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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

Overview

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Highlights

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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

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

2025/06/16

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

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

2025/06/16

Overview Shownote Highlights Transcript Chapters Pins

Shownote

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 ...

Highlights

Larry Aschebrook, Founder and Managing Partner of G Squared, shares his journey from humble beginnings to managing over $5 billion in investments. Known for bold bets on companies like SpaceX, Palantir, Alibaba, and Twitter, Larry also discusses significant losses and the lessons learned along the way. His unique approach to venture capital emphasizes strategic investments, liquidity management, and avoiding common pitfalls.

03:40

Larry started as a fundraiser before entering venture capital

06:11

Started buying shares of early Uber, Twitter, and Spotify during business school

09:05

Fewer institutions helped companies go public post-crisis.

14:08

Diversified entry strategy focuses on fewer companies for liquidity

17:26

Past funds allowed acquiring assets at 35 cents on the dollar

18:00

Direct secondary buyers interact with founders and access primary-level data.

22:40

Using the mosaic theory for due diligence in early-stage investments.

24:21

Invested $380M in Spotify, turning it into a billion-dollar outcome.

27:41

Tripled down on an investment at a 50% discount, reaching a 380-million-dollar pool.

30:09

Lost 20 cents on the dollar in Uber but made 3x on Lyft.

32:11

Companies reaching high valuations and avoiding cycle ends is crucial.

34:00

The manager argues they're doing what they're hired for, generating capital velocity.

38:38

Got $800M back to LPs on Coursera and exited Toast at $76 per share

51:21

Avoided a disastrous Theranos investment by trusting his 'Spider sense'.

Chapters

From Broke to Billion-Dollar Bets

00:00

The $800M Coursera Windfall

03:40

Lyft Made Millions, Uber Lost $50M

06:10

“We Fcked Up”: The Billion-Dollar Vintage

09:05

How a $150M Spotify Bet Made a Billion

11:50

The Gut Call That Dodged Theranos

15:10

Vampires vs Zombies: The Coming Startup Purge

18:00

When Success Almost Killed the Firm

20:30

DPI Is King, MOIC Is Bullsht

24:20

Why I’d Buy Anthropic at $61BN Today

27:40

Losing $70M on 23andMe

30:05

The Janitor of Venture Capital

32:10

The Getir Deal That Nearly Broke Me

34:00

Does Money Actually Make You Happy?

36:25

What Cal Ripken Jr. Taught Me About Venture

39:00

Transcript

Larry Aschebrook: I mean, we made ridiculous sums of money for LPs in that period. We were the largest shareholder of Coursera. $800 million back to LPs on Coursera. We made a ton of money on Lyft and we lost money on Uber. 40% of my third fund went into S...