since you’ve been back out on your own, that you are the most proud of.

The Milestone That Brandon’s Most Proud of As a Digital Entrepreneur

Brandon Lewin: A milestone. Being on your show is a big one.

Jerod Morris: Thank you.

Brandon Lewin: No problem. I think really a milestone for me is putting up my podcast. I have a podcast called Sell More. I hope you don’t mind if I shamelessly plug it.

Jerod Morris: We already talked about it in the intro, so you’re good.

Brandon Lewin: Awesome. My podcast, it’s been a dream of mine for three years. Even when I was back working for somebody else, I wanted to really dive into it. I’ve always been a big, big fan of podcasts. I believe that you have to take advantage of the downtime that you have. It might not be the most productive time, but whatever you can put in between your head and in your earbuds really makes the difference, so I’ve always been a big fan of podcasts.

When I got that launched, it was a big milestone for me. Then what was even a bigger milestone after that was being recognized, having people like yourself and others reach out and ask me to be on their podcasts. To me, having that ability to be, and having people recognize me for that, that is a big, big accomplishment for me.

Jerod Morris: All right. Now let’s go to the flip side. Tell me about the most humbling moment in your career as a digital entrepreneur and what you learned from it.

The Epiphany That Led to Brandon Changing His Approach with Clients

Brandon Lewin: Oh, man, I have those every single day. I have to say, you deal with a lot of customers, and not every customer is satisfied. I’ve had a few that weren’t. Luckily, we’ve been able to work through those trials and tribulations and bumps and bruises. There was this one moment I think was the most humbling was that I worked with a client.

Both him and I worked endlessly for about a month, just trying to come up with this plan. We came up with a plan to go out and reach out to partners — bloggers, other people — and do an outreach established through relationships to sell these products that he has. He sells leather journals. They do beautiful work. It’s all handmade. It’s all done in New Mexico, and so it’s US-based. People love it.

He’s been doing it forever, but he just didn’t have a big enough following. We thought that partners were the way to go. It was one of these things where I was beating my head against the wall. We were reaching out, and people just weren’t responding — or weren’t responding the way we wanted them to. Everyone seems to charge for guest posts nowadays, and we were looking for a real strong strategic partnership, and that didn’t come to fruition. The goal was really just to grow the email list and to leverage other people’s opportunity.

One day, I just went back, and I said, “Hey, have you ever actually used your current email list,” which was about 12,000 at the time. He’s like, “What do you mean?” I said, “Well, have you ever asked them to make a referral to maybe their friends and family?” He’s like, “No. I’ve actually never thought about that.” We wrote up this real quick email, sent it out, just basically asking people. We were giving away this free little leather journal. It was like a retail value about $9, $10, but it was free. You just had to pay for shipping and handling. We sent it out, and in the first two weeks, we had about 5,000 people sign up or so.

Jerod Morris: Wow.

Brandon Lewin: It wasn’t super viral, but it got put up on Reddit. Reddit just blew up from there. A huge amount of traffic and conversions were coming from Reddit. That was a very humbling moment, just thinking that I knew the way to go, and we worked so hard on doing that when it just simply came back to just to re-evaluate it. It was both a success but also very humbling. It’s helped me tremendously, though.

That happened about two years ago when I first started, when I went back on my own. Ever since then, I take a much different approach with clients and just suggestions with people. That was a big humbling moment for me.

Jerod Morris: Boy, it’s always great when those humbling moments can turn into successes and teach us great lessons that we can then use in the future.

Brandon Lewin: Exactly.

Jerod Morris: That’s what you want to happen, so that’s great.

Brandon Lewin: Absolutely.

Jerod Morris: Let’s fast forward to now. What is one word that you would use to sum up the status of your business as it stands today? One word.

Why Brandon Sees Limitless Possibilities for His Business

Brandon Lewin: One word. I would say ‘limitless.’

Jerod Morris: Limitless.

Brandon Lewin: Yeah.

Jerod Morris: I would say, when you’re trying to reach five billion people, that’s a good word for it to be.

Brandon Lewin: Absolutely.

Jerod Morris: Why limitless? Why is that the word that came to mind?

Brandon Lewin: I think what I’ve done and how I’ve positioned the business and what we’re doing, as far as giving away information and the direction that we’re going, we’ve removed the ceiling — and not just from the business perspective, but from a mental perspective. I think, as human beings, we’re naturally programmed to think negatively.

