Jessie Itzler

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

Entrepreneurs are great to study because they’ve done the thing rather than talk about the thing. Sure it’s an N of 1  but there are still things to be learned. Tyler Cowen put it this way:

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Can we extend this to business advice? For the most part. Though everyone liked Shoe Dog. Can we do this for Itzler? Let’s find out.

Itzler’s interview on The Investor’s Podcast focused on Marquis Jet. Itzler had no experience with planes but he took a ride in a private jet and said it was like a Wizard of Oz moment when everything turns from black and white to color.

These see-it-to-believe-it moments are the seeds of growth. Judd Apatow and Joe Rogan saw comedians. Alton Brown went to Tuscany. Ezra Klein read a blog. Richard Thaler read Value Theory.


But interestingness needs gumption to lead to action. Don’t worry that you don’t know it all, that’ll help. “Not knowing what you don’t know,” said Itzler, “is a gift.”

If you knew how hard this was going to be, you wouldn’t do it.

Okay, notice things and just start. After that, you have to hire for your weaknesses. Itzler knew zilch about aviation so he hired people who did. At this point you’ll start to hear doubts, that’s okay too. Good ideas are different ideas and different ideas are the big ones.

Itzler said, “when my wife started Spanx if she would have asked her parents or her close friends about footless pantyhose they would have been like, ‘if it’s such a good idea, Sara, why haven’t the big guys done it yet?’ and that might have scared her off.”

Leigh Drogen said “Union Square Ventures finds that when they go into a partner meeting with an idea they want to see a barbell of, ‘I think that’s an awesome idea’ and ‘you’re freaking crazy, why would we ever do that?’ Their worst investments are the ones where everybody thinks, ‘yeah that makes total sense.'”

Jason Calacanis said about VC investments “If it’s clear that it’s going to work you should not invest.”

Andy Rachleff said about the Howard Marks Matrix (below), “I also believe this framework can be applied to entrepreneurship….To be non-consensus and right you have to have tremendous knowledge of your domain…When we started the idea of people trusting their money to be managed exclusively by software was a radical idea.”


If you have an interesting idea then it’s time to get the business growing. For Modern Monopolies this is the chicken and egg problem. It’s when founders do things that don’t scale. Itzler did this too, filling every plane seat with people. “We out-cared everybody and that created word-of-mouth.” That and good PR which “is so inexpensive compared to advertising.”

As the company grew Itzler focused on getting the product right. He followed Scott Galloway’s advice: “People come to me and I tell them, ‘build a better mousetrap and the brand will take care of itself.'”

Itzler also suggests taking time to think and said “I’m sure Bill Gates takes time to think.” Well not only that, but he spends a whole week doing it.

I learned from that video that part of the goal of Think Week (for Gates) is to let good ideas percolate up.

“We’ve institutionalized it as a grassroots process. This is a way that somebody just a year or two into the company – and has ideas that may or may not relate to the group they’re in – can write something up.”

Good organizations have decision makers interact with customers. Think Week Papers may be a channel where the front line staff can communicate what they see with the C-suite. Talking with his customers helped Itzler sell to Berkshire, that’s good business.


Thanks for reading, I’m mikedariano.

See everything I’m learning here:

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