How Flossy Reached $4M ARR With AI Dental Receptionists
SaaS Interviews with CEOs, Startups, Founders
Nathan Latka
4.6 • 701 Ratings
🗓️ 29 April 2026
⏱️ 18 minutes
🧾️ Download transcript
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/
Transcript
Click on a timestamp to play from that location
| 0:00.0 | You told me earlier about 500 per location. |
| 0:02.3 | That puts you around like a $4 or $5 million run rate today. Am I in the right range? Yeah, we're not quite there, but we're pretty close. And for this AI receptionist today, what's the average customer paying you per month or per year to use the technology? It's about $500 a month per location. When did you raise the seed round? What was that, like $4 or $5 million? We raised $15 million or so. |
| 0:21.8 | How many people in 2024 did you have to fire to right size the team? About 30, I think. 60 to 70% month-per-month growth. Does that mean you're adding like $50 to $100K of new ARR per month? Some months have been more than that, yeah. It's growing very, very, very fast. If someone came and offered you today, $40 million, |
| 0:36.8 | all cash up front miles, no strings attached, |
| 0:39.2 | do you take the deal? very, very, very fast. If someone came and offered you today, 40 million bucks all cash up front |
| 0:37.8 | Miles, no strings attached, do you take the deal? |
| 0:41.4 | Hey folks, my guest today is Miles Beckett. He has been around the startup block, his first |
| 0:46.7 | company Everyday Health, built and sold over six years back in 2013, next built and sold over |
| 0:51.8 | another six years in 2019. Now working on flossie going face first |
| 0:56.0 | into the space of AI for dentists leaning and launched in 2020 and now six years into the journey |
| 1:02.3 | we're going to talk about how we launched how we grew and already sees the space going miles you |
| 1:05.6 | ready to take us to the top yeah for sure all right but take me back to the launch story here because you were in this in 2020, |
| 1:12.6 | which is before everyone was building sort of AI wrappers on top of the most recent LMs and foundation models. |
| 1:17.9 | How did you just even discover the issue of dental practices and an ability to use AI to make them faster? |
| 1:24.3 | Yeah, so I think like all great companies, we are a pivot. |
| 1:27.2 | So we launched the company in |
| 1:28.9 | 2020 as a tech-powered dental discount plan. So we had sold Silver Sheet, my prior business, to |
| 1:36.6 | AMN Healthcare, the big staffing firm. And my partner and I were looking at new areas to innovate |
| 1:42.3 | within health care and adjacent. And we just felt |
| 1:45.1 | like dental was ripe for opportunity. And specifically, the way people pay for dental care |
| 1:50.3 | didn't make a lot of sense. Dental insurance is really not worth it when you look at the numbers. |
| 1:54.9 | So we started as a discount plan. We were matching patients to Dennis and basically passing the |
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