SaaS Interviews with CEOs, Startups, Founders

How do you build a $16.5M vertical SaaS company with 24% EBITDA margins with zero paid acquisition, zero outside funding, and your wife as co-founder? Rohit Garg is the co-founder and CEO of Practice by Numbers, an all-in-one dental practice management platform serving 1,300 customers across 2,000 locations. He started building it in 2015 because his wife is a dentist and he was the one running SQL queries to answer her business questions. Today they are bootstrapped, profitable, and sitting on $2 billion in untouched payment GMV from their existing customer base. You'll learn: Why Rohit built the entire platform by sweat equity while working a full-time job at Philips Healthcare How Practice by Numbers went from $2M in 2021 to $16.5M in 2026 without spending a dollar on paid ads Why their customers generate almost 2x the national average in dental practice revenue — and why that drives retention without any loyalty program The $2 billion in payment GMV sitting in their system right now that they have not started converting yet Why Henry Schein and Patterson, who own the biggest competitors, simply cannot move fast enough to build what Practice by Numbers has built How 100% inbound word of mouth growth leads to 22 to 24% EBITDA margins at $12.5M in revenue The AI receptionist and agentic workflow roadmap that will let dental office managers run the entire practice without touching a screen What Rohit actually said when Nathan asked if he would sell for $180M all cash to the company that owns Dentrix Why COVID cut the company at its knees in 2020 and what it took to relaunch and 8x revenue in five years The vision for $100M in revenue within 10 years and why Rohit thinks it will happen faster than expected Connect: YouTube: youtube.com/@NathanLatkawatch Practice by Numbers: practicenumbers.com Founderpath: founderpath.com

How do you build a $10M business by teaching robots to write handwritten notes with real pens, and do it with zero outside investment for 12 straight years? David Wachs sold his text message marketing company for eight figures in 2012, started Handwrytten the next day, and has bootstrapped it to 200 custom-built robots in a Phoenix facility sending 350,000 notes per month. He owns 100% of the company, took $350K in profit last year, and is targeting $10 to $11M in revenue this year. You'll learn: Why David thinks physical CapEx is now a competitive moat in the AI era, and why he is glad he can't be vibe coded away in a weekend How Handwrytten went from $1M in 2018 to $9.4M in 2024 without raising a single dollar The veterinarian euthanasia franchise that has been sending 80,000 robot-written notes per quarter for 8 straight years Why a $5 Google ad click from a realtor generates only 20 cents in contribution margin and what that forced them to do instead How they built a paper feed system that can write on a stuffed envelope without mismatching a single card across hundreds of thousands of sends The robot leasing model: 30 units in the field at $1,000 to $1,250 per robot per month going to 3PL facilities and swag companies How integrations with HubSpot, Shopify, Claude MCP, Zapier, and Salesforce turned Handwrytten into a fully automated marketing channel Why David would sell for $100M today and what roll-up strategy Nathan pitched him live on camera The SEO playbook that drives 40,000 organic clicks per month with zero agency spend and one in-house writer What it actually costs to build a robot when you manufacture them yourself in Tempe, Arizona Connect: YouTube: youtube.com/@NathanLatkawatch Handwrytten: handwrytten.com Founderpath: founderpath.com

How do you go from a pricing experiment inside a failing product to $3.6 million in annual revenue with 10,000 customers — in under two years and with zero paid marketing? Eugene Cheah is the co-founder and CEO of Featherless.ai, the largest open source LLM inference provider on Hugging Face. He co-created RWKV, the first attention-free AI architecture under the Linux Foundation, and today runs a 27-person team serving customers that pay anywhere from $25 a month to $2 million a year. You'll learn: Why Featherless started as an accident — a pricing experiment that outperformed the original company within days How they grew to 10,000 customers with zero paid marketing using only Reddit posts to AI communities The enterprise sales motion that closes $1 to $2 million per year contracts by showing startups how to cut their OpenAI or Anthropic bills in half Why supporting 6,700 models versus competitors' 100 is the moat — and why no one else is doing it How the RWKV architecture has the potential to reduce AI inference costs by over 1,000x compared to today's transformer models Why the bottom 50% of AI model usage — the fine-tuned, niche, non-English models — is where the real money is hiding What happened when servers caught fire from user growth and the team had to add capacity faster than they could hire How a $20 million Series A in December 2025 finally gave them enough server capacity to breathe Why Eugene believes AI models today are massively over-parameterized — and what a human brain tells us about where efficiency is actually going The refund guarantee Eugene made live on camera and what it says about their confidence in the product Connect: YouTube: youtube.com/@NathanLatkawatch Featherless: featherless.ai Founderpath: founderpath.com

