How Flossy Pivoted to an AI Dental Receptionist and Grew 60-70% Month Over Month

You 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?

It's about $500 a month per location.

When did you raise the seed round?

What was that? Like, 4 or 5,000,000? We raised 15,000,000 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 a 100 K 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 $40,000,000, 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, on 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 the space going. Miles, you ready to take us to the top?

Yeah. For sure.

Alright. 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?

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 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

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.

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. 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 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.

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.

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 five hundred locations or a thousand locations or 10 locations?

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.

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. 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 his 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 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 twenty twenty four, fast forward to today, we're recording here in late January of twenty twenty six. 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.

Fair to say between a hundred and five hundred 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, one k 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. Yeah. Okay. Tell us more about the Fiona product.

When I see

it 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?

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 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 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 dentist.

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

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.

Guys 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

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?

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...

Or 5,000,000?

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

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.

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

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

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 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?

No. The venture markets changed completely.

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

Sure. I mean, I mean, as a founder... I mean, you're always... If your friends are backed, you're close to running out of money almost all the time. Not all the time, but you know what I mean. 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.

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 8 figures of revenue.

Yeah. So... Yeah, we did.

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

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.

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

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.

Okay. Was that... Or did you consider that a win at the time? 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 great. 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.

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

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.

Oh, 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.

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.

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

About 30, I think.

And what are you in terms of FTEs today?

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.

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.

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 4 or 5,000,000 run rate today. Am I in the right range? Yeah. We're we're we're not quite there, but we're we're pretty close. Yeah.

We're... And and again, we're growing like, you know, we're growing like 60, 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.

So 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?

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,

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.

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 twenty twenty, twenty one at the peak is not gonna do well. That's just the reality.

Yep. That vintage, that cohort is

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

Yep. 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?

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

Guys, 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

500 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.

Thank you.

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