Episode
How Flossy Reached $4M ARR With AI Dental Receptionists
- Published
- Apr 29, 2026
- Duration seconds
- 1060
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Summary
How do you survive shutting down during the pandemic, pivot a heavily funded business model, and rebuild a team of 8 into a $4M ARR AI powerhouse? Miles Beckett is the CEO of Flossy, a verticalized AI receptionist that automates patient booking and engagement for dental practices. After successfully building and exiting two previous startups for tens of millions, Miles raised a $15M Series A for a dental discount plan. When the market shifted, he pivoted the company entirely to voice AI, made hard cuts to the team, and found explosive product-market fit. Today, Flossy is growing 60 to 70 percent month over month. You'll learn: Why vertical AI agents beat general tools like Intercom How to sell $500/month software to PE-backed roll-ups The reality of firing 30 people to save a company's burn rate How a $1 million breakup fee saved a past acquisition deal Why they rejected a theoretical $40 million buyout The math behind adding $100,000 in new ARR each month How they used a $3M seed round to survive 2020 lockdowns The mechanics of multi-location enterprise SaaS deals Miles is a seasoned operator who previously built and sold Equal to Everyday Health for $30M, and Silver Sheet to AMN Healthcare, before diving into the dental tech space. Watch this episode on YouTube: https://www.youtube.com/watch?v=U2RAjHVdHZM Connect with Miles: https://www.flossy.com/ Connect with Nathan: https://founderpath.com/