How Flossy Reached $4M ARR With AI Dental Receptionists

Summary

Podcast Summary: How Flossy Reached $4M ARR With AI Dental Receptionists

Podcast: SaaS Interviews with CEOs, Startups, Founders
Host: Nathan Latka
Guest: Miles Beckett, CEO of Flossy
Date: April 29, 2026
Episode Theme:
How Flossy, led by serial entrepreneur Miles Beckett, pivoted from a dental discount plan to become a fast-growing AI-powered dental assistant platform (“Fiona”), scaling to a $4M+ ARR by serving dental practices and DSOs with vertical-specific AI receptionists and engagement tools.

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1. Episode Overview

Nathan interviews Miles Beckett, exploring Flossy’s journey from its 2020 inception to its status as a leading AI receptionist and patient engagement product for dental practices. They discuss the company’s critical pivot, scaling efforts, customer acquisition strategies, fundraising path, and how vertical AI is disrupting “old school” verticals like dental. Practical insights are shared on product-market fit, weathering funding & market shifts, and prioritizing scale over exits.

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2. Key Discussion Points & Insights

The Pivot: From Dental Discount Plans to AI Receptionist (00:08–01:24)

• Original Model (2020): Flossy launched as a tech-powered dental discount plan, addressing dental insurance inefficiency by matching patients to dentists and passing on insurer rates.
• Personal Motivation: Beckett and his partner, after selling Silversheet to AMN Healthcare, were searching for innovation in healthcare.

  “Dental insurance is really not worth it when you look at the numbers.” – Miles Beckett (01:10)

• AI ‘Aha’ Moment: The arrival of LLMs and ChatGPT in 2023 sparked their interest in AI, first for internal tools, then creating an AI receptionist to automate call agents, ultimately driving their business pivot.

Product & Customer Value Proposition (05:44–07:31)

• What Makes Fiona Different: Unlike generic tools (e.g., Intercom), Flossy's AI is deeply verticalized: focused on patient booking, retention, rescheduling, and engaged reactivations.

  “In dental, the number one most important thing for a dentist... is booking those patients.” – Miles Beckett (06:18)

• Customization over Generic Software: Scheduling, rebooking, and phone integration are deeply tailored to the dental workflow.

Scaling & Customer Growth (02:55–05:38, 05:02–05:34)

• Customer Profile: Primarily serving DSOs (Dental Service Organizations) via enterprise-ish sales, but started with a hybrid of bottom-up and top-down approaches.

• Land & Expand: Largest customers are DSOs with up to 100+ signed locations, with some upcoming contracts for 500+ locations.

• Current Scale: Hundreds of brands (potentially 300-500), nearing 1,000 active locations.

• Pricing: ~$500/month/location, average.

  “We have very deep relationships in the private equity world... we’ve signed multiple, hundred-location-plus DSOs.” – Miles Beckett (02:57)

Growth Channels & Motion (04:02–05:02)

• Early rollout to known practices, then strong use of conferences (“We really sold a lot to surgery centers at our last business by going to conferences”), and now targeting decision-makers at scale via PE/DSO ecosystem.

Fundraising, Capitalization & Market Timing (07:31–10:13)

• Seed Round: $3M in 2020; sat on cash during COVID closures, didn’t pay themselves; careful capital usage.
• Series A: ~$15M raised in Spring 2022 right before market crash.
• Pivot Timing: Big move into AI-based business in 2023/24, benefitting from both internal conviction and market needs.
• Experience with Down Markets: Miles discusses the constant pressure of cash, referencing prior exits and close-calls with cash balances.

Leadership, Team, and Recap (13:19–13:56)

• Layoffs and Headcount: 30 let go in 2024 for right-sizing; now at ~25 FTE (mid-20s), previously as low as 8.
• Return of Talent: Some cut team members later rejoined.

