How Flossy Reached $4M ARR With AI Dental Receptionists

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/

• 0:00Speaker 00

  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?

• 0:05Speaker 01

  Yeah, we're not quite there, but we're pretty close.

• 0:07Speaker 00

  And for this AI receptionist today, what's the average customer paying you per month or per year to use the technology?

• 0:13Speaker 01

  It's about 500 bucks a month per location.

• 0:16Speaker 00

  When did you raise the seed round? What was that, like four or five million?

• 0:19Speaker 01

  We raised 15 million or so.

• 0:21Speaker 00

  How many people in 2024 did you have to fire to right-size the team?

• 0:24Speaker 01

  About 30, I think.

• 0:26Speaker 00

  60 to 70% month-over-month growth. Does that mean you're adding like 50 to 100K of new ARR per month?

• 0:31Speaker 01

  Some months it's been more than that, yeah. It's growing very, very, very fast.

• 0:34Speaker 00

  If someone came and offered you today 40 million bucks, all cash upfront, miles, no strings attached, do you take the deal? Hey folks, my guest today is Miles 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 Fosse, 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. Miles, you ready to take us to the top?

• 1:06Speaker 01

  Yeah, for sure.

• 1:08Speaker 00

  All right. But take me back to the launch story here, because you were in this in 2020, which was 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?

• 1:24Speaker 01

  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. 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.

• 2:10Speaker 01

  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 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.

• 2:38Speaker 00

  And for this AI receptionist today, what's the average customer paying you per month or per year to use the technology?

• 2:44Speaker 01

  It's about 500 bucks a month per location. That can go up or down depending upon usage.

• 2:50Speaker 00

  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?

• 2:55Speaker 01

  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 rollups 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.

• 3:19Speaker 00

  Can I ask, don't obviously name their name, but what's the largest customer in terms of number of locations on your platform?

• 3:24Speaker 01

  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 will sign pretty soon.

• 3:35Speaker 00

  Well, avoid saying their name. I don't want you to divulge anything confidential. I'm just asking on general, I mean, are you, is your largest one 500 locations or 1,000 locations or 10 locations?

• 3:43Speaker 01

  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.

• 3:50Speaker 00

  Interesting. Okay, that's great. And did you, 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?

• 4:02Speaker 01

  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 to surgery centers. So we went to a lot of conferences in the space and that worked well. So it started out more bottoms up. Simultaneously, we were having

• 4:47Speaker 01

  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.

• 5:02Speaker 00

  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?

• 5:14Speaker 01

  Hundreds. I don't know the exact number, but hundreds of customers at this point. Yeah, it's grown really, really fast.

• 5:21Speaker 00

  Fair to say between 100 and 500 customers?

• 5:23Speaker 01

  Yeah, higher than, yeah, probably at least three to 500, maybe more.

• 5:28Speaker 00

  Okay, great. And is a customer a location or is that a brand that could have multiple?

• 5:31Speaker 01

  That would be brands that could have multiple locations. Yeah.

• 5:34Speaker 00

  Okay. So are you over the special 100, sorry, 1K location mark yet?

• 5:38Speaker 01

  I don't know if we are. I'd have to check. We might be, maybe in terms of signing.

• 5:43Speaker 00

  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, of their sort of page? What's the answer to that?

• 5:58Speaker 01

  Yeah. So I think what you find is that in all of these verticals that are very specific and a little old school. So whether it's dental, healthcare more broadly, you know, veterinary, even frankly, restaurant, you know, restaurants, like,

• 6:15Speaker 01

  Like tech companies and maybe big, big companies that are very tech focused are going to 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, they're not focused on scheduling. They're focused on conveying information. It's more like customer support. And if you look at what Fiona does, and we have some other products we haven't announced

• 6:59Speaker 01

  yet, but that are one, one that's like, we're actually selling right now behind the scenes. Like it's all very focused on booking patients, engaging, re-engaging with patients, getting them to come back for appointments. It's a more active motion. And so the product is a little bit different. And then the business logic behind the scenes is totally different. Like being able to really nail scheduling is critical. And we had a lot of prior experience with that from our original business because we were booking patients to go to Dennis.

• 7:31Speaker 00

  Tell us more about how you capitalize this business, Miles. I think, I mean, you're successful entrepreneur. You've exited two companies and the third one here, have you said, you know, let me do it myself or did you go out and raise?

• 7:40Speaker 01

  We raised money. Yeah, we raised venture capital for the original business model. We've raised more money since then, post pivot, all from, you know, traditional VCs.

