140 Angel Investments and 12 Unicorns
The Story
Over five years, Lenny Rachitsky invested in 140+ companies. Twelve became unicorns (valued at $1 billion or more), with 10 more projected to reach that status (Source 1). His portfolio includes Figma, Vanta, and Webflow (Source 2). AngelList ranked him in their top 20 investors (Source 1).
His most surprising finding: only one-third of his best-performing investments received “Great” confidence ratings at the time. Two-thirds of major successes came from deals he rated “Good” or “OK,” suggesting a broad portfolio approach outperforms selective picking (Source 1).
“Access is more important than picking winners” (Source 1, attributed to Jack Altman). Over two-thirds of his biggest winners were “hot deals” — competitive rounds where access trumped analysis (Source 1).
He started investing in friends leaving Airbnb. Early investments were 70% from friends; the ratio later reversed, with most deals coming from other investor networks (Source 1). He targets approximately 10% of net worth for angel investing and describes it as a “very expensive hobby” (Source 2).
80% of founders he meets subscribe to or know of his newsletter, making it his primary deal-flow engine (Source 2). He uses weekly deal-sharing emails with select angel friends to maintain access (Source 1).
AngelList research corroborated his experience: early-stage seed investors maximize returns by investing broadly rather than selectively picking winners (Source 1).
Lesson for Creators
Lenny’s angel investing story is a case study in how a creator’s audience becomes an asset beyond content revenue. His newsletter gives him deal flow (80% of founders know him), credibility (top 20 on AngelList), and a portfolio of 12 unicorns. But the counterintuitive insight is that conviction doesn’t predict returns. Two-thirds of his winners came from deals he wasn’t even that excited about. For creators considering angel investing, the lesson is: build access first, invest broadly, and accept that you can’t predict which bets will pay off.
Related
- The One-Person Media Empire — the newsletter that powers the deal flow
- Project Avoid Getting a Real Job — angel investing as one-third of the post-Airbnb plan