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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.

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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.

The Transcript

Sean McCabe’s Tried-and-True Techniques for Getting More Meaningful Work Done

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 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. I am your host, Jerod Morris, the VP of marketing for Rainmaker Digital, and this is episode No. 26.

On this week’s episode, I am joined by someone who is passionate about helping other people make a living from work that fulfills them. Someone who’s goal is to “demystify the path toward building a sustainable, profitable, audience-driven business.” He recently took the month of July to write his book Overlap. He’s the host of a couple of podcasts: one on creativity in business and another with the goal of helping others build a thriving, sustainable business and achieve huge goals.

He is the founder of the brand called seanwes, where he teaches two courses. One is on how to grow your business with writing, Supercharge Your Writing, and the other is focused on how to stop trading time for money and start pricing your work on value, Value-Based Pricing.

He is Sean McCabe, and he is a digital entrepreneur.

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

Jerod Morris: Real quick, before I bring you my discussion with Sean, I want to let you know about a webinar that I participated in recently with Brian Clark and Chris Garret that you may want to check out. You’ve heard us talk a lot about the Rainmaker Platform here on The Digital Entrepreneur. Rainmaker, of course, is the complete solution for digital marketing and sales, giving you more power, less pain, and higher profit. It was designed by digital entrepreneurs, the team at Rainmaker Digital, for digital entrepreneurs, people like you.

Well, did you know that Rainmaker now includes integrated email marketing as well? It’s true. It’s called RainMail, and it’s built right into the platform, integrating with all the other features of Rainmaker — like landing pages, marketing automation, and memberships. You can really create an adaptable, personalized experience for your audience when email is baked right into your online platform, like it is now for Rainmaker with RainMail. Oh, and your first 999 subscribers? They’re free, as in they’re included in your regular platform payment. You don’t pay a dime extra.

Want to see how RainMail works? Well, one way to do it is to check out the replay of the webinar that Brian, Chris, and I did recently. The live event was only for Rainmaker Platform customers because we wanted to answer customer questions, but we’re happy to share the replay with prospective Rainmaker customers like you so you can see what RainMail is capable of.

To watch the replay, go to RainmakerPlatform.com/Webinar1. It’s about a two-hour replay, but the nice thing is, on that page, we actually have a bulleted list of all the topics and questions. It was based on a lot of FAQs that we often get, plus some use cases and examples, so we could show folks what RainMail can do and how you can use it on your site, too. So again, RainmakerPlatform.com/Webinar1 — the number ‘1,’ not spelled out like one.

And now, here’s my interview with digital entrepreneur Sean McCabe.

Mr. McCabe, welcome to The Digital Entrepreneur.

Sean McCabe: Hey, Jerod. Thanks so much for having me.

Jerod Morris: It’s great to have you on here. Let’s begin here, Sean. 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 benefit of digital entrepreneurship do you appreciate the most?

The Two Biggest Benefits Sean Derives From Being a Digital Entrepreneur

Sean McCabe: Freedom is a big one for me, for sure. I’m also an introvert, so I love working from home. I love the ability to work from anywhere. Usually, that’s home. I wrote a book last month, and I was thinking, “I’m going to travel,” because I like this romantic idea of getting a cabin and looking over the scenery, but my friend said, “Do you get your work done really well at home, or do you get distracted at home?” I was like, “Oh I focus great at home. I have so much focus at home.” He’s like, “Why are you going to go anywhere else?” I’m like, “You’re right, you’re right. This is where I get my work done.”

So I like being able to work from home. It was just me at first. I was a solopreneur. Now we’ve got a team of eight people, including myself. I consider the people I work with to be some of my very best friends, so it’s also fulfilling to give them freedom as well and give them the ability to do work they enjoy. We have a remote team, like you guys do at Rainmaker, and it’s such a joy to give them a sense of fulfillment as well.

