How to Find and Tap into Unmet Demands

My guest today is a successful author and screenwriter and has written a book and produced a movie about his life, called I Hope They Serve Beer in Hell.

His books have sold over 3 million copies and have been translated into 30 different languages.

My guest also founded (and sold) Tropaion Publishing, which pioneered the idea of author as publisher. He later co-founded Book in a Box after a busy entrepreneur asked if she could write a book without actually writing it.

The company’s mission is to help people turn their wisdom, knowledge and ideas into professionally published books without having all the hassle that comes with it. Book in a Box made an amazing $200,000 in its first two months and is still going strong.

Now, let’s hack …

Tucker Max.

In this 29-minute episode Tucker Max and I discuss:

  • Making decisions based on emotions
  • How failure forces you to learn, change, and adapt
  • Why you need to learn lessons the hard way
  • The positives of being fired

The Show Notes

How to Find and Tap into Unmet Demands

Jonny Nastor: Hack the Entrepreneur is part of Rainmaker.FM, the digital business podcast network. Find more great shows and education at Rainmaker.FM.

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Voiceover: Welcome to Hack the Entrepreneur, the show which reveals the fears, habits, and inner battles behind big name entrepreneurs and those on their way to joining them. Now, here is your host, Jon Nastor.

Jonny Nastor: Hey, hey, welcome back to Hack the Entrepreneur. I’m so glad you decided to join me today. I’m your host Jon Nastor, but you can call me Jonny.

My guest today is a successful author and screenwriter and has written a book and produced a movie about his life called I Hope They Serve Beer in Hell.

In total, his books have sold over three million copies and have been translated into 30 different languages. My guest also founded and sold Tropaion Publishing, which pioneered the idea of author as publisher.

He later co-founded Book in a Box after a busy entrepreneur asked if she could write a book without actually writing it. The company’s mission is to help people turn their wisdom, knowledge, and ideas into professionally published books without having all the hassle that comes with it. Book in a Box has made an amazing $200,000 in its first two months, and it’s still going strong.

Now, let’s hack Tucker Max.

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Welcome back to another episode of Hack the Entrepreneur. Today, we have someone extra special. Tucker, thank you so much for joining me.

Tucker Max: So do you mean extra special like in a way that you have to wear a helmet or extra special in a way that I’m actually amazing? You can read that both ways. I can be both retarded and amazing, or either or.

Jonny Nastor: Well, I am wearing a helmet, but that’s just kind of how I roll. All right. Let’s do this. Tucker, as an entrepreneur, what is the one thing that you do that you feel has been the biggest contributor to your successes so far?

Making Decisions Based on Emotions

Tucker Max: There’s obviously a lot, but if I had to nail it down to one thing. I was very successful as a writer and as a creative artist, whatever you want to call it, for a while and then started getting into business and entrepreneurship, and I was nowhere near successful. In fact, I was a failure for my first couple of entrepreneurial attempts. Not catastrophic failures, but basically did all the iconic entrepreneurial startup mistakes you can make. I made all of them.

I really had to figure out what was going on. Why could I be so successful in an area that seems to be a lot harder to succeed in — creativity, writing, and arts — to be in the top 1 percent of writers but not be able to even start a functional business. What was wrong? It took me a while to realize what was going on, and I was the problem.

Basically, I was making all of my decisions based on my identity and what was emotionally right and then rationalizing them all after the fact instead of analytically thinking through the right way to do it and taking my identity out of the decision. You can be totally irrationally identity-based when you’re writing about yourself, and it can actually work — but you can’t do that making a business.

Ultimately, a business boils down to you need to make things that people want. Whereas as an artist, you can be successful making things that you want. Now, obviously, at some point, other people have to want them, too. But your decision process, you can fool yourself. You can think that, “Making things that I want is what other people want so that I’m the genius here.”

If you’re a successful artist, that’s actually how you think. It’s really weird. You don’t think people want what they want, and you’re providing it. You think, “People want what I make. I’m making it somehow. People just want it because it’s me” — which is, of course, the worst thing you can think as an entrepreneur because you’re going to totally fool yourself. You’re going to make things that you want without thinking about whether anyone else wants them, too.

That was the real lesson I had to learn when I moved from writing to entrepreneurship. Now, I’m explicitly making things for other people, and I have to really think about those people and not think about myself. Before, because what I wanted to write overlapped with what people wanted to read, I thought I was just some genius and everyone wanted me. That’s just not the way it works, you know?

Jonny Nastor: Yeah, and it makes sense. That’s an interesting way of looking at. It’s probably completely correct. So here’s you, Tucker, “I write these bestselling books, and I’m a genius. All these other people start businesses, too. Why don’t I? I’m a genius. I can do this.”

