Terrence Rohan and Lenny Rachitsky are speaking here according to their newsletter.

There are endless posts and podcasts about how investors pick startups. But Lenny and I were curious about a quiet class of employees who seem just as good as—if not better than—the most famous VCs at spotting generational companies before they blow up.

How do these rare folks keep joining world-changing companies before most of the world even notices them ?

To find out, we interviewed five people whose resumes include some of Silicon Valley’s most remarkable companies : Palantir, OpenAI, Facebook, Stripe, Linear, Figma, Notion, Slack, Box, Spotify, and Dropbox.

Each joined at least two of these companies early—an extraordinary feat, especially since they committed as full-time employees, not diversified investors. Their “hit rate” is phenomenal.

We were curious : What did they see ? How did they choose ? Are there lessons to take from their experiences ?

Across their stories, we saw three distinct factors that mattered most.

Though originally written for job seekers, these insights apply much more broadly—for founders, investors, or anyone trying to recognize greatness early.

Here’s what to look for.

1. Ambition bordering on “ludicrous”

This was the most novel takeaway for us : One of the clearest markers of a future generational company, according to our interviewees, is ambition. It came up again and again.

2. Founders, founders, founders

Building on the above insight, every interviewee emphasized the same point : the founders matter above all else. Not as one variable among many—this was the variable.

How to judge founders

Joining a company with great founders is easy to say and hard to do. What exactly makes a founder great ? Many people call out intelligence, and we have a whole section highlighting the importance of ambition. But our interviewees mentioned some less obvious traits. Here are some characteristics of founders :

a) Ability to adapt

b) Ferocity

c) market fit

Founder always asked himself, “Do these people seem like they’re doing what they’re meant to be doing, and is there no question that no one else can do it as well as them ?”

3. Judging today’s product is a trap

You’d think that for legendary product companies like Stripe, Figma, Slack, Notion, and Facebook, you could tell how special they were going to be by how good their early product was. It turns out this way of thinking is a trap.