  “One of our sales people came back. One of our customer success people came back. So that was kind of gratifying.” – Miles Beckett (13:50)

Revenue and Growth Metrics (00:00–00:31, 14:09–14:58)

• Current ARR: $3-$4M, growing rapidly.
• Growth Rate: 60–70% month-over-month since launching Fiona, sometimes adding over $100k in new ARR each month.

  “We’re growing like 60, 70% month over month since launch.” – Miles Beckett (14:10)

• Projected Dominance: Miles believes Flossy will clearly win the vertical by the end of 2026.

Why Not Take the Money? (16:12–16:51)

• Exit Offer Hypothetical: Would not sell for $40M cash today:

  “We want to build a very big business here...there’s a really big opportunity.” – Miles Beckett (16:28)

• Expansion Plans: Intends to move into adjacent verticals (e.g., veterinary, healthcare practices).

  “I think by the end of this year, it'll be clear that we've won in dental.” (16:40)

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3. Notable Quotes & Memorable Moments

• On Pivoting and Market Fit:
  “Like all great companies, we are a pivot.” – Miles Beckett (01:24)

• On Unique Value to Dentists:
  “It’s really about scheduling and booking...if you look at what Fiona does...it’s a more active motion.” – Miles Beckett (06:10)

• On the Funding Environment:
  “2020, 2021 at the peak is not going to do well. That’s just the reality.” – Miles Beckett (15:39)

• On Personal Experience with Cash Crunches:
  “When we sold [my first] company...we had to borrow $500,000 from them [the acquirer].” – Miles Beckett (10:35)

• On Resilience and Growth:
  “We’re growing like 60, 70 percent month over month since launch.” (14:10)

• On Layoffs and Team Loyalty:
  “One of our sales people came back. One of our customer success people came back. So that was kind of gratifying.” – Miles Beckett (13:50)

• On the Bright Future:
  “We want to build a very big business here and I think there’s a big opportunity. I think we are rapidly becoming the dominant platform in dental.” – Miles Beckett (16:28)

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4. Timestamps for Key Segments

• 01:24 – 02:38: Flossy’s founding story and pivot to AI.
• 03:44 – 05:02: Scaling to large dental enterprise accounts (DSOs).
• 05:44 – 07:31: Fiona product differentiation and vertical focus.
• 07:31 – 10:13: Fundraising timeline and managing through COVID/market crash.
• 13:19 – 13:56: Team resizing, layoffs, and rehiring.
• 14:09 – 14:58: Current run rate, growth, and scale.
• 16:12 – 16:51: Founder’s perspective on not selling, vision for expansion.

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5. Flow & Tone

The interview is candid, brisk, and tactical—with Nathan probing on deal metrics, growth data, and product-market decisions, while Miles responds with openness and humor about the realities of startup life (pivoting, near-cashouts, firing, and hiring). The pair’s founder-to-founder rapport keeps the episode practical, focusing on lessons applicable to SaaS builders and investors.

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6. Final Takeaways

• Flossy’s success stems from a bold pivot, deeply vertical product focus, and smart leveraging of relationships in fragmented, old-school industries (like dental).
• The Fiona AI receptionist is carving a massive niche by going beyond general chatbots to solve the true revenue-critical scheduling and engagement for dental offices.
• Miles sees further upside, betting on category dominance and eventual expansion into similar “appointment-heavy” services.
• The founder’s tactical transparency about pivots, layoffs, cash management, and not chasing premature exits make this a must-listen for SaaS operators growing in vertical AI.

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Curious for more? Visit flossy.com to see the Fiona product in action.

Transcript

[A]

You told me earlier about 500 per location. That puts you around like a 4 or 5 million run rate today. Am I in the right range?

[B]

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

[A]

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

[B]

It's about 500 bucks a month per location.

[A]

When did you raise the seed round? What was that, like 4 or 5 million?

[B]

We raised 15 million or so.

[A]

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

[B]

About 30, I think so 60 to

[A]

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

[B]

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

[A]

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 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 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?

[B]

Yeah, for sure.

