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Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down

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 01:06 Mag7 Earnings: The "Super Bowl" of Tech Results 04:59 Google's Cloud Explosion & The AI Search "Disruption" That Never Came 14:46 Microsoft's $190B Bet: Is AI the Only Thing Keeping Growth Flat? 21:24 Meta's $150B Future Bet vs Wall Street's Need for Spreadsheets 28:14 Palantir's Home Run: Why Big Companies Spend Big Money on AI 39:42 Apple's Quiet Consistency & The Stealth Inflation of Memory Chips 42:37 The SaaS Apocalypse Over? Atlassian and Twilio Lead the Re-acceleration 01:04:17 Anthropic's $50B Raise & The Math Behind Token vs. Salary Spend 01:10:57 Sierra's $15B Valuation: Replacing the $400B Customer Service Labor Market 01:19:30 Musk vs Altman Trial 01:23:49 The End of Managers? Brian Armstrong & The Rise of the "Individual Contributor" ---------------------------------------------------------------------------------------------- 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 #mag7 #palantir #anthropic #sierra #google #microsoft #meta #apple

Rory O’DriscollguestHarry StebbingshostJason Lemkinguest
May 7, 20261h 36mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Mag7 earnings reveal AI capex winners, SaaS rebound, private-market frenzy

  1. Alphabet is framed as the earnings-season standout as Search resilience and surging Cloud backlog/capex signal that incumbents are “leaning in” rather than being disrupted by LLMs.
  2. Microsoft and Meta are contrasted on AI spend: Microsoft’s growth is portrayed as heavily AI-dependent while Meta’s larger capex is punished because the ROI path is harder to model in spreadsheets.
  3. Palantir’s blowout quarter is interpreted as evidence that enterprises want large, CEO-level AI transformation programs and will pay $10M+ checks to credible, implementation-heavy vendors.
  4. Public SaaS shows signs of life (Atlassian, Twilio) but the hosts argue “SaaSpocalypse” isn’t broadly over; winners either monetize AI into the base and/or add net-new customers, especially near infrastructure.
  5. Private markets look overheated yet rationalized by AI capex math: Anthropic raising huge sums reduces IPO urgency, while Sierra’s premium valuation bets on labor replacement and category expansion beyond customer support software.

IDEAS WORTH REMEMBERING

5 ideas

The Mag7 are entering an unusually aggressive, incumbent-led investment regime.

The discussion characterizes the quarter as “the most aggressive” because the largest firms are simultaneously accelerating growth and expanding capex fast enough to consume much of free cash flow, aiming to prevent disruption rather than respond defensively.

Google’s win is about ‘everything working at once,’ not just AI.

They highlight Search/ads staying strong despite LLM fears, while Cloud backlog nearly doubling signals sustained demand; the main constraint becomes allocation of GPUs/compute across internal and customer needs.

Hyperscalers’ AI revenue is still largely ‘selling picks and shovels’ to LLM labs.

A core critique is that Big Tech growth is boosted by hosting/training spend and reselling tokens, while foundational-model IP value may accrue disproportionately to OpenAI/Anthropic—creating uncertainty about who ultimately captures the profit pool.

Microsoft’s valuation sensitivity to AI is higher than many assume.

Rory argues that excluding AI-related growth, Microsoft’s broader business looks flat, implying that if the AI bet disappoints, growth expectations—and therefore the equity multiple—could reset meaningfully even if the company remains profitable.

Meta is penalized because its AI capex is harder to tie to near-term, attributable revenue.

Unlike Google/Amazon, Meta’s justification is framed as qualitative (future experiences, chatbot-native social) or indirect (ad lift) and therefore resists the Wall Street spreadsheet approach to ROI, increasing the discount rate investors apply.

WORDS WORTH SAVING

5 quotes

This is leaning in like you've never seen leaning in before. This is the top of the distribution pulling away.

Rory O’Driscoll

Without the AI initiative, Microsoft the corporation is flat revenue.

Rory O’Driscoll

Anyone on LinkedIn that talks about their team, fire them. "My team this." They're all so precious about their team. Lead from the effing front with AI.

Jason Lemkin

Two of them full-time, two full-time human equivalents, $254 a month.

Jason Lemkin

There is no such thing as too much cash on your balance sheet. There is no such thing.

Rory O’Driscoll

Mag7 earnings and AI capex arms raceGoogle Cloud backlog growth vs AI-search disruption narrativeMicrosoft growth attribution to AI and capex riskMeta capex skepticism and “unmodelable” ROIPalantir enterprise AI transformation spend and compressed buying cyclesSaaS re-acceleration: Atlassian vs Twilio dynamicsAnthropic raise, IPO timing, and token-vs-salary economicsSierra valuation and AI agents replacing CX laborMusk vs Altman trial: distillation, standing, and statute of limitationsCoinbase/Brian Armstrong and the shift from managers to ICs with AI

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