In college, I played a political simulation game where I was a stonemason in Ancient Greece named Lithicles of Scambonidae. I spent most of my time securing lucrative contracts to rebuild the walls of Athens while quietly plotting to overthrow the government. The Athenians tried to ostracize me and narrowly failed. Democracy crumbled soon after, replaced by a dictator who wasn’t me. A guy with a construction business, a thing for walls, and a botched attempt to overthrow the government… thank goodness that’s all ancient history.

Sparta had torn down the walls after the war, and critics argued that walls built from fresh stone wouldn’t really be the walls of Athens, just an expensive reminder that we’d lost. One of my pitches for rebuilding them anyway was the Ship of Theseus: replace every plank and it’s still the same ship, so new stones would still make them the walls of Athens. (Every stone also happened to be a contract for me.) A few years later I watched a company I loved get rebuilt plank by plank, and I wasn’t so sure anymore.

Intuit acquired Mailchimp for $12 billion in 2021. Mailchimp was, in a lot of ways, a genuinely weird company. Founded in 2001, bootstrapped the entire way, no board of directors (though there WAS a board room… walls covered floor-to-ceiling in vintage skateboards that Dan collected):

A wall in Mailchimp's board room covered floor-to-ceiling with vintage skateboard decks
Mailchimp's board room. Photo by Kate Kiefer Lee, quoted by Tony Hawk.

No investors to please, so we could plan more than one quarter ahead. When I joined in 2017, the independence was tangible. Things were lax. The vibe was quirky. It was occasionally chaotic. At one point we were sending physical postcards… yes, actual paper postcards in the mail. But it was ours, and the people who built the product genuinely cared about the small businesses using it.

Then the planks started coming out. You know the list, because every acquisition has the same one: new processes, a founder stepping down, the brand’s offbeat humor tempered into something more “corporate,” decisions that used to take hours now taking weeks of cross-departmental approvals, layoffs. Some of it was bad. Some of it wasn’t: Intuit brought a more mature technical foundation and genuinely smart people. It just didn’t look like the thing I’d joined.

I’m not going to pretend that list is interesting. It’s the most predictable story in tech. What I didn’t expect was how badly the Ship of Theseus framing fits it, because it asks the wrong question.

There’s a second half to the thought experiment that almost nobody tells. Hobbes added it: suppose someone collected every old plank as it was pulled off, and assembled them into a second ship. Now you have two. Which one is the Ship of Theseus?

That’s the version I actually lived through. Some colleagues were thrilled with the new ship… more resources, bigger scope, a real career ladder. Others quietly carried their planks out the door and started rebuilding something scrappier somewhere else. A lot of us landed in the middle, nostalgic and curious at the same time, not sure whether we were watching an evolution or an ending. “Is it still the same ship?” turned out to be unanswerable and kind of beside the point. The question people were really answering, one resignation or promotion at a time, was whose ship is it now?

So whose ship is it? It’s not the product. Klaviyo, Constant Contact, ActiveCampaign… they all do roughly similar things, but none of them are Mailchimp. And it’s not the code… though I suppose you could argue that as long as you’re still running your in-house proprietary PHP MVC framework, it’s definitely still the same ship. (Please don’t think too hard about that one.) It was the people: a specific group making specific bets for small businesses and being a little odd about it. Intuit’s slogan is “Powering prosperity around the world,” which… sure. I guess accounting software is prosperity-adjacent. Same direction, maybe. Very different ship.

Back in Athens, I thought the Ship of Theseus was an argument for continuity: swap out every stone and the city still owns its walls. I don’t buy that anymore. The Mailchimp I joined isn’t sitting in an Intuit org chart. It’s scattered across a hundred other companies, in the people who left and took the weirdness with them. It isn’t one ship anymore, but pieces of it are out there right now, hopefully making tech a little better.