Do investors who have lived through prior market cycles add distinctive value during downturns?

Michael Eisenberg · Dec 6, 2021

Who sits around the board table and who your co-investors are matters enormously, and today many boards lack steady hands who have seen a downturn

Learned from 1999-2000 that fears and true colors come out in hard times; entrepreneurs listen to their board, and investors who have never seen a 50% drawdown or who fear reporting bad news at Monday partner meetings will drive founders and boards crazy

30:19 20VC: Bill Gurley and Michael Eisenberg on The First Signs of an Impending Bust, What Happens with a Market Crash, How Do Public Markets Impact Private Valuations & The Biggest Lessons from 20 Years Investing in Venture

Hunter Walk · Jan 30, 2023

Partnering with someone who has lived through multiple business cycles produces better decision frameworks, provided you don't over-learn the lessons of past eras

Satya's experience of institutional venture in 1998-2000 and 2007-2011 prevented Hunter's bad ideas while letting the good unconventional ones through, generating good debate and decisions

Scope: markets today are not the same as the nineties, so past lessons shouldn't be over-applied

41:27 20VC: Homebrew's Hunter Walk and Satya Patel on Why $100M is Not Enough To Execute a Seed Strategy Today | Why They Decided not to Raise New External Funds | Where Are We in the Cycle & What is Truly F***** | Why Founders Should Take Secondaries Earlier

Kevin Systrom · Feb 22, 2023

People who have lived through prior cycles do better than first-timers because they recognize patterns and stop extrapolating the present

Zero interest doesn't last forever; when the music stops there aren't enough chairs, and pattern recognition makes you quicker to correct mistakes

Scope: you still make the same mistakes, just fix them faster

58:33 20VC: Instagram Founders Kevin Systrom and Mike Krieger on Why Social Networks Should Be Less Social & The Next Wave of Social | Why San Francisco Will Return with a Vengeance and The Future For Remote Work | Let's Get Personal: Relationships to Money, Be

Eléonore Crespo · May 9, 2025

The most experienced investors add value in shaky markets because they've seen the cycle before and can hold the long-term macro picture.

They know a shaking market recovers in a few years, so they push for aggression rather than transmitting panic.

42:49 20VC: Four Traits of the Most Successful Founders | How to Hunt and Close Talent Like a Pro and Where All Founders Go Wrong | Lessons Raising $397M From the Best Investors in the World with Eléonore Crespo @ Pigment