Hustle Fund Partner Reflects on Missed Unicorns, Citing Luck Over Brilliance

On November 12, Hustle Fund partner dunkhippo33 posted a long thread systematically reviewing a batch of strong companies she passed on, concluding that luck matters far more than smarts in early-stage investing. She said the team has a pile of similar cases on its books and will keep tracking them and drawing lessons, with the goal of "seeing good companies even if we don't always make the right call."

Confirmed

• Airalo (eSIM): the partner looked at it at an $8M valuation but thought eSIM was commoditized and the space crowded; it is now valued at over $1B, and she admits the space actually has many winners.
• Ajaib (Indonesian investment platform): now valued at $1.35B.
• GC AI (legal-industry AI): she didn't even take a meeting because she thought the space was crowded; the founder is now thriving.
• Workstream: it was right in Hustle Fund's coworking space, yet they didn't invest; she praised founder Desmond.
• WindBorne (balloon-based weather forecasting): she thought the team's tech was excellent and they were close to founders in her portfolio, but "weather forecasting with balloons" didn't look like a business and she "didn't get it"; the company just raised $37M at a $250M valuation.
• Passport: looked at it at a $4M valuation; despite Passport and Around's founders being among the best serial entrepreneurs, she passed, missing what she estimates was a 50x+ return; Passport was later acquired by Global (the acquirer) for $350M.

Why it matters

• It's a rare public list of misses from a frontline fund, vividly showing the scale of opportunity that common rejection reasons like "crowded space" and "I don't get it" can cost.
• She stresses that among timing, opportunity, the state of the world, plus skill and effort, luck plays a huge role, and "you get more humble every year in this job" — a useful reference for founders and new investors judging which rejection reasons hold up.

2026-11-12 ~ 2026-11-12 · 6 related posts

• [source] Hustle Fund passed on Airalo at $8M; Ajaib now valued ~$1.35B — dunkhippo33 · 2026-11-12
• Hustle Fund passed on GC AI for feeling 'too crowded' — founder now thriving — dunkhippo33 · 2026-11-12
• Hustle Fund missed WindBorne, which just raised $37M at a $250M valuation — dunkhippo33 · 2026-11-12
• Hustle Fund saw Passport at a $4M post-money; Global-e later bought it for $350M — dunkhippo33 · 2026-11-12
• [source] Hustle Fund partner on missed unicorns: 'luck is huge, and it keeps getting more humbling' — dunkhippo33 · 2026-11-12

1 near-duplicate retellings: dunkhippo33