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How Jay Baer is Navigating New Waters With His Latest Digital Product
29th September 2016 • The Digital Entrepreneur • Rainmaker Digital LLC
00:00:00 00:39:01

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This week’s guest on The Digital Entrepreneur wants to hug you … even if you hate him!  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.

Listen to The Digital Entrepreneur below ...

The Show Notes

The Transcript

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

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

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

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

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

All right, so on to my guest this week. He’s the founder of, 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...