Uploaded October 2025 | Updated September 2026, 3 weeks ago
Nine out of ten people might tell you you're crazy. The tenth might see what you see.
Garry, Harj, Jared, and Diana talk about contrarian bets — the ideas that look impossible until they work. From Uber and Coinbase to DoorDash and Flock Safety, they share how founders find opportunity where others see dead ends.
Chapters:
0:00 - Intro
2:00 - AI verticals are becoming more crowded
6:22 - Non-obvious successes
9:50 - End users can get regulations changed
18:05 - Finding contrarian ideas, what founders should look for
25:10 - Flock Safety and selling to local governments
33:40 - The sci-fi founder and "impossible" big ideas
36:42 - Outro
Apply to Y Combinator: ycombinator.com/apply
Work at a startup: ycombinator.com/jobs
Nine out of ten people might tell you you're crazy. The tenth might see what you see.
Garry, Harj, Jared, and Diana talk about contrarian bets — the ideas that look impossible until they work. From Uber and Coinbase to DoorDash and Flock Safety, they share how founders find opportunity where others see dead ends.
Chapters:
0:00 - Intro
2:00 - AI verticals are becoming more crowded
6:22 - Non-obvious successes
9:50 - End users can get regulations changed
18:05 - Finding contrarian ideas, what founders should look for
25:10 - Flock Safety and selling to local governments
33:40 - The sci-fi founder and "impossible" big ideas
36:42 - Outro
Apply to Y Combinator: ycombinator.com/apply
Work at a startup: ycombinator.com/jobs
