Serendipity in the Real World & Why Big Events Work

I still get butterflies when we have our large events. We do them a few times a year in Boston and New York, and once annually in San Francisco.

How will it turn out? Will it be too loud? Who will show? Will the food be good?

Last night was our annual SF Founder & Friends cocktail event, and I heard so many interesting stories, connections made, and friends reunited that I was reminded why large-scale gatherings still matter so much in this business.

Here are just a few of the things I heard:

• Two people who’d known each other for years discovered they were both from Montreal.
• One of our portfolio companies brought a product demo.
• Another ended up meeting two new prospective investors.
• I caught up with an investor looking at one of our companies – someone I’d never actually met in person.
• And the most hilarious: a founder and a VC accidentally swapped jackets and met up later that night to exchange them.

All of that — in one night.

That’s the magic of being together in person: the randomness, the collisions, the small human moments that no algorithm could ever script.

Big groups can feel a bit like weddings – they bring the same mix of energy and nerves. You talk to everyone for five minutes and no one for long enough. You see someone across the room, and by the time you make your way over, they’re gone. You leave wishing you’d had just a little more time for deeper conversations.

But in venture, so much happens in the in-between – the side chats, the laughs, the quick introductions. Turns out you need enough “n” number of people to sometime foster this randomness (just like the VC business itself).

It’s another example of the thousand little things you have to do that make all the difference.

I left that night thinking: serendipity doesn’t scale, but it compounds.