Tapping Into the Serendipity of Silicon Valley

If you’ve been a reader of my newsletter for any length of time, then you know that I’m a huge proponent of founders (and investors) spending time in San Francisco / Silicon Valley. But I regularly meet founders who travelled to the Bay Area only to come away disappointed.

They didn’t meet anyone particularly interesting. They didn’t have any life-changing epiphanies. Sure, it was cool to visit. But they didn’t get it.

In contrast to the never-ending stream of posts about amazing SF experiences, it doesn’t make a lot of sense. So many people claim that San Francisco is open and welcoming. They assure you that it’s easy to get in the proverbial door. That it’s all about “paying it forward”.

But not everyone has that experience. What gives?

It boils down to two things: time and a willingness to say ‘yes’.

Silicon Valley is a fast-moving ecosystem, but relationships still take time to develop. Many founders come to San Francisco for a weekend or a week, hoping to “tap into the magic.” But a week isn’t long enough.

Because San Francisco serendipity works in hops.

Consider the following scenario:

You fly to SF, having done your research and found some events to attend on SF IRL. The first couple of meetups you go to are duds, but on the third day you strike gold. While at a hackathon, you start up a conversation with some like-minded founders, who casually drop the opportunity,

“You should totally come to X with us on Tuesday.”

Too bad you’re leaving town the next morning… 🤷‍♂️

These types of conversations happen every week in San Francisco — it’s a big part of how the ecosystem operates. Many events don’t have formal invites. The details spread through word-of-mouth, text messages and group chats. It’s easier than it might seem to get into the “inner circle”, but it starts with being able to say yes.

Which means you have to visit for more than a few days.

When we first conceived of last month’s Game On Canada experiment, one of the key questions was, “how long should the program be?” One of my objectives was to help the visiting founders build the beginnings of genuine personal and professional networks in the Bay Area. That meant having them visit San Francisco long enough that they could say “yes” — not only to the first hop of serendipity, but to the ones that came after.

We eventually landed on three weeks. In theory, that would be enough time to get the lay-of-the-land, attend a number of “entry level” events and meetups (both those we held and ones they found themselves), and then go deeper with some of their burgeoning relationships.

At the end of the program, I asked the founders to export their LinkedIn connection graphs for me. I wanted to see if that part of the experiment worked. Were the founders able to make connections in the Bay Area? Here’s what I saw:

LinkedIn Connections (Baseline as of 1/1/25)

LinkedIn connections certainly don’t provide a complete picture of anyone’s relationship graph (I’m connected to plenty of people who I don’t remember and have many friends who I’m not “LinkedIn official” with). But when I first saw this graph, I immediately smiled. Not only did every single founder have a meaningful increase in LinkedIn connections during the program, but a significant number had their rate of connections “accelerate” as the program went on.

On the last day of the program, I asked the founders to share their experiences meeting people in San Francisco. As we went around the room, almost all of them told stories of meeting people who invited them to something, where they met other people who then invited them to something else. Hackathons, art exhibits, dinners, conference parties, after parties, hikes,… — almost all of the founders were able to tap into the serendipity of Silicon Valley!

And almost every single one referenced the fact that they had met people that they intended to stay in touch with after returning home.

That, to me, is success.

Is three weeks the correct number for everyone? I don’t know — but it feels like a good place to start. It’s obviously not easy to pickup and relocate for three weeks, but if one of your goals is to build genuine connections in San Francisco / Silicon Valley, see if you can make it happen.

And be sure to say yes.