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Wall St's $725BN AI Question | The Rise of Open Source & How it Threatens OpenAI & Anthropic

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 01:09 Google Loses Two Generational Scientists in 48 Hours to Anthropic 13:28 Why Being #3 in AI Is the Most Dangerous Position 18:00 DeepSeek's $7.4B Series A at a $50B Valuation: Is China Winning? 29:00 Wall St’s $725B AI Question: Who's Actually Going to Pay for AI? 49:09 Gross Margin Is Now the New Growth 53:00 Menlo Ventures Raises $3B: Why Not More After the Anthropic Win? 1:04:30 Accenture Plummets 19%: Why AI Is Destroying the Consulting Business 1:12:22 Work From Home Is White Collar Fraud 1:18:10 OpenAI Launches the Jalapeño Chip 1:19:07 Open Source Is Hollowing Out the Middle of the AI Market ---------------------------------------------------------------------------------------------- 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 #deepseek #wallstreet #google #openaichip #jalapeno #saas

Jason LemkinguestHarry StebbingshostRory O’Driscollguest
Jun 25, 20261h 28mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
June 25, 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 01:09 Google Loses Two Generational Scientists in 48 Hours to Anthropic 13:28 Why Being #3 in AI Is the Most Dangerous Position 18:00 DeepSeek's $7.4B Series A at a $50B Valuation: Is China Winning? 29:00 Wall St’s $725B AI Question: Who's Actually Going to Pay for AI? 49:09 Gross Margin Is Now the New Growth 53:00 Menlo Ventures Raises $3B: Why Not More After the Anthropic Win? 1:04:30 Accenture Plummets 19%: Why AI Is Destroying the Consulting Business 1:12:22 Work From Home Is White Collar Fraud 1:18:10 OpenAI Launches the Jalapeño Chip 1:19:07 Open Source Is Hollowing Out the Middle of the AI Market ---------------------------------------------------------------------------------------------- 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 #deepseek #wallstreet #google #openaichip #jalapeno #saas

SPEAKERS

  • Jason Lemkin

    guest

    Founder of SaaStr and a venture investor/operator focused on SaaS and enterprise software.

  • Harry Stebbings

    host

    Founder and host of 20VC, interviewing and debating with leading founders and investors.

  • Rory O’Driscoll

    guest

    Venture investor known for analytical commentary on tech market structure and unit economics.

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Jason Lemkin and Harry Stebbings, Wall St's $725BN AI Question | The Rise of Open Source & How it Threatens OpenAI & Anthropic explores open source AI, soaring capex, and the coming enterprise ROI reckoning Anthropic’s hiring of top DeepMind scientists is framed as both a better research environment and a faster shipping culture that incumbents like Google struggle to match.

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