How Failure Forces You to Learn, Change, and Adapt

Tucker Max: Exactly. “People want what I do. So I can do anything, and it will work.” That’s the way an arrogant, egotistical mind that is full of hubris works. Here’s the thing. For years, everyone’s like, “Oh failure, failure’s the quickest way to succeed.” Then there came a reaction to that, all this failure porn, and people are like, “No, failure is terrible. You want to succeed. That’s the point.”

I think what the people who were all into the failure porn didn’t really understand how to communicate, for most people, failure is very critical to success, but the reason why is because all success teaches you how to do is do what you’ve done in the past. Failure forces you to learn, forces you to change and adapt, and forces you to find the right way.

My first attempt at writing worked spectacularly well — don’t get me wrong, I worked really hard to become a good writer. But I didn’t have 10 years of toiling away in darkness. Basically, the emails I wrote to my friends became a massive, genre-creating bestseller.

So it’s very easy to get tricked into thinking your sh*t just does not stink when you do that and thinking that you’re some magical genius who can produce things that work out of thin air. I didn’t really have to fail my way to success in a lot of ways. I succeeded, and the worst part is, I succeeded a lot of ways by accident. Don’t get me wrong, I had talent. I worked hard. My stories are funny, and millions of people bought these books.

At the same time, I could not have accurately told you why my stories were working when I was doing them. I was just doing it, and it worked. So it just taught me to do the same thing over and over, and I did. It worked for a while, but I didn’t actually understand what I was doing. Failure forces you to understand what you’re doing because what you’re doing isn’t working, so you’ve got to try new things until you find what does work. That usually forces you to learn a whole field.

Why You Need to Learn Lessons the Hard Way

Tucker Max: I don’t want to say I’m a good entrepreneur now, but I’m a very successful entrepreneur now because I failed so much at entrepreneurship at the beginning. It hurt my ego, dude. That was the thing. I had to learn that I wasn’t special. I wasn’t some magical genius, and people didn’t actually care about me. They cared about what I produced that mattered to them — whether it’s funny stories or a product or a business that provides a service that they want. I had to learn that lesson the hard way.

Now, because I learned that lesson, business is actually, I don’t want to say it’s easy, but it’s so much easier because now. I focus on what I’m actually doing. I’m not focusing on like, “Oh, I’m going to build a monument to my ego because I think I’m amazing.” Now I’m focused on, “How do we make something that people want?” That’s how businesses work. Sell people a product or a service that they want.

Jonny Nastor: Exactly. Okay, I don’t know if this is going to be a stretch for you, but to me, you putting out your first book, that is still entrepreneurial in the sense that you’re creating something out of nothing — creating something from yourself, making money from it, building a business around it, and avoiding having to go and actually work for somebody.

Is this something you’ve kind of always done, or was that sort of the beginning? Did you work for other people, and then like, “I can’t do this,” or else, “I need to make something bigger in this world”? What was it that caused you to have to do this?

The Positives of Being Fired

Tucker Max: You want to know the real true story is I got fired.

Jonny Nastor: Nice.

Tucker Max: I would love to tell you some magical Paul Bunyan origin story about how amazing I am, I sprung from the head of Zeus, and I knew all along. That’s all BS. I actually tell this story in my very first book. The first law firm I worked for, I got super drunk and basically made a huge spectacle at this big firm event. Then, one of the senior female partners propositioned me, and I turned her down and told everyone in the company that she did this.

They, of course, had to fire me because I was an unguided missile of debauchery, and they had to get me out of the company. I don’t even blame them. It was Fenwick & West, which is a famous tech law firm. They fired me. I was in law school at the time.

Then I wrote an email about it to my friends. Of course, my friends are a-holes, so they forwarded it to everyone. It spread all across every law firm in North America. This is 2000. This is back when email forwards were a thing, so of course, I couldn’t getting a job anywhere at a law firm. I would have to be a public defender or something awful like that, and I wasn’t about to do that.

So I went to work for my family. My dad has some restaurants in south Florida. The true story there is my dad fired me from the family business. There’s a lot of reasons why. Basically, I lost an internal power struggle between all the butt-kissing sycophants he had in his company. I wanted to actually do really cool stuff, and they wanted to protect their power.

I thought, “Well, my name’s on the door, and I’m right. Of course my dad’s going to back me” — not understanding anything about the way people work or office politics or dynamics. Then I made it really easy on the people who hated me because I would hook up with girls in the bathroom of the restaurant and stuff like that, which was obviously not smart. So my dad fired me from the family business. I was basically forced to carve my own path. I wish I could tell you that I had the courage to do it on my own. I did do it, but part of the reason I did it is because I had to.