Typically — and I know I personally have gone through this a lot, where I’ve done some self-sabotaging efforts — the mental part of it is a big part, which I don’t think enough entrepreneurs work on it, but it’s a big part of it. I’ve done a lot of work into removing that from both the business perspective, but also from my own mental perspective.

As soon as I started doing that, things have just skyrocketed. That’s why I would describe it as limitless. It starts off with the head, the person running and everything and how their mentality is, and then what they preach to everyone else that’s working within the organization. Then that also transitions into the business and how the business is taking off, too. That’s why I would describe it as limitless.

Jerod Morris: Can you give us a brief description of the business, exactly what kind of clients you’re serving, and what your main revenue streams are?

A Quick Breakdown of Brandon’s Business

Brandon Lewin: In a nutshell, really what we do is we help businesses achieve the goals that they’re looking to achieve by doing unconventional, strategic, scientific, and a lot of times, just bold moves in digital marketing. What we’re really good at is being generalists and being able to piece together content, marketing automation, emails, sales funnels, pulling all these together to produce results.

We work with anywhere from one-person shops to mid-sized companies. I really don’t go beyond that because what I like to focus in on is these up-and-coming purposeful businesses, businesses that are focused on making a difference more so than making a profit. What I find is that typically the small- to mid-sized companies, those are the ones that have that type of focus. There are Fortune 500 companies that like to take that approach, at least from the outside, but from my own experience, I’ve never really met one quite yet that has really practiced that internally.

That’s what we’re doing. We do a couple different things. We’ll either consult, come in, help them, work with their team to put together different processes and systems and making sure things are actually working and moving in the direction that they want to go, or we’ll actually train them. Then there’s online digital programs that we offer as well that allows people to understand how these different processes work.

Then we have a do-it-for-you service as well. We’ll come on, and we’ll actually handle all these different services. Sometimes it’s all of them, and we’re almost like an outsourced marketing department. Then in some cases, it’s one specific piece of the puzzle that we’ll actually do for people. Something that we’re really focusing heavily right now is sales funnels, but also marketing automation. That’s a big piece where a lot of small businesses aren’t taking advantage of that quite yet, but it’s moving in that direction.

Jerod Morris: It sounds like sales funnels, marketing automation is kind of at the top of your priority list. What specifically are you doing right now to incorporate those more, both in what you’re doing and what your clients are doing?

Why Brandon’s Embracing Marketing Automation and Lead-Nurturing Programs

Brandon Lewin: It’s amazing. Some of the companies and clients that we work with is that it’s just about incorporating the software and then building out these lead-nurturing programs. The age-old saying has always been it takes, on average, seven, eight times to touch somebody to actually convert into a sale. That actually can be a lot more, especially in the online world. In some cases, it can be a lot less, but you really need to get them to know who you are and build that trust, get them to like you, provide value. Then you can go ahead and ask.

We’re just developing these processes that basically takes whatever company if they have an offline process, we help them transition to an online process, building out different sequences, and then helping them draw people in, doing ebooks, webinars, or evergreen webinars, which are becoming more and more popular — and more and more effective, too. People just like to have the on-demand focus instead of being able to be nailed down to one time.

We’re building out these processes and just helping them convert, and then analyzing the results from it and segmenting audiences out to give them more specific topics. I would say it’s anything that isn’t being done already by a lot of people, but there’s a certain market of customers that are just not taking advantage of it quite yet because they’re not educated about it. We’re finding a lot of B2B companies are like that, but then there’s coaches and all these types of different industries that are up-and-coming that need help with this process.

Jerod Morris: Yeah. Tell me a little bit about the biggest challenge that you’re facing right now in your business.

How Brandon Consciously Chooses the Right People to Work With to Create His ‘A-Team’

Brandon Lewin: The growing pains, man. That’s always been a challenge of mine — finding the right type of help. Bringing on people that buy into the vision, but also have a specific skillset and are willing to stay focused. It’s hard because a lot of times those rock stars, though, are the ones that are off on their own or really want to just stay on as a freelancer or a contractor.

What I’m finding, though, is actually just teaming up with those people instead of trying to hire employees or getting people just to focus on just my business. It’s just finding the people that are best suited for that specific project, so building up almost like a rock star or what I call an ‘A-team of contractors’ to work on these different projects. Whatever it entails and whatever skillset is necessary, it’s just bringing in the right people to take care of that.