• 7:50Speaker 00

  Guys, remember I am not just a YouTuber. I'm investing in my third fund. We've deployed $250 million into 550 software companies so far. Again, at founderpath.com. If you're interested in capital, I would love to cut you a check because I know you're investing in your education. You watch my show. So sign up at founderpath.com. And when you get the onboarding email, I reply and I see all those, just reply and say, Nathan, I found you through YouTube and I'll make sure to prioritize you. I would love to cut you a check. Check out founderpath.com. Can you take us through that storyline a bit? How, you know, when did you raise the seed round?

• 8:22Speaker 01

  So we raised a seed round for the original business in 2020. Right when the pandemic hit, we actually closed on the financing. We actually didn't do anything with the money. So we went the like literally.

• 8:36Speaker 00

  Four or five million or?

• 8:38Speaker 01

  It was like three million. And. Like again, we, the economy shut down or the, everybody shut down. Everybody was, you know, in, at home, isolated and dental offices were closed. And so we were like, oh no, like, what do we do here? So we actually didn't pay ourselves anything. You know, we had some money, so we were comfortable and we didn't, we didn't need it. And we literally just sat on the cash and we were kind of like, does this business even work? Should we fully change to a different model like with this cash? I don't know. We had a lot of conversations with our investors and between my co-founder and I. And actually, when we had raised the money, the original model was to be like a better type of dental insurance, but we were actually going to be an insurer.

• 9:24Speaker 01

  And coming out of those conversations, we decided to do this discount plan. And we started talking to some dental practices and figuring out what their pain points were. And so we, we actually built the product. We didn't start hiring people and building it until fall of 2020. And then we launched that original discount plan model in spring of 2021. And then we raised a series A. I don't remember exactly when that was. I think it was in spring of 22, right before the market crashed. And we raised, I don't remember the exact amount, but you know, call it 15 million or so from that.

• 10:04Speaker 01

  And then we grew again, we grew that model. We were in, you know, a dozen or so states. We were in a bunch of local markets. We raised a little bit more money.

• 10:13Speaker 00

  Something, I'm, I'm, I'm, there's something here I don't understand because you ultimately moved away from the discount plan model, but it must have been extremely well if you raised a series, a 15 million series A in 2022. Did something crazy happen between 2022 and 2023 where that revenue line just collapsed?

• 10:27Speaker 01

  No, the venture markets changed completely.

• 10:30Speaker 00

  Were you ever close to running out of cash completely and shutting the company down in that period?

• 10:34Speaker 01

  Sure. I mean, I mean, as a founder, I mean, you're always, if you're venture backed, you're close to running out of money almost all the time, not all the time, but you know, yeah. Sure. All the time. Yeah, every business is like that. My first company, when we sold that company, and it was actually called Equal, we sold to Everyday Health. When we sold to Everyday Health, we had to borrow $500,000 from them so we didn't run out of cash and we could actually close the transaction.

• 11:01Speaker 00

  How did you get that done, though? You lost all your leverage. Didn't they just pound you on valuation? It looks like you grew it over eight figures of revenue.

• 11:07Speaker 01

  Yeah, so, um, yeah, we did. Um, the short, I don't know, but I think it's because we had a breakup fee. So we had, we had signed a term sheet with them. Uh, that term sheet expired. We had a competing offer. Uh, we had two competing verbal offers and we had one competing term sheet. We got them back under term sheet, but as part of that, we required them to have a million dollar breakup fee. So I think the answer is probably because of the breakup fee. They, I mean, they wanted to buy us, but I think that that was the, the pill that they didn't want was to not close the deal and pay us a million dollars.

• 11:47Speaker 00

  Was it public? Did they release, or can you share what this exit was for?

• 11:50Speaker 01

  Um, I think it, I don't know if it was public or not, but I think it's out there. It was around 30 million.

• 11:55Speaker 00

  Okay, was that, did you consider that a win at the time?

• 11:57Speaker 01

  Oh, yeah. I mean, we had raised very little money. I mean, it was, it was, I mean, it's like, it's not a massive venture exit, but everyone made money. We had some, we had a, some investors at 10x their money. Everybody made 2x or more. It was very personally meaningful for me and my co-founder and even, you know, senior people on the team. Yeah, it was definitely one.

• 12:15Speaker 00

  That's great.

• 12:16Speaker 01

  Every, every, so, you know, knock, knock on wood, every company so far has been a net positive for investors and some, you know, better multiples than other and, and everybody's done well on the team.

• 12:28Speaker 00

  Which one was bigger in terms of revenue when you exited, uh, AMN Healthcare or the one that you sold to Everyday Health?

• 12:34Speaker 01

  Yeah, so Equal, which we sold to Everyday Health, was quite a bit bigger in revenue than Silver Sheet, which we sold to AMN Healthcare, but the Silver Sheet was a much bigger exit. Interesting.

