Tyler Willis

Supported by Greenhaven Road Capital, finding value off the beaten path.

Jerry Neumann again chatted with Patrick O’Shaughnessy on Invest Like the Best. Neuman is kind and curious and we’ve looked at some of his ideas already:

He also turned us on to Rob Fitzpatrick, author of The Mom Test. Recently Neumann invested in Unsupervised and he said, “One founder is one of the few people in the commercial world who understands this (machine learning) technique and the other founder has worked at startups before and is an awesome outside facing person.”

There are two parts to any business; doing then telling. If neither is done well, startups won’t succeed. Josh Wolfe told O’Shaughnessy, “There are amazing credible people. And there are amazing salesman. And sometimes those two people are one. When they are you have an amazing entrepreneur. But often times they’re not.” So you get two. You get someone like Tyler Willis, that “outside facing” person.

“I was not a good traditional student,” Willis said. We hear this a lot and it’s helpful to think of school as one type of education. Another type is to do. Tom Goodwin said, “Leaving school and starting out, or leaving school and traveling the world and writing, or leaving school and creating a documentary are actually pretty remarkable ways to learn.”

However, Willis said, “If you’re going to drop out you need to work harder than you would have in school.” That’s kind of what he did and does. “So I tried to do things. I became a fairly voracious reader. I read a lot of nonfiction to understand different people’s opinions about different things. I read history, biographies, a lot of varied topics.”

But Willis also gives a reason to stay in school. “If you don’t know which way to go, the default should be to stay in school.” Defaults, base rates, and distributions are all mathematical fences to corral our psychological guesses. Michael Mauboussin is fond of citing Daniel Kahneman’s work, and no wonder. Kahneman observed – academically – our self-aggrandizement.

Base rates are for other people. Right?

Ramit Sethi said that for the second edition (10th anniversary) of his book, I Will Teach You to be Rich, he was coaching a group of readers through the content. He asked them, What would you do with $10,000? They’d be canny of course. Ramit said they were full of baloney. “According to these answers, we have a bunch of Mother Theresa’s in the group. They will pay down debt, give to charity, do this and that.”

These were people who had enrolled to be coached through a book on better financial decisions. But it’s not just them. It’s all of us. Even Kahneman fell for it, thinking he could write Thinking Fast and Slow in less time than the base rate might suggest.

Willis is familiar with the work of Ramit who champions good designs. Dan Lockton has done lots of good work on designs too and noted that designs only do so much. Lockton said, “When people feel they are being influenced in a way that doesn’t match their understanding of the situation they will rebel.”


In 2014 Willis spoke about growth. First, “You have to create a product of value before you can grow your product.” Then, “The number one thing is that speed beats everything else. The faster that you iterate, the more you win…You could be one standard deviation better than the next guy but if he has 20% more cycles he’s going to beat you.”

Jerry Murrell messed up a lot of businesses before starting Five Guys. Anson Dorrance told his soccer players that goals only happen every seven shots or so. Scott Adams compares life to a slot machine that costs little and has “rare and uncertain payoffs.”

Mauboussin titled one of his books, The Success Equation. The formula is some luck mixed with some skill. Mauboussin’s goal was to look back to peek forward at expected values. His advice might be, ‘do more skill dependent things.’ But for some people it’s even simpler, ‘do more.’ Think of marketing as an MVP process too said, Willis.


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2 thoughts on “Tyler Willis”

  1. […] Tyler Willis saw this too, noting that he became a wiser person when, “I became a fairly voracious reader. I read a lot of nonfiction to understand different people’s opinions about different things. I read history, biographies, a lot of varied topics.” […]


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