Jerod Morris: Yeah. Working from home is so interesting because it can be a blessing and a curse in so many ways. You really have to learn how to manage it for yourself. I’m the same way. I can focus really well at home. And then there’s every now and then where I find my focus is jumbled, and I’ve got to get out somewhere else and spend a day somewhere else. But then usually I can come back and my focus is back.

That really is a big benefit, just to be able to have that freedom. Especially for me now starting a family, it’s been really nice to have that flexibility. That’s definitely a big benefit.

Sean McCabe: Yeah for sure. And then nothing beats waking up in the morning and finding out you made a few thousand dollars, right?

Jerod Morris: Right, exactly. You said something interesting there. You said last month you wrote a book. Did it only take you a month to write the book? This is a pretty big project for you, isn’t it?

How Sean Wrote a Book in a Month

Sean McCabe: Well, it’s been in my head for several years, so I did actually write a book in a month. I actually set a really ambitious goal, really, really ambitious, which was to write three books in a month just because I’m crazy. I set out on this goal to write three books in a month. I figured they would be about 80,000 words apiece, which means I would need to have written 240,000 words. That comes out to about 8,000 words a day, which I have done before. I’ve topped 10,000 words in a day, but this was going to be an intense sprint.

During the process of this, I was actually journaling the whole process. I was doing a live stream every morning, just sharing the writing process. On day four, I decided, “You know what? This three-part series really should be a single book. I really should put it all in one book because it’s for the same person.”

I was at first thinking, “Oh this is for different people,” but it’s really for the same person in different stages. I decided, “I’m going to compile it all into one book. I’m going to make it nice and concise, condensed, nothing that you don’t need.” And because I set that super-big goal of trying to write three books in a month, I actually wrote the one book in 14 days. That’s 75,000 words.

Jerod Morris: That’s the Overlap, right?

Sean McCabe: Yes, the book is called Overlap. It’s on getting from the life you have to the life you want, basically like a really practical, step-by-step guide. Especially people who are in a day job and they want to be able to start their own thing, it’s just a really practical guide for getting where you want to be.

Jerod Morris: Let’s talk a little bit about your story, then, of getting from where you wanted to be to where you are now. Take me 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?

How an Interest in Hand-Lettering Led to the Burgeoning Online Empire Sean Now Oversees

Sean McCabe: Well, honestly, Jerod, I started pretty young. My first business was a computer repair business when I was 17 years old. Before that, I was three stories up, washing windows.

Jerod Morris: Oh my.

Sean McCabe: We had a 32-foot ladder leaning against a three-story residential building, and then on top of the roof, there was another window, yet another window, a little bit higher, maybe a good 12 feet up or so. We had a four-foot ladder on top of this roof, on top of the 32-foot ladder, and my partner was holding this ladder because the roof was slanted. I was standing on the top of the four-foot ladder where it says “Do not stand,” reaching as far as I could to wipe the drops of water from the corner of the window. At that point, I started thinking, “Maybe I should do something else.”

Jerod Morris: My fear of heights is getting activated just listening to the story.

Sean McCabe: It was an exciting time, but not what I wanted to do forever. I ended up starting a computer repair business just in high school, passing around flyers, learned the importance of relationship marketing and referrals, got into this nice … basically, a retirement community where everyone had computers they didn’t know how they worked, and they wanted to pay someone else to fix them. They just kept referring me and referring me, so that’s basically how I got into business.

Jerod Morris: Talk about how hand-lettering fits into this because that was your entryway into working online, correct?

Sean McCabe: Yeah. I’m a musician. I’m a creative person, but also very logical. I enjoy business. I enjoy computers. When I started the computer repair business, I stepped down from a band, and what I didn’t anticipate was losing that creative outlet. I eventually started a web firm with a partner, and I enjoyed creative work.

I started pursuing things in my nights and weekends, just creatively, creating hand-lettering — so drawing letters by hand, kind of like the Coca-Cola logo type. It’s not a font. It’s drawn by hand. I was really enjoying this process, and I started sharing my work. No one really noticed it for a couple years, but after about two years into it, people started to notice my work. They were asking for T-shirts and prints. You know, “Can I hire you to design my logos,” and I ended up going full-time freelance. I sold my other businesses. We hibernated the web firm, and I went full-time freelance.

