VC dunkhippo33 advises angel portfolios of 50 to 100 companies

Investor dunkhippo33 posted a long angel investing thread on October 12, tackling the question of how many companies an angel investor needs to back to have a shot at landing a big winner. His advice: early-stage angels should build a portfolio of 50 to 100 companies.

Confirmed

The rationale is that roughly 9/10 startups fail, so you need enough shots on goal to reasonably hit a super-winner; he admits the 50-100 number often sounds crazy to people.
He believes both the "spray and pray" camp and the "concentrated bets" camp are right — it depends on whether a company has reached product-market fit: companies with validated PMF can warrant concentrated bets.
Ordinary people can do angel investing too — no need to be super wealthy: spread the 50-100 company portfolio over 5-10 years, i.e., 5-20 investments per year.
He believes consistently investing across bull and bear cycles is itself the best way to invest.

Why it matters

dunkhippo33 cautions that the first few years will feel awful: failed companies shut down first, while winners may take 10+ years to show their scale, so sticking with building the entire portfolio is the premise that makes this strategy work.
The thread offers everyday investors a quantifiable, actionable path into angel investing, breaking down a seemingly high-barrier asset class into a long-term discipline of 5-20 deals per year.

2026-10-12 ~ 2026-10-12 · 9 related posts

Primary sources

Angel investor: build a portfolio of 50-100 companies to catch a big winner — dunkhippo33 · 2026-10-12 01:01 (UTC+08:00)
Why angels should build 50-100 company portfolios: 9/10 fail — dunkhippo33 · 2026-10-12 01:01 (UTC+08:00)
You don't need to be ultra-wealthy to angel invest: 5-20 companies a year over 5-10 years — dunkhippo33 · 2026-10-12 01:01 (UTC+08:00)

VC argues angel investors need 50-100 company portfolios to hit a big winner — dunkhippo33 · 2026-10-12
Spray and pray vs concentrated angel investing hinges on PMF, says VC — dunkhippo33 · 2026-10-12
Round names are broken: AI startups raise $100m+ with no product — dunkhippo33 · 2026-10-12
In 1997 Benchmark put $6.7M into eBay when it was already profitable — dunkhippo33 · 2026-10-12
[source] Why angels should build 50-100 company portfolios: 9/10 fail — dunkhippo33 · 2026-10-12
[source] Angel investor: build a portfolio of 50-100 companies to catch a big winner — dunkhippo33 · 2026-10-12
Angel investing is a claw machine: drop 50 quarters and the law of large numbers works for you — dunkhippo33 · 2026-10-12
[source] You don't need to be ultra-wealthy to angel invest: 5-20 companies a year over 5-10 years — dunkhippo33 · 2026-10-12
Angel investing feels awful early: winners take 10+ years to show — dunkhippo33 · 2026-10-12