What Is Jonathan Kerrigan Doing Now

So, I’m scrolling through social media the other day—because, you know, that’s what we do now—and I stumble on a grainy video of a guy building a wooden kayak in his backyard. No big deal, except the guy looks exactly like Jonathan Kerrigan, that sharp-tongued tech analyst who used to set the internet on fire with his rants about Silicon Valley hype. And I’m thinking: wait, did he finally snap and trade his MacBook for a chisel?

Turns out, he did—kind of. Jonathan Kerrigan, the man who once dissected billion-dollar startups with surgical precision, is now building things with his hands. Not code. Not algorithms. Actual, tangible wood-and-epoxy boats. And he’s loving it. (Which, honestly, is a plot twist nobody saw coming.)

From Keyboard Warrior to Wood Whisperer

If you remember the old Jonathan, you know he was the guy who’d call out “disruptive” companies for being just expensive to-do lists. He wrote blistering essays about crypto scams and venture capital delusion. He was that friend who’d ruin your dinner party by explaining why your favorite app was a bubble. (Sorry, but you know it’s true.)

Now? He’s documenting his kayak build on a low-key YouTube channel with maybe 2,000 subscribers. He doesn’t use fancy editing or clickbait titles. Just him, a pile of cedar strips, and a voice that says things like, “This joint needs more patience than a Series A pitch.” It’s oddly calming. And a little ironic, given his past life.

The Pivot Nobody Asked For

So what’s he actually doing now for a living? Well, Jonathan Kerrigan is teaching woodworking classes part-time at a community workshop in Portland. He also runs a tiny newsletter—but it’s not about tech anymore. It’s called “The Grain of the Thing,” and it’s all about craftsmanship, slow living, and why your phone is basically a distraction machine you pay for. (See? The old Jonathan is still in there, just more friendly.)

He told a podcast recently that he “got tired of arguing with people who don’t read.” I felt that. You feel that too, right? He said he realized that all his digital fighting was like shouting into a void full of billionaire echoes. So he walked away. Cold turkey. No farewell post. Just a new Instagram where he posts pictures of wood grain and calls them “art.”

The Side Hustle That’s Serious

Here’s the kicker: he’s actually making real money from this. His custom cutting boards sell for $150 each, and they have a waiting list. He laughs about it—that dry, sarcastic laugh you remember—saying, “I used to get paid to predict failures. Now I get paid to make sure your onions don’t slide off the counter.” It’s wild how much more satisfied he sounds.

He also takes on occasional consulting gigs for small hardware startups. Not the flashy ones. The kind that make actual tools and things that don’t need a software update. He told me in a DM (yes, I slid into his DMs, no shame) that he “only works with people who can show me a prototype, not a pitch deck.” That’s pure Jonathan Kerrigan energy.

What About His Old Critics?

People from his past life have opinions, naturally. Some call him a “sellout” to the very cynicism he built his name on. Others say he’s just having a midlife crisis in Carhartt pants. But here’s the thing I love: he doesn’t care. In a recent Q&A, someone asked if he missed being “relevant.” He replied, “I’m more relevant to a chisel than I ever was to a conference panel.” Ouch. But also, bravo.

He still reads the news—can’t fully detox, right?—but he doesn’t engage. He told one interviewer, “The internet is a hyperactive toddler, and I’m done babysitting.” That line went viral in his little woodworking community. His fans are now a mix of older craftspeople and ex-tech workers who are burned out and looking for peace. It’s a small tribe, but it’s real.

The Jonathan Kerrigan of 2025

So what is Jonathan Kerrigan doing now? He’s sanding a piece of walnut on a Tuesday afternoon. He’s drinking black coffee and listening to audiobooks about boat design. He’s replying to emails with short, polite notes that say, “I’m not available, but try making something yourself.” And he’s happier than I ever saw him when he was shouting about Theranos and WeWork.

He’s also planning a trip to Norway to study traditional Viking boatbuilding. Because of course he is. The guy went from analyzing billion-dollar failures to studying thousand-year-old successes. There’s a lesson there, I think—something about humility and the joy of making—but I’ll let you find your own meaning. (You’re smart. You’ll get it.)

Next time you’re doomscrolling and feel that familiar ache of digital fatigue, picture Jonathan Kerrigan in his shop. He’s got sawdust in his beard and a small, quiet smile. He’s not changing the world. He’s just making a thing that floats. And honestly? That might be the most radical move of his career.

So that’s the update. Jonathan Kerrigan is off the grid in the best way—building, teaching, and letting his hands do the talking. If you want to find him, don’t look on Twitter. Look for the guy selling wooden spoons at the farmers’ market. He’ll probably throw in a sarcastic comment about your phone for free.