Explore every episode of the podcast Top Founders

Atticus LeBlanc, CEO of PadSplit, rents furnished rooms for under $30 a night, has 25,000 of them filled tonight, and owns none of the real estate. PadSplit is the largest co-living marketplace in the US: 82 units at the end of 2018, 34,000 today, over $250M a year in rent flowing through the platform, and 70% growth three years in a row.

In this interview, Nathan Latka breaks down the marketplace business model behind it: an 8% take rate (roughly $60,000 per day), the 10-day rent clawback that funds customer acquisition, an 8-day average room refill time, and a 9.5-month average stay where 25% of tenants stay 12+ months. Atticus also explains why he chose the Airbnb model over owning property like Invitation Homes, how real estate investors and small landlords earn higher yields renting by the room, and how a crowdfunding partner is buying up performing PadSplit homes.

On the funding side: 77 investor meetings for his 2021 Series B and one yes, $40M in total equity raised, and a new Orix credit facility that landed after he got the company near break-even. He answers "hell no" to a $150M all-cash offer and explains why.

Topics: affordable housing, co-living, real estate investing, rental property, proptech, marketplace business model, two-sided marketplace, take rate, venture capital vs debt financing, public benefit corporation, bootstrapping to break-even, Atlanta startups.

Subscribe on YouTube: https://www.youtube.com/@NathanLatkawatch?sub_confirmation=1
Subscribe on iTunes: https://podcasts.apple.com/us/podcast/top-founders/id1023761733
Subscribe on Spotify: https://open.spotify.com/show/3AA9buFn8oxJf8WSDOUks5

Looking for funding? Visit https://founderpath.com/

Jonathan Adly spent 15 years as a licensed pharmacist before writing the first line of code for TJM Labs in November 2024 — and 18 months later he's at $25M ARR, 40% EBITDA, 450 pharmacies, and $100M raised without ever making a pitch deck.

His pharmacy AI agents cost $45,000 a year, replace 2–3 human technicians each, and now fill 500,000 prescriptions every day.

In this episode he breaks down the $1M → $15M → $25M ARR run, why he took a $75M Series B from Elephant while already profitable, how he values an AI company at 15X+ off public comps, and the napkin math from 450 pharmacies to a $1.8B opportunity.

Vadim Yasinovsky, co-founder of pdfFiller and CEO of airSlate (parent of pdfFiller, signNow, DocHub, US Legal Forms, airSlate Flow), breaks down how a plain-looking PDF editor page became a $106M/year product with 866,000 paying customers — inside a company doing $200M in revenue across 1.1 million customers at an average of $180/year.

He raised just $150M total (last round: $52M at a $1.25B valuation in June 2022) and now says the company is optimistically worth $800M — despite doubling revenue since. He bought signNow at $3M and grew it to $35M. He built an SEO machine on 4.8 billion keywords and 35 million pages, and now says that playbook is dead within 9–12 months as ChatGPT and AI search take over.

In this episode:

• Why 650 employees are split into siloed 120-person product teams with no shared tech
• Why airSlate didn't become Harvey despite 85,000 lawyer-built legal forms as a training set
• Why Vadim says the "ChatGPT SEO" gurus are "b.s." and his influence on search drops from 80% to 30%
• His unannounced AI product (bizdraft.com) and why he won't monetize it
• The path from $200M to $400M: 20–30% from existing products, the rest from vertical AI
• His M&A filter: product-market fit, domain expertise, $5–10M+ revenue minimum
• His advice to founders: raise as late as you can, cash is king, preserve it now

Topics: SaaS, SEO, programmatic SEO, AI search, ChatGPT, document automation, e-signature, PDF editor, legal forms, SMB software, bootstrapping, vertical SaaS, M&A, capital efficiency.

Jeff Lu quit Google Cloud in 2022 to build his own AI video models at Akool, a generative AI platform for avatars, face swap, and video translation. He skipped the giant foundation models and trained small ones for specific tasks on rented servers, then watched revenue go from $100K in 2022 to $3M in 2023, $13M in 2024, $25M in 2025, and over $3M in June 2026 alone. He breaks down why Coca-Cola picked him over the foundation models and now pays him $4m per year. He'll share how he's driven huge usage (500,000 images and videos created daily) and what he'd say if Google offered $500M cash.

Akool revenue data: https://getlatka.com/companies/akool.com

Antoine Fort launched Qobra in 2020 with a $100K pre-seed from 7 angels, and his first investor was also his first customer. He started by cold calling with a phone list from a provider later shut down over European privacy law (GDPR), charging $10K/year. Today Qobra is at about $30K/year per customer, 250+ customers, and roughly $7–8M ARR. Along the way, one meme ad closed an $80K/year deal, and a single sales rep on the platform earned $1.5M in commissions (75x the average). So when Nathan asks if he'd sell for $100M cash today, his answer is surprisingly honest.

