How Flossy Reached $4M ARR with 300 Dental Brands on Its AI Receptionist Platform (Interview with Founder Miles Beckett)

Host teaser and key metrics preview

Nathan Latka

00:00You told me earlier about 500 per location. That puts you around like a 4 or 5,000,000 run rate today. Am I in the right range? Yeah. We're not quite there, but we're 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?

Miles Beckett

00:13>> It's about $500 a month per location.

Nathan Latka

00:16When did you raise the seed round?

Miles Beckett

00:18>> What was that? Like, 4 or 5,000,000? We raised 15,000,000 or so.

Nathan Latka

00:21How many people in 2024 did you have to fire to right size the team?

Miles Beckett

00:25>> About 30, I think.

Nathan Latka

00:2660 to 70 month over month growth. Does that mean you're adding like 50 to a 100 K of new ARR per month?

Miles Beckett

00:31>> Some months it's been more than that. Yeah. It's growing very, very, very fast.

Nathan Latka

00:34If someone came and offered you today $40,000,000, all cash upfront, Miles, no strings attached. Do you take the deal?

Guest introduction: Miles Beckett and Flossy background

Nathan Latka

00:41Hey 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 flossy, going face first into the space of AI for dentists, leaning in launched in 2020, and now six years into the journey. We're gonna talk about how he launched, how he grew, and where he sees

01:04the space going. Miles, you ready to take us to the top?

Miles Beckett

01:06>> Yeah. For sure.

Nathan Latka

01:08Alright. 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?

Launching Flossy in 2020 as a dental discount plan

Miles Beckett

01:24>> 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

01:51>> 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 book 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 moment for us. And we started building a lot of internal tools at the

02:18>> 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.

Pivoting to the Fiona AI receptionist

Nathan Latka

02:38And for this AI receptionist today, what's the average customer paying you per month or per year to use the technology?

Pricing: $500 per location per month

Miles Beckett

02:44>> It's about $500 a month per location. That can go up or down depending upon usage.

Nathan Latka

02:50Interesting. And do most people sign up for one location, or are you going to the parent company and selling to 600 locations at once?

Selling to PE-backed dental roll-ups

Miles Beckett

02:55>> Yeah. Most are signing up from 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.

Nathan Latka

03:19Can I ask don't obviously name their name, but what's the largest customer in terms of number of locations on your platform?

Miles Beckett

03:24>> 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.

Nathan Latka

03:35Well, 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 five hundred locations or a thousand locations or 10 locations?

Miles Beckett

03:44>> About a 100 or so signed, and then there's a couple right now that are, like, 500 plus that we're pretty far along with.

Nathan Latka

03:50Interesting. 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.

Miles Beckett

04:02>> Sure.

04:03>> 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 his discount plan. When we pivoted to AI, we started out with about half a dozen locations that we

04:28>> 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 conversations with larger DSOs and then private equity firms that own the DSOs. And as we've

04:54>> 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.

Nathan Latka

05:02And so Miles, using conferences as growth specifically for your pivot to the Fiona product in mid to late twenty twenty four, fast forward to today, we're recording here in January 2026. How many individual customers are you working with today?

Customer count and location scale today

Miles Beckett

05:14>> Hundreds. I don't know the exact number, but hundreds of customers at this point. Yeah. It's grown really, really fast.

Nathan Latka

05:21Fair to say between a hundred and five hundred customers?

Miles Beckett

05:24>> Yeah. Higher than yeah. Probably at least three to 500, maybe more.

Nathan Latka

05:28Okay. Great. And is a customer a location or is that a brand that could have multiple

Miles Beckett

05:31>> locations? That would be brands that could have multiple locations.

Nathan Latka

05:33Yeah.

05:34Okay. So are you over the special 100 sorry, one k location mark yet?

Miles Beckett

05:38>> I don't know if we are. I'd have to check. We might be. Maybe in terms of sizing.

Nathan Latka

05:43Okay. Cool. Yeah. Okay. Tell us more about the Fiona product.

Miles Beckett

05:46>> When I see

Nathan Latka

05:47it on your website, again, I'm 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?

Why vertical AI beats generic tools like Intercom

Miles Beckett

05:58>> 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, health care more broadly, you know, veterinary, even frankly restaurant, you know, restaurants, like 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

06:32>> 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. And if you look at what Fiona does, and we have some other products we haven't announced yet, but that are one

07:01>> 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

07:29>> were booking patients to go to dentist.

Nathan Latka

07:31Tell us more about how you capitalize this business, Miles. I think, I mean, you're a successful entrepreneur. You've exited two companies. And the third one here, have you said, you know what? Let me do it myself, or did you go out and raise?

Miles Beckett

07:40>> 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.

Nathan Latka

07:50Guys remember, I am not just a YouTuber. I'm investing into my third fund. We've deployed $250,000,000 into five fifty 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

Capitalizing the business: seed and Series A

Nathan Latka

08:13YouTube, 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?

Miles Beckett

08:22>> We raised a we raised the 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

Nathan Latka

08:36or 5,000,000?

Miles Beckett

08:37>> It was like 3,000,000. And like, again, we we the economy shut down, or the 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. We didn't we didn't need it. And we literally just sat on the cash. And we were kind

09:04>> 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 gonna be an insurer. And coming out of those conversations, we decided to do this discount plan.