How do you build a $15M revenue business by teaching autonomous drones to find missing sneakers in warehouses, and get customers to more than double their spend every single year? Sankalp Arora is the founder and CEO of Gather AI, a physical AI company that uses autonomous drones and computer vision to track inventory in real time across warehouses. He holds a PhD in robotics from Carnegie Mellon, built the world's first safe autonomous helicopter for DARPA, and today has 30 to 40 customers paying an average of $500K per year with net revenue retention of 170%. You'll learn: Why Sankalp spent three years writing code with zero revenue before getting his first customer in 2021 How a $2 warehouse pick turns into a $15 pick because of one inventory location error, and how Gather cut that by 70% for Barrett The land and expand math: customers start with 5 facilities and expand to 100 within three years at $500K per facility network Why 170% net revenue retention is possible when your product is embedded in daily warehouse operations How Gather AI built neural nets that can read barcodes a standard grocery store scanner cannot, with no human annotation required Why Sankalp passed on big-name VCs and chose Smith Point Capital, founded by Keith Block, former CEO of Salesforce The forklift vision product that turns any warehouse into an Amazon Go store using off-the-shelf hardware from Best Buy How Sankalp was carrying suicidal thoughts since his teenage years and only discovered life without them a year and a half ago, while building a company past $9M in revenue The Series B math: $40M raised at roughly $270M to $400M valuation selling 10 to 15% of the business at $15M in revenue Why Gather AI is touching just 0.1% of its addressable market today, and what 1% would actually mean in dollar terms Connect: YouTube: Nathan Latka Gather.ai: gather.ai Founderpath: founderpath.com

How do you go from $10,000 left in the bank and a down round to $100 million in annual revenue — without ever seriously considering quitting? Krenar Komoni is the founder and CEO of Tive, a hardware-plus-SaaS company that tracks shipments in real time across trucks, ships, and planes worldwide. He started in his basement in 2015, charging his father-in-law $19.99 a month, and today has 1,300 customers — nine of which pay over $1 million per year — at a $545 million valuation. You'll learn: Why Krenar almost went bankrupt twice and laid off 75% of his team — and what kept him going The pricing mistake that nearly killed the company: manufacturing a tracker for $150 and selling it for the same price How hiring two college kids to cold call strangers became the GTM playbook that took Tive from $2.5M to $10M in revenue Why 60% of new revenue at Tive comes from existing customers expanding, not new logos The patent that creates a physical switching cost competitors can't replicate: ping-rate configuration based on shipment events How Krenar negotiated a down round from $21M to $11M valuation with $10K in the bank — and why he doesn't regret it What it actually takes to land a million-dollar-per-year customer when you sell physical hardware on monthly contracts Why Krenar thinks AI agents will fully automate the supply chain in 24 to 36 months — and how Tive is already building toward that The secondary liquidity story: why his Series A1 investor had to push him to take money off the table before he had the courage to ask How Tive went from $250K revenue in 2019 to $100M run rate in 2026 — the full year-by-year breakdown Connect: YouTube: https://www.youtube.com/@NathanLatkawatch Tive: https://www.tive.com/ Founderpath: https://founderpath.com/

How do you build a $53M ARR software company, stay profitable for eight straight years, and give 60% of the cap table to your employees — without ever taking a venture check? Mike Zisman is the founder and CEO of Golf Genius, the dominant tournament management and handicapping platform for golf clubs worldwide. He self-funded $10M of his own money as interest-free debt, did 10 acquisitions before hitting $60M in revenue, and today sits on $14M cash while printing 20% EBITDA margins with 300 employees across the US and Cluj, Romania. You'll learn: Why Mike structured his entire $10M founder investment as debt instead of equity — and how it created a tax shield that paid him back on the way out How the USGA handicapping contract in 2019 transformed Golf Genius from a niche club tool into the infrastructure layer of global golf How Golf Genius went from $0 to $1M ARR in 8 years, then from $1M to $53M in the next 8 — and what the USGA relationship had to do with the inflection point Why 50% of his 300-person team are engineers based in Cluj, Romania — and how that structural cost advantage funds 20% EBITDA while competitors burn cash The exact three-phase acquisition strategy: legacy desktop customer rollups, league expansion, then B2C mobile apps with 8M+ users How Mike negotiated the GolfShot acquisition — and why he forced their entire cap table behind a single LLC before closing Why employees own 60% of the cap table at $53M ARR and how that drives 6-7% annual attrition across the entire company including Romania What Mike would say if a PE firm offered $400M all cash today — and why he says he's more excited about what's next than he's been in years Why he thinks AI will make SaaS companies radically more productive, not obsolete — from a founder whose doctoral thesis in 1977 was already on artificial intelligence The rule of 40 reality at $53M ARR: why growth slows as companies scale and what Mike does to stay above the 10% industry average Connect: YouTube: youtube.com/@NathanLatkawatch Golf Genius: golfgenius.com Founderpath: founderpath.com