Jerod Morris: Yeah. Let’s open up your tool box, if you’ll allow us to. What is one technology tool that contributes the most to your success as a digital entrepreneur?

How Marketing Automation Has Benefited Brandon’s Business

Brandon Lewin: I would say the marketing automation. To me, I use ActiveCampaign personally, and it’s been one of the better tools I’ve found, just from a price-point standpoint. Marketing automation, man, I constantly just come back to my dashboard and look, and there’s a new subscriber and another new subscriber.

I have it set up where it’s almost like a 72-day nurturing sequence. They just get content after content, and podcasting is a big part of it. They just get that, and then there’s a few asks in there. Then there’s some segments that go. In my mind, what marketing automation is, is that it’s just like having another employee, actually a couple of employees, because you can use it for different points of the business. It can help with the nurturing, the marketing, and the transition to sales.

In the world of sales, nothing beats a conversation, but what I’m finding is a lot of people don’t want to have conversations anymore. They’re comfortable with just making that decision, as long as they’re getting the right information, but doing that. Then once they do become a customer, how are they getting customer service? So following up with them and having that automated.

The key, I find, is that you have to make it not seem like it’s automated. You have it a very personal approach. That takes some finesse. That’s something that I’ve been working on and have worked on for a very long time. It works tremendously once you figure it out. Marketing automation I would say is definitely the tool that we’ve been using more and more often.

Jerod Morris: Yeah. And when you do it well, your content can almost serve as your sales force.

Brandon Lewin: Yup.

Jerod Morris: Then as your service team. Obviously, at a certain point, people may need a little bit more than that, but like you said, if you can finesse it, it can really work out well. That’s a good one. What about a non-technology tool that contributes the most to your success?

The Value of Relationship Building

Brandon Lewin: Relationship building. It’s so funny. I’ve been following Gary Vaynerchuk for a very long time ever since he came out with Crush It. I remember I read that book, and it just completely changed my philosophy on things, just more so about not what he was doing, because I was doing a lot of what he was doing as well — obviously, not on such a large scale as he was — but just being the person that you are and just being comfortable with who you are. I think he’s the best at just not giving a sh*t at what other people think about him, but at the same time, still giving a crap. I apologize. I don’t know if you’re allowed to swear on this.

Jerod Morris: It’s all right.

Brandon Lewin: Luckily, this was only the first time that I did that. That relationship, he talks about EQ, emotional intelligence. That’s what I have really always been good at. It’s just something that I’ve picked up. I’m a child of divorce. I went through that when I was 11. Ever since that I was in therapy. Because of that, I think I really have been well-trained in how to pick up different people’s emotions and figuring out what’s wrong, even when they won’t tell you something is wrong. I can pick that up from clients and be able to bring that up and avoid bigger blow-ups and have a conversation about that, and then be civilized and just work through those problems.

Even if it comes down to partners and people that you’re working with, and people who are employees, it comes to all parts of it, but being able to really find out what makes them tick. I think that’s really important, especially with clients, too. The clients, you got to find out what’s below that surface. It’s not just the tip of the iceberg, but it’s really what is that driving motivation for them to do these things that they want to do and then also transitions to the people that are working with you, underneath you, for you, however you want to describe it. See what their motivations are, and identify what their strengths and weaknesses are as well.

They might tell you one thing, but a lot of times, what I find is, especially with weaknesses, you got to find out what it is and quickly nip that in the butt and gear it more towards their strengths, so they can just work better for everybody. The faster you can set them up for success, the better off the entire organization is going to be.

Jerod Morris: Absolutely. Earlier, I asked you for one word that you would use to sum up your business as it stands today, and you said limitless. If we talk again in a year, what would you want that one word to be?

Why Brandon Is Doubling-Down on Limitless Possibilities for the Future of His Business

Brandon Lewin: Oh man. Describe my business in one word in a year from now. Honestly, I wouldn’t want it to be anything but ‘limitless’ because, if I’m going to hit that five billion mark, Jerod, it’d better be limitless for a very long time.

Jerod Morris: That’s right. That is right.

Brandon Lewin: I’m going to stick with that answer. That’s my final answer.

Jerod Morris: Okay. Because of the special circumstances, we’re going to allow it.

Brandon Lewin: All right.

Jerod Morris: No one else comes on here claiming they want to impact five billion people, but when you do, then we’re going to allow you to use a word like limitless twice.

Brandon Lewin: Awesome. I appreciate that.

