Behind every good alumni syndicate is a great community

Last month, I shared a tactical guide to launching an alumni syndicate. It was useful, but incomplete.

As one of the founders of the Xtripe syndicate, I overlooked the real reason it works: the community.

When we launched the Xtripe syndicate in 2021, I learned a good deal about deal structure, tooling, process, and compliance from founders of alumni syndicates at Palantir, Uber, Airbnb, etc. Most advice centered on logistics, the operational backbone of running a community-based investment group. That was the focus of my last post.

But in the past few months, while working with alumni syndicates emerging from Figma, OpenAI, Snowflake, Ramp, Plaid, and Databricks, one thing has become unmistakably clear:

The most important input isn’t process. It’s people.

Let me paint a picture.

Today, Stripe has 2,000+ alumni community.

And it’s still growing. That’s wild.

We’ve built a digital space, mostly on Slack. It’s where former colleagues trade ideas, gossip, celebrate wins, and spin up side quests. The syndicate is just a subreddit of that broader community. And that’s exactly how it should be.

We also have dozens of affinity channels:

• #anime and #metal

• #sf, #nyc, and #london

• #payments, #api, #sales, #risk

We’ve got #yakshak (pure chaos), #equity (sharpened thinking), and a legendary group of #diamondstripes—hodlers of the still-illiquid $TRIPES (🙃).

But two of my favorite channels are:

• #intro-yourself — where new (or newly reappeared) alums reintroduce themselves to the community. Every week, a few familiar faces pop up with a “hi again 👋” and receive a flood of reacjis, welcome-backs, and the digital equivalent of seeing an old friend at the party.

• #shipped — our celebration channel. A place where builders quietly post new launches, side projects, startups, or even memes. It’s Stripe-y in the best way: low ego, high output, and deeply supportive of the next thing.

Today, Stripe processes 1–2% of global GDP. In a recent interview, Patrick said that while it’s a lot, it also means there’s a long way to go. Stripe will keep growing. That means more incredible people will join, and more will eventually move on to build the next thing.

That also means our alumni community is nowhere near done.

The eternal “we haven’t won yet” mantra still applies.

Of course, none of this happens on its own. Communities aren’t automatic; they’re stewarded. Xtripe owes a debt to the people who’ve put in real work—welcoming new members, keeping the vibes high, and helping the whole thing stay alive and useful.

Marty has quietly become the backbone—administering Slack, answering questions, and reminding us that even if you left Stripe years ago (he did in 2018), you’re still very much part of the crew.

Sandro spent 7 years at Stripe, and still finds the community to be a source of inspiration and energy.

Kevin put it best: "This isn’t just a few people broadcasting. It’s a real network. Intros, convos, side projects. That’s true community."

Milo andDanika have been incredible partners on the investing front—helping make the syndicate feel like an extension of the culture, not a separate room. JT also shows up thoughtfully and consistently in the investment channels.

Lachy somehow keeps the entire place both high-signal and high-spirited, even though he’s doing a million things at once.

Jane reminded me that the magic of Stripe was always the people—witty, surprising, brilliant in ways that often had nothing to do with your actual job. The fact that you still can’t always tell what someone does here? That’s a feature, not a bug.

And Michael, a more recent joiner, said it perfectly: “I knew my time working at Stripe was done. But I also know my time working with Stripes is far from done.”

The point is this: it takes a constellation. And somehow, it still feels like one team.

If you’re thinking about starting a syndicate, do it.

But start by building a community.

A living, breathing space where people show up with ideas, intros, co-conspirators, and investments. Where people want to hang out. A place with legs. A place that doesn’t rely on any one person. A place that welcomes the next generation of alums who may someday lead the thing themselves.

Slack makes it easy. We’re already there, hanging out. And every once in a while, that casual drop-in leads to something new and exciting.

If you're trying to build this at your company and want a hand, I’d be happy to help. Just shoot me a note: ak@thegp.com.

The best communities don’t scale because of one founder. They grow because someone opened the door, and others decided to stay.