The Transcript

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