Jerod Morris: Yeah. You are the exception.

Brandon Lewin: Nice.

Jerod Morris: Do you have time for a few rapid-fire questions here?

Brandon Lewin: Yeah. Let’s do it.

The One Book Brandon Would Insist You Read

Jerod Morris: Okay. If you could have every person who will ever work with you or for you, or as part of your A-team of contractors that you mentioned earlier, if you could have all of those people read one book, what would it be?

Brandon Lewin: Wow, one book. Man, you make it hard with this one thing. I don’t know. I’m going to take it to one of the more recent ones that I’ve read, Chop Wood Carry Water.

Jerod Morris: Ooh. I like that title.

Brandon Lewin: Yeah. It’s a newer book. I wouldn’t say it’s on any New York Times Best Seller lists yet, but if you go check it out, it’s Chop Wood Carry Water by Joshua Medcalf. It is awesome. It’s all about enjoying the process of being great and achieving greatness. It is a process. I think a lot of people get caught up, especially as entrepreneurs, we don’t have patience.

We want everything immediately. Sometimes we’ll shoot ourselves in the foot by thinking too short term instead of understanding that this is an entire process. It really just opens your eyes and appreciates everything that’s happening, and all you can do is learn from it and grow and continue to move forward and appreciate that process.

Jerod Morris: That’s a great one. That book sounds wonderful.

Brandon’s Ideal 30-Minute Skype Call to Discuss His Business

Jerod Morris: If you could have a 30-minute Skype call to discuss your business tomorrow with anyone, who would it be? Anybody.

Brandon Lewin: To discuss my business.

Jerod Morris: Yup, 30 minutes.

Brandon Lewin: Thirty minutes. Brian Clark.

Jerod Morris: Ooh, okay.

Brandon Lewin: I follow everything that you guys have done. He’s done a beautiful thing of just transitioning from one business to another. He’s grown this empire that I see, at least from the online perspective, and I would love to just be able to, for 30 minutes, pick his brain and see how everything has gone through that entire process — how it started, what were some trials and tribulations, now what he’s doing with his life, and the business side of it. That would be definitely one person that I’ve always wanted to have a conversation with.

Jerod Morris: That would be a value-packed 30 minutes. No question.

Brandon Lewin: Absolutely.

Jerod Morris: No question.

The One Email Newsletter Brandon Can’t Do Without

Jerod Morris: Okay. What is the one email newsletter that you can’t do without?

Brandon Lewin: I think it’s Neville Medhora. I don’t know if you know him. He’s at Kopywriter Kourse. It’s with a K. I just got one from him this morning. He’s actually a local guy here in Austin. His claim to fame was that he was the copywriter for AppSumo and does SumoMe.

His writing, though, is just beautiful. If you ever talk to him in person, it’s the same thing. It just transitions beautifully. He just talks about things that are relevant to my business and what I’m doing and what I’m trying to do. Copywriting is also always a skillset of mine that I’m always trying to develop. Whether it’s reading his, or Copyblogger is a big one, too, that I enjoy. So yeah, his I would definitely say I can’t live without it.

Jerod Morris: Okay, Neville Medhora, you said?

Brandon Lewin: Yeah. Yup.

The Non-Book Piece of Art That’s Had the Biggest Influence on Brandon as a Digital Entrepreneur

Jerod Morris: Okay. What non-book piece of art has had the biggest influence on you as a digital entrepreneur?

Brandon Lewin: I am a big fan of Michael Jordan.

Jerod Morris: Ooh, okay. We share that.

Brandon Lewin: Yup. Awesome. I grew up in Chicago, Midwest guy like yourself. I was about nine, 10 years old, when the six championships happened. I grew up watching it, stayed up late. I remember the first championship when they were tipping over cars. I have a poster of Michael when he’s doing it from the free throw line, the slam dunk contest, his famous dunk. Anything from him inspires me, even that piece. It’s just a poster. It’s black and white. His jersey’s red. I would call it art. That just inspires me.

I had these little different posters in my office of people like that. Some of them have quotes on them. Some of them don’t. His definitely inspires me because he’s the epitome of greatness and also failure, too. He’s failed, and that’s a big part of his story. I love everything that he talks about when he talks about his drive to success and his journey. I would say that’s the biggest one. That’s been the most influential to me.

Jerod Morris: I would say that Michael Jordan playing basketball definitely qualifies as art.

