Make striving cool again
Striving, startup failure rates, and a celebratory NFT (Stew's Letter #100)
Howdy, happy Sunday.
Thank you to everybody who read my annual review. It ended up being my most-read piece of all time. Thank you all for the support and input.
This is the 100th Stew’s Letter. To celebrate, I’m gonna mint an NFT and give it to somebody.
Reply to this email with your ETH address and I’ll let you know if you’ve been chosen.
To all the new readers, welcome. Thanks for taking a risk on this.
Haters, absolutely body slam that “unsubscribe” button.
Let’s get to it!
Make striving cool again
I will never forget the condescending, confused reaction one my frat bros in college gave me when I showed him the iPhone app I had just spent months building.
It was my junior year (or “third year” as we pretentiously said at UVA) and I had started to teach myself programming. I knew I wanted to eventually start a tech company, but unfortunately I hadn’t known that when I first started school and so I was already halfway through an economics and religious studies double major.
To course-correct, I began spending hours each day sitting in on computer science courses and watching programming tutorials on YouTube. After many months of self-directed learning and building, I had finally done it: I had built my first iPhone app.
The app was admittedly stupid; it let people buy “binaural beats” that induced specific states of mind. It resembled what I suspect pharmacies in the metaverse hood might look like. But, by God, I had built the thing and it was functional.
I enthusiastically showed the app to a few friends, most of whom were indifferent but supportive. But one particular friend was clearly puzzled by why I’d spend my free time toiling away at what appeared to be a trivial skill and certainly a trivial project. He laughed out loud when I showed him the app and just very clearly didn’t understand why I had built it.
His reaction helped made realize what I already suspected: we occupied two different realities. He would likely fall into a well-paid job after graduation, and I would not. He was on “the path,” and I was scrambling to figure out how the game worked. His family was rich, mine wasn’t.
It wasn’t obvious to him why I’d spend so much of the supposed best years of my life to gain as many skills as humanly possible.
In retrospect, though, I think there was something else going on. I think my try-hard energy may have triggered something else: disdain. As Elizabeth Spiers recently wrote in The New York Times:
In the United States, we love a good Horatio Alger story, in which a person who starts out with very little applies hard work and ambition and becomes a success — but only in the abstract. In real life, American elites abhor a try-hard as much as any European aristocrat might.
Elites are often socialized into affecting “ease” and eschewing displays of effort.
That reflected my experience in college, where most of my better-off classmates seemed to get by with relative ease. Plenty of them worked hard, but I felt I was working just as hard, if not more, and barely treading water. There seemed to be a myriad of unspoken rules I had to work just a little bit harder than them to learn.
Luckily for me, though, the work ethic and skills I developed in college served me well: the tech startup I co-founded shortly after shipping that first app ended up finding some relative success. That catapulted me into a career I would have expected to take much longer to build.
Today, I’ve found myself in a different dilemma. A decent number of my friends have fairly “normal” jobs and seem somewhat confused by the amount of time I spend working. I think it’s because, in part, they view “work” as a single, catch-all category.
But I’m lucky enough to be the co-founder of most of the projects I work on full-time, which is fundamentally different (not better or worse!) than a job. Elizabeth Spiers again:
There is a difference between pointlessly toiling away for a company and working hard because you enjoy it, or you care about what you do, or most crucially, you are trying to economically advance. There’s nothing wrong with wanting to do better than your parents did.
Finally, the people who do partially get this assume that working super hard is unhealthy. They’re often right in the short-term, but I’ve found there’s often an unspoken assumption that those who work unusually hard have been infected by the capitalist mind virus. They’re another casualty of “hustle culture.”
It’s worth considering, but I often find that I just see things differently.
I’m busting ass to build an exciting future for myself and future family. Entropy ensures that won’t happen; effort increases the likelihood that it will. It’s tough and I’ll burn out from time-to-time, but I believe a much better future is possible given enough effort, skill, and luck.
In other words, there’s a difference between trivial, mind-numbing work and future-altering, effortful striving. May we never lose our understanding of and, dare I say, appreciation for the latter.
Now, time to get back to work ;)
🌶 Medium-spicy take: Startup failure rates are not 90%
I wrote a short & sweet thread on why I think startup failure rates are much lower than 90%:
💭 Thought of the week
Language can never capture the full human experience, but that's what makes writing so much fun.
It's a game: how much of the human experience can I capture with words?
The delight is in surprising yourself and realizing it's more than you think.
🔥 Fire TikToks
This one kicked me directly in the feelies. Wholesome AF.
In other news, I will pledge my loyalty to whichever airline hires this man as a pilot.
Until next time,
I like the idea of "striving." I read Daymond John's "Rise and Grind" a few years ago. My fiancée met him during a venture capital program and gave me the book.
John's path is certainly impressive and I have nothing but admiration of his accomplishments and drive, but man, do I dislike the term "Grind."
To me, people are not made to "grind." There's nothing inspirational about grinding out wins in games, although coffee grinds are important.
Thanks for brining a different perspective to working to achieve. Cheers!
Loved this one, Stew. I’m a striver to my bones but I wouldn’t have it any other way.