20VC

Harry Stebbings × Mike Mignano

With OpenAI, Anthropic, and xAI building the infrastructure layer, Mike Mignano sees the application layer entering its value-creation window, though the buildout is not finished.Labs may lose the app layer to regulatory clearance, organizational context, and focused distribution, while startups can maximize token spend and exploit the 70% of markets left beyond the winner.The key variables are recursive self-improvement versus model commoditization, agent trust, routing economics, energy demand, and whether fund size matches repriced ownership and cash-on-cash math.

Harry Stebbings × Josh Browder

Josh Browder’s one-man accelerator combines sub-$5M pre-seed entry, founder cohabitation and hands-on screening, producing 33 deals in fund four and a Micro 1 return well over a thousand X.His broader signals are that framing can flip funding outcomes, he thinks Anthropic will get to a trillion in revenue, and Nevada land serves as his hedge against both post-economic abundance and tech going to zero.

Harry Stebbings × Jake Paul × Geoffrey Wu

Anti-Fund’s core bet is that attention, cultural fluency, and response-generating access will appreciate as AI commoditizes coding and financial analysis.Its $30 million vehicle targets roughly ten exceptional late-stage companies, with an ambition to manage $10–$20 billion and extend the distribution advantage into public markets.

Harry Stebbings

AI-native firms below $100M ARR averaged -126% FCF margins versus -56% for non-AI, making burn multiple useful but vulnerable to churn, CapEx and runway distortions.Public software’s valuation reset remains unresolved: 30%-growth companies trade around 15–20× revenue versus a historical 6–7× NTM benchmark.Fivetran’s dbt acquisition, at roughly $400M and $100M ARR, signals consolidation’s potential to turn a crowded unicorn backlog into IPO-scale businesses.

Harry Stebbings

GPT-5’s underwhelming launch shifts attention from AGI speculation to software economics, with pricing 8–10x below Anthropic’s high-end token loads pressuring coding revenue and benefiting Cursor.AI CapEx is rewarding co-attached suppliers as Datadog posted a record $260M net-new ARR quarter yet fell 10%, while Palantir’s 45% growth and $843M US commercial bookings confront a roughly 120x-revenue valuation.

Harry Stebbings × Johannes Reck

GetYourGuide’s near-failure after its 2013 Series A shows the cost of VC-driven expansion, senior hiring and diluted focus.Reck’s reversal—internal promotions, core-market focus and preserving engineers through COVID—preceded 10x growth, profitability and five-times pre-pandemic scale.SoftBank’s $450M round proved existential six months before COVID, while Europe’s growth capital, visas and AI productivity remain key variables.

Harry Stebbings × Niklas Östberg

Food delivery is a scaled, multi-winner market where execution drives roughly 80% of outcomes, challenging winner-take-all assumptions.Delivery Hero’s logistics bet and Germany sale supported international execution, while cohort data across roughly 70 markets pointed to 10–13% margins; Gorillas’ nearly $200 million loss and COVID-era debt choice leave capital allocation and quick-commerce economics as key risks.

Harry Stebbings × Shervin Pishevar

Pishevar alleges Benchmark engineered Travis Kalanick’s 2017 removal, destroying value; his counterfactual is a trillion-dollar Uber versus Dara’s $175bn outcome.The live catalyst is a pending appeal over Fusion GPS discovery, while tokenized venture and AI-quantum claims remain high-upside but unverified possibilities.