Qobra is an AI-first sales compensation and commission software platform. Antoine covers his $5M seed and $10M Series A, the $2M in debt he raised to limit dilution, the $200K–300K/year he spends on LinkedIn, YouTube and Google ads, his G2 and SEO glossary playbook, and the three AI agents Qobra is building to replace commission consultants.

Sevan Marian, co-founder and CEO of Fleet, bootstrapped his Paris-based laptop rental company for 7 straight years to roughly $40M in annualized revenue and close to $10M in yearly profit (EBITDA), without raising a single dollar of VC. His trick: customers pay about $50/month on 36-month contracts, and Fleet sells each contract to a bank that pays it upfront on day one. That's how he's financed 50,000+ devices across 20 countries without holding inventory. In early 2026 he sold about 25% of the company at a $100M valuation, and every dollar went out to the team: employees cashed out 100% of their shares, worth several million euros.

At 23, Alex Jekowsky started building Cents, an all-in-one software, hardware, and payments platform for laundromats, dry cleaners, and shared laundry rooms.

In 2025, Cents generated $60 million in revenue, up 67%, with just 80 employees and EBITDA margins above 20%. The company now has 99% customer retention, powers laundry rooms in nearly 7,000 apartment buildings, and recently raised a $140 million Series C at an approximately $800 million valuation.

In this episode, Alex reveals:

• How Cents grew from $700,000 to $60 million in four years
• Why its first customer was a 73-location laundry operator
• How Cents combines software, payments, and custom-built hardware
• Why the company generates roughly $750,000 in revenue per employee
• How Cents maintains 99% customer retention
• Why Alex acquired a hardware company instead of continuing to build everything internally
• How the $140 million financing included a $30 million employee tender
• Why founders should avoid raising at valuations that eliminate future options
• How Alex plans to turn an overlooked industry into a multibillion-dollar company

Froda generated $57 million in revenue in 2025 by lending to the small businesses traditional banks often overlook.

In this episode, Nathan Latka sits down with Froda co-founder Oliver Mohseni to unpack the economics behind the startup bank. Froda has supported 150,000 businesses across seven markets and funded approximately $3.45 billion since launch.

Oliver explains how Froda uses retail deposits, automated underwriting, and embedded partnerships with banks, fintech companies, payment providers, and software platforms to scale its lending operation.

Listen to learn:

• How Froda makes money on an average loan of just $23,000
• Why its banking license and retail deposits create an advantage
• How it prices loans at approximately 16% APR while managing credit losses
• Why embedded lending helped Froda expand across Europe
• How the company built a roughly $500 million active loan book

Carl Turner, founder of Swipe.by, built an AI marketing platform for restaurants to $3.5M ARR growing 400% year-over-year — with $0 spent on ads and every customer closed by a rep knocking on doors. He breaks down the exact rep comp plan (6 locations/month, $6K ACV, 30–40% commission), why he took $450K from Founderpath instead of Stripe, and why he gives away websites and online ordering for free. Then he turns down a $15M cash offer and explains the 2x liquidation preference math that could leave a founder with nothing. SaaS, bootstrapped, AI, restaurant tech, outside sales, SMB, Nathan Latka, Top Founders

Raphaël Boukris is the co-founder and Chief Revenue Officer of Didomi (didomi.io), the Paris-based consent management platform that helps enterprises comply with GDPR, CCPA, and privacy laws worldwide. Roughly 2% of all global web traffic passes through Didomi's SDK, and the company processes billions of consent decisions every month for customers including Bloomberg, Sky, and Adyen.

In this interview, Raphaël breaks down the full financial history on the record: three funding rounds, two acquisitions, and a majority sale to private equity. He raised under €300k from angels, then €5m from Breega in late 2019, then a €34m ($40m) Series B led by Elephant and Breega in summer 2021 — priced, he says, at above a 10x ARR multiple. Eight months later the market collapsed. He never burned through the money. In April 2025, Marlin Equity Partners took majority control, and Didomi immediately acquired Addingwell and Sourcepoint. Today the group does $40–60m ARR across 3,500 customers with fewer than 200 employees, and has at least one customer paying over $1m per year.

