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How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price?

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 00:53 Did Jason Just Kill Replit? 03:49 Why Claude Lies To You and Cannot Be Trusted 06:28 You Cannot Trust Agents. Period. 08:48 Why Windsurf Was Dead Without Claude 11:43 Cursor vs. Lovable: What’s the Better Bet? 12:49 Should You Still Invest in Cursor at $28B? 20:24 Would You Bet on Anthropic at $100B or OpenAI at $300B? 25:22 Inside OpenAI’s Secret Weapon: The Calvin French-Owen Memo 28:44 Perplexity Just Crushed ChatGPT and Claude 35:08 Figma’s IPO at $16B: Outrageous or Fair Game? 44:36 90% of Seed Funds Are Cooked: Is Rob Go Right? 52:40 How Often Do You Meet a Founder Who Can Return the Fund? 01:16:09 Which Seed Fund Would You Back Today? 01:20:39 Coldplay Concert: Astronomer’s Situation 01:22:55 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 #cursor #windsurf #chatgpt #replit #cloude #loveable #vibecoding #perplexity

Jason LemkinguestRory O’DriscollguestHarry Stebbingshost
Jul 24, 20251h 26mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
July 24, 2025
Duration
1h 26m
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 00:53 Did Jason Just Kill Replit? 03:49 Why Claude Lies To You and Cannot Be Trusted 06:28 You Cannot Trust Agents. Period. 08:48 Why Windsurf Was Dead Without Claude 11:43 Cursor vs. Lovable: What’s the Better Bet? 12:49 Should You Still Invest in Cursor at $28B? 20:24 Would You Bet on Anthropic at $100B or OpenAI at $300B? 25:22 Inside OpenAI’s Secret Weapon: The Calvin French-Owen Memo 28:44 Perplexity Just Crushed ChatGPT and Claude 35:08 Figma’s IPO at $16B: Outrageous or Fair Game? 44:36 90% of Seed Funds Are Cooked: Is Rob Go Right? 52:40 How Often Do You Meet a Founder Who Can Return the Fund? 01:16:09 Which Seed Fund Would You Back Today? 01:20:39 Coldplay Concert: Astronomer’s Situation 01:22:55 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 #cursor #windsurf #chatgpt #replit #cloude #loveable #vibecoding #perplexity

SPEAKERS

  • Jason Lemkin

    guest

    Founder of SaaStr and a venture investor focused on B2B SaaS.

  • Rory O’Driscoll

    guest

    Venture capitalist known for enterprise/Series A investing and market/IPO analysis.

  • Harry Stebbings

    host

    Founder of The Twenty Minute VC (20VC) and podcast host interviewing leading investors and founders.

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Jason Lemkin and Rory O’Driscoll, How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? explores aI platform dependency, agent trust risks, plus Figma IPO pricing debate AI coding agents can silently alter production code and data, so “vibe coding” speed creates new security and governance failure modes for non-engineers.

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