Jerod Morris: Wow. So tell me about the milestone or the moment in your career as a digital entrepreneur. Maybe take us from where you were doing what you were doing with the hand-lettering and then to what you’re doing now, which is teaching people how to build their own online businesses. Tell me about a milestone or a moment that you are the most proud of.

The Essential Lesson Sean Learned From Launching His First Course

Sean McCabe: I’d have to say the moment that made me realize that it was possible was when I launched my first course. I had a bunch of people … they were buying my products and hiring me, but a lot of people wanted to learn how to do what I did. I took about six months to create a course and launched this course.

During that time, I was learning from a bunch of people, especially people on Rainmaker and Copyblogger, and books, articles, and videos, everything I could learn about marketing online. I applied that knowledge to the first launch of my course, and thanks to people who were willing to share what they learned for free with me, my course actually made six figures in the first three days of launching. That was when it was like, “Wow, this is actually possible. I can actually do this.”

As much as I actually enjoyed doing design and being an artist, people started asking me, “How did you do that? How are you able to launch a course and make so much money in a few days?” I said, “You know, I’m just going to share it.”

I started sharing on my podcast. I started sharing articles and case studies. I’m just trying to help people, and I started seeing, over time, these people were taking this advice and they were going on and starting their own businesses, quitting their day job, moving across the world. Even more than actually doing the work of art, or design, or working with clients, I found a lot more fulfillment in helping others realize their dreams.

Jerod Morris: A good story. When you talk to people who have been successful in digital entrepreneurship, especially a teaching kind of digital entrepreneurship like what you’re doing, that love for helping people and helping people achieve their goals just comes out time and time again. It’s such an important lesson to remember. The more that you help other people get what they want, the more that you’ll get what you want. It’s such a beautiful cycle in that way.

Sean McCabe: Completely agree.

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

How Hiring Full-Time Employees Changed Sean’s Perspective

Sean McCabe: I think the most humbling moment for me was when I started to hire. This was my third business, Sean Wes, but it was the first business that I had full-time employees. I’ve had contractors before, but I brought on five or six full-time employees in a year and really quickly started to feel that the gravity, the weight of that. You think, “I want to hire employees for my business so they can do work for me,” but you realize you’re actually supporting their livelihood.

I don’t have kids. I’m the oldest of 13 kids, so I have a little bit of an idea of what it’s like. Especially growing up, when they were young, I changed probably 1,000 diapers, so I’ve got kind of an idea.

Jerod Morris: Thirteen kids? Wow.

Sean McCabe: Yeah. Never a dull moment. They’re super awesome. I never had kids myself, but I can only imagine I’m getting a glimpse of that as a business owner. I obviously have my own dreams and ambitions, but somehow those really fade away in the face of having your own employees and realizing it often comes to you to take care of these people. That becomes your number one priority, or at least for me it did.

Jerod Morris: In episode 162 of your podcast, you talked about how people put other people into boxes, and I really enjoyed this. What did you mean by that, and why is that important to recognize?

How to Project That One Thing You Want to Be Known for Next

Sean McCabe: Probably the simplest way to start would be to refer people to Dunbar’s number, which is to say that we really can only process about 150 close relationships, give or take. People can’t process the complexities of individuals beyond that. On a surface level, we can. You can obviously follow more than 150 people on Twitter, if you want, but you can’t get super deep on those relationships.

What we tend to do is categorize people. “What is this guy about? What do I think of when I think of Jerod?” People put them in a box. They say, “Okay, you are a podcast guy. You are an entrepreneur. You are an artist, a designer, a developer.” They put you in a box based on what you share, what you project.

