Scrap and Claw: Fred Wilson on Winning the Rounds You Missed
Key points
Key takeaways from a conversation recorded at the USV CEO Summit shortly after Labour Day in 2026, between Union Square Ventures founder Fred Wilson and investment partner Nikhil Raman, on the state of the VC business:
Earn the right to advise. At 29, Wilson showed up at his first board meeting—— of Ron Shriber's and Jordan Levy's second company—— and started lecturing the founders; Jordan stopped him: do every job in the company for a week first. He flew to Buffalo, worked customer support, sat with engineers and the marketing team—— and only then would they entertain his advice. Young VCs, he says, must work harder to understand the business and earn founders' trust.
Founder mode, the Don Valentine way. Wilson recalls the 2x2 that Don Valentine showed Roelof Botha at Sequoia—— great-vs-good founders against hard-vs-easy to get along with—— with the money quadrant being great founders who are hard to get along with: "We make all our money here." He still bets on that type—— founders with great conviction and great courage who may not be great communicators—— and links it to Mark Pincus's definition of founder mode: staying true to your instincts and willing the company where you want it to go, not letting board or management push you.
Missed deals can be chased back. USV passed on FOMO when it first met the company in September 2025. Wilson kept using the app, concluded he'd been wrong, and—— rather than angel alone—— pressed USV to reinvest; six months of showing up—— including the company's holiday party—— and a couple of graciously declined offers later, the firm got its allocation while the company had tripled or quadrupled in size.
Helpfulness buys allocations. When USV couldn't lead the latest round at the startup behind Hermesbecause it was raising more than USV could write, Wilson still earned an allocation by introducing the founders to investors and corporates who'd be good partners. "That's the way the game is played now"—— you have to win with the founder and prove they want you on the cap table.
A less collaborative business. Wilson grew up in a venture industry built on syndication reciprocity, but today firms are larger, founders allocate rounding they want,and you can't expect other firms to hand you allocations. Every opportunity is a jump ball: someone's going to get it,so you're going to get it.
Conviction first, consensus second. His advice to young investors: treat the firm's money as your own. He wasted early years wondering whether partners would like a deal; he eventually realised he had to like it first, then convince them—— never the other way round. "You can overcomplicate the investment business if you start thinking of yourself as a steward of someone else's capital."
Simplify the story. Wilson's self-described gift is helping founders craft a very simple story to tell when raising, and reframing the question the board is actually deciding;sometimes a founder has been trying to say it for 20 minutes. Raman's take: gravitas comes from doing the work and understanding the business—— it doesn't always have to be the advice.
Read more: Fred Wilson on X · USV on YouTube
