20VC

Harry Stebbings × Rory

SpaceX’s all-stock Cursor takeover, completed within a week and carrying a breakup fee, highlights AI M&A’s currency and clearance advantages while testing premium pricing against forward revenue.Stripe’s OpenRouter bet monetizes routing complexity but faces model drift, while Workday’s take-private underscores system-of-record durability without guaranteed upsell; AI-budget ceilings and agentic roadmaps remain key risks.

Harry Stebbings × Fred Turner

Curative turned a failed lab-license wind-down into roughly $5 billion of COVID-testing revenue, scaling from 7 to 7,000 employees in nine months through an orthogonal supply chain built for 10x capacity.Its structurally loss-making troughs contrast with Claude agents cutting credentialing to 20 cents and Gwen contracts to $70, making administrative automation an earnings lever incumbents may struggle to copy.

Harry Stebbings × Paul Erlanger

FOMO raised a $75M Series B at a $550M post-money valuation from Index and USV, with founders anchoring the price before receiving a term sheet.Its 17-person, AI-enabled organization has no meetings, 1:1s, or hierarchy, while founder-grade equity aligns a small group for a decade-long build.Pre-IPO perps and thesis-driven trading could define its global wedge, but SpaceX’s retail performance and prediction-market regulation remain key tests.

Harry Stebbings

Anthropic’s filing alongside a $65B raise and Cursor’s potential $60B exit reset startup scale and public-market timing.Token budgets are the battleground: Uber capped spend at $1,500/month, agent-attached software rose, and classic per-seat SaaS weakened.Watch whether tokens reach 33% of engineering compensation, or whether capex intensity and PE software returns constrain the upside.

Harry Stebbings × Sebastian Siemiatkowski

Siemiatkowski argues that near-zero software creation costs and one-click data migration could push threatened SaaS revenue multiples from 5–10x toward utility-like 1–2x, while enterprises reorganize around secure Lego-like components and agents.Klarna’s workforce fell from more than 7,000 to fewer than 3,000, with fewer than 2,000 possible by 2030, but whether AI-driven information compression reduces compute demand or consumer generation overwhelms those savings remains unresolved.

Harry Stebbings

Brex’s $5.15B sale to Capital One resets the comparison for Ramp’s roughly $32B mark: a real-money acquisition applied about seven times revenue to Brex’s roughly $700M, while Discover’s closed network gives Capital One a structural interchange advantage.Anthropic’s inference costs ran 23% above expectations even as gross margin improved to roughly 40%, leaving mid-tier SaaS economics and AI-capex sustainability unresolved.

Harry Stebbings × Alan Chang

Fuse Energy has grown revenue 10x annually—from £2M to £20M and over 200 this year—while raising 70 at a 5 billion valuation.Chang credits speed, quality-engineering hiring, and parallel bets—not capital—while diversified products offset Revolut’s near-zero interchange revenue during COVID lockdowns.The next test is roughly 5x growth, with hiring speed the stated constraint and UK planning barriers, grid bottlenecks, and renewable intermittency worth monitoring.

Harry Stebbings

SpaceX combines exceptional rocket and Starlink businesses with roughly $15 billion of revenue growing about 30%, yet its $800 billion mark exceeds 40x run-rate revenue.The valuation embeds an Elon premium and leaves downside if growth decelerates, while 2026 IPOs from SpaceX, Anthropic, and Databricks could unlock liquidity without fixing private-market overpricing.

Harry Stebbings × Tarek Mansour

Kalshi’s $1 billion raise at an $11 billion valuation funds global marketing, hiring and regulated-exchange reserves as the already profitable company expands beyond roughly 110–120 people.Sports currently drives volume, but Tarek frames markets as an attention-linked media layer spanning elections, Fed decisions and culture, with CNN and CNBC extending distribution.The October 7, 2024 legal victory and Polymarket rivalry validated the category, while organizational scaling, marketing and trust-based neutrality remain key execution and regulatory moats.

Harry Stebbings

OpenAI’s restructuring removes its corporate obstacle to raising another $100–200 billion and moves a potential IPO one enormous step closer, while Microsoft retains IP rights, revenue share, and prospective Azure business. a16z’s $10 billion scale supports optioning and follow-ons, but Mercor’s $350 million round at a $10 billion valuation depends on three to five more years of AI CapEx hypergrowth despite pass-through margins and two customers reportedly exceeding 50% of revenue.