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Keith Rabois on Rejoining Khosla Ventures | E1102

Notion combines your notes, docs, projects into one space that’s simple and beautifully designed, with the power of AI built right inside — not a separate AI tool or browser tab. Try Notion for free when you go to notion.com/20vc --------------------------------------------- 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. ----------------------------------------------- Timestamps: (0:00) Intro (00:53) Moving to Khosla from Founders Fund (06:00) Founders Fund vs. Khosla Strategy (10:01) Investment Regrets at Khosla (14:11) Investment Price Sensitivity (18:00) Lessons from Investing in Ramp (25:29) Ideal Seed Funding (31:58) Role of Operators in Venture Capital (34:45) Current State of Growth Funds (38:19) Strategies with Khosla's $3BN Fund (43:05) Khosla Ventures' Youthful Approach (45:21) VC Firm Preferences Among Founders (49:45) Returning to Khosla and Starting a Fund (51:05) Current Motivations for Keith (01:00:21) Timing for Selling Investments (01:07:40) Quick-Fire Round --------------------------------------------- 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? --------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Keith Rabois on Twitter: https://twitter.com/Rabois Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact --------------------------------------------- #harrystebbings #20vc #business #venturecapital #podcast #keithrabois #khoslaventures #foundersfund

Harry StebbingshostKeith Raboisguest
Jan 12, 20241h 15mWatch on YouTube ↗

CHAPTERS

  1. 0:00 – 0:53

    Intro

  2. 0:53 – 6:00

    Moving to Khosla from Founders Fund

  3. 6:00 – 10:01

    Founders Fund vs. Khosla Strategy

  4. 10:01 – 14:11

    Investment Regrets at Khosla

  5. 14:11 – 18:00

    Investment Price Sensitivity

  6. 18:00 – 25:29

    Lessons from Investing in Ramp

  7. 25:29 – 31:58

    Ideal Seed Funding

  8. 31:58 – 34:45

    Role of Operators in Venture Capital

  9. 34:45 – 38:19

    Current State of Growth Funds

  10. 38:19 – 43:05

    Strategies with Khosla's $3BN Fund

  11. 43:05 – 45:21

    Khosla Ventures' Youthful Approach

  12. 45:21 – 49:45

    VC Firm Preferences Among Founders

  13. 49:45 – 51:05

    Returning to Khosla and Starting a Fund

  14. 51:05 – 1:00:21

    Current Motivations for Keith

  15. 1:00:21 – 1:07:40

    Timing for Selling Investments

  16. 1:07:40 – 1:15:47

    Quick-Fire Round

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