What a lot of people do is they project everything that they do. I was a full-time designer for about six or seven years, and during that time, I did all kinds of things — illustration, animation, user interface design, logos, screencasts, all kinds of things — and I was projecting all of them. Whenever I made a new piece of work, I wrote on something, or I produced a video, I shared that. I think I might have gotten a few followers. My audience grew a little bit, but the inflection point in my growth, especially the growth of my audience and revenue online, was when I started to curate what I shared.

What I mean by ‘curate’ is selectively projecting a single focused thing. Just taking one thing of the many things you do — we all do many things, we’re all good at many things — but projecting just that one thing that you want to be known for next.

It doesn’t necessarily have to be for the rest of your life. We go through seasons, and everything is a stepping stone. But putting up that one thing that you want to be known for helps people process you because they’re going to simplify. They’re going to simplify, simplify, simplify. They can’t process all of your complexity, so if you project everything, you become known for nothing. What you can’t control is the fact that people will put you in a box. What you can control is what box they put you in. You can define that box by what you share.

Jerod Morris: Great advice. If you project everything, then you project nothing. That’s great. 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 Clarity That Comes From Recognizing What Metrics Best Track Your Business Growth

Sean McCabe: Growing.

Jerod Morris: That’s good.

Sean McCabe: This year’s been a lot of growing pains, really getting a solid idea of what our business model is. I think a lot of us stumble into revenue, and we don’t actually understand the core fundamentals of business and what our business model is. I put myself in that category. I stumbled into things that were working. I kind of figured out ways to make revenue here and there, but I didn’t have a solid idea of our business models that we spent the past year really refining that. It’s been a growing year.

Jerod Morris: What was the biggest thing you learned about your business model, maybe that surprised you?

Sean McCabe: I think that monthly revenue isn’t necessarily the right metric to track. It depends on your business model. I have my ear in a lot of industries. I pay attention a lot to the SaaS app industries, and I listen to a lot of the people in those spaces. We are developing a SaaS app behind the scenes, so I try and pay attention to that stuff. But our revenue right now is not at all coming from SaaS.

We are the very definition of the digital entrepreneur in every sense. We have a membership site. We have digital products. We have physical products. We have our community, a podcast network, a conference — everything you can think of. But we don’t currently have a SaaS app.

I’ve been so obsessed over this monthly revenue figure that it’s actually been hindering for me. This is the kind of clarity you get when you go on a mastermind and have smarter people give you advice from the outside. Our business model is more conducive to being seen over a 12-month period and really planning out everything we do holistically.

Jerod Morris: That’s an important realization to have.

Sean McCabe: It was a moment of clarity for me.

Jerod Morris: Yeah. So what’s at the top of your priority list right now, and what are you doing to get there?

The Biggest Challenge Sean’s Currently Facing in His Business

Sean McCabe: Top of the priority list right now is getting our consistent revenue to surpass our payroll and expenses. That sounds really scary, but we hired really quick. I got my start by launching online courses, and what you’ll recognize and realize quickly when you get into online courses is you have these really big spikes of revenue and then not so much in between, for the most part, even if it’s an evergreen type of a situation.

It’s been, for me, transitioning from that spike-driven revenue of a business to something that’s more diversified and more sustainable, where I can not have to worry like, “Okay, it’s going to be a dry spell for three or four months, and make sure everyone gets paid,” but something a little more reliable.

Jerod Morris: What are some of the specific ways that you’re trying to do that and smooth that out?

Sean McCabe: We are diversifying our course offerings. Basically, we’re wanting to be the place where people go to build and grow a sustainable business. We want to give them the resources for that. We want to give them access to a community of people who are doing the same thing. Diversifying our flagship courses, which are separate purchases, as well as inflating the value of our membership — because obviously that recurring revenue is a lot more steady.

Jerod Morris: You just mentioned a challenge that you’re facing here — getting your consistent revenue to surpass payroll and expenses. Are there any other big challenges that you’re facing right now, or would you say that one’s the biggest?

