Traynor on growing Fin and why selling AI products is genuinely hard, from a founder who bet the company on it.
A Cheeky Pint with Intercom Cofounder Des Traynor
Cheeky Pint (John Collison, Stripe) 2025
Watch on YouTube youtube.com →Users do not care that a feature uses AI; they care whether it removes a slow, painful, judgment-heavy step from their day. Start from a specific friction point in your existing workflow, not from the technology, and be honest about whether AI is a checkbox for investors or a real 10x on time saved. The strongest AI features sell the finished work (a resolved ticket, a drafted document), not a fancier tool.
20 resources.
Traynor on growing Fin and why selling AI products is genuinely hard, from a founder who bet the company on it.
Cheeky Pint (John Collison, Stripe) 2025
Watch on YouTube youtube.com →How Superhuman designed Summarize and Instant Reply so users send 72% more email per hour.
Upfront Ventures Mar 2024
Watch on YouTube youtube.com →Four consumer investors on why subtle product choices now matter more than raw model quality.
a16z (Anish Acharya, Olivia Moore, Justine Moore, Bryan Kim) Dec 2025
Open a16z.com →Veteran product leaders on AI at the core versus AI at the edge, the distinction most founders miss.
Lenny's Podcast Sep 2025
Open lennysnewsletter.com →YC group partners distil patterns from hundreds of AI startups they funded, including what users reward.
Y Combinator (Lightcone Podcast) 2024
Open ycombinator.com →Vohra applies his famous product-market-fit engine to deciding which AI features earn their place.
Product School (Rahul Vohra) 2025
Open productschool.com →A clear decision framework for the exact moment every founder faces: bolt on AI, ignore it, or rethink the product.
Vasil (Founder Prompts) 2025
Open founderprompts.com →The UX research heavyweights on why novelty chatbots harm products and what user value actually looks like.
Nielsen Norman Group 2024
Open nngroup.com →VC-grade market data on which AI product categories are actually winning, so you bet where demand is proven.
Bessemer Venture Partners 2025
Open bvp.com →A blunt scorecard of which AI product ideas changed user behaviour and which quietly flopped.
a16z Dec 2025
Open a16z.com →The canonical reframe: sell the finished work, not a 15% productivity tool, and your market gets 10-50x bigger.
Sarah Tavel (Benchmark) Aug 2023
Open sarahtavel.com →Tavel pressure-tests her own thesis with what she has since seen in real AI startups.
Sarah Tavel (Benchmark) 2024
Open sarahtavel.com →The full transcript, including the memorable rule against force-feeding users AI they never asked for.
Cheeky Pint (Stripe) 2025
Open cheekypint.substack.com →A rare honest post-mortem from a product team on which AI bets worked in production and which had to be killed.
Hex 2024
Open hex.tech →Includes Carta's hard-won lesson on separating model behaviour from UX when shipping AI features.
First Round Review Dec 2025
Open review.firstround.com →A top consumer investor answers the exact question, drawn from hundreds of a16z Speedrun applications.
Andrew Chen (a16z) May 2025
Open x.com →A data company's candid recap of which of its own AI features users adopted and why.
Amplitude 2025
Open amplitude.com →A case study of an incumbent rebuilding around one AI feature that customers demonstrably pay for.
Bessemer Venture Partners 2025
Open bvp.com →The sharpest counterargument you will read; know the backlash before you ship an unwanted AI feature.
Ted Gioia (The Honest Broker) 2025
Open honest-broker.com →A respected discovery coach documents what surprised her when she actually built an AI product herself.
Teresa Torres (Product Talk) 2024
Open producttalk.org →The same ground, over in Build the product, our Starting Up track.