Brandon Lewin: Yes.

Jerod Morris: Number two, one of the greatest commercials he ever had was the commercial where he talked about how he succeeded because he has failed. He goes over all of his different failures and says that’s why he succeeded. Oh man, is there anybody who grew up around the time we did and in the Midwest that didn’t just love Michael Jordan? You didn’t have to be in the Midwest.

Brandon Lewin: No.

Jerod Morris: He was the man.

Brandon Lewin: He was the man.

Brandon’s Biggest Productivity Hack for Doing Meaningful Work

Jerod Morris: Okay. What productivity hack has had the biggest impact on your ability to get more meaningful work done?

Brandon Lewin: Health in general. This has been something that I’ve really focused a lot in the last year, but really, really heavily in the last three to four months that has completely turned things around. I have never been so productive in my entire life.

There’s other things of course, like scheduling and all that, but just having the right type of energy and being in a right state of mind helps you tremendously into achieving so much during the day. It’s not always about how much you do. It’s not about working 16 hours in a day, but it’s about how much you can get done in that 16 hours — or even if it’s just eight hours. How much can you get done?

A lot of people can get a lot done in eight hours, nine hours, and not have to work those grueling 16-hour days, although sometimes they’re necessary. I’ve just been taking care of my body, eating clean, exercising regularly, taking nutritional supplements that have helped tremendously, a combination of those three, and then sprinkle in some meditation in the morning and affirmations, and that really has been the recipe of success for me.

Jerod Morris: That’s huge. I have found that in my own life as well. That’s a really good one. I echo that.

Brandon Lewin: Thank you.

How to Get in Touch with Brandon

Jerod Morris: Finally, what is the single best way for someone inspired by today’s discussion to get in touch with you?

Brandon Lewin: Single best way? Email. Email is always the easiest way. It’s Brandon@BrandonMLewin.com. I respond the quickest outside of text messages, but as of right now, I don’t want random people texting me.

Jerod Morris: These are not random people. These are Digital Entrepreneur listeners.

Brandon Lewin: Of course, I would love that. Don’t get me wrong.

Jerod Morris: But you still probably shouldn’t give out your phone number over the podcast.

Brandon Lewin: Yeah. When someone texts me, I’m like, “Hey.” They’re like, “Hey.” I’m like, “Hey. Who the hell is this?”

Jerod Morris: Yes.

Brandon Lewin: Yeah, email would be great for right now. Then whenever we need to transition into it, that would be awesome, or transition to a text message or phone call. Yeah, email is the best way.

Jerod Morris: Cool, so Brandon@BrandonMLewin.com.

Brandon Lewin: Yup.

Jerod Morris: Excellent. Well, Brandon, that brings us to the end of this episode. It has been a pleasure. Thank you so much for your time.

Brandon Lewin: Jerod, thank you, man. This has been an absolute pleasure and a lot of fun. I hope everyone gets something out of this.

Jerod Morris: Yup. I look forward to someday sharing that Mosaic with you, and we can reminisce about Michael Jordan and the Bulls.

Brandon Lewin: Absolutely, man.

Jerod Morris: All right, man. Take care.

Brandon Lewin: You too.

Jerod Morris: All righty. Thank you very much for being here, for listening to this episode of The Digital Entrepreneur. My thanks to our guest this week, Brandon Lewin. Really appreciate his time, his insight, and his candor.

My thanks also to the production team here at The Digital Entrepreneur, everybody at Rainmaker.FM, Toby Lyles, editing, Caroline Early and Will DeWitt, who helped me produce the show, really appreciate the help there. Thanks to you, as always, for being here.

Again, if you want to see the webinar we did about RainMail, maybe you have questions about RainMail, maybe you’re just hearing me say RainMail for the first time and you’re like, “What is this? Email marketing baked into a platform? This sounds kind of cool. I want to learn more,” go to Rainmaker.FM/RainMail. It will redirect you to the webinar replay page.

The nice thing is, Will actually went through and created a table of contents. It’s a two-hour webinar. You don’t have to go through the whole two hours looking for what question you may have. You can actually look at the table of contents, and see if there’s a specific question that maybe you have or a topic that you want to see if we covered. Look, see if it’s there, and you can actually skip ahead in the video to watch it. Again, Rainmaker.FM/RainMail.

All righty. We will back next week with another brand-new episode of The Digital Entrepreneur. Until then, take care, and we will talk to you soon.