20VC Exclusive: Keith Rabois on Rejoining Khosla Ventures

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?