Never Take That Shot Again
I scrubbed the list on purpose. Here's what Stretch Four is now.
Conceptually, I was supposed to be a professional basketball player. My career hit a snag on the first day of practice in college.
The coach — who had just spent nine months recruiting me to my alma mater James Madison University — yelled, “Never take THAT shot again in this gym in your life.” I can’t even remember if it went in. It didn’t matter. It was a corner three off a kickout, and I was wide open. First practice. It felt like a good shot. In 2026 it would be an afterthought. In 2006 it was a crime.
I was a freshman big man, and my job was to not know what I was doing, and it was definitely not to shoot threes with that type of confidence. We went 7–23 that year (4–14 in conference). I averaged 0.7 points, 0.3 rebounds, and 0.1 assists per game and played sparingly in 18 of our 30 games. The coach who yelled at me coached one more year, then never coached another minute of college basketball again.
That’s how the “stretch four” thing started. My second coach, two seasons later, told me he wanted me to stick around — as long as I never shot a shot inside the three-point line again. I listened and played more in my last two years to the point where my career ended shooting three to five three pointers again and making close to 40%.
I feel like my whole life has gone against the grain ever since. Maybe I’m just disagreeable. But I tend to want to do the thing I’m told not to do. I’ve launched more than five companies since my last nine to five over a decade ago — several of which failed — and I’m now building a new one, ClearFirm.
So I write for people who do unconventional things. And lately I’ve been more interested in what want change as opposed to what is constantly changing. Writing about what won’t change, in a world of tech, entrepreneurship, and AI that seems to change every hour. feels like shooting that corner three pointer almost 20 years ago.
That’s the whole idea here. The thing I think about most isn’t what’s new this week — it’s what won’t change over the next year, the next decade, the next century. That’s where I’ve decided to spend my energy. I recently started working through Will Durant’s The Story of Civilization, eleven volumes about exactly that: the things that recur no matter what the technology of the moment happens to be.
So here’s what you’ll get from me, every Thursday: essays aimed at being timeless — about the things that don’t get disproportionately rewritten week to week. I’ve historically used this channel to cover tech news and venture fundraising. In the last two years, that beat has changed more than almost anything with companies raising over $100 billion in one round of funding — which is exactly why I’m leaving it behind. I’ll stick to what lasts: my love for basketball, the unglamorous machinery of taxes, and the boring industries still decades behind the bleeding edge everyone else is chasing.
I scrubbed this list down to the people who actually wanted to be here, and I’m starting over on purpose. If that’s you, here’s the deal:
Essays here every Thursday.
And a new show — Unglamorous Billions — on Substack and YouTube, where I take the boring problems nobody wants to talk about and show you why they’re quietly worth billions.
I took the shot in that gym in 2006. twenty years later, I’m still taking it.
See You Next Week.
— Matt