7 things I learned about startups from Duke Fightmaster

Odds are, you’ve never heard of Duke Fightmaster. And I know what you’re thinking: “There’s no one named Duke Fightmaster. No one normal anyway.” Well, there is a Duke Fightmaster (his real name), and no, he’s not normal. But his story is fascinating and offers some great lessons on tackling a huge challenge, dealing with the risks, and knowing when to call it quits. Basically the same things any entrepreneur struggles with.

I learned about Duke Fightmaster on a recent episode of This American Life that told the story of his quest to take Conan O’brien’s “Late Night” spot. Duke apparently had no broadcasting or comedy experience, but about three years ago, he was fed up with his job as a debt counselor and decided (on a whim, apparently) to be the next Conan O’brien and have his own national TV talk show.

Ok, goal defined. What now?

Go out and start your own show, of course. So Duke Fightmaster immediately went out and gathered a few friends to be his guests and audience members and started filming this thing in his bedroom. The first episode was…ahem…amateurish, and a little hard for me to watch. He put it on Youtube and got essentially zero views.

But Duke was undeterred. Despite having two kids and a mortgage, he quit his job after the first episode and started working on the show full-time. So what if no one was watching? He just kept going, and every show got a little better and his audience got a little bigger until after twenty-something shows, he had 30 people crammed into his bedroom and had racked up hundreds of thousands of views on Youtube.

Duke decides to go for it and starts renting space at a local Veteran’s hall and enlisting the help of more and more people. A local reporter gets wind of it and he gets news coverage. He starts booking better guests like good local comedians. Things are looking up.

But there’s already a warning sign: moving the show out of the bedroom now requires a lot more work for setup and teardown, the volunteers helping with the show are flaky, and Duke is no longer having fun. But he already quit his job and he has his grand vision, so he presses on.

As I was listening to this story, I felt like it could have gone either way at this point, though I knew that the fact I’d never heard of Duke Fightmaster before this episode probably wasn’t a good sign. And sure enough; it’s all downhill from here.

I’ll spare you the gory details, but Duke spends almost three years shooting more than a hundred shows, but never making any real money from it. His family loses their home to foreclosure, their vehicles to repossession, and their credit to bankruptcy. In the end, all the other volunteers bail and Duke is back to essentially doing the show alone, like he started. Finally, after three years and on the verge of a nervous breakdown and divorce, Duke hangs it up and gets a job.

Depressing, right? Maybe, but maybe not.

The first half of this story bears incredible resemblance to the stories that many, many successful entrepreneurs tell about their early struggles. Struggling and scraping to build their fledgling enterprises while narrowly dodging bankruptcy, divorce, and nervous breakdowns. In fact, one of the things Duke mentions as a contributing factor to his blind determination to keep going for so long is that he’d heard so many other entrepreneurs say they had long stretches where it seemed hopeless, but they just put their heads down and kept on trudging. So that’s what Duke did, but his big payoff never came.

1. Don’t be afraid of humble beginnings

I admire this guy so much for being willing to create something laughably bad and put it out there for the world to see. It’s easy to look at that first episode and assume the show will never go anywhere. But look at the first version of Google, or Facebook, or Apple. Greatness rarely starts out great, and people laughing at you shouldn’t be a deterrent.

2. Dream big

I love that this guy didn’t dream about having his own local talk show on a public access station. He went right to the top and wasn’t afraid to dream the biggest dream he could think of. Crazy? Naive? Delusional? Absolutely. Most successful entrepreneurs are all three, at least to some extent.

3. Know your limits when you start

The hard part of any venture is knowing when you’re just spinning your wheels and need to try something else. In the thick of it, it’s hard to see the forest for the trees, so it might have been helpful to Duke and others like him to have a sense of what he was willing to sacrifice, or what benchmarks he needed to hit to really feel that this venture had a future. This is especially true when you have a family, because you can only take as much risk as your family can take, and that might be less.

4. Be careful when you lose the sense of fun

A huge warning sign for me was when Duke said that the show was no longer fun for him. It won’t always be fun, but especially in the early days, at least some of it should be fun. Gary Vaynerchuk argues in Crush It! that you should focus on things you’re passionate about as a way of controlling risk; if it never goes anywhere, it doesn’t matter because you were having fun regardless.

5. Manage your downside

The other big warning sign to me was jumping all-in so early, with basically no validation. It sounds brave but I’m really skeptical that it was necessary. The show was filmed weekly, so it seems very likely he could have held down a job for the first year or so until the show was making at least some money. Ditto for moving the show out of his bedroom (free space) and into the Veteran’s hall (paid space). If you’re starting a business that you absolutely have to quit your job for, this might be a good case for raising money. If you can’t raise money because it’s too deemed risky, maybe it’s too risky for you, too.

6. Figure out why whatever success you have is working, and focus on that

I wonder if the whole “bedroom” aspect of the show could have ended up driving it to be a huge internet phenomenon. It’s quirky and fun, but once you “grow up” and try to be like the big boys, you lose some of what made you special. Ze Frank wouldn’t have been a big hit if he had tried to imitate Jay Leno; he had his own style and his audience loved it. Why change?

7. The road less traveled is often risky, and that risk is very real

At the end of the day, though, the biggest lesson that I took is that this is what risk actually looks like most of the time. Thanks to survivorship bias, we hear so much from successful entrepreneurs about their early struggles that it’s easy to confuse risk with difficulty. Taking risks means that sometimes you will fail. Badly. Painfully. With very real costs. And it might look like Duke Fightmaster’s failure, or even worse. Before you start down a risky road, remember that it’s not as easy as just pushing through. You might just fail, no matter how hard or long you struggle, and there won’t be any talk shows or SXSW panels waiting to hear you talk about it on the other side.

And sometimes taking that risk is really the only way, but remember what you might be in for.