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This essay was originally published here.
Within five minutes of meeting Michael, I was talking to a guy I couldn’t keep up with.
It was a year ago today, as we stood at a bar on my 44th birthday. I was waiting to order a beer when a guy a few seats down looked over and asked, “Are you Justin?”
Jennifer and I were at a brewery in the middle of nowhere in Upstate New York, so I was taken by surprise as I confirmed.
“Oh, cool, man. I follow you on Twitter. Nice to meet you. I’m Michael Kauffman.”
Michael was easy to talk to right out of the gate. And when I got around to asking him what he does for work, he told me he writes a newsletter called Catskill Crew.
Now that was a funny coincidence, because I’d been reading his newsletter religiously since I moved Upstate. And Jennifer and I had wondered, more than once, who in the world was the guy publishing this newsletter? Because it’s not your average newsletter.
It has the look and feel of a country store bulletin board, brimming with all kinds of information about what’s going on around the Catskills. Events. Bird Sightings. When the moon rises and sets. If it’s happening in the Catskills, it’s in the Catskill Crew.
“I read your newsletter every week,” I told him. “I love it.”
Just two guys having a beer, in a small town with 158 residents, who happen to follow each other’s work online. The internet is wild.
And then Michael’s energy just exploded. He pulled a box from under the bar to reveal a Catskills-themed Monopoly game he’d been working on. He came up with the idea, worked out the design, and manufactured the physical product. He was at the brewery that day to drop off the first few copies to his friends who own the place, and he was excited to show me his new invention.
The following week, Michael was throwing a happy hour at Foxfire Mountain House in Mt. Tremper. Did I want to come? Give him my number, and he’d get me a ticket. Then he whipped out his phone to show me some new merch he was designing, this designer ballcap, with the word “TROUT” splashed across the front with some fish. It was going to be huge up here.
And he was getting ready to start mailing a physical newsletter to his subscribers every quarter. I’m talking paper and stamps. It would include a fishing report, events, games, you name it. And did he mention the rotating dinner parties he was kicking off, so people around the Catskills can meet up with strangers to make new friends? Or the holding company he and his buddies had created to start investing in, and rebuilding an entire town up here?
I was just trying to keep up.
Michael and I became fast friends. And over the last year, I’ve watched him ship ideas at a pace that puts most entrepreneurs to shame. The Monopoly game. The trout hat. Dinners where strangers get matched to become friends. Cookouts and mushroom foraging days. Entrepreneur meetups. Puzzles. Fly-fishing excursions. And the most surprising one, that physical newsletter that arrives in my mailbox once a quarter.
I remember getting my first copy and thinking, Who the hell does this?
Someone who thought it would be fun, that’s who.
Not someone who read some X thread or marketing lead magnet about differentiating through “hands-on experiences.” Michael just thought it would be cool to send his readers actual mail, so he printed thousands of mailers and started doing it. He’s the kind of guy who gets an idea and thinks “Why not?” He’s willing to give just about anything a try as long as it’s fun and helps his readers.
Last week, Michael threw a little party at his house, and we were all watching the US vs. Bosnia-Herzegovina game. At one point, I started chatting with his friend Ben, who told me a bunch of other entrepreneurs up here have tried to copy what Michael’s doing. The newsletter, events, merchandise thing. But they can’t make a dent.
“They’re trying to build a business,” Ben said. “But Michael’s just doing what Michael does.”
Michael’s self-created job was born out of his love for this little corner of the world. And his whole mission is to help other people love it too. He’s the man about town, promoting small businesses, connecting this person to that person, and throwing events so that good people can get together and meet each other the old-fashioned way, over a beer.
You can hear it in his voice. You can read it in his newsletter. And you can feel it at his events. Michael’s having fun. Michael is Catskill Crew.
The people copying Michael probably aren’t lazy or dumb. They’re just doing what most entrepreneurs do. They studied something that was already working, launched their own newsletters, tried to throw some events, and made the merch. A proven playbook generally works, right? And just a few years ago, maybe that would have been enough. Competent execution plus marketing was basically the whole game. Intense passion was a nice-to-have, or faked through a well-orchestrated “founder story.”
But AI has flipped all that on its head. Anyone can produce good content at scale now. Writing, visuals, systems, and entire funnels can be built in an afternoon, for a few hundred bucks. Discipline and competence are getting easy to replace.
And from a purely technical perspective, Michael’s online work could probably be replicated by someone with the same tools.
I built my whole career that way. I was always defining strategy, figuring out systems, and building dashboards, products, and funnels to make it all work. And it did work for a long time. That skill set built everything I have in my business.
But watching Michael has forced me to think about something uncomfortable. That almost everything I got good at over the last twenty years is getting commoditized by AI.
But what Michael is doing can’t be replicated. Because fun is a moat AI cannot cross.
Today is my 45th birthday, and if I’m lucky, I’m just hitting halftime. And I’ve decided the entire second half of my life is going to be built around one filter: having fun.
Is this the thing I’d do anyway?
Writing has always passed the test. A few other things I’m cooking up pass as well. Spending more time with interesting and passionate people in this space is something I want to continue to lean into and build toward. But anything that doesn’t feel like fun? It’s time for that stuff to go. Tools have never been cheaper or easier to use, so the boring, mundane, miserable parts of work can be automated.
What’s rare and special is the person having an absolute blast.
That’s Michael.
Getting to know him has made an impression on me. I still think about meeting him at that bar as he dropped off his board games and told me about mailing letters and selling trout hats, because he loves where he lives and can’t stop sharing it with people. He’s inspired me to reconsider what’s possible at the intersection of life and work.
So here’s the question I’ll leave you with today:
Is the thing you’re building today the thing you’d do anyway, if nobody paid you?
Because if it isn’t, somewhere out there is a Michael who would.
And he’s going to win.
Cheers
Justin Welsh
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Fun is an underrated business advantage because it makes the work easier to sustain and harder to fake.
People can copy tactics, but they cannot easily copy the energy behind someone who actually enjoys the game they are playing.
I loved this essay so much. The Catskill Crew newsletter has been so inspiring for the work I do in my community, too. Thanks for distilling why.