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

20VC Exclusive: Keith Rabois on Rejoining Khosla Ventures

Jan 12, 2024

Keith Rabois, Managing Director @ Khosla Ventures, talks about his decision to rejoin Khosla Ventures from Founders Fund. He compares the investing styles and price discipline of the two firms. Keith shares his lessons on liquidity and capital planning in venture investing. The chapter also explores the importance of finding the right match between founders and investors and discusses the trade-offs of success, Bitcoin adoption, and predictions for 2024.

01:06:14

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Keith Rabois

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Quick takeaways

Keith Rabois decided to rejoin Khosla Ventures from Founders Fund due to aspects that he missed and personal factors that were appealing to him.

When comparing Founders Fund and Khosla Ventures, Keith discussed their investing styles, price discipline, and the depth and quality of investment decision-making.

Keith emphasized the importance of having a comparative advantage and leveraging it to make successful investments in venture capital.

Deep dives

Keith Reboi's Motivation Behind Joining Coesler Ventures

Keith Reboi, legendary founders fund investor, recently made the move back to Vinod Coesler and Coesler Ventures. He explained that there were certain aspects of KV (KV4, KV5, and KV6) that he missed, as they contributed to the successful track record of those funds. Additionally, he mentioned personal factors that were appealing to him as an individual, aside from his professional goals. The decision to join Coesler Ventures was motivated by a combination of professional aspirations and personal factors.

The Risk and Price of Seed Funding

01:46

Elements for success in VC market

03:05

How kv $3bn is going to make money

02:30

What’s make Vinod special

02:50

Introduction

3min

Reflections on Returning to CoSLA Ventures

15min

Concerns about Pricing and Conviction in Seed Stage Investing

16min

The Importance of Finding the Right Match

21min

The Trade-offs of Success, Bitcoin Adoption, and Predictions for 2024

4min

Deciding which first meetings to take and the strategy of going public early

2min

Discussing the Teal Fellowship, Europe's Decline, Venture Strategies, and Keith's Future Plans

2min

Discussion on LPs and Sponsored Content

3min

Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Just last week, Keith announced he would be rejoining Khosla from Founders Fund, where he spent an immensely successful 5 years as a General Partner. Prior to Founders Fund, Keith started his career at Khosla where he spent 6 years and led investments in DoorDash, Opendoor, Webflow and more.

In Today's Episode with Keith Rabois We Discuss:

1. The Decision to Rejoin Khosla Ventures:

Why did Keith decide to rejoin Khosla Ventures from Founders Fund?
What did Keith miss most that Khosla did, that Founders Fund did not?
How did Delian take the news?

2. Comparing Two Great Firms: Founders Fund vs Khosla Ventures:

Investing Style: How does Keith compare the investing styles when analyzing FF and KV?
Price Discipline: Which firm is more price-disciplined? Does price discipline even matter?
What are the single biggest mistakes Keith has made on price? How did it change how he invests?
Founder Type: What sort of founder would choose KV? What founder would choose FF?
How did the depth & quality of investment decision-making compare between KV and FF?

3. What It Takes To Win in Venture in 2024:

Liquidity: What have been Keith's biggest lessons on when is the right time to sell positions?
Capital Planning: What have been Keith's biggest lessons on the most effective use of reserves?
Why does Keith believe if you do not lose some deals as an investor, you are not competing for the right companies?
Khosla Ventures recently raised $3BN. How important is the ability to support companies across their lifetime in 2024 vs stage specific?

4. Where is The Best Place to Invest:

Why does Keith think seed is the best place to be investing today?
Why despite the better risk/reward profile, does Keith think Series A is not the best place to invest?
Does Keith believe we will see the return of growth investing in 2024?
What does Keith predict for the M&A market in 2024? Did Figma kill all activity?
When will the IPO windows open again? Why would Stripe go out this year?

5. Keith Rabois: AMA:

Why did Keith not want to start his own fund? Will he ever?
What have been Keith's biggest lessons from working with Vinod Khosla and Peter Thiel?
What were Keith's biggest lessons from Roelof Botha on what it takes to be an effective board member?
How does Keith think about bitcoin in 2024?

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

20VC Exclusive: Keith Rabois on Rejoining Khosla Ventures

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

Keith Reboi's Motivation Behind Joining Coesler Ventures

Key Lessons and Future Plans for Keith and Coesler Ventures

Risk and Price Sensitivity in Venture Investing

Series A investment strategy

The broken state of growth investing

The Risk and Price of Seed Funding

Elements for success in VC market

How kv $3bn is going to make money

What’s make Vinod special

Get the Snipd
podcast app

AI-powered
podcast player

Discover
highlights

Save any
moment

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

20VC Exclusive: Keith Rabois on Rejoining Khosla Ventures

Episode guests

Podcast summary created with Snipd AI

Quick takeaways

Deep dives

Keith Reboi's Motivation Behind Joining Coesler Ventures

Key Lessons and Future Plans for Keith and Coesler Ventures

Risk and Price Sensitivity in Venture Investing

Series A investment strategy

The broken state of growth investing

The Risk and Price of Seed Funding

Elements for success in VC market

How kv $3bn is going to make money

What’s make Vinod special

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