Jonny Nastor: Nice. That’s fair enough. All right. You’re an awesome writer. You have figured out how to be a great entrepreneur. You are not that good maybe at working for people, but you’re good at getting drunk and just making an ass of yourself. That’s awesome.

In your business now, you’ve figured out what it takes to be an entrepreneur — how it’s not about you, it’s about what the customer needs. Can you tell us something in the day-to-day business that you are just absolutely terrible about?

Finding the Ying to Your Yang

Tucker Max: Oh man, that’s a long list. How long do we have? I’m actually writing a piece now about how to pick a good co-founder because I’ve messed up on that a couple of times. I’ve picked people that I’ve liked or people that fed my ego and not people who were really great at things that I’m not great at.

This time around, my co-founder Zach Obront, he’s not like my best friend. We’re good friends. We get along really well, but we’re not like drinking, butt buddies, taking showers together, or whatever. He doesn’t feed my ego at all, but he is fantastic at things that I’m terrible at.

I’m really good at high-level thinking, high-level strategy. I’m really good with building relationships with people. I’m really good at inspiring people. The company that I’m doing now, it’s basically book writing and publishing as a service. Sort of like ghostwriting, but way cheaper and way better. So I’m good at building that process and understanding all of that stuff.

I’m really bad at getting day-to-day minutia that is tedious done. He’s really good at that. You can give him a messy pile of nonsense, he’ll turn it into a checklist, and get it all done. I hate dealing with finance. He loves looking at the numbers every day. I don’t have to think about that. Every day, he’s like,
“Oh, blah, blah, blah.” I’m like, “Okay, that’s great, Zach. I don’t care. Just tell me what I need to know to sell more stuff.”

Jonny Nastor: Sounds like a good co-founders.

Tucker Max: Exactly. He does the stuff I hate. I do the stuff he’s not good at. It really is a fantastic balance.

Jonny Nastor: So do you feel like you can bring the money in, and he can take control of it once it’s there?

Tucker Max: Oh yeah. He’s pretty good at sales actually. I’m really good at getting us on people’s radar and getting them jacked up about working with us. Then I pass them to him, and he closes them and gets their money.

Jonny Nastor: Nice, wow.

Tucker Max: I’m not really good at asking for money. I’m not so good at closing. It feels creepy to me even though it’s not. These are people who think what we’re doing is amazing, and it’s a bargain, and blah, blah, blah. I’m just not good at that last mile. He’s fantastic at the last mile.

Jonny Nastor: So this is cool. Book in a Box, to me, looks like an amazing service. It looks brilliant. I want to know, with all the things you’ve done, all the opportunities that you’ve had from speaking, from writing, from all the publicity you’ve had, there’s probably a lot of offers, a lot of ideas that people put to you, that you could partner with, and do this, do this, do this, do this, do this. How do you decide that Book in a Box is something that, “This is a project that I need to act on, and I need to go all in on and see where it goes.”

Recognizing the Unicorn and Running with It

Tucker Max: That’s an excellent question. That’s literally what happened. We’re maybe eight months old now. I had like three different quasi-consulting company things I did. I was active angel investing. I’m in 50 companies. I had like two or three side projects. I was spread very thin, and Book in a Box came about by accident. Then, once I saw, I realized what I had.

Here’s the thing. Think about it like venture capitalist. A VC invests, they look at a thousand companies a year, and they invest in 200. They expect that, of those 200, 190 are going to either fail or return less than 2x, and that’s not enough to keep the fund alive. The fund as a whole has to return at least 10x for it to be considered a success.

They’re expecting most of them aren’t going to work, but the reason they do all that stuff is because, maybe in 200 investments, you might have one that returns 10,000x, two that return 1,000x, and three that return 100x. That’s all your money is from those five. In fact, if you actually look at the numbers, a lot of times, the top two investments will return more than all the rest combined.

A good venture capitalist would tell you, “We get into as many companies as we can because, once we’re in a unicorn, then we double, triple, quadruple, 10x down on that unicorn, and that’s where we make all of our money.” For me, I was looking for something that I could double down on. I could eliminate all my side projects, virtually all of them, and I can say, “This is an amazing opportunity that excites me and gets me up in the morning, so I need to focus on that.” The only way you can create outside success is by extreme, ridiculous focus, so I didn’t have anything like that.

Then Book in a Box came along. I’ll tell you why I picked Book in a Box. We had product market fit before we even knew we had a company. When people are giving you money for something that you’re not even officially selling, that’s when you know you’ve hit a crazy lucrative market. You’ve tapped into an unmet demand. The story was kind of funny.