Sean McCabe: Well, it’s definitely the biggest. There’s some articles going around that are like, “Everyone’s saying video is the next big thing, and it’s not the only thing.” Honestly, I think video is the next big thing. Video is already big, but it’s going to get even bigger and bigger. Especially with the coming virtual reality world, you’re going to want to be good on video. You should be doing live streaming. You should be doing way more video.

We’re trying to ramp that up, and I’d say the most difficult part of that is having a remote team. We have tens of thousands of dollars of equipment in our office here where I am, but our team is remote. Getting more of them on video, up to our quality standards, it’s difficult.

Jerod Morris: That’s a good one.

The SaaS App at the Top of Sean’s Toolbox

Jerod Morris: Let’s open up your toolbox, then. You mentioned some of the video equipment that you have there. Let’s open up your toolbox a bit. What is the one technology tool that contributes the most to your success as a digital entrepreneur?

Sean McCabe: Am I allowed to say something we built?

Jerod Morris: Of course, absolutely.

Sean McCabe: For the past several years, we’ve been building a system for our community. We have several hundred people inside our community, and this system is what could best be described as a live chat system. However, it’s something we would like to build into something that’s … it’s so hard to describe, but I would say a hybrid between archivable, long-form discussions and real-time discussions.

Basically, we are wanting to eradicate forums. We’ve had forums. There are some issues with forums that we don’t like. We have chat, but there are some things that chat can’t quite do. So we’re developing this feature called ‘Conversations,’ which threads discussions, makes them searchable, makes them filterable.

You can essentially zoom in and out of what you want to hear and what you don’t want to hear, get notified by follow-up responses. It has live-streaming built in, both audio and video. You’ve got people with profiles. They have badges for whether or not they’re going to the conference or whether or not they took a certain course. We can send push notifications from it. It’s very, very powerful. We can use it for live events as well, so it’s good for people who stream their podcasts, do webinars, or are community organizers.

We have commands where we can toggle a call to action button, so people who are watching a live event video and at the right moment, while it’s live — it’s not even a timer, like how people do that with recorded videos — on cue, we can animate the video where it zooms down to the side, and there’s a button right there, whatever color, whatever call to action text you want, going to whatever link or add to cart you have.

It’s a very, very powerful system, but as many of our members really, really want this for their own communities, I’m dedicated to making this the best it can be for our own community before I make it available to others. I know when I turn this into a SaaS app, our customers and clients of the software will become the primary people we focus on. They’re going to ask for features. They’re going to ask for things, and we’re going to need to address those.

If we keep it in-house first … this system was built around the needs of a community. When people are like, “I wish I could do this. I wish I could do that … ,” we build it. I want to preserve that as long as possible, and I really want to make sure this is built around the needs of the user.

Jerod Morris: Wow, that sounds like a really, really interesting product. It really is.

Sean McCabe: It is absolutely our strongest piece, by far.

Jerod Morris: Wow, very cool. What about the non-technology tool that contributes the most to your success?

The Two Life Hacks That Have Contributed the Most to Sean’s Success

Sean McCabe: I would just say getting your back against the wall. Commit to something, and schedule it. A lot of us wait for a motivation to find us. We see it as a source, and really motivation is a result. It’s a result of making a commitment and showing up consistently.

I started my podcast and said, “I’m going to podcast twice a week.” This was before I knew how hard podcasting was, or editing, and newsletters, and show notes, and all that stuff. I set a commitment, and I did it for the better part of two, two and a half years. We did two episodes a week, and I think that has really helped us.

It’s not just podcasting, but anything that you do. I would say get your back against the wall. You’re capable of more. Just make the commitment. Say, “I am going to do this weekly.” Tell your friend you’re going to do it weekly. Tell yourself. Write it on a note and put it next to your bed. Tell your audience you’re going to do it weekly. Be consistent. Get your back against the wall.

