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The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI

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 01:25 SpaceX Completes Acquisition of xAI in $1.25 Trillion Merger 10:39 The Rehabilitation of the IPO and the End of "State Private Forever" 18:13 The 2026 SaaS Massacre: Public Market Collapse 30:15 Next-Gen CRM War: Hubspot Down 50%+ vs Next Gen Heavily Funded 48:10 Microsoft's $360 Billion Market Cap Loss & the Shift in AI Narrative 53:43 Nvidia's Strategic Retreat: The Dispute Over the $100 Billion OpenAI Investment 01:07:10 Waymo Raises $16 Billion at a $110 Billion Valuation 01:23:11 The Launch of OpenClaw & Moltbook: 1.5 Million Agents Join a Social Network ---------------------------------------------------------------------------------------------- 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 #spacex #xai #twitter #elonmusk #microsoft #saas #nvidia

Rory O’DriscollguestJason LemkinguestHarry Stebbingshost
Feb 5, 20261h 37mWatch on YouTube ↗

Episode Details

EPISODE INFO

Released
February 5, 2026
Duration
1h 37m
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 01:25 SpaceX Completes Acquisition of xAI in $1.25 Trillion Merger 10:39 The Rehabilitation of the IPO and the End of "State Private Forever" 18:13 The 2026 SaaS Massacre: Public Market Collapse 30:15 Next-Gen CRM War: Hubspot Down 50%+ vs Next Gen Heavily Funded 48:10 Microsoft's $360 Billion Market Cap Loss & the Shift in AI Narrative 53:43 Nvidia's Strategic Retreat: The Dispute Over the $100 Billion OpenAI Investment 01:07:10 Waymo Raises $16 Billion at a $110 Billion Valuation 01:23:11 The Launch of OpenClaw & Moltbook: 1.5 Million Agents Join a Social Network ---------------------------------------------------------------------------------------------- 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 #spacex #xai #twitter #elonmusk #microsoft #saas #nvidia

SPEAKERS

  • Rory O’Driscoll

    guest

    Venture capital investor focused on software/SaaS and public-market tech analysis.

  • Jason Lemkin

    guest

    SaaS investor and founder of SaaStr, known for SaaS operating and go-to-market insights.

  • Harry Stebbings

    host

    Founder and host of 20VC (The Twenty Minute VC), interviewing leading venture and tech figures.

EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Rory O’Driscoll and Jason Lemkin, The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI explores aI capital hunger reshapes IPOs, SaaS valuations, and agentic future now SpaceX’s acquisition of xAI is framed as Elon Musk “load-balancing” capital needs and as evidence that even top private companies are being pushed back toward public markets to fund AI-scale capex.

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