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

In this episode of 20VC, Harry Stebbings interviews Larry Aschebrook, founder of G Squared, about his journey in venture capital, starting from fundraising for academic institutions to managing over $5 billion in assets. Larry shares his early investments in companies like Twitter, Uber, and Spotify, as well as the challenges and losses he faced with companies like Theranos and Gettier. He discusses his investment strategies, the importance of generating quick returns for LPs, and the evolution of his firm's approach to direct secondary buying. Larry also reflects on mistakes made during the 2020-2021 period, emphasizing the need for guardrails and a focus on data-driven decisions. He touches on the current AI landscape, his investment in Anthropic, and his views on liquidity and firm building.

Outlines

Part 1: Genesis and Early Strategy

Part 2: Guardrails, Mistakes, and Lessons Learned

Part 3: Strategy Evolution and Reflections

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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

Part 1: Genesis and Early Strategy

The Genesis of G Squared: From Fundraising to Early Investments

The Thesis and Early Fund Formation: Capitalizing on Private Market Growth

Investment Strategy and the Spotify Story: Concentration and Data-Driven Decisions

Securing the Spotify Deal and Early Successes: Concentration and Contrarian Bets

Part 2: Guardrails, Mistakes, and Lessons Learned

Guardrails and DPI: Protecting Against Irrationality and Delivering Returns

The Sins of 2020: Believing the Bullshit and Overpaying for Assets

Saving the 2020 Vintage: Selling Overvalued Assets and Learning from Mistakes

Theranos and 23andMe: Lessons in Due Diligence and Selling

Gettier: The Perils of Fighting Too Hard and the Importance of Walking Away

Part 3: Strategy Evolution and Reflections

Co-Investment Strategy and Revolut: Balancing Risk and Opportunity

Personal Reflections: Money, Happiness, and Maintaining the Edge

Firm Building and Leadership: Humility, Openness, and Productive Paranoia

Quick Fire: Admiration, Change, and Advice

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

Part 1: Genesis and Early Strategy

00:00The Genesis of G Squared: From Fundraising to Early Investments

The Genesis of G Squared: From Fundraising to Early Investments

07:08The Thesis and Early Fund Formation: Capitalizing on Private Market Growth

The Thesis and Early Fund Formation: Capitalizing on Private Market Growth

15:29Investment Strategy and the Spotify Story: Concentration and Data-Driven Decisions

Investment Strategy and the Spotify Story: Concentration and Data-Driven Decisions

24:51Securing the Spotify Deal and Early Successes: Concentration and Contrarian Bets

Securing the Spotify Deal and Early Successes: Concentration and Contrarian Bets

Part 2: Guardrails, Mistakes, and Lessons Learned

31:03Guardrails and DPI: Protecting Against Irrationality and Delivering Returns

Guardrails and DPI: Protecting Against Irrationality and Delivering Returns

37:00The Sins of 2020: Believing the Bullshit and Overpaying for Assets

The Sins of 2020: Believing the Bullshit and Overpaying for Assets

45:59Saving the 2020 Vintage: Selling Overvalued Assets and Learning from Mistakes

Saving the 2020 Vintage: Selling Overvalued Assets and Learning from Mistakes

52:03Theranos and 23andMe: Lessons in Due Diligence and Selling

Theranos and 23andMe: Lessons in Due Diligence and Selling

1:01:31Gettier: The Perils of Fighting Too Hard and the Importance of Walking Away

Gettier: The Perils of Fighting Too Hard and the Importance of Walking Away

Part 3: Strategy Evolution and Reflections

1:07:33Co-Investment Strategy and Revolut: Balancing Risk and Opportunity

Co-Investment Strategy and Revolut: Balancing Risk and Opportunity

1:17:03Personal Reflections: Money, Happiness, and Maintaining the Edge

Personal Reflections: Money, Happiness, and Maintaining the Edge

1:23:11Firm Building and Leadership: Humility, Openness, and Productive Paranoia

Firm Building and Leadership: Humility, Openness, and Productive Paranoia

1:30:31Quick Fire: Admiration, Change, and Advice

Quick Fire: Admiration, Change, and Advice