The other thing I would say is all of our team … maybe not all of our team, but most of our team have adopted the habit of going to be early and waking up early. I know you’ve heard this a million times. You hear successful people wake up early. You maybe have even read articles that say, “Wake up whenever you want. It doesn’t matter.” I would just say, try it for yourself. Try it. Just go to bed early, wake up early, and log your output.

Are you a writer? How much do you actually write at night? You go throughout your whole day. You’re getting all this baggage. Your mind is full with the day’s events. I’m a night owl by heart. I don’t like waking up early. I like the person that I am when I do.

I would say, if you’re a writer, if you’re anything, just log your output. Whatever your output looks like, log it. Log it right now for several weeks. How much are you getting done? Then try this out. Wake up early, and log your output. This is what I did because I wanted to prove the early birds wrong. I was like, “I’m going to show them that it doesn’t matter,” and I doubled my output.

As much as I like being right — Jerod … I love being right — as much as I like being right, I like being successful more. Even though I was wrong, I’m like, “I’m sold. I’m going to do this.”

If you try this out, this would be my recommendation for the transition. Instead of thinking of this ideal where you go to bed super early, at 9:00 or something, you wake up at 4:00, you write several articles, you go on a run, and then you eat this healthy breakfast … instead of picturing this ideal that’s super hard to get to, start by defining success by when you go to bed. That’s all it is.

It starts the night before. Successful morning routine starts the night before. Just say, “If I can go to bed by X,” whatever that is for you, “This is a success.” Even if I don’t wake up early, even if I don’t write the next day, just define it as a success if you go to bed when you said you wanted to. Do that for a few weeks. Just a couple weeks, try that. Then, start redefining success. Redefine success as when you wake up. Then define success by whether you went on a run or whether you started writing.

Jerod Morris: How important is that, to have your own definitions for what success is, and to make them like that? Not easy, necessarily, but simple, and maybe outside of what people would think because I think they would think, “Well, success is writing 5,000 words,” but you’re redefining it by saying, “No, success is going to bed at this certain time, before then.” How important is that as a mindset shift for people?

Sean McCabe: In terms of defining success, no one can or should define success for you. If you’re able to live the life you want with the people you love, that’s what it’s all about. Getting to that point, it takes individual steps, and what’s overwhelming is looking at the conclusion and the place you want to be and saying, “That’s success. Everything I do in between that isn’t perfectly that is a failure, and I’m a loser.” That’s why I like defining success as the next step. Then just redefining it as I basically level up.

Jerod Morris: All right, let’s look forward now. Earlier, I asked you for the one word that you would use to sum up the status of your business as it stands today, and you said ‘growing.’ If we talk again in a year — and hopefully we will, we’re going to talk, certainly, in six or seven weeks at Digital Commerce Summit, which will be fun — if we talk again in a year, what would you want that one word to be?

Sean McCabe: I am very much looking forward to the conference. That’s going to be a fun time.

Jerod Morris: It is.

Sean McCabe: I would say ‘thriving,’ and to add onto that word, once our business is in a place that we want it to be, and once we have our solid business model and we’re sustaining ourselves and our people, I then want to start by defining our success by our members’ success and our students’ success. I really admire the people who, they don’t toot their own horn and say, “We’re so great. This is what we’ve done,” but, “This is what the people that we’ve helped and the people that we serve have done.”

Jerod Morris: I like that. I like that a lot. All right. Are you ready for some rapid-fire questions here to close this out?

Sean McCabe: Let’s do it.

The One Book Sean Would Insist You Read

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

Sean McCabe: I require them to read The 10X Rule.

Jerod Morris: Do you?

Sean McCabe: I buy it for them even.

Jerod Morris: Very nice. Why that one?

Sean McCabe: The 10X Rule, it’s by Grant Cardone. He’s basically saying “You’re not taking enough action. You’re not taking enough action. You have this goal, you have this thing you want to do, and you do the amount of action that you think it will take to reach the goal. That’s 1X action. You need to do 10 times the amount of action that you think it will take to reach your goal.”