What we cover:

(01:02) What Didomi actually sells, and why every cookie banner in Europe is a business
(01:51) Why roughly 2% of global web traffic runs through their SDK
(02:12) Processing billions of consents per month — and who is not the customer
(03:00) Pricing on monthly unique visitors, and why AI agents and bots are breaking that model
(04:32) The Addingwell acquisition: a few million in ARR, a few thousand euros ACV, profitable enough to pay dividends
(05:10) Why he bought a second product instead of building one
(06:56) Every round, in order: sub-€300k angel, €5m Breega, €34m Series B
(07:50) Above a 10x multiple in 2021 — and how he ran Elephant through a roadshow to get it
(09:44) Secondaries in the Series B, and managing a team whose options went underwater
(10:06) The year he crossed $1m ARR, and the year he crossed $10m
(12:18) The question he answers "absolutely not" — was he ever close to shutting it down
(13:09) What growth equity actually pays in 2025, and the range he'd give
(14:22) Buying Sourcepoint, a company that had raised $48m, for its ACV and its US enterprise base
(15:07) 3,500 customers, one paying over $1m/year, under 200 people
(16:44) The combined group revenue number: $40–60m ARR

Full metrics, funding history, and revenue timeline: https://getlatka.com/companies/didomi.io

Stéphane Donzé has bootstrapped AODocs and Talarian to a combined $60m in 2026 revenue without raising capital. His top three customers each pay more than $2m per year, including Google, which pays him millions annually to control the documents behind its data center builds. He funded fourteen years of R&D off a cloud consulting business, never burned more than $200k in a month, and has fielded private equity calls four times a week declining $600m offers. 

He bootstrapped to $16.5m ARR selling software to 2,000 dental offices. Zero dollars raised, 24% EBITDA, and $1.5m in free cash flow last year. COVID cut him back to $2m in 2021; he's added $14.5m since, charging $13k per dental office per year. When I asked what happens if Henry Schein shows up with $180m cash, he gave a surprising answer. 

How do you go from a Chrome extension with no sales team to $15M in revenue in five years, while raising less money than most startups spend in their first year?

David Chevalier is the co-founder and CEO of Surfe, the leading CRM enrichment and waterfall data platform for B2B sales teams. He bootstrapped for two years, grew to $1.5M purely through HubSpot and Pipedrive marketplace rankings, and has never taken a dollar of personal secondary despite being six years into the company. Today Surfe processes 50 million data points per year and is the third partner inside HubSpot's AI prospecting agent next to ZoomInfo and Apollo.

You'll learn:

• How Surfe got to $1.5M in revenue with zero salespeople by becoming the number one app in HubSpot and Pipedrive marketplaces
• The waterfall enrichment model that aggregates 15 data providers and why building it at scale is much harder than it looks
• Why a third of their $15M revenue now comes from API usage and credits rather than seat licenses
• How David revealed his company revenue publicly for the first time ever on this show
• The Google partnership that started three and a half years ago and helped Surfe build the waterfall before the market even knew what it was
• Why their largest customer now pays over $1 million per year and how many more are approaching that threshold
• What happened when David tried to hire salespeople before the product was ready, and how many failed hires it took to find their CCO Eric
• How Surfe doubled from $9M to $15M in one year with 20 AEs each carrying $700 to $800K in quota
• Why 40% of their revenue comes from the US despite being founded in Paris and what it took to make that happen
• What David would do differently if he could go back and negotiate secondary at his pre-Series A round

Connect:
YouTube: youtube.com/@NathanLatkawatch
Surfe: surfe.com
Founderpath: founderpath.com

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/

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 customer service calls for transportation, retail, and healthcare brands.

After realizing their Cornell ridesharing app was a dead end, Brian and his co-founder Sam pivoted into voice AI. Today, Flip automates up to 90 percent of routine support calls for over 250 enterprise companies and recently raised a $20M Series A at a $100M valuation.

You'll learn:

• How to successfully pivot a failing startup model
• Why verticalized AI beats horizontal platforms
• How to implement usage-based pricing at $1.50 per call
• Why "listen mode" is their best sales tactic
• How to maintain 75 percent gross margins with AI
• Why they rejected a theoretical $150 million acquisition offer
• How to select the right industries for expansion
• Why competitive B2C markets are best for AI tools

Brian started his entrepreneurial journey at Cornell's eLab accelerator. He navigated the near-total collapse of transportation revenue during the pandemic to build a highly efficient business growing 3X year over year.

Watch this episode on YouTube: https://youtu.be/gtFt5exyCaI 

Connect with Brian:  https://flipcx.com/

Connect with Nathan:  https://founderpath.com/ 

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 coordinating people and spaces for hybrid work.

After realizing his wireless charging startup was a "vitamin, not a painkiller," Dan pivoted during the pandemic to help companies like Nasdaq, Revolut, and Boeing manage their office space. Today, Kadence serves over 600 enterprise customers.

You'll learn:

• How to manage board expectations during a hard pivot 
• The exact mechanics of resetting a cap table for new investors
• Why shifting from SMB to enterprise accelerated revenue
• How they achieved over 130 percent net dollar retention
• Why seat-based pricing still works in the enterprise
• The math behind saving half a billion dollars in leasing costs
• How launching SpaceOps AI drives multi-product expansion
• Why high-ticket dinners replaced SEO for customer acquisition

Dan started his career managing technology for a church before founding his first IoT business. He moved his family to the Bay Area just before the pandemic forced him to rethink his entire company operations.

