In one of my favorite talks, “Runnin’ Down A Dream,” the venture capitalist Bill Gurley explains that while studying the career trajectories of three of his heroes—the restauranteur Danny Meyer, the coach Bobby Knight, and the musician Bob Dylan—he noticed a pattern: They studied the career trajectories of the icons in their respective industries. They studied how others successfully got their foot in the door then climbed to the top of their profession. And then, they took similar steps towards doing the same. “Greatness isn’t random,” as Gurley puts it. Instead, it’s usually a predictable step along a studied path of strategically modified emulation and, of course, determination. That’s the theme of this SIX at 6.
Go For The Moon, Miss, And Discover A New Planet
Before John Mayer joined Dead & Company, he held a false assumption about The Grateful Dead. “I always thought the unique Grateful Dead sound was an intentional invention,” Mayer said. But as Mayer spent more and more time with the original Grateful Dead members, he learned, the unique Grateful Dead was a product of modified emulation. “The sound of the Grateful Dead,” Mayer explains, “is a misinterpretation in the attempt to sound exactly like their musical heroes. Their aspiration has always been to be on the same level as every artist they’ve ever looked up to.” Artists like Miles Davis, Wilson Pickett, Bill Evans, and The Texas Playboys. “It’s like, they went for the moon, missed, and discovered a new planet,” Mayer said.
The Harvey Keitel Part
As he was struggling to break into Hollywood, Matt Damon read about how Quentin Tarantino did it: Essentially, he got a big-name actor (Harvey Keitel) to want to star in Tarantino’s first movie (Reservoir Dogs) then leveraged that to get the movie funded. “And so,” Damon said, “We wrote ‘Good Will Hunting’ and that part that Robin [Williams] eventually took—we called it ‘the Harvey Keitel part.’” “Ben [Affleck] and I wrote the movie specifically because we wanted the parts as actors…But we knew [we needed] a big-name actor who could get us some money because Ben and I were worth nothing. And so we wrote ‘the Harvey Keitel part’ really open-ended. So we could adjust it: if Morgan Freeman or Denzel Washington wanted to come in and play it—we could make that character from Roxbury [a neighborhood in Boston], and we could explore the historic racial tension in Boston. If Meryl Streep took the part—instead of a father-son relationship, we could make it a mother-son relationship. So we really left it open-ended because we wanted to cast as wide a net as possible because we were just trying to get the movie made.” “And then once we got Robin to sign up to do it, that’s really what got us a green light to make it…He changed our lives.”
I Studied Him and I Studied Him and I Studied Him
When he was 14 years old, Wayne Gretzky moved from a small town in Canada to the mecca of hockey, Toronto. He was undersized and after his first practice, his coach pulled him aside. “When you go home tonight,” the coach told Gretzky, “the Leafs are playing the Philadelphia Flyers—watch Bobby Clarke play.” Clarke was an undersized player on the Flyers who went on to be inducted into the NHL Hall of Fame. “And I studied him and I studied him and I studied him,” Gretzky said. “I would take out a piece of paper and draw a rink and then without looking at the paper, I’d watch the hockey game on TV, and I would take my pen and I’d follow the puck.” When Clarke got off the ice, Gretzky would look down at the paper and look for patterns. He observed that Clarke “played the game out of the corners, not so much in front of the net.” Gretzky emulated, with some modifications, Clarke’s style, and on the ice himself, “I started playing out of the corner and from behind the net…And I started using the net as a decoy. Consequently, I wasn’t standing in front of the net, getting knocked over, and being on my keister the whole time.” Consequently, Gretzky went on to set 61 NHL records—many of which he still holds—including most career regular season goals (894), assists (1,963), and points (2,857).
Creativity Is A Modified Emulation
In 1985, Nike held a 24-hour shoe design contest. Nike was struggling. Their stock dropped 50%. They had to lay off people. Adidas, Converse, and Reebok were all selling more shoes. So in a panicked attempt to find creative talent, Nike held a shoe design contest. The winner was a corporate architect named Tinker Hatfield. “Two days after the competition,” he said, “I wasn’t even asked—I was told that I was now a footwear designer for Nike.” As he got to work on his first official shoe design, he thought about a building he had studied in architecture school: The Centre Pompidou in Paris. The Centre Pompidou is an inside-out building, meaning that the structural, mechanical, and circulation systems are all exposed. “That building,” Tinker said, “was describing what it was to the people of Paris. And I thought, ‘Well why not do that with a shoe? Let’s cut a hole in the side and show what’s in the shoe.’” So Tinker designed an inside-out shoe: The Air Max 1. The Air Max 1 was a massive success, and it steered Nike’s design direction from then on. “To this day,” Tinker says, “Phil Knight says I saved Nike.” Had he not studied that building in Paris, Tinker says, he couldn’t have created the Air Max. Creativity, he says, is a function of the “library in your head.” “When you sit down to create something…what you create is a culmination of everything you’ve seen and done previous to that point.” What you create is a modified emulation of everything you’ve seen and done previous to that point.
Focus, Above Else, On Acquiring Knowledge and Skills
At one point in a car ride with Robert Greene on December 11, 2021, he asked me about working for Ryan Holiday. I love it, I said, but I also battle the nagging thought that my friends are on more traditional career paths making more money. “Don’t worry about money,” Robert told me. “At this point in your life, above all else, focus on acquiring knowledge and skills. Knowledge and skills are like gold—a currency you will transform into something more valuable than you can imagine.”
So I began to focus, above all else, on acquiring knowledge and skills. I adopted, with some modifications, Robert and Ryan’s reading and note-taking system. I took all that I’d been learning as Ryan’s writing assistant and, with some modifications, emulated it in my own content. I took what I’d learned in observing him grow his newsletters and social media accounts to grow my own.
And almost exactly 19 months after that car ride with Robert, on July 10, 2023, I received an email from a publisher and an editor at Penguin Random House. We read your newsletter, they said, have you thought about writing a book? Of course. I sent them a 4-page document roughly outlining an idea for a book I’d been kicking around. After they responded with excitement about the idea, I fleshed out a fuller 60-page proposal. And, two weeks ago, almost exactly 23 months after that car ride with Robert, I’m excited to announce it here** first: I sold my first book, The Work Is The Win (for publication in 2025), to Penguin Random House’s imprint Portfolio.
**I’ve been going back and forth about saying anything publicly at this stage of the process. Initially, I decided to wait until the book is closer to publication. But then, earlier this week, I was working on a chapter related to Category 2 motivation and realized I wanted to express my appreciation for the people who are in that category for me. So thank you for reading this newsletter, for supporting my work, and for helping me home in on some of the ideas going into the book. OK, back to work on The Work is the Win!