Number one, you have no idea what it’s going to take to get there. Number two, worst case is you surpass your goal, which is awesome. The other thing he says is, “Success is your duty.” The author sees it as unethical not to fulfill his potential. It’s just all around an awesome book.

Jerod Morris: Very cool.

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

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

Sean McCabe: I wouldn’t mind talking to the author, Grant, but if not him, I would say Gary Vanderchuck. He’s an intense guy, and he knows the value of a few minutes. He could turn around your life and your business in a three-minute conversation, for sure.

Jerod Morris: He could, and you’d be able to have 10 of them in 30 minutes. That would be an intense 30 minutes if it was with Gary.

The One (or Two) Email Newsletter(s) Sean Can’t Do Without

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

Sean McCabe: While Gary’s on my mind, I do have to give him credit. He has an incredible newsletter, and it’s very straight to the point. You can glance at it in 30 seconds and get a little hit of motivation, and he’s also started giving things away. He’s partnering with people, and if you open a newsletter early enough, there’s legit stuff in there, pretty solid.

The other guy, I would say, is Ramit Sethi. Brilliant guy. If you’re like me, the first year or two you heard about him, you’re like, “Eh, I don’t know about this guy.” When you come back around, really pay attention. There’s so much, so many layers to everything he does that you can learn from.

Jerod Morris: There was a really interesting episode recently of the Tim Ferriss podcast that reintroduced me to him, which was really beneficial, so two really good recommendations there.

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

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

Sean McCabe: One of my community members sent me an original watercolor painting. He’s an incredible watercolor artist. His name’s Eric Lin. If you search for ‘Eric Lin watercolor,’ his work is amazing. I would say he’s the next Bob Ross, but he’s really the next Eric Lin. That’s how good he is. He made a painting from a photo that I shared on Snapchat of a mastermind retreat that I was at in San Diego just of the guys in front of me walking along the beach, and it’s absolutely gorgeous.

But honestly, it’s more the gesture that he felt like he had received so much value from me, he wanted to create this, and send it to me. It hangs in the foyer of my house, and I’m just super proud of it.

Sean’s Biggest Productivity Hack for Doing Meaningful Work

Jerod Morris: Finally, what productivity hack has had the biggest impact on your ability to get more meaningful work done? You may have actually already mentioned this one when we talked earlier.

Sean McCabe: I’m going to say it again. I’ll say either get your back against the wall and commit, or just try the waking up early and log your output.

How to Get in Touch with Sean

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

Sean McCabe: If they made it this far, I think they probably like podcasts, so I would say check out the seanwes podcast at seanwes.com/podcast and feel free to drop me a line. We talk all about the intersection between creativity and business, marketing, online entrepreneurship. That’s the best place to find us.

Jerod Morris: You have several different podcasts there, too, right? You’ve got Lambo Goal podcast, and then several other ones in your network.

Sean McCabe: Yeah, we do have a network there. It’s really all about helping people with everything they need to do business online, whether you want to start a podcast, we’ll start talking about client work and pricing, video, all that good stuff.

Jerod Morris: Excellent. Well, Sean, thank you so much for joining us on this week’s episode, and I look forward to seeing you in a couple of months in Denver.

Sean McCabe: I’m very excited about that. Thank you again. Really appreciate the opportunity, Jerod.

Jerod Morris: Absolutely. Thank you, Sean. All right. Well, thank you for joining me on this episode of The Digital Entrepreneur. Happy to be back. We will get back with our regular schedule of weekly episodes, so check back next week for another brand-new episode of The Digital Entrepreneur.

Again, go to RainmakerPlatform.com/webinar1. Check out that webinar about RainMail, see how it works. There’s a good chance that if you have questions about RainMail, they are probably answered in that webinar, so go check it out. Get your questions answered. Check out some use cases, some examples. See if it’s for you. If it is, you’ll be right there at RainmakerPlatform.com. You can take the platform for a test drive, see if you like it.

Thank you for listening, and I will join you next week on another brand-new episode of The Digital Entrepreneur.