Virtual Serendipity

I once met an investor in the hallway of a small conference in Tucson. He ended up funding a startup I was advising at the time. It felt like pure luck: “Right place, right time, right person.” But if you think about it, there’s a pattern to these seemingly random encounters. You go to a place where the kind of people you hope to meet are likely to be. You walk around enough that a few collisions are guaranteed. It’s structured happenstance. “Serendipity” is never really an accident.

These days, many of us are scattered across different cities or working from home. The old approach—show up physically in the right location—doesn’t translate easily. Yet the longing for serendipity remains. So we try online communities, Slack groups, and Zoom conferences, hoping to replicate those “hallway collisions.” It can be overwhelming. The number of people we can connect with online is so vast that we often end up not connecting at all.

So how do we bring the advantage of random collisions into the digital realm without drowning in noise? I see that as the core puzzle Momentum is solving. The platform sets up these small “serendipity windows” once a week: a match with someone you didn’t explicitly request, but that the AI suspects you’ll value. It’s not random, but it is surprising. You’ll often realize you share a challenge or a passion with the other person. Maybe they mention something that sparks your next idea. Maybe you have a resource or introduction they need. Real serendipity emerges from that cross-pollination.

What I love about this model is how it democratizes chance. In a physical environment, you have to be in the right city, at the right event, and at the right moment in the hallway. Virtual serendipity says: “Let’s do that every week, for everyone.” You don’t have to be wealthy enough to attend a pricey conference. You don’t have to guess if the people you need to meet are actually going to be at that event. Instead, you rely on a system that picks among thousands of possibilities—then gently nudges them into your path.

Sometimes people worry that a structured approach kills the magic. Isn’t serendipity supposed to be uncontrolled? In my experience, it’s not the randomness that makes serendipity magic; it’s the unexpected alignment of interests. If an AI can accelerate that alignment, it doesn’t feel any less special. If anything, you have more time to enjoy the conversation, rather than grappling with the awkwardness of “Why are we talking?” I’ve seen folks come away from these meetings with a sense of wonder, as if they just lucked out. That’s the same wonder you get from discovering a hidden gem at a conference or stumbling into someone who transforms your path.

The great irony is that we’re using algorithms to restore something that used to happen spontaneously in the physical world. It’s like replacing the concept of “bumping into someone in line at Starbucks” with code. But once you realize how scattered everyone is, it makes sense. We can’t rely on pure happenstance to bring us the people we need. We have to orchestrate it. And yes, the result is that many more people get to experience these “lucky breaks.”

I suspect we’re only at the beginning. Eventually, this kind of structured serendipity will be everywhere—events, workplaces, public forums. It’s already how forward-thinking companies match mentors with mentees or how some communities do “random coffee” pairings. Momentum is one of the first to make it a full-blown routine, coupling it with daily knowledge bites so you always have something new to say. If this is the future, it’s a future in which location matters less, and your willingness to show up to weekly calls matters more. That sounds a lot fairer to me. And ironically, it might lead to even more collisions than we ever had in real life.

At its core, “virtual serendipity” is a reminder that meaningful connections aren’t about being physically near powerful people. They’re about being open to conversation with interesting folks whose paths cross your own in some intangible way. By bringing an element of design to that, we’re giving more people a chance to realize they might have something to learn from each other. It’s still up to you to show up and follow through. But if you do, you’ll find that serendipity is very much alive—just living in your calendar, waiting for you to take that meeting you didn’t know you needed.