This female entrepreneur, really smart, really cool, meets me, and she’s like, “Oh I hear you’re the publishing guy. I want a book, but I don’t have the time to do it. I don’t want to figure out the publishing industry because it’s so complicated and such nonsense. How can you give me a book without me having to do all of that?”

I looked at her and like, “Yeah, I want to be a success without doing any work, too. There’s no way to have a book without writing it and then publishing it.” I lectured her about hard work for a little while, and this woman has done way more than I have. She rolled her eyes at me, and she’s like, “Tucker, I’m an entrepreneur, and my job is to solve problems. What is your job?” I was like, “Oh, all right. All right. Okay, okay. Fine.”

Of course, I obsessed over this because she called me out, and she was right. I came up with this method to turn her ideas into a finished published book with her only having to spend about 12 hours on the phone. I didn’t think it was going to work, to be honest. I was like, “I can’t imagine this is going to work, but we’ll try it.” It ended up working amazingly.

We basically talked to her on the phone for about 10 hours and turned those conversations into like a perfect resuscitation of her ideas and a really fantastic book. That book turned into millions of dollars of business for her, and she was super excited.

It was funny. I did a podcast with Lewis Howes a few months after we finished with her thing, and Lewis was talking about how he was starting on a book. And Lewis is dyslexic, so he couldn’t write it. This is on the podcast interview. I told him what we were doing. I was like, “Hey, try this process. We’ll do it with you if you want, and Lewis is like, “That’s an awesome business idea.” Then he’s like, “What do you call it?” I was like, “I don’t know, Book in a Box.” I made it up.

I think I might have called it a name in the pre-interview when Lewis was asking what we were going to talk about. After the podcast was recorded — it was prerecorded, obviously, because it’s a podcast — his sound engineer called us up and wanted to buy this. I was like, “Zach, we need to put up a landing page because Lewis’ podcast comes out in two weeks, and we might sell some of this.

So the podcast comes out, and we get four clients who pay us $10,000-$15,000 a piece to do this. I was like, “Zach, this is a company.” Then I started talking about it to other people, and really smart people I know who were really skeptical about startup ideas and businesses, they weren’t just like, “This is a good idea,” they started signing up. People I know that never think any idea is good, who are investors, are like, “Dude, can you take me on as a client? I have this idea for a book, and I just don’t have the time to write it,” and I was like, “Yeah, okay.” So we sold six packages our first month.

Jonny Nastor: Wow.

Tucker Max: Then I really flushed the idea out of my head. I saw the end game. I saw the ways we can get there, and I was like, “This is a home run. This is my unicorn, not as an investor, but as an entrepreneur.” I shut down almost all my other things I was working on. I was an advisor of seven companies. I resigned from four of them as an advisor. I cut everything else out of my life except for my family and one hobby side project. Now, this is what I do. It’s going amazingly well, but that’s how I decided. I saw that we had not just product market fit, but we had tapped into something.

For 10 years, people have been asking me, “How do I get a book?” The implication, even if it’s unstated, is, “How do I get a book without having to write it?” I could have thought of this five or 10 years ago. I felt stupid actually. I really did. I felt stupid that I didn’t think of this earlier.

Then once we got that product market fit and once I realized that product market fit was hitting this massive, untapped demand, I’m like, “This is the definition of a great idea, and I’m the perfect person to run with it,” and Zach was the perfect co-founder. So here we are.

Jonny Nastor: You are the perfect person to run with it. As you say that, yeah, you should have thought of this because you’ve built up this authority and presence within being an author, getting published, and writing bestsellers. Everybody that comes up to you and meets you is probably like, “How do you do that?” And you’re like, “Well, I’ll show you a way. Go to this website.” It’s genius.

Tucker Max: Yeah, I know. It’s one of those things I’m really generally proud of it, but I also feel really stupid. Here’s a great example. I feel like I was so arrogant in my notions of what a writer had to be that I didn’t see this idea, not because the technology didn’t exist. We’re using all off-the-shelf technology, and our process is very simple to explain. It does require a little expertise to do it really well, but it’s simple to explain.

I could have done this off-the shelf technology at least five years ago, but I was so arrogant in my thought of, “Well, a writer has to be someone who does the work. Then I was like, “That’s so stupid. That can be a writer, but what if you just want a book of your ideas. What if you just want to turn your ideas into a professional, well-written book, but you don’t have the time to write it. How can you do that?”

