Santiago Zavala sat me down in front of the 500 Global community in San Francisco.
The room was full of founders spending a few weeks in the Bay trying to crack the city.
So Santiago pushed me on the one thing I get asked most: how do you actually break into Silicon Valley?
Here’s what I think now after 5 years in SF:
Skip the big events (SF Tech Week, SaaStr, Salesforce). They’re built (mostly) for tourists, but the locals are who you came for.
San Francisco is a city that happens indoors. Deals close at dinner parties. Friendships start at birthday BBQs and soccer pickup. You have to hack your way into the indoors.
Don’t network. Just live a life you enjoy. The most successful people I’ve met in this city, I met playing soccer. Some of them run top venture firms in the Valley.
Stop asking what you can get from SF. The investors and founders worth knowing are exhausted by coffees from people they’ll never see again. Show up with something to give and the city opens.
Capital follows the circle of trust. SF investors will pass on a business they love if your LinkedIn shows zero connections in common. The YC and Stanford logos are shortcuts into that network, not substitutes for it.
The real reason to come isn’t the capital or the talent. It’s what this city does to your mindset.
You don’t realize you needed it until you leave and notice you came back a different person.
Santiago and I kept going from there. We talked about AI, the founders I’m betting on now, and what content survives in the AI era.
[YouTube] → [Spotify] → [Apple Podcast]
Also in this episode:
[10:35] Why San Francisco Runs on Abundance, Not Scarcity
[14:55] Silicon Valley’s Real Advantage Is the Circle of Trust
[22:15] Why VC Conviction Is Becoming More Psychological Than Rational
[34:15] Why AI Makes “Informative” Content a Losing Game
[43:50] Why San Francisco Happens Indoors
