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Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors

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. 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. ----------------------------------------------- Timestamps: 00:00 Intro 01:28 OpenAI Misses Growth Targets: Is This a Real Problem? 07:20 The Rise of AI Agents: Why Humans No Longer Pick Models 18:45 $45B Floods into Anthropic from Google & Amazon 27:11 "Compute ≠ Revenue": The First Crack in the AI Business Model 30:55 Why Google May Be the Biggest Winner in AI Infrastructure 34:59 China Blocks $2B Manus Deal 42:19 Thoma Bravo Hands Medallia to Creditors: $5B Wiped Out 01:06:28 The Collapse of Private Equity Exit Routes in VC ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: https://x.com/harrystebbings Follow Jason Lemkin on X: https://x.com/jasonlk Follow Rory O’Driscoll on X: https://x.com/rodriscoll 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/con... ----------------------------------------------- Legal Disclaimer: The content of this podcast is for informational and entertainment purposes only and does not constitute financial or investment advice. Any discussion of stocks, public markets, or investment strategies reflects the personal opinions of the speakers and should not be relied upon when making investment decisions. Figures, valuations, and financial data referenced may be estimates or subject to error. Always consult a qualified financial adviser before making any investment decision. The views expressed are those of the individual speakers and do not represent the views of 20VC or its affiliates. ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #anthropic #openai #thomabravo #manus #ai #aiagents

Rory O’DriscollguestHarry StebbingshostJason Lemkinguest
Apr 30, 20261h 28mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
April 30, 2026
Duration
1h 28m
Channel
The Twenty Minute VC
Watch on YouTube
▶ Open ↗

EPISODE DESCRIPTION

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. 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. ----------------------------------------------- Timestamps: 00:00 Intro 01:28 OpenAI Misses Growth Targets: Is This a Real Problem? 07:20 The Rise of AI Agents: Why Humans No Longer Pick Models 18:45 $45B Floods into Anthropic from Google & Amazon 27:11 "Compute ≠ Revenue": The First Crack in the AI Business Model 30:55 Why Google May Be the Biggest Winner in AI Infrastructure 34:59 China Blocks $2B Manus Deal 42:19 Thoma Bravo Hands Medallia to Creditors: $5B Wiped Out 01:06:28 The Collapse of Private Equity Exit Routes in VC ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: https://x.com/harrystebbings Follow Jason Lemkin on X: https://x.com/jasonlk Follow Rory O’Driscoll on X: https://x.com/rodriscoll 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/con... ----------------------------------------------- Legal Disclaimer: The content of this podcast is for informational and entertainment purposes only and does not constitute financial or investment advice. Any discussion of stocks, public markets, or investment strategies reflects the personal opinions of the speakers and should not be relied upon when making investment decisions. Figures, valuations, and financial data referenced may be estimates or subject to error. Always consult a qualified financial adviser before making any investment decision. The views expressed are those of the individual speakers and do not represent the views of 20VC or its affiliates. ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #anthropic #openai #thomabravo #manus #ai #aiagents

SPEAKERS

  • Rory O’Driscoll

    guest

    Venture capitalist and recurring 20VC panel guest focused on enterprise/SaaS investing.

  • Harry Stebbings

    host

    Founder and host of 20VC (The Twenty Minute VC).

  • Jason Lemkin

    guest

    Founder of SaaStr and SaaS-focused investor/commentator.

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Harry Stebbings, Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors explores aI compute economics shift as agents reshape software, exits, PE OpenAI’s reported growth miss is framed as a backward-looking reflection of last year’s model leadership gap versus Anthropic, rather than a definitive signal of long-term weakness.

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