Fundraising Strategies

ClickHouse CEO: AI Margins Need to Improve | Revenue Concentration Should be a Concern

Aug 31, 2026 · 1:05:57

Aaron Katz, co-founder and CEO of ClickHouse, tells Harry Stebbings the AI cycle is 'just getting started' — revenue growth is unprecedented, but the biggest risk is revenue durability because agentic apps have low switching costs. He accepts lower gross margins if expansion is possible, measures AI token spend by ROI, and predicts agents will have identities, budgets, and pick their own infrastructure. He argues open-weight models won't win the enterprise over trust concerns, and sees enterprises moving back on-prem. ClickHouse revenue went 0, 12, 50, 200, finishing north of 500 this year, with >200% NDR; Katz would take the under on $1B ARR by December 2027. He calls the $2B Series B with no product the priciest round; revenue concentration matters — AI customers are under 12% of revenue.

Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated

Aug 27, 2026 · 1:26:44

Jason Lemkin, Rory O’Driscoll and Harry Stebbings say the AI boom now depends on Nvidia and hyperscalers financing frontier models, as shown by Nvidia's $6B Poolside purchase and $1B at a $12B pre-money valuation. They dissect OpenAI's promised 2027 IPO, arguing it has no choice as Anthropic outraces it and 'it's all about code'; they call Anthropic's $30T TAM claim delusional and OpenAI's $200 plan a losing consumer business. Also covered: Mercor's $20B round, Hugging Face's $13B sale risk, Citadel unwinding 80% of Leopold's fund, Stripe's 41% growth, agents' data leaks, and why customer support, humanoid robotics and AI services are the dumbest categories. Their verdict: we're less than a third of the way through the cycle and addicted to tokens.

Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?

Aug 20, 2026 · 1:17:47

Harry Stebbings, Jason Lemkin and Rory O'Driscoll analyze SpaceX's $60B Cursor takeover, Stripe's $7B OpenRouter deal, Anthropic's first profit, Silver Lake's $43B Workday bid and Lovable's $13.3B round, arguing all reward speed and growth over margin. Musk got Cursor at ~10x forward revenue; Microsoft, not Meta, is the real loser. OpenRouter is a niche that may vanish in five years, yet could become 20-30% of Stripe revenue. Anthropic's first profit on $11.5B Q2 revenue was inevitable at ~40% gross margin; only 2027-28 projected revenue matters for its IPO. Workday is a 5.3x-revenue system-of-record LBO baseline versus 70x trailing for OpenRouter, and Higgsfield's $5.5B and Lovable's $13.3B are compared to Cursor, with Lovable 'not radically off' as AI apps accrete moats.

Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash

Aug 17, 2026 · 1:09:44

In a rare interview, Uber President and COO Andrew Macdonald tells 20VC host Harry Stebbings that autonomy is existential for ride-hailing and distribution beats superior technology. He says Uber One is the most efficient long-term lever — membership beats price incentives — and admits he was wrong to resist it. On AI, Uber blew through a year's budget in four months because usage is vertical; ROI is real but hard to quantify, so he advises combining compute and headcount budgets. Recounting Uber China, Uber burned $52 million a week on subsidies before exiting to Didi, a deal he calls successful. He also explains the Delivery Hero acquisition, why Uber Eats trails DoorDash, and leadership lessons from Travis Kalanick and Dara Khosrowshahi.