SaaS Interviews with CEOs, Startups, Founders
How Flossy Reached $4M ARR With AI Dental Receptionists
29 Apr 2026
Chapter 1: How did Flossy pivot during the pandemic?
you told me earlier about 500 per location that puts you around like a four or five 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 bucks a month per location when did you raise the seed round what was that like four or five million we raised 15 million or so how many people in 2024 did you have to fire to right size the team
about 30 i think 60 to 70 month over month growth does that mean you're adding like 50 to 100k of new arr per month some months it's been more than that yeah it's growing very very very fast if someone came and offered you today 40 million bucks all cash up front miles no strings attached do you take the deal Hey folks, my guest today is Myles Beckett.
He has been around the startup block, his first company, Everyday Health, built and sold over six years back in 2013. Next, built and sold over another six years in 2019. Now today, working on Flossie, going face first into the space of AI for dentists, leaning and launched in 2020, and now six years into the journey.
We're going to talk about how he launched, how he grew, and where he sees the space going. Myles, you ready to take us to the top? Yeah, for sure. All right.
Chapter 2: What inspired the launch of the AI dental receptionist?
But take me back to the launch story here, because you were in this in 2020, which is before everyone was building sort of AI wrappers on top of the most recent LLMs and foundation models. How did you just even discover the issue of dental practices and an ability to use AI to make them faster?
Yeah, so I think like all great companies, we are a pivot. So we launched the company in 2020 as a tech-powered dental discount plan. So we had sold Silver Sheet, my prior business, to AMN Healthcare, the big staffing firm. And my partner and I were looking at new areas to innovate within healthcare and adjacent. And we just felt like dental was ripe for opportunity.
And specifically, the way people pay for dental care didn't make a lot of sense. Dental insurance is really not worth it when you look at the numbers. So we started as a discount plan.
Chapter 3: How does Flossy's pricing model work for dental practices?
We were matching patients to dentists and basically passing the insurance rate on to the patients that booked through us. And we got super into AI in 2023, like when ChatGPT launched, similar to I think many people. It was kind of an aha moment for us. And we started building a lot of internal tools at the original kind of business model using AI.
So we built like an LLM-powered pricing algorithm. We built some internal call analysis tools. And then we started building this internally. AI receptionist with the idea that we could replace some of the call agents that we were using on our team. And that's what really set us down the path.
And for this AI receptionist today, what's the average customer paying you per month or per year to use the technology?
Chapter 4: What strategies did Flossy use to acquire customers?
It's about 500 bucks a month per location. That can go up or down depending upon usage.
Interesting. And do most people sign up for one location or are you going to the parent company and selling to 600 locations at once?
Yeah, most are signing up for multiple locations. I think one of our advantages is we have very deep relationships in the private equity world. And so there's a lot of these dental roll ups that are private equity backed.
So, you know, we've signed, you know, multiple, you know, 100 location plus DSOs that are then doing like varying degrees of rollout, sometimes in chunks, sometimes location by location.
Can I ask, don't obviously name their name, but what's the largest customer in terms of number of locations on your platform?
Yeah, I mean, we don't really talk about specific customers, but I can tell you that like there are multiple ones that you've heard of that, you know, we've either signed or we're pretty far along conversations with and we'll sign pretty soon.
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Chapter 5: How did Flossy manage layoffs and team restructuring?
Well, avoid saying their name. I don't want you to divulge anything confidential. I'm just asking on general. I mean, is your largest one 500 locations or 1,000 locations or 10 locations?
About 100 or so signed. And then there's a couple right now that are like 500 plus that we're pretty far along with.
Interesting. Okay, that's great. And were you always sort of going this top-down approach or back in 2020 when you launched, were you going more bottoms up? I'm just trying to get a sense if there was a transition from sort of PLG to enterprise motion or something in between.
Chapter 6: What role did venture capital play in Flossy's growth?
Sure.
Yeah, so with the discount plan, it was very much, well, it was kind of a hybrid. So we signed a deal with a nationwide dental network. So we sort of had a roster of dentists, very large one nationwide. But we still had to go location by location by location, getting individual dentists to opt in to being part of this discount plan.
When we pivoted to AI, we started out with about half a dozen locations that we had prior relationships with really to kind of prove the product out. And then we started going to conferences. You know, we found with our last business, Silver Sheet, that we really sold a lot of surgery centers. So we went to a lot of conferences in the space and that worked well. So it started out more bottoms up.
Chapter 7: Why did Flossy reject a $40 million buyout offer?
Simultaneously, we were having conversations with larger DSOs and then private equity firms that own the DSOs. And as we've gotten more traction with them, we've been a little bit more focused on the top down. Although we are going to like, you know, a lot of conferences this year.
And so Miles, using conferences as growth specifically for your pivot to the Fiona product in mid to late 2024. Fast forward to today, we're recording here in late January of 2026. How many individual customers are you working with today?
Hundreds. I don't know the exact number, but hundreds of customers at this point. Yeah, it's grown really, really fast.
Chapter 8: What is Flossy's vision for the future of dental AI?
Fair to say between 100 and 500 customers?
Yeah, higher than, yeah, probably at least three to 500, maybe more.
Okay, great. And is a customer a location or is that a brand that could have multiple locations?
That would be brands that could have multiple locations. Yeah.
Okay. So are you over the special 100, sorry, 1K location mark yet?
I don't know if we are. I'd have to check. We might be. Maybe in terms of signing.
Okay, cool. Okay, tell us more about the Fiona product. When I see it on your website, again, I'm a total novice here, right? Just meeting you today. I'm looking at it going, well, why wouldn't someone just use like an intercom or a general support tool in the bottom right of their sort of page? What's the answer to that?
Yeah, so I think what you find is that in all of these products, that are very specific and a little old school. So whether it's dental, healthcare more broadly, veterinary, even frankly restaurants, like tech companies and maybe big, big companies that are very tech focused are gonna use things like Intercom, but they're really not specific to the industry vertical. So as an example in dental,
The number one most important thing for a dentist in terms of communication with patients is booking those patients. It's really about scheduling and booking. So right off the bat, if you look at an intercom or a fin or, you know, one of those types of products, they're not focused on scheduling. They're focused on conveying information. It's more like customer support.
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