[A]

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?

[B]

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 silversheet, my prior business, to AMN Healthcare, the big staffing firm. And my partner and I were looking at new areas to innovate within health care 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 onto 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 intern 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.

[A]

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

[B]

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

[A]

Interesting. And do most people sign up for one location? Are you going to the parent company and selling to 600 locations at once?

[B]

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, hundred location plus DSOs that are then doing like varying degrees of rollout, sometimes in chunks, sometimes location by location.

[A]

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

[B]

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.

[A]

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 1500 locations or a thousand locations or 10 locations?

[B]

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.

[A]

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.

[B]

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 into being part 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.

[A]

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?

[B]

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

[A]

Fair to say between 100 and 500 customers?

[B]

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

[A]

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

[B]

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

[A]

Okay, so are you over the special 100, sorry, 1k location mark yet?

[B]

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

[A]

Okay, cool.

[B]

Yeah.

[A]

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 Intercom or a general support tool in the bottom right of their, of their sort of page? What's the answer to that?

[B]

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, 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 one of those types of products, they're not focused on scheduling, they're focused on conveying information. 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 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 dentists.

[A]

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 what, let me do it myself or did you go out and raise.

[B]

We raise money.

[A]

Yeah.

[B]

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

[A]

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. [e-mail] 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 [e-mail] 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?

[B]

So 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 4 or 5 million or it was like 3 million and like again the economy shut down or the everybody shut down. Everybody was at home isolated and dental offices were closed. And so we were like, oh no, what do we do here? So we actually didn't pay ourselves anything. We had some money so we were comfortable, 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 had 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. 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 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. 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.

[A]

Something, there's something here I don't understand because you ultimately moved away from the discount plan model. But it must bring 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?

[B]

No, the venture markets changed completely.

[A]

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

[B]

I mean, I mean, as a founder, I mean, you're always, if you're friends, you're 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.

[A]

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 to figures of revenue.

[B]

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 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 pass a million dollars.

[A]

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

[B]

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.

[A]

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

[B]

Oh yeah. I mean we had raised very little money. I mean it was a, it was, I mean it's. Look, 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.

[A]

That's great.

[B]

Every, every cup. 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.

[A]

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

[B]

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.

[A]

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

[B]

Just combination of that? Equal was a media business and so we sold for a smaller multiple on Reven 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.

[A]

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

[B]

About 30, I think.

[A]

And what are you in terms of FTEs today?

[B]

We're about mid 20s, 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 we had to do. I did more layoffs at Equal that was. And we didn't really do a layoff at Silversheet but we kind of outsourced a team at Silver Sheet. But it's always really hard. I would say we have a couple people from the OG team that actually came back. One of our sales people came back. One of our customer success people came back. So that was kind of gratifying.

[A]

That's great. Well, I mean it seems to be working. Can I take the 300 or 500 brands and around maybe approaching 1000 locations today. You told me earlier about 500 per location. That puts you around like a 4 or 5 million run rate today. Am I in the right range?

[B]

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. 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.

[A]

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

[B]

Yeah, it's actually, in some months it's been more than that. Yeah, I mean, it's accelerating. It's growing very, very, very fast. You know, and I' Go ahead. I was going to 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 will work, are going to 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, 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 billion in like eight or ten 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 going to do great. I get it. Like it happens. You know what's going to happen? Almost everybody who invested in 2020, 21 at the peak is not going to do well. That's just the reality.

[A]

Yeah, that vintage, that cohort, it's, that

[B]

vintage is, is, is very, very hard. Yeah. Yeah. Unless you do things like we did, you know. Yeah.

[A]

So as we wrap here, you're a hot AI company. You're growing 60 to 70% month over month. You're doing between caught 3 and 4 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?

[B]

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 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 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.

[A]

Guys, there you have it. Miles founded flossie 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 FL 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 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 [e-mail] Miles, thank you for taking us to the top.

[B]

Thank you.

[A]

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