CP on losing money by holding on to Slack stock

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The speaker recalls holding onto Slack stock during the pandemic instead of distributing it, leading to a significant loss of money. Despite initially believing in the company and being amped up about it, the pandemic caused panic and a rushed distribution decision, leaving substantial money on the table. This experience taught the speaker a valuable lesson to never hold onto stock for others when it's liquid, to promptly distribute it, and only hold for personal shares with a clear point of view. The speaker emphasizes the regret and the 50% loss incurred from trying to hold on against the market conditions.

This conversation was recorded LIVE at the All-In Summit in Miami and included slides. To watch on YouTube, check out our All-In Summit playlist: https://bit.ly/aisytplaylist

0:00 Bill Gurley & Brad Gerstner break down the state and historical significance of 2022's market downturn

12:27 How VCs will handle capital commitments from LPs, underwriting startups in the new reality

24:14 Bull run mistakes, why VCs don't underwrite lower valuations, handling distributions

33:52 Gurley's take on WeCrashed & Super Pumped TV series, how sophisticated investors got "gaslit" by the market, influx of capital creating consumer-surplus businesses

47:54 Brad predicts the market for next year, Bill gives post-Benchmark plans

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