Still the single best 25 minutes on founder sales; drill these fundamentals in your AI roleplay.
How to Sell, by Tyler Bosmeny
Y Combinator 2019
Watch on YouTube youtube.com →Two loops make first-time founders dangerous fast: roleplay before the call, and review after it. AI roleplay bots (Hyperbound, or a well-prompted ChatGPT persona) let you rehearse discovery and objections without burning real prospects, and feeding your recorded calls back through AI shows you your talk ratio, missed questions, and weak answers. Pair the practice with the YC sales talks so you are drilling the right fundamentals, not just getting fluent at bad habits.
16 resources.
Still the single best 25 minutes on founder sales; drill these fundamentals in your AI roleplay.
Y Combinator 2019
Watch on YouTube youtube.com →The Monzo founder's tight process for landing real recurring revenue as a first-time seller.
Y Combinator Aug 2025
Watch on YouTube youtube.com →The ex-Brex CRO's crash course in selling when you are the whole sales team.
Y Combinator May 2024
Watch on YouTube youtube.com →Watch real call teardowns to calibrate what good actually sounds like.
30 Minutes to President's Club 2025
Open youtube.com →Tactical, no-fluff call tactics you can feed straight into your practice reps.
Nick Cegelski and Armand Farrokh 2025
Listen on Spotify open.spotify.com →The practical setup for rehearsing discovery and objections against a realistic AI buyer.
Hyperbound 2025
Open hyperbound.ai →A founder-led-sales case study of the roleplay company itself, double lesson in one read.
Founder Led Sales Stories 2025
Open founderledsalesstories.substack.com →Explains why practice at scale beats manager shadowing, even for a team of one.
Uhubs 2025
Open uhubs.ai →Ready-made scenarios so your first practice session starts in minutes.
Federico Presicci 2025
Open federicopresicci.com →An enablement expert compares the roleplay tools including the free ChatGPT route.
Federico Presicci 2026
Open federicopresicci.com →A wider comparison if Hyperbound's enterprise pricing is out of reach.
PitchMonster 2026
Open pitchmonster.io →Free scripts and frameworks that give your AI coach a quality bar to grade against.
30 Minutes to President's Club 2025
Open 30mpc.com →Six tactics for founders who dread selling, from operators who coached hundreds through it.
First Round Review 2024
Open review.firstround.com →The Founding Sales author's curated reading list, the syllabus behind your AI drills.
Peter Kazanjy 2023
Open kazanjy.svbtle.com →The benchmark to grade your own recordings against after every call.
Salesprep 2025
Open salesprep.ai →The leading purpose-built roleplay bot, trained on real winning calls rather than generic personas.
Hyperbound 2025
Open hyperbound.ai →The same ground, over in Get your first customers, our Starting Up track.