Sahil Lavingia once believed his startup was headed for unicorn status, but his journey through Silicon Valley—the viral launch on Hacker News, $8 million in venture capital, the glowing press—led to a very different outcome. In this episode, Sahil reflects on life outside the literal and figurative confines of Silicon Valley, and the satisfaction he gets from building a sustainable business.

Show Notes

"Is Venture Capital Worth the Risk?" (The New Yorker) - 00:51

"The deal Jeff Bezos got on Basecamp" (Signal v. Noise) - 1:55

Sahil Lavingia on Twitter | Gumroad - 2:05

Vibram shoes - 6:00

Jon Wheatley founded DailyBooth, a YCombinator company - 7:22

"Pinterest Has Already Pinned Down $10M At A $40M Valuation" (TechCrunch) - 7:31

Bebo is a now-defunct social networking company - 7:54

"SoftBank's Vision Fund Is a Graveyard of Broken Tech Startups" (Vice) - 9:47

"Gumroad Gets $7 Million Series A From Kleiner Perkins For Indie E-Payment Platform" (TechCrunch) - 11:43

Basecamp Personal - 15:45

Her (film) on Wikipedia - 21:01

The 4-Hour Workweek - 29:10

Sahil's big essay on his experience, "Reflecting on My Failure to Build a Billion-Dollar Company" (Medium) - 32:58

The Road Out Of Startupland

REWORK