How I Invest with David Weisburd · Sep 30, 2026 · 1h 7m · 49m saved
With Nnamdi Okike, Co-Founder and Managing Partner of 645 Ventures, previously at Insight Partners
645 Ventures returned about 35% of its first fund by selling half of a single holding. The company was later acquired for a fraction of the price the firm sold at.
Most venture capitalists describe good early-stage investing as instinct. Nnamdi Okike said it is closer to science: a set of founder traits and market conditions that can be studied, scored and checked against results.
"Our belief is that it's really not instinct."
Okike, co-founder and managing partner of 645 Ventures, on How I Invest with David Weisburd, started in 2002 cold-calling founders for Insight Partners, co-founded 645 with an $8 million first fund twelve years ago, and now runs a $200 million main fund as the firm heads into its fifth vintage.
The full interview is covered here so you can skip it. 67 minutes of audio, 18 minutes of reading.
Here are the 18 lessons that matter.
Key Takeaways
645 Ventures sold half of one position and returned about 35% of its first fund
Selling all of it would have returned close to 70%; the buyer later paid a fraction of that price
Massive seed rounds are bad for companies, Okike said, because they kill the discipline that scarcity creates
Venture valuations, round sizes and revenue multiples show signs of exuberance again, so 645 is slowing its pace before fund five
Founder motivation matters more than early traction, and 645 prefers "missionaries" to "mercenaries"
A startup needs a change in the world behind it, not only a good team
He took the idea of "inflections" from Mike Maples's book Pattern Breakers
The best seed companies change their business model, and 645 passed on Squire at seed because it missed that
Stablecoins are the biggest driver in fintech, mainly for cross-border payments and for savers in weak currencies
Five decades-old vendors run most US bank technology, and 645 is backing startups that go after them
Firm capital loss ratio of about 4% or 5%, which he credits to patience
1. Science, Not Instinct
The host opened with the view that venture investing comes down to instinct. Okike disagreed.
Investing reflects the sum of experience, and it can be measured
He said founder quality has been hard to quantify because many data points are subjective, so an investor has to go a level deeper and work out the key drivers.
"And so our belief is that there is real science behind it, but you need to really unpack the elements and understand the key drivers." — Nnamdi Okike
"It's not purely a ones and zeros game." — Nnamdi Okike
