After 8 Pivots and a Failed Startup, YC Founder's Second Company Hits $200M Annualized Revenue
mon__lim · x · 2026-10-22
A startup anecdote quoted by calvinchen: a YC batchmate broke up with a co-founder mid-batch, pivoted 8 times, and finally built an AI personal shopper that also shut down. His second company just emerged from stealth doing over $200M in annualized revenue.
Calvin Chen adds his own reflections: you don't learn much from failure—most of his learnings came from his last year working on Proximal; he "probably should have quit earlier and joined a fast-growing startup much sooner"; and there's no overnight success, you just rewrite history to ignore the period before becoming "successful."
Related event: YC Founder Fails After 8 Pivots, Second Startup Hits $200M ARR(2 posts)→
More from Venture
- Just 1% of companies account for 80% of OpenAI and Anthropic spending — and growth has stalled — SumitGup · 2026-10-22
- Indie dev shares nostalgia game site earnings nearing $100/day via Adsterra ads — ezshine · 2026-10-22
- Ashlee Vance: A New Hard-Tech India Is Rising in Hoskore, Backed by Lachy Groom and Shruti Rajagopalan — kyliebytes · 2026-10-22
- SiteData x TrustMRR integration shows verified MRR of any website you browse — yihui_indie · 2026-10-22
- Anthropic accounts for $90B of $157B neocloud deals, powering the GPU rental boom — FinanceYF5 · 2026-10-22
- Founder Used Claude to Mine Old Emails, Tested 14 GTM Motions Before One Worked — julianweisser · 2026-10-22