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

This week’s guest on The Digital Entrepreneur wants to hug you … even if you hate him! πŸ˜‰ He founded one of the world’s most popular online resources for marketers and business owners, hosts one of the world’s most influential social media and marketing podcasts, and is the author of several exceptional books. He is … Jay Baer

In this 37-minute episode, Jay Baer and I discuss:

  • How the real estate market crash in 2008 led him to where he is today
  • His most humbling time as a digital entrepreneur, which he is currently going through as he develops his first online course
  • Jay’s guidance on how to balance advice from others and your own ideas about how to do things when those two conflict
  • The one technology tool that contributes the most to his success as a digital entrepreneur
  • What he believes holds every digital entrepreneur back
  • Why he’s adding proactivity and wisdom to the business development process

And much more.

Plus, Jay answers my patented rapid-fire questions at the end of the episode, which unveiled which email newsletter he can’t go without and his productivity hack to get more work done.

Don’t miss it.

The Show Notes

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, 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 … let me know if there’s an easier URL to say.

Jay Baer: Just go to

Jerod Morris:, 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 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 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 We created our own proprietary ranking algorithm, lots of custom database work, built it on WordPress. It was slick, man. It’s still there. It still works. We launched it — really proud of it, really proud of the technology — but I had built that project because I was mad that it didn’t exist.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Jay Baer: We haven’t had people associated with that work. Obviously, we know how to do it. We do that kind of consulting for clients all the time, but we’ve never done it ourselves. We’ve never said, β€œHey, 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, 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,

Jerod Morris: Then 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.