Harry Stebbings

Harry Stebbings × Jean-Denis "JD" Grèze

Town converts more than 15% of trial users to paid and generates over $700 per user annually despite losing 30% at its mandatory email-and-calendar gate, while teams spend at least $75K per engineer on AI tools.Its agent-to-agent network effect could make team switching difficult, but zero pricing power at the frontier leaves economics dependent on whether inference costs fall and how much workload remains frontier.

Harry Stebbings × Cliff Weitzman

Speechify’s owned-GPU strategy compares $35,000–50,000 annual H100 rental with roughly $30,000 to buy, potentially lowering compute costs.NVIDIA’s deal with Blackstone, BlackRock, Apollo and Goldman Sachs could create a liquid secondary market and price floor through buybacks up to 25% of GPU value.Weitzman calls missing B2B his biggest strategic mistake; Simba 3.2 costs $10 per million characters versus ElevenLabs’ $100, but execution against an “unstoppable” rival remains unresolved.

Harry Stebbings

NVIDIA delivered a record $96.2B quarter and guided to 70% growth for the fiscal year ending January 2028, with end-user demand and share loss the key risks.The reported near-$12.9B Hugging Face deal, not finalized or confirmed, would reinforce open-source compute economics and NVIDIA’s push to win every segment.Agents are becoming software buyers, supporting the cases for Clay at $7B and Linear at $2.5B, while cyber exposure and reward hacking remain unresolved.

Harry Stebbings × Aaron Katz

Aaron Katz rejects the AI-bubble thesis, citing unprecedented adoption and revenue acceleration.ClickHouse grew from zero to over 500 in revenue, with over 99% gross retention and over 200% net dollar retention.AI customers remain below 12% of revenue, but agentic applications’ low switching costs leave durability unresolved.

Harry Stebbings × Eno Reyes

AI may be priced by outcomes rather than tokens, favoring open models for commodity work and proprietary post-trained specialists for high-value workflows.That challenges frontier-model TAM as Anthropic’s $2T framing depends on Claude Code amid fierce developer-tool competition, model lock-in and margin risk; watch whether the harness becomes the durable application layer.

Harry Stebbings

NVIDIA’s $6B Poolside licensing deal, $1B investment at a $12B pre-money valuation, and 109-engineer transfer show frontier-model capital intensity pushing capable startups toward strategic “failure” exits.OpenAI’s 2027 IPO appears compelled by Anthropic’s $60B mid-year run rate versus under $30B this year, while enterprises’ $200–400B AI-spending capacity remains the key test.

Harry Stebbings × Julien Bek

Sequoia’s hunter culture rewards conviction over consensus: Citadel Securities came from years of persistence, while a one-vote SpaceX proposal became one of the firm’s best investments.After underestimating Anthropic and later investing $2.5B, Julien Bek sees exponential AI, agent traffic reaching parity with humans, and outcome-priced Sierra as major signals, while warning that new AI labs face brutal selection risk.

Harry Stebbings × Jerry Murdock

Murdock places a potential AI-bubble correction between October 2026 and March 2027, citing hyperscaler debt, narrow private-debt spreads, and Japan’s Treasury sales as possible triggers.At least half of neoclouds could disappear within 36 months, while Fireworks stands out on capital efficiency; OpenRouter’s 5% markup may face disruption within three to five months, with sandbox security unresolved.

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 × Andrew MacDonald

Uber’s AI efficiency story is less about line-item ROI than tighter headcount constraints: a 30-person team cut pricing allocation from 15 hours to 2 and marketing QA from two weeks to two days.MacDonald calls autonomy existential and Uber One a compounding consumer lever, while cheaper modes, the pending Delivery Hero deal, and AV dollar-share concentration shape the next growth and competitive tests.