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| ISSUE №167 · ENTREPRENEURSHIP |
“Too Dumb To Know When To Quit”
It's the start of the holiday weekend here in the United States, where we blow shit up, celebrate ourselves relentlessly, regardless of our worthiness, and look around with wonder at what we have created.
There is a great myth of American exceptionalism that feels really quite true in many respects. We have the platonic ideal of the rugged individualist - The Marlboro Man - or the hero who lives by a code and does the right thing at great risk to life and limb, like many of John Wayne's characters. Those were the icons that shaped the ideal of an American for the first 75 years of the 20th century.
Post-Vietnam, after the horrors of war showed up on our television sets and in our living rooms for the first time, we switched from rugged individualists fending for themselves to rugged capitalists creating empires. We celebrated fictional makers of wealth like Gordon Gekko and modern-day entrepreneurial wunderkinds like Steve Jobs, Bill Gates, and later Mark Zuckerberg, Sam Altman, and others.
In so many respects, the idea of a hero didn't change. It was always a self-contained man (always a man, ugh…) Who triumphed over insurmountable odds in the form of the American West, or a train-robbing gang, or the stifling of creativity by corporate mono-speak.
A few years ago, someone asked me what my definition of an entrepreneur was, and I gave this definition:
AN ENTREPRENEUR IS SOMEONE WHO IS TOO DUMB TO KNOW WHEN TO QUIT.
Are Entrepreneurs Heros?
To tell you the truth, I have no idea - if you look at many of the most obviously successful entrepreneurs today, I would say that they aren't heroic because they've focused on the accumulation of wealth rather than the implementation of wealth. That could just be my East Coast liberal thinking coloring my reflection. But there are elements to being an entrepreneur that seem heroic.
The act of entrepreneurship is really a battle against entropy. When you start a company, you are trying to enforce your idea of how things work into a system full of variables that you do not fully understand. The delusion of that madness is stunning.
So let's start with the conceit that likely every single one of you reading this email is totally nuts. In my book, that is generally a net positive. Each of you that are entrepreneurs in the traditional sense, meaning that you have started your own company and are trying to lead something, or those of you who are simply entrepreneurial in the employ of someone else, you are trying to accomplish things in a way that is different than expected.
There is enormous power in your unwavering delusion that you can make it work. That delusion, I would argue, is the essence or truly the actuality, behind the self-aggrandizing myth of American exceptionalism. Throughout the last 250 years, the idea that when you are up against it, facing insurmountable odds, all you need is your sense of what is right and what is possible to make success inevitable.
Americans aren't exceptional. The current version of America isn't exceptional. but that cultural truth behind the myth of American exceptionalism is truly exceptional.
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My Time As An Uber Driver
There was a time when my oldest son wanted a Playstation 5, a new TV, and other sundry luxuries. I told him that wasn't in the budget, and that he needed to earn some of that money. He wallowed in his angst about not getting what he wanted for a while, and he kept on asking me how he could make some money. Every idea that I gave him, he dismissed as not worth it or impossible to make the amount of money that he was seeking.
When my son was a little guy, it was so easy to change his mindset by making something a competition. So even though he was in his late teens, I pulled out that tactic and said, "Let's each work 100 hours, and whoever makes the least amount of money has to buy the PlayStation."
He started doing odd jobs in the neighborhood and other places, and because my daily schedule is really busy, I needed something that was completely flexible, so I decided to drive for Uber. While I was driving Uber, I was exposed to an extraordinary array of people.
Therethere was a schizophrenic man who wondered out loud what would happen if he stabbed me in the back of the head. There was a young woman who asked for help on how to choose between two men, but there two that stick in my mind today as we are talking about entrepreneurship and America:
The Georgian Trade Envoy: I picked up a woman from a Boston hotel, and she was dressed in an incredible evening gown. She was in her late 50s or early 60s and had a life of hard Eastern European times etched into her face.
I complimented her on her dress and asked what sort of event she had been to. In her thick accent, she told me she was from Georgia, not the state, but the country. I laughed and she went on to tell me that she was an economics professor at a mid-level university in Georgia, and she was here as part of a U.S.-Georgian trade mission.
After a little chit chat and as we got closer to her hotel (which was not quite as fancy as the one she has left), she took in a deep breath and said, "I love your country."
This was in Trump's first term, and I was feeling not very great about our country. I asked her to explain why, and she said, "This is a place that you can breathe deeply, say anything that you wish, and accomplish anything that you can put your mind to."
I asked if the same wasn't true in her country - after all, she was a professor, she traveled internationally representing her country, and was working for the economic benefits of her fellow citizens. She said, "No, I am a professor because my deceased husband was a trade minister. I have freedom to talk frankly about what our country needs, as long as I do so in a way that no other Georgian can hear. But I could not tell my students about the inefficiencies, corruption and the oppression of our government.”
I said that we have inefficiencies and corruption and oppression in our government as well. she laughed and she said, "I know. I read about that in this morning's New York Times. I can only say it here when I am asking my ex-countrymen to invest their American success back into their homeland."The Jamaican Raconteur: Another night, I picked up a Jamaican man in his thirties. He was smiling and laughing and asked if he could have the aux. in our forty-five minutes of him talking about Bob Marley and Peter Tosh, he told me about how beautiful Boston is. As a lifelong Bostonian. I agree with him, but with our history of racism and segregation, it's hard to imagine that the most shameful part of a city I love has healed itself to the point where this man, who is so clearly outside of what is expected, would see beauty.
I told him about the subtle and not-so-subtle racism that I grew up with - shamefully, when I was growing up, my father was involved in local town politics, and he publicly opposed the development of subsidized housing in our town. Publicly, he said that it would be a burden on the town's infrastructure, but privately he didn’t want “those people” in his children's schools. and I told him about my two brown sons, on whom my well-educated, liberal, woke neighbors have called the police because they were concerned about “those kids”.
He laughed and said that “The beauty is that you know it’s not OK! I drag my Jamaican ass all over this town, singing songs, making art, and trying to make friends with the people that do not want to be my friend. And every day I make a new friend - and today, because you drove me, I have now made two friends.”
BTW, after 100 hours, I bought the Playstation.
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What Do Those Stories Have To With Entrepreneurship?
My thinking really started with the story of my son, whom I used a parental psychological reversal trick to get him to believe that he could accomplish something. But I suspect if I had just said no long enough, he would have gotten frustrated enough to take action on his own.
These two people showed me that my concept of our country and our culture was wrong. Now, in Trump’s second term, I am even less thrilled about the direction our country is headed in, and I have real concerns about the impact that this detour away from representative democracy will have.
But my Georgian friend reminds me to breathe deep and accomplish something because there is accountability. Here we don't have to hide our flaws from ourselves. We can focus on them, call them out, and change them.
My Jamaican friend tells me that action creates change. That singing and making art and trying to make friends with people who don't know that they yet want to be your friend creates enormous change both for the befriender and the befriendee.
So I might be dumb for saying this, but I believe in the capacity for entrepreneurship to make change. I believe in the capacity of the delusion that you can order the universe in the way that you see best, which can create opportunity for everyone that comes into contact with you. I believe that if my Georgian friend and my Jamaican friend could speak to those entrepreneurs who have focused on accumulation rather than implementation of their wealth, our ability to create an exceptional America is well within our grasp.
I’m just too dumb to know when to quit.
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