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Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero?

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 01:16 Anthropic's $10 Billion Fundraise 08:59 Has Claude Code Beaten Cursor Already 16:08 OpenAI Could Still Go to Zero 25:58 Andreessen Horowitz's $15 Billion Fundraise 46:33 The Middle is Dead: Boutique vs. Large Platforms in Venture 53:27 The Future of Venture Capital 01:12:14 The Impact of Wealth Taxes on the Industry ---------------------------------------------------------------------------------------------- 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... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #anthropic #openai #claude #cursor #elevenlabs #a16z

Rory O’DriscollguestHarry StebbingshostJason Lemkinguest
Jan 15, 20261h 30mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
January 15, 2026
Duration
1h 30m
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 01:16 Anthropic's $10 Billion Fundraise 08:59 Has Claude Code Beaten Cursor Already 16:08 OpenAI Could Still Go to Zero 25:58 Andreessen Horowitz's $15 Billion Fundraise 46:33 The Middle is Dead: Boutique vs. Large Platforms in Venture 53:27 The Future of Venture Capital 01:12:14 The Impact of Wealth Taxes on the Industry ---------------------------------------------------------------------------------------------- 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... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #anthropic #openai #claude #cursor #elevenlabs #a16z

SPEAKERS

  • Rory O’Driscoll

    guest

    Venture capitalist (GP at Scale Venture Partners) focused on software investing and fund strategy.

  • Harry Stebbings

    host

    Founder and host of 20VC, interviewing leading investors and operators in tech.

  • Jason Lemkin

    guest

    Founder of SaaStr and an early-stage SaaS investor and operator.

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Harry Stebbings, Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? explores aI mega-rounds reshape venture capital: scale, risk, and policy shocks Anthropic’s reported $10B raise is framed as potentially pre-IPO and arguably rational on forward revenue math if current extreme growth persists another year.

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