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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 ↗

At a glance

WHAT IT’S REALLY ABOUT

AI capital hunger reshapes IPOs, SaaS valuations, and agentic future now

  1. 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.
  2. The panel argues public SaaS is facing a “massacre” driven less by churn spikes and more by structural growth deceleration, seat compression, budget diversion to AI, and a valuation reset toward free-cash-flow multiples net of dilution.
  3. Venture and public markets are said to be bifurcating: companies either sustain extreme growth/acceleration or become effectively unfundable/uninvestable, changing how quickly investors and founders abandon slow trajectories.
  4. Microsoft’s $360B one-day market-cap drop is interpreted as a narrative shift: strong corporate development around OpenAI but weak owned AI products/models, plus investor concern that OpenAI-linked Azure RPO may not translate into profitable revenue.
  5. NVIDIA–OpenAI investment ambiguity and the Waymo mega-round illustrate a “dispersion” market where capital concentrates in perceived future-defining winners despite weak current revenue multiples, while agents (OpenClaw/Moltbook) hint at powerful—yet risky—agent-to-agent networks.

IDEAS WORTH REMEMBERING

5 ideas

AI scale is forcing a return to public markets—even for elite private companies.

They argue the planet’s private capital is insufficient for data-center/compute spend, pushing companies like Anthropic (IPO talk) and indirectly OpenAI/xAI toward public-market access; the SpaceX–xAI combination is treated as a capital-structure maneuver as much as an industrial one.

The “SaaS massacre” is primarily a growth-and-attention problem, not immediate churn collapse.

For systems of record (e.g., ServiceNow/SAP/Oracle), churn may remain stable, but new logo growth slows as markets saturate and CIO mindshare/budgets shift to AI; seat reductions at renewals amplify SMB pain.

Valuation floors appear only when markets price software like cash-flow assets—net of dilution.

Rory’s “bottom” framework is a shift from revenue multiples that ignore losses/SBC to free-cash-flow multiples that explicitly account for ongoing dilution, implying longer resets for decelerating software names.

Venture incentives now reward faster triage—sometimes at the expense of salvage value.

Harry and Jason describe a “heat-seeking missile” partnership dynamic where opportunity cost (missing the next hyper-grower) drives earlier write-offs, while Rory cautions that abandoning five ‘dogs’ hoping for one 10–20x can backfire in weaker vintage outcomes.

Next-gen CRM only works if it truly replaces labor, not if it’s “old CRM + AI sprinkles.”

They reconcile HubSpot/Salesforce low public multiples with high private CRM funding by distinguishing agentic systems that generate pipeline/bookings (easy to sell at high ACVs) from mere workflow replicas; churn risk remains high when promises don’t match each customer’s go-to-market reality.

WORDS WORTH SAVING

5 quotes

What you just saw is the rehabilitation of the IPO, and I'm gonna call it the end of stay private forever.

Rory O’Driscoll

Compute and revenue have a one-to-one correlation, so as long as that holds, it makes sense to consume every single penny of capital on all of planet Earth.

Jason Lemkin

Inference is the new sales and marketing.

Jason Lemkin

The good news is I believe in a balanced scorecard. The bad news is revenue growth rate is 95% of the balance.

Rory O’Driscoll

If you look at the basket of the top 25 public software stocks, every quarter their growth rate declines. Every single quarter, right? ... that is a slow death. That is dying of cancer in 20 years.

Jason Lemkin

SpaceX–xAI $1.25T merger mechanics and dilutionIPO reopening driven by AI capital intensityCompute/inference as the new growth engineSaaS valuation reset to FCF multiples and dilution awarenessCRM disruption via agentic “do the work” productsMicrosoft’s AI product gap vs OpenAI ownershipNVIDIA–OpenAI investment ambiguity and circular capitalWaymo’s robotaxi economics and cost-structure constraintsOpenClaw/Moltbook agent networks, virality, and security

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