The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Mag7 Earnings: Google & Amazon Win - Meta and Microsoft Falter | Anthropic's $50BN Raise & What it Means for a Potential IPO | Atlassian, Twilio and Five9 Beat: The SaaS Apocalypse Over? | Sierra's $15B Valuation: Peak or Potential
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May 7, 2026 
Jason Lemkin, founder of SaaStr and veteran SaaS investor, joins Rory O’Driscoll, a Scale Venture Partners VC focused on software and AI. They dig into Google and Amazon’s standout earnings, Microsoft and Meta’s AI-fueled pressure, Palantir’s enterprise AI surge, whether Twilio and Atlassian signal a SaaS rebound, Anthropic’s massive raise and IPO timing, Sierra’s $15B valuation, and the Musk-Altman courtroom drama.
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Amazon Benefits From the App Explosion
- Jason Lemkin prefers Amazon because AI is driving not only token sales but also an application-building boom that expands AWS demand.
- He puts Meta last because it misses both layers of upside: infrastructure monetization and the explosion of new apps being built on top.
Palantir Fits the Budget Size of Big AI Mandates
- Palantir wins because CEOs need one large AI initiative they can report to boards, and Palantir can credibly absorb $10 million-plus enterprise-wide mandates.
- Rory O’Driscoll says startups often sell point solutions, while Palantir sells transformation at a scale comparable to old IBM-style strategic programs.
Twilio and Atlassian Show Two AI Comeback Paths
- Jason Lemkin says the SaaS apocalypse is not over, but Atlassian and Twilio proved some incumbents can reaccelerate by monetizing AI or winning new AI-native customers.
- His distinction matters: Atlassian sold Rovo into its base, while Twilio also appears to reignite net-new customer growth from AI companies like 11Labs.
