20VC

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.

Harry Stebbings × Cliff Weitzman

Speechify expects token spending to exceed engineering salaries next year, with great companies reaching that point in 3 years.It tests 1,000 AI-generated ads daily plus 8,000 human creatives monthly on proprietary tooling and is among 200 companies provisioned for OpenAI ads.Single-digit inference costs versus Eleven Labs’ $70–100 support profitability, but undisclosed valuation and the OpenAI-Anthropic contest remain key watchpoints.

Harry Stebbings × Andrew Dudum

Hims & Hers is down 66% in six months to a $4.35B market cap on over $2.3B of revenue, while Andrew Dudum says weight loss remains one of a dozen clinical categories, not the core business.Its consumer-platform model is reshaping pharmaceutical distribution, using lower-priced GLP-1 access, AI-enabled productivity, and loss-leading diagnostics to build a broader healthcare front door; retention decay remains the key risk to monitor.

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 × Severin Hacker

Duolingo used AI to add 148 courses in one year after taking 12 years to build its first 100, moving toward real-time personalized exercises while humans retain curriculum control.Its competitive evidence remains retention built through thousands of A/B tests, while AI support and content generation improve unit economics; OpenAI's motivation-based threat, European funding constraints and public-market demands for predictability remain unresolved risks.

Harry Stebbings × Ernest Garcia

Carvana’s refusal to become a software layer preserved vertical control of logistics, reconditioning, finance, and customer experience, but added at least one near-death experience.With AI the relatively weakest layer, infrastructure that “clearly supports 3 million” cars, and focus shifting from profitability back to growth, execution and balance-sheet cushion remain key watchpoints.

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 × Solly Solomou

Solly Solomou turned a “low thousands” Facebook-page acquisition into a profitable public company with 500 people, over 500 million followers and 3,000-plus views every second, while combining advertising with youth-culture consultancy.LADbible’s delayed US expansion, possible dual listing and TikTok Shop’s projected one trillion market frame the next growth phase, alongside unresolved questions around culture, AI discovery and platform competition.

Harry Stebbings × Dan Gill

Carvana’s journey from a $2BN IPO to $60BN, down to $500M and back to $50BN reflects a model built to capture financing and other transaction profit pools around a commodity product.Vertical integration, 60% finance attach, paid long-distance shipping, and eight-team prioritization improved unit economics, while deterministic systems create an AI advantage; investors can monitor whether logistics scale and OEM distribution ambitions widen the flywheel.