Watch this episode on YouTube: https://youtu.be/2ySF3YMDcnY

Connect with Dan: https://kadence.co/
Connect with Nathan: https://founderpath.com/

How do you build a construction SaaS to $2M in revenue with just $500K raised and get 95% of growth from SEO?

Hmayak Tigranyan is the founder and CEO of Buildern, a construction management software platform serving around 300 customers and generating roughly $2M in revenue today. The company helps residential and commercial builders manage finances and workflows, and it is doing about $160K in monthly revenue with roughly $40K in monthly profit.

What makes this business interesting is that it scaled in a legacy industry without paid acquisition or outbound. Buildern built an inbound engine around high-intent SEO, stayed profitable, and is only now adding a sales team as ACV moves closer to the range that can support quota-carrying reps.

You'll learn:

• How Buildern found an underserved construction software niche.
• Why Hmayak shut down a $3M dev shop to go all in on SaaS.
• How the company raised just $500K and sold only 10%.
• What $160K in monthly revenue looks like at a $40K profit level.
• Why 95% of revenue came from SEO-driven inbound.
• How Buildern chooses long-tail keywords in construction.
• Why transparent competitor comparison pages rank well.
• How internal SEO execution beat the need for an agency.
• What changed once the company started hiring sales reps.
• How pricing moved from roughly $6K ACV toward $7.5K to $8K.
• What AE quotas and compensation look like at this stage.
• How a profitable vertical SaaS company scales with a global team.
  
  

Hmayak came into Buildern after years in SaaS development, travel software, and running a dev shop that peaked at about $3M in annual revenue. He launched Buildern in 2021, spent the first two years without paying customers, then used industry-informed angels and product iteration to find the right shape of the product.

This episode is for founders building in old industries, operators trying to scale efficiently, and investors who care about profitable SaaS growth. It is a useful masterclass in vertical SaaS positioning, SEO-led demand generation, and disciplined capital use.

Watch this episode on YouTube: https://youtu.be/An0n18v4j8E 

Connect with Hmayak: https://buildern.com/ 

Connect with Nathan: https://founderpath.com/ 

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 launched Allo as its first product. Allo is an AI phone system and dialer for small businesses, now serving around 5,000 customers with average revenue above $160 per month and a goal of reaching $10M in revenue in 2026.

This business is interesting because Jeremy did not stop at a self-serve PLG motion. He started there, saw the churn and activation issues, then layered in demos, lead routing, CRM-based qualification, and expansion to raise ACV and improve retention. The result is a high-volume SMB SaaS business built on strong distribution, fast onboarding, and clear activation metrics.

You'll learn:

• Why Jeremy moved from pure PLG to a sales-assisted motion.
• How Allo increased average revenue from $18 to over $160 per month.
• The exact activation metric that predicts churn.
• How the team uses demo routing based on CRM and team size.
• Why retargeting was one of the cheapest acquisition channels.
• How Allo won SEO with long-form content and original screenshots.
• The keyword prioritization system behind their content strategy.
• Why 50% of new revenue now comes from expansion.
• How the team thinks about CAC quality instead of lowest CAC.
• Why Jeremy raised early without waiting for a co-founder.
• How he kept about 50% ownership after raising around $20M.
• What it takes to sell into SMBs at high volume with only 17 people.

Jeremy previously led growth at Spendesk before starting The Mobile First Company. He launched the company as a solo founder, raised a $5M pre-seed on his own, then built the team around him while keeping significant ownership. His long-term goal is not just one product, but a broader suite of vertical SaaS tools built under separate brands.

If you care about SMB SaaS, PLG versus sales-assisted growth, SEO-led distribution, or building a multi-product software company, this episode is a masterclass for SaaS builders.

Watch this episode on YouTube: https://youtu.be/PUZMvjyS3xw 

Connect with Jeremy: https://www.withallo.com/ 

Connect with Nathan: https://founderpath.com/ 

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 launching in 2024. The company serves enterprise sales teams with contracts ranging from $24K to $250K annually, with its largest deals exceeding seven figures.

What makes TitanX interesting is its approach to building a moat. Instead of competing as another data provider, the company sits between data sources and execution layers, using proprietary signals and AI to improve outbound performance. The business scales through high ACV sales, expansion revenue, and strategic acquisitions.

You'll learn:

• How Joey turned a $200K IP purchase into a $100M company
• Why buying IP can be faster than building SaaS products
• How TitanX structures pricing from $24K to $250K ACV
• The role of proprietary data in building defensibility
• How inbound, outbound, and referrals drive pipeline
• Why expansion revenue is core to growth strategy
• How acