20VC: How We Made $800M on Coursera | We Lost Money on Uber and Made Money on Lyft | We Did 3x on Postmates in 18 Months | DPI is King, MOIC is BS | We Dodged Theranos and I Still Lost Millions with Larry Aschebrook @ G Squared

20VC: How We Made $800M on Coursera | We Lost Money on Uber and Made Money on Lyft | We Did 3x on Postmates in 18 Months | DPI is King, MOIC is BS | We Dodged Theranos and I Still Lost Millions with Larry Aschebrook @ G Squared

Larry Aschebrook is the Founder and Managing Partner of G Squared in what is one of the wildest stories of venture capital. Larry started G Squared with nothing, dialling for dollars having personally invested in Twitter and Uber. In his first fund, Larry made sizable bets into SpaceX, Palantir, Alibaba and Twitter. Larry has also had mega losses along the way (discussed in the show) in Getir, 23andme and more. Today, Larry manages over $5BN and has invested in all the best from Wiz to Spotify to Revolut and Anthropic.

Agenda:

00:00 – From Broke to Billion-Dollar Bets

03:40 – The $800M Coursera Windfall

06:10 – Lyft Made Millions, Uber Lost $50M

09:05 – "We Fcked Up": The Billion-Dollar Vintage

11:50 – How a $150M Spotify Bet Made a Billion

15:10 – The Gut Call That Dodged Theranos

18:00 – Vampires vs Zombies: The Coming Startup Purge

20:30 – When Success Almost Killed the Firm

24:20 – DPI Is King, MOIC Is Bullsht

27:40 – Why I'd Buy Anthropic at $61BN Today

30:05 – Losing $70M on 23andMe

32:10 – The Janitor of Venture Capital

34:00 – The Getir Deal That Nearly Broke Me

36:25 – Does Money Actually Make You Happy?

39:00 – What Cal Ripken Jr. Taught Me About Venture

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