How to Sell, by Tyler Bosmeny
Still the single best 25 minutes on founder sales; drill these fundamentals in your AI roleplay.
Watch on YouTube youtube.com →
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How can I use AI to practice sales calls and coach myself when I have never sold before?
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.
Go deeper
16 resources.
The sales playbook for founders, Tom Blomfield
The Monzo founder's tight process for landing real recurring revenue as a first-time seller.
Watch on YouTube youtube.com →
Founder-led sales for YC Demo Day, Sam Blond
The ex-Brex CRO's crash course in selling when you are the whole sales team.
Watch on YouTube youtube.com →30MPC on YouTube
Watch real call teardowns to calibrate what good actually sounds like.
Open youtube.com →30 Minutes to President's Club
Tactical, no-fluff call tactics you can feed straight into your practice reps.
Listen on Spotify open.spotify.com →How to use AI for sales roleplay practice
The practical setup for rehearsing discovery and objections against a realistic AI buyer.
Open hyperbound.ai →From boba shops to $1M ARR: how Hyperbound turned AI roleplay into sales success
A founder-led-sales case study of the roleplay company itself, double lesson in one read.
Open founderledsalesstories.substack.com →How Hyperbound is reinventing roleplay practice
Explains why practice at scale beats manager shadowing, even for a team of one.
Open uhubs.ai →9 sales roleplay scenarios with Hyperbound AI bots
Ready-made scenarios so your first practice session starts in minutes.
Open federicopresicci.com →Best AI sales roleplay software, expert review
An enablement expert compares the roleplay tools including the free ChatGPT route.
Open federicopresicci.com →Top 8 tools for sales role-plays: comparison and review
A wider comparison if Hyperbound's enterprise pricing is out of reach.
Open pitchmonster.io →30MPC site: courses and templates
Free scripts and frameworks that give your AI coach a quality bar to grade against.
Open 30mpc.com →Founder-led sales
Six tactics for founders who dread selling, from operators who coached hundreds through it.
Open review.firstround.com →Sales, marketing and recruiting resources for founders
The Founding Sales author's curated reading list, the syllabus behind your AI drills.
Open kazanjy.svbtle.com →Talk-to-listen ratio: what 100k sales calls show
The benchmark to grade your own recordings against after every call.
Open salesprep.ai →Hyperbound: AI sales roleplay and coaching platform
The leading purpose-built roleplay bot, trained on real winning calls rather than generic personas.
Open hyperbound.ai →More in CRM & Sales Calls
- How do founders use AI notetakers and call analysis (Granola, Fireflies, Gong-style tools) to close more deals? 20 →
- Why let AI update the CRM, draft follow-ups, and forecast pipeline? 23 →
- Which AI notetaker should I actually pick: Granola, Fathom, Fireflies, or Otter, and what will it cost? 18 →
- Do I need a CRM at the pre-seed stage, and should I pick an AI-native CRM like Attio over HubSpot or Zoho? 18 →
- How are founders using AI tools like Clay and Apollo to run outbound prospecting and personalized cold email? 20 →
- Do AI SDRs actually work, or are they hype? 16 →
- Is it legal and OK to record sales calls with an AI notetaker? 17 →
- How do founders turn sales call transcripts into product insights and sharper messaging? 19 →
- How do founders use AI for pre-call research and meeting prep? 18 →
- How can AI help me qualify and score leads so I chase the right deals? 19 →
- What does an affordable AI sales stack look like for an early-stage Indian startup? 19 →
Also in Starting Up
The same ground, over in Get your first customers, our Starting Up track.
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