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Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19

Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. ----------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 01:25 Databricks hits $100B: Bubble or just the beginning? 04:14 Is Databricks actually undervalued at 25x revenue? 13:27 Can Andreessen’s Databricks bet return $30B+? 19:13 Is the return of Chamath’s SPACs the ultimate bubble signal? 29:24 Should OpenAI staff be cashing out billions in secondaries? 35:44 Founder raises $130M… then walks away. Is this the new normal? 38:40 Nubank’s $2.5B profit: The best FinTech in the world? 52:36 CoreWeave takes on $11B in debt: smart bet or ticking time bomb? 01:12:07 Will AI spend really hit trillions—or is it all hype? 01:26:43 Kalshi Quick-Fire Round ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #chatgpt5 #databricks #datadog #openai #coreweave #nubank

Jason LemkinguestHarry StebbingshostRory O’Driscollguest
Aug 21, 20251h 34mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
August 21, 2025
Duration
1h 34m
Channel
The Twenty Minute VC
Watch on YouTube
▶ Open ↗

EPISODE DESCRIPTION

Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. ----------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 01:25 Databricks hits $100B: Bubble or just the beginning? 04:14 Is Databricks actually undervalued at 25x revenue? 13:27 Can Andreessen’s Databricks bet return $30B+? 19:13 Is the return of Chamath’s SPACs the ultimate bubble signal? 29:24 Should OpenAI staff be cashing out billions in secondaries? 35:44 Founder raises $130M… then walks away. Is this the new normal? 38:40 Nubank’s $2.5B profit: The best FinTech in the world? 52:36 CoreWeave takes on $11B in debt: smart bet or ticking time bomb? 01:12:07 Will AI spend really hit trillions—or is it all hype? 01:26:43 Kalshi Quick-Fire Round ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #chatgpt5 #databricks #datadog #openai #coreweave #nubank

SPEAKERS

  • Jason Lemkin

    guest

    SaaS investor and operator, founder of SaaStr.

  • Harry Stebbings

    host

    Founder and host of 20VC, venture capital interviewer and commentator.

  • Rory O’Driscoll

    guest

    Venture capitalist and tech investor.

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Jason Lemkin and Harry Stebbings, Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 explores aI boom fuels mega-valuations, debt bets, and fintech breakouts worldwide Databricks at roughly $100B is framed as potentially “reasonable” or even undervalued given ~4B ARR and ~50% growth, but only if growth persistence holds long enough to grow into the multiple.

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