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second-time founder

also referred to as: second time founders · second-time founders

10 statements across 9 episodes · 5 bullish · 0 bearish · 8 people on the record · first statement Nov 6, 2020 by Zach Weinberg · across every show →

Everything said about second-time founder, oldest first

Nov 6, 2020 bullish
Insight
Weinberg: Second-time founders with small first exits are the best investments
“I have found that second time founders who had a good but small first outcome are by far and away the best people to invest in.”
Zach Weinberg Nov 6, 2020 ▶ 14:04 20VC: Zach Weinberg on Whether A Company is a Democracy, The Importance of Ownership, The Rise of Pre-Emptive Rounds, Multi-Stage Funds Entering Seed and How he Approaches Both Risk and Personal Capital Allocation
Feb 22, 2023
Insight
Systrom: Second-time founders fire fast while first-time founders struggle
“And if it's not the right fit for whatever reason, you just, you move on it. And I think that's something a second-time founder will do that a first-time founder has a lot of trouble doing.”
Kevin Systrom Feb 22, 2023 ▶ 56:42 Kevin Systrom & Mike Krieger: The Founders of Instagram Reveal their New Project "Artifact" | E981 · 20VC with Harry Stebbings
Mar 20, 2023 positive
Assertion Not checkable as stated
Ackman: Plenty of Capital Exists for Second-Time Founders Who Failed
“There's plenty of capital available for people who are second time founders and the first one was not a successful exit.”
Bill Ackman Mar 20, 2023 ▶ 12:51 Bill Ackman: SVB Collapse; Biden vs Trump; How I Lost $400M on Netflix; Bill's 10-Year Long | E991 · 20VC with Harry Stebbings
Sep 18, 2023 neutral
Opinion
Stebbings: Second-time founders view VC funding as a deal, not partnership
“I find like second time founders, especially, I get it, you're selling cash with some advice, which is great, but it's a deal.”
Harry Stebbings Sep 18, 2023 ▶ 30:40 Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
Sep 27, 2023 bullish
Opinion
Stebbings: Paying a valuation premium for second-time founders is worth it
“I always say, like, I would so much rather invest in second-time founders and pay a premium, because I think the lessons that you've learned prevent you from making so many very significant mistakes”
Harry Stebbings Sep 27, 2023 ▶ 14:24 Christian Lanng: "How Being a Founder Almost Killed Me" | E1065 · 20VC with Harry Stebbings
Nov 15, 2023
Prediction Not checkable as stated
Traynor: Second-time founders hire slower to avoid eventual layoffs
“I would bet your second time founders don't they hire slower is my guess because I just think it's an easy way to like burn up opportunity and ultimately lead yourself in a position where you might have to riff.”
Des Traynor Nov 15, 2023 ▶ 1:20:46 Des Traynor: How to Survive and Thrive in a World of OpenAI | E1082 · 20VC with Harry Stebbings
May 8, 2024 neutral
Insight
Hulme: Second-time founders strongly prefer passive investors over value-add ones
“First time founders are looking for investors that add a lot of value. Those that are second time around understand it, bias, and skew wildly towards the passive.”
Tom Hulme May 8, 2024 ▶ 6:14 Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings
May 8, 2024 positive
Insight
Hulme: Second-time founders handle overfunding better than first-time founders
“Again, one of the reasons second time founders do so well is they would be less affected. No one is unaffected, but they would be less affected.”
Tom Hulme May 8, 2024 ▶ 11:13 Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings
May 15, 2024 neutral
Insight
Siroker: First-Time Founders Brag About Headcount; Serial Founders Brag About Lean Teams
“First time founders brag about how many employees they have, second time founders brag about how few employees they have.”
Dan Siroker May 15, 2024 ▶ 7:29 Dan Siroker: Second-Time Founders Are More Investable & Why Not To Hire People Out of College |E1153 · 20VC with Harry Stebbings
Aug 7, 2026 positive
Insight
Frankel: Moderately Successful Second-Time Founders Outperform Prior Massive Winners
“And I think overall we've done a little better on second time founders who didn't do that great up front. They didn't, they did okay, right? It's life changing. Like the first million dollars is so life changing. But they're really hungry. They've learned some…”
David Frankel Aug 7, 2026 ▶ 59:46 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
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