Co-founder + GP @outcastvc. Former GP @coatuemgmt @kleinerperkins @cia. Early in Figma, Distyl, Scale. Still tinkering in my garage.
SF
Joined March 2011
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Over 300 first meetings turned into 70+ work trials. Several teams incorporated. Some already have customers and term sheets.
The best co-founder usually isn’t the person you already know.
It’s the person worth searching for.
… It was how quickly complete strangers started acting like co-founders.
They challenged each other’s ideas. Stayed late after dinner. Built prototypes over the weekend. Interviewed customers together. Talked through how they would handle conflict. They weren’t trying to become just friends. They were figuring out whether they wanted to spend the next decade building together.
That’s the point of these dinners.
They’re an extension of Catalyst, our founder formation program, and designed to bring together people who would likely never cross paths otherwise.
If that’s you, or someone you know, RSVP for our 7/8 dinner: luma.com/98n4ukj3
That makes co-founder selection more important, not less.
Most founders don’t deliberately choose a co-founder. They default to whoever is nearby: a friend, former coworker, or someone already in their orbit.
We’re hosting the next one in SF at the @OutcastVC office.
We think the next few years may be one of the best company formation environments in a decade. For the last few years, many of the strongest builders were concentrated inside a handful of AI companies.
Today, more of that talent is becoming available to start companies of their own.
@heyamylin and I regularly host dinners for founders looking to meet potential co-founders.
The room includes repeat founders behind $1B+ exits, along with staff and founding engineers from Applied Intuition, Robinhood, Airbnb, Stripe, Character AI, Open AI, Splunk, Affirm, and more.
Join me for a private dinner in SF for founders looking to meet potential co-founders.
luma.com/98n4ukj3
Chart data in collaboration with @coatuemgmt coatue.com/c/takes/chart-of-…
The labs haven’t become less important.
The opportunity cost of leaving has changed.
If history is any guide, the next generation of iconic AI companies won’t emerge simply because the models improved.
They’ll emerge because exceptional people are becoming available to build them.
We’re starting to see a similar dynamic in AI.
For the last few years, the rational decision for many top engineers was to join OpenAI, Anthropic, or one of the frontier labs. Today, we’re seeing more of those same people join earlier-stage companies or start companies themselves.
Part of that shift is simple economics. Cursor’s $60B acquisition is the latest example of talent mobility. Over the last year, OpenAI, Anthropic, and several other leading AI companies have enabled employees to cash out about $14 billion. Many early employees are now financially independent and asking a different question: not “Where can I maximize compensation?” but “What do I want to build?”
Most people think innovation waves start with technology.
We think they start when talent becomes available as technology alone doesn’t create companies.
People do.
The mobile era wasn’t just driven by the App Store. It also coincided with the GFC, when ambitious builders suddenly had fewer reasons to stay put. What followed were companies like Uber, Airbnb, Stripe, WhatsApp, and Instagram.
Yesterday's $60B Cursor acquisition means a group of exceptional builders suddenly has the freedom to leave and start companies of their own.
At @OutcastVC , we track this through The Talent Mobility Index: our framework for understanding when exceptional technical talent is locked up, when it becomes liquid, and when it becomes free to build.
Catalyst applications officially closed last night but we're accept late submissions. We can't guarantee a response by April 13 midnight but we do read every application.
outcastventures.com/catalyst…
The hard questions most people avoid until things start breaking.
The best founding teams I've backed didn't leave this to chance. They got explicit early on risk, on ambition, on life stage, on who owns what when things get hard.
And they always get hard.
These are the same questions @heyamylin and I worked through before starting @outcastvc. Not a casual "let's grab coffee and see if we vibe." Hours of conversation over months.
Who makes the final call?
What do we look like at our worst?
What would make us resent each other?
After 20 years recruiting technical talent, I've seen that skills can be developed. Mindsets are nearly impossible to shift. That's why the questions are organized from the inside out. Who someone is, how you'll work together, and only then what they can do.
This is the question I get asked more than any other:
I'm grabbing coffee with a potential technical co-founder. What do I ask?"
So I wrote down 100 of them: outcastventures.com/essays/1…
