How Flossy Reached $4M ARR With AI Dental Receptionists
SaaS Interviews with CEOs, Startups, Founders
Release Date: 04/29/2026
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info_outlineHow 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/