• 12:47Speaker 00

  Oh, interesting. Why silver sheet was under eight figures of revenue then if the one report was bigger, but they exited for a higher, a higher, I guess, total dollar value. Why was that?

• 12:57Speaker 01

  Yeah. A combination of that equal was a media business. And so we sold for a smaller multiple on revenue than silver sheet, which was a SaaS business. And also the market at the time in 2019, it wasn't 2021 craziness levels, but multiples were still pretty crazy for SaaS businesses.

• 13:19Speaker 00

  How many people in 2024 did you have to fire to right size the team?

• 13:22Speaker 01

  About 30, I think.

• 13:23Speaker 00

  And what are you in terms of FTEs today?

• 13:25Speaker 01

  Uh, we're about mid twenties, but we were, we got down to about eight. I think we were eight when we did the last. And you know, it's always tough. I mean, I, we had to do, I did more layoffs at equal. Um, that was, and we did, we didn't, uh, we didn't really do a layoff at silver sheet, but we did, we kind of outsourced the team at silver sheet, but it's always really hard. Um, you know, then I would say we have a couple of people from the OG team that actually came back. One of our salespeople came back. One of our customer success people came back. So that was kind of gratifying.

• 13:56Speaker 00

  That's great. Well, I mean, it seems to be working. Can I take the 300 to 500 brands and around, I mean, maybe approaching a thousand locations today? 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?

• 14:10Speaker 01

  Yeah, we're, we're not quite there, but we're, we're pretty close. Yeah. We're, and again, we're growing like, you know, we're growing like 60, 70% month over month since launch. It's Yeah, yeah. And then like I said, you know, we're really expanding into other AI agents for dental practices. Really focused on customer engagement, customer retention, patient bookings, patient rebookings, phone calls. Fiona now does, you know, phone call, text, web chat, et cetera. So it's really become pretty rapidly like a full customer acquisition and engagement platform.

• 14:50Speaker 00

  So you're comfortable sharing 60, 70% month over month growth. Does that mean you're adding like 50 to 100K of new ARR per, per month?

• 14:58Speaker 01

  Yeah, it's actually in some months it's been more than that. Yeah, I mean, it's accelerating. It's it's it's growing very, very, very fast, you know, and I'm also good. I was gonna say, I'm also an investor in a lot of companies and I've done SPVs in companies. And, you know, prior to the market change and like some of those businesses that will work and are gonna work out and some aren't. And like, you know, it really comes down to were investors and management realistic about valuation and cap table? And did they take necessary measures to fix things? And I think the answer in most cases is people did not. And, you know, there's been a lot of debate right now about the Brex exit, which I'm sure you saw. And like, you know, the Brex outcome was a great outcome. Like, the reality is that was a great outcome. That was a win.

• 15:44Speaker 01

  They sold a company for $5 billion in like eight or 10 years. They crushed it. You know, it's not their fault that they raised at a $12 billion valuation prior. And like those investors aren't gonna do great. I get it like it happens. You know what's gonna happen? Almost everybody who invested in 2020, 21 at the peak is not gonna do well. That's just the reality.

• 16:04Speaker 00

  Yep, that vintage, that cohort.

• 16:05Speaker 01

  That vintage is is is very, very hard. Yeah. Yeah, unless you do things like we did, you know?

• 16:12Speaker 00

  So as we wrap here, I mean, you're a hot AI company. You're growing 60 to 70% month over month. You're doing between call three and four million bucks of revenue. If someone came and offered you today 40 million bucks, all cash upfront miles, no strings attached. Do you take the deal?

• 16:26Speaker 01

  No, I mean, not for me. I mean, you know, we're still trying to, we want to build a very big business here. And I think there's a big opportunity. I mean, I, I think we are rapidly becoming the dominant platform in dental.

• 16:39Speaker 01

  And I think we will be, I think by the end of this year, it'll be clear that we've, you know, won in dental. We think that there are adjacent verticals that are similar to dental that we can go into as well. And so we think there's a really big opportunity.

• 16:51Speaker 00

  Guys, there you have it. Miles founded Flossy back in 2020, seed round of 3 million, 15 million Series A in 2022 on a totally different business model, discount plan, but in the same space, dental. He then pivoted in 2023, 2024, going all in on Flossy and his agent Fiona, which helps critically dental offices never missed a potential to book a meeting. That is their lifeblood. That's how they make revenue. Fast forward to today, he's working with 300 to 500 dental brands, approaching 1,000 locations, doing between three and four million bucks of revenue with his team of 25, and adding call between 50 and sometimes more than 100K of new ARR per each month. It's growing rapidly. He's recapped the business so everyone is properly incentivized and he wants to go big. Check it out at flossy.com. Miles, thank you for taking us to the top.

• 17:33Speaker 01

  Thank you.

• 17:34Speaker 00

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