09:30>> 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 twenty twenty. And then we launched that original discount plan model in spring of twenty twenty one. And then we raised a series a, I don't remember exactly when that was, I think it was spring of twenty two, right before the market crashed, and

09:56>> we raised, I don't remember the exact amount, but you know, call it 15,000,000 or so from that.

10:04>> 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.

Nathan Latka

10:13Something 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 be extremely well if you raised a series a 15,000,000 series a in 2022. Did something crazy happen between 2022 and 2023 where that revenue line just collapsed?

Miles Beckett

10:27>> No. The venture markets changed completely.

Nathan Latka

10:30Were you ever close to running out of cash completely and shutting the company down in that period?

Miles Beckett

10:34>> Sure. I mean, I mean, as a founder I mean, you're always

Nathan Latka

10:37if your friends are backed,

Miles Beckett

10:38>> you're close to running out of money almost all the time. Not all the time, but you know what I mean.

Nathan Latka

10:43Yeah. Sure.

Miles Beckett

10:44>> All the time. Yeah.

Nathan Latka

10:45Every business is like that.

Miles Beckett

10:47>> 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.

Nathan Latka

11:01How 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 8 figures of revenue.

Miles Beckett

11:07>> Yeah. So yeah, we did.

11:12>> 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, that term sheet expired. We had a competing offer. 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

11:38>> 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.

Nathan Latka

11:47Was it public? Did they release? Or can you share what this exit was for?

Miles Beckett

11:50>> I think it I don't know if it was public or not, but I think it's out there. Was around 30,000,000.

Nathan Latka

11:54Okay. Was that or did you consider that a win at the time?

Miles Beckett

11:57>> Oh, yeah. I mean, we had raised very little money. Mean, it was a bit it was I mean, it's look, it's not a massive venture exit, but everyone made money. We had some we had some investors at 10 x their money. Everybody made two x or more. It was very personally meaningful for me and my cofounder, and even, you know, senior people on the team. Yeah. It was definitely one. That's

Prior company exits and lessons learned

Nathan Latka

12:15great.

Miles Beckett

12:16>> 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.

Nathan Latka

12:28Which one was bigger in terms of revenue when you exited, AMN Healthcare or the one that you sold to Everyday Health?

Miles Beckett

12:34>> 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.

Nathan Latka

12:47Oh, interesting. Why why why so Silver Sheet was under 8 figures of revenue then if if if the one before it was bigger, but they Yeah. Exited for a higher a higher, I guess, total dollar value. Why was that? Just Yeah.

Miles Beckett

12:57>> A combination of that equal was a media business, and so we sold for a 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.

Layoffs, rebuilding the team, and current headcount

Nathan Latka

13:19How many people in 2024 did you have to fire to right size the team?

Miles Beckett

13:22>> About 30, I think.

Nathan Latka

13:24And what are you in terms of FTEs today?

Miles Beckett

13:25>> We're about mid twenties, but we were we got down to about eight. I think we were eight when we did the layoffs. And you know, it's always tough. I mean, I I we had to do I've I did more layoffs at equal. That was and we did we didn't didn't really do a layoff at Silver Sheet, but we did we kinda outsourced the team at Silver Sheet. But it's always really hard.

13:46>> You know, then I I would say we have a couple of people from the OG team that actually came back. One of our sales people came back. Of our customer success people came back. So that was kinda gratifying.

ARR, growth rate, and monthly new ARR

Nathan Latka

13:56That'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 5,000,000 run rate today. Am I in the right range?

Miles Beckett

14:08>> Yeah. We're we're we're not quite there, but we're we're pretty close. Yeah.

14:12>> We're and and again, we're growing like, you know, we're growing like 70% month over month since launch. It's A Fiona. 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, etcetera. So it's really become pretty rapidly like a full customer acquisition and engagement platform.

Nathan Latka

14:50So you're comfortable sharing 60 to 70% month over month growth. Does that mean you're adding like 50 to a 100 k of new ARR per per month?

Miles Beckett

14:58>> 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 go ahead. Go ahead. 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 are working are gonna work out and some aren't. And like, you know,

15:18>> 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.

15:44>> They sold a company for $5,000,000,000 in like eight or ten years. They crushed it. You know, it's not their fault that they raised it a $12,000,000,000 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.

Expanding Fiona into a full engagement platform

Nathan Latka

16:04>> Yep.

16:04That vintage, that cohort is

Miles Beckett

16:05>> gonna That vintage is is is very, very hard.

Nathan Latka

16:07Yeah. Yeah. Unless you do things like we did. You know?

16:11Yep. 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 it, 3 and $4,000,000 of revenue. If someone came and offered you today $40,000,000, all cash upfront, Miles, no strings attached, Do you take the deal?

Would Miles sell for $40M today?

Miles Beckett

16:26>> No. I mean, not for me. I mean, you know, we're still trying to we wanna build a very big business here, and I think there's a big opportunity. I mean, I think we are rapidly becoming the dominant platform in dental, 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

16:47>> can go into as well. And so we think there's a really big opportunity.

Closing recap and wrap-up

Nathan Latka

16:51Guys, there you have it. Miles founded flossy back in 2020, seed round of 3,000,000, 15,000,000 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

17:14500 dental brands approaching a thousand locations, doing between 3 and $4,000,000 of revenue with his team of 25 and adding call between 50 and sometimes more than a 100 k 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.

Miles Beckett

17:33>> Thank you.

Nathan Latka

17:34You won't believe this CEO's revenue. Click here to watch the next episode right now.