How Flossy Reached $4M ARR With AI Dental Receptionists

How Flossy Reached $4M ARR With AI Dental Receptionists

Author: Nathan Latka April 29, 2026 Duration: 17:40

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/


Ever wonder what the actual numbers look like behind a successful software company, or what crucial decision made the difference between stalling and scaling? SaaS Interviews with CEOs, Startups, Founders cuts straight to that chase. Host Nathan Latka sits down each day for a focused fifteen-minute conversation with the people building the software businesses shaping our world. These aren't abstract discussions; you'll hear founders detail their precise revenue figures, customer acquisition costs, team structures, and the sometimes messy realities of growth. The guests on this podcast represent the full spectrum of the journey, from those just launching an MVP to leaders managing companies with thousands of customers, from bootstrapped operators to those navigating venture funding. By tuning in, you get a daily dose of unvarnished data and tactical stories, stripping away the hype to understand how real SaaS businesses are built, run, and monetized. It’s a resource for entrepreneurs, operators, and anyone curious about the mechanics of modern software entrepreneurship, offering a clear window into the strategies that work and the pitfalls to avoid. Latka’s direct approach ensures every interview delivers concrete takeaways, making this podcast a unique and valuable listen for the business-minded.
Author: Language: English Episodes: 100

SaaS Interviews with CEOs, Startups, Founders
Podcast Episodes
How 1Mind Hit $1M in 3 Months Selling $100k AI Sales Agents [not-audio_url] [/not-audio_url]

Duration: 25:08
How do you hit $1 million in contracted revenue in three months and achieve 211% net dollar retention in your first year? Amanda Kahlow is the founder and CEO of 1Mind, an AI platform building go-to-market superhumans th…
Selling Check for $400M, Now Building a $1.5M ARR AI Startup [not-audio_url] [/not-audio_url]

Duration: 24:18
How do you build a $1.5 million ARR enterprise AI platform after previously selling a fintech startup for nearly $400 million? Ahikam Kaufman is the CEO of SafeBooks AI, an agentic data automation platform for the office…
Flip Reaches $12M ARR with AI Voice Support for 250 Brands [not-audio_url] [/not-audio_url]

Duration: 24:34
How do you pivot a banned college ridesharing app into a voice AI company handling 300 million customer service calls? Brian Schiff is the co-founder and CEO of Flip, a verticalized AI voice assistant that automates cust…
Kadence Reaches $15M ARR Managing Hybrid Work for Revolut & Boeing [not-audio_url] [/not-audio_url]

Duration: 20:32
How do you completely reboot a dying hardware startup, restructure a heavy cap table, and pivot into a SaaS product doing $15M ARR? Dan Bladen is the co-founder and CEO of Kadence, a workplace operations system coordinat…
How Allo Reached $10M Revenue With 5,000 Customers [not-audio_url] [/not-audio_url]

Duration: 22:36
How do you grow an AI phone system to 5,000 customers and roughly $3M ARR in under two years while still aiming for $10M in revenue this year? Jeremy Goillot is the founder and CEO of The Mobile First Company, which laun…
How TitanX Hit $9.7M ARR After Buying IP for $200K [not-audio_url] [/not-audio_url]

Duration: 15:40
How do you turn $200K into a $9.7M ARR SaaS company with a $100M valuation by buying IP instead of building from scratch? Joey Gilkey is the founder of TitanX, a sales intelligence platform generating $9.7M ARR after lau…