Then I took out all the goofy cultural tropes about what a writer is and what writing is, and I realized the book is just a way to get an idea from one head to another. It’s just a medium for expression. If you can remove the friction from that medium, you can connect ideas between heads so much easier. That’s actually what books are supposed to do. It’s just a whole culture of people have romanticized writers as separate from the point of writing.

It took humility for me to understand that. The only way I’ve ever learned how to be humble is failure. Some people can be humble without failure. Those people are way better than me, and I wish I could be like that, man. I have to fail, and I have to see my arrogance crushed before me before I get humble.

Jonny Nastor: Nice. Beautifully, beautifully said. I like it. So, Tucker, I do want to thank you so much for joining me. We’ve mentioned your business now and all through the conversation, but can you specifically tell the listener where to go find out about you and this business we’re talking about?

Tucker Max: Yes. Our packages are 15 grand, so we’re not cheap. But if you have an idea for a book and you want to turn it into a book but you don’t have the time to write it, then just go to It explains the entire process.

We’re actually going to come out with a book that explains the process, so if you don’t have the money, we’ll tell you exactly what to do. You can just do all the work yourself. That will be great for people who have a lot of time but no money. That book’s coming out soon. So either way, if this sounds appealing to you, just go to All the information is there.

Jonny Nastor: Excellent. I will link to that in the show notes for everyone, so it’s very, very easy to find. Tucker, thanks so much for joining me and just keep doing what you’re doing because it’s pretty awesome to watch.

Tucker Max: Thank you, man. Thank you for having me.

Jonny Nastor: Well, that was a lot of fun. I thank you so much, Tucker, for coming on the show and for sharing so much. You just are spewing knowledge out of you. It was just a really, really fun conversation, and I hope you out there listening enjoyed it as much as I enjoyed participating in it. It was a lot of fun.

Tucker said a lot. Literally, I’d ask a question, he would just go off. It was amazing. He knows how to talk. He’s a writer who has a lot of ideas in his head and can really get them out to you, so it’s a really cool conversation. But then going back through it, trying to find something that really resonated with me, there was three things. Then I got it down to two, and then there was one.

There was that one thing that Tucker said, and it just stuck with me. Did you get it? Did you hear it? Let’s do it. Let’s find the hack.

Tucker Max: For most people, failure is very critical to success, but the reason why is because all success teaches you how to do is do what you’ve done in the past. Failure forces you to learn, forces you to change and adapt, and forces you to find the right way.

Jonny Nastor: And that’s the hack.

Yes, Tucker. Exactly. In the hack, we don’t get into failure as much anymore as we once did. As Tucker said, it’s been discussed over and over, but this is a brilliant way of looking at it. This is so true. You know it’s been flagged to death, that failure is kind of a key to success, but not for the reasons you think.

Tucker says success, the only thing it does is get you to do the same thing. Why would you change it if it’s successful, right? Exactly. You wouldn’t. You would just keep doing the same thing and the same thing. It doesn’t push you to learn more. It doesn’t push you to grow. It doesn’t push you to do even what you’re doing successfully better because, if it isn’t broke, don’t fix it, right? It’s the adage that we use, and that’s how we talk about.

So I love that he says, “The failure causes you.” That’s when we literally sit down, we stare at our computer, we’re like, “Okay, what went totally wrong? What went wrong here, and what can I do differently to change this so that I don’t continue failing?” And that’s awesome. It’s almost like we need to push ourselves to failure so that we learn, so that we grow, so that we figure things out, and so that we do better in our businesses and in our lives in general. I really, really like that.

Success keeps you doing the same thing. Failure forces you to grow and forces you to learn. It really gets no simpler than that. That’s really just a great way. Don’t let it defeat you. Don’t let it knock you down. Don’t let it destroy your ideas, your goals, and your ambitions of what you can do. Literally, just take it as, “Oh, this will force me to learn.” But then, also, when you get to the successes, you got to push harder to push yourself from success to failure so that you do then learn and grow even further. Tucker, thank you. That was awesome.

All right. That wraps up another episode, and it’s been a lot of fun. As always, I thank you so much for stopping by. Reviews, rating, I would absolutely love them. iTunes, so if you are on an Apple device. You can leave me a rating and a review there, and it will help so much. Put your Twitter name in there, @YourName if you can. I’ll go on Twitter and thank you personally. I would love to do that.

If you are on any other kind of device, go to Stitcher. You can go, and it will take you right there to my page. You can leave me a rating and a review there. That will absolutely help the show so much.

It’s been fun. I hope you know how much it means to me that we get to hang out together like this. I hope you enjoyed Tucker Max as much as I did.

Please, until next time, keep hacking the entrepreneur.