How do you build a $100M SaaS company by charging apartment residents $5 a month to keep rats out of their bedroom? Justin Clements is the co-founder and CEO of PestShare, an on-demand pest control platform embedded inside property management software. He bootstrapped from 2019 to 2020, raised just $5M over two rounds, then closed a $28M Series A at a $100M valuation in 2025, the same year he crossed $10M ARR. You'll learn: — Why PestShare's revenue model is structured like a warranty, and why that makes it nearly impossible to churn — The difference between contracted ARR and live ARR, and how that gap almost killed their valuation story  — How embedding into the lease instead of selling direct to residents creates structural GRR that VC-backed competitors can't replicate — What it actually took to raise at 10x ARR from an investor that only backs 9 companies at a time — Why Justin's Series A investor pushed him to take $3M in personal secondary and why he says it made him take bigger swings  — How IGP's PE background forced a full COGS and gross margin rebuild right after closing the round — Why "if you don't see pests it means the product isn't working" is the exact wrong way to think about pest control retention — How PestShare went from $1M (2022) to $5M (2024) to $10M (2025), doubling every year with under 1x ARR in prior capital raised — What property managers actually pay vs. what residents pay and how PestShare navigates that split without losing either side — Why Justin chose a hyper-concentrated, low-profile fund over a brand-name VC, and what they got in return   Connect: YouTube: youtube.com/@NathanLatkawatch PestShare: pestshare.com Founderpath: founderpath.com

How do you go from 0 to $30 million in ARR in just 3 years while purposely losing money on every single free user? Richard White is the founder and CEO of Fathom, a free AI meeting assistant used by hundreds of thousands of professionals daily. After running UserVoice for nearly two decades, Richard entered the hyper-competitive AI transcription war against giants like Zoom, Otter, and Firefly. Instead of playing the traditional VC game, he gave the product away, lost $50 per user, and built an absolute rocket ship that dominates through bottom-up distribution. You'll learn: — Why purposely losing $50 per user per month was the ultimate growth hack. — The 5-step framework to sequence risk (Retention -> Onboarding -> Acquisition -> Referral -> Monetization). — How to hit $100k MRR in your first 30 days of monetization. — Why Richard hired three enterprise salespeople before writing a single line of code for the premium product. — The exact strategy to gamify fundraising by reserving 15% of your Series A for your users. — Why open data, MCP servers, and local agents are replacing walled-garden SaaS models. — How to scale to $30M ARR by pricing bottom-up teams at $25 per seat. — The reality of stepping down as CEO from a $10M ARR company after 18 years.   Watch this episode on YouTube: https://youtu.be/UavacWr2jbQ  Connect with Richard:  https://fathom.ai/ Connect with Nathan:  https://founderpath.com/

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 that replace SDRs, AEs, and sales engineers. You'll learn: - How to sell AI software for $100,000 to $400,000 using flat subscription pricing instead of metered models.  - The unit economics of replacing 89 SDRs and 19 sales engineers with a single custom agent.  - How they maintain 80 to 90 percent SaaS margins while running heavy LLM operations.  - The strategy behind 1Mind's 600 percent year-over-year growth rate.  - Why most enterprise customers purchase a second AI agent within 90 days of going live.  - How 1Mind uses their own AI agent to source 78 percent of their eight-figure pipeline.  - The reality of managing founder dilution and secondary sales after building a $380 million business.  - Why AI agents are expanding past chat interfaces and joining live Zoom calls to run product demos. Amanda is a three-time entrepreneur who previously founded and served as CEO of 6sense, scaling the company through multiple funding rounds and a $380 million valuation before stepping down. Watch this episode on YouTube: https://youtu.be/lFX0n3uYTkw  Connect with Amanda: https://www.1mind.com/ Connect with Nathan: https://founderpath.com/

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 of the CFO. You'll learn: - How to charge $125,000 ACVs by pricing against the cost of an accounting headcount. - Why the company raised a $15 million seed round just to build their initial data architecture. - How they landed a $300,000 engagement in their first year of going to market. - The exact strategy Ahikam used to distribute $25 million in retention bonuses during a past acquisition. - Why building a proprietary graph database is the only way to prevent AI hallucinations in finance. - How SafeBooks scaled to 15 paying enterprise customers. - The economics of automating the quote-to-cash process across disparate CRMs and ERPs. - How to manage founder dilution while building a venture-backed tech company. Ahikam is a veteran fintech executive who previously co-founded Check, which he scaled and sold to Intuit in 2014 for nearly $400 million, creating over 10 millionaires in the process. Watch this episode on YouTube: https://youtu.be/JQA3RX9PsHw Connect with Ahikam:  https://safebooks.ai/ Connect with Nathan:  https://founderpath.com/

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/

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An engineer from a young age, previously CTO/R&D manager in a number of Israeli startups, ex-Googler turned entrepreneur and CEO, changing the US education financing. Running a successful all-remote company now for 5 years, and a strong believer in remote as a way of life.

Massimo Chieruzzi, CEO of AdEspresso. His company, founded in 2013, is now so profitable that he says they don't need fundraising! Massimo sees only growth for AdEspresso in the future as Facebook ads continue to evolve and improve.   Famous Five:   Favorite Book? – Predictably Irrational What CEO do you follow? — Rand Fishkin Favorite online tool? — HubSpot Do you get 8 hours of sleep?— No If you could let your 20 year old self know one thing, what would it be? — Don't start a startup. Get some experience for a corporate business first.   Time Stamped Show Notes: 01:05 – Nathan introduces Massimo 01:30 – AdEspresso was first on The Top on Episode 70 01:50 – Focus on growing and reducing churn 02:25 – Revenue is about $400k/month 02:38 – 2015 total revenue was $3M 02:50 – Fundraising has reached $1.8 Million 03:30 – "We have been profitable this last year, so we don't need the money." 04:00 – More than 4000 customers 04:45 – Learn about AdEspresso at Adespresso.com 05:00 – Churn is 7% and is decreasing 06:00 – How long their customers stay 07:10 – 35 people on their team 07:20 – Monthly expenses are around $280k 07:45 – They are growing by at least 15% every month 08:00 – How the company is sustainable 08:30 – Customer acquisition is less than $10 08:45 – Paid acquisition is only content promotion 09:20 – They were founded in 2013 09:30 – What would Massimo sell his company for? 10:20 – @MassimoCw on Twitter or [email protected] 12:10 – The Famous Five   3 Key Points: Allow yourself to gain knowledge from different experiences. Find ways to lower your acquisition costs. Get into an industry that has a long life ahead of it.   Resources Mentioned: Host Gator – The site Nathan uses to buy his domain names and hosting for cheapest price possible. Freshbooks - The site Nathan uses to manage his invoices and accounts. Leadpages  – The drag and drop tool Nathan uses to quickly create his webinar landing pages which convert at 35%+ Audible – Nathan uses Audible when he's driving from Austin to San Antonio (1.5 hour drive) to listen to audio books. HubSpot – Massimo's favorite online tool Show Notes provided by Mallard Creatives

Amit Kothari. He spent ten years in London dealing with some of the largest companies and organizations in the world and helping them with collaboration technology. After seeing a lot of failures in that industry, he realized he needed a very structured process with unstructured, human conversations to make his business succeed. Famous 5: Favorite Book? – The Innovator's Dilemma What CEO do you follow? — Jack Welch and Warren Buffett Favorite online tool? — DropBox, Xero Do you get 8 hours of sleep?—Yes If you could let your 20 year old self know one thing, what would it be? — "Never confuse movement with action." –Hemingway Time Stamped Show Notes: 01:10 – Nathan introduces Amit 01:45 – Tallyfy 02:05 – The company's program helps remove routine processes throughout the day 02:30 – They started in Chili with a grant in 2014 03:00 – Then they got a grant from the US 03:30 – First year had no revenue 03:45 – $300k in 2015, with $600k total 04:15 – Paying customers 04:50 -- $39/month is the average that customers pay 05:15 – Monthly revenue 06:00 – They have several different services and processes 06:35 – Pure MRR in April -- $4000 07:10 -- Professional services is a huge chunk of revenue 08:20 – Starting out with professional services brings in a lot of revenue 08:50 – Team size is 5, with a few freelancers 09:05 – Total capital $500000 10:10 – Amit and his wife are cofounders 10:25 – They have a rule to stop talking about work after 6 pm 11:00 – They believe in their business 11:45 -- tallyfy.com and @tallyfy on Twitter 12:00 – Consistency is the secret to a growing company's success 14:20 – The Famous Five 3 Key Points: Start a business that you believe in. Look for grants and funding opportunities. If you want to scale your business, you have to put effort into consistency. Resources Mentioned: Host Gator – The site Nathan uses to buy his domain names and hosting for cheapest price possible. Freshbooks - The site Nathan uses to manage his invoices and accounts. Leadpages – The drag and drop tool Nathan uses to quickly create his webinar landing pages which convert at 35%+ Audible – Nathan uses Audible when he's driving from Austin to San Antonio (1.5 hour drive) to listen to audio books. The Innovator's Dilemma – Amit's favorite business book DropBox – One of Amit's favorite online tools, that allows businesses to share files online Xero – Online accounting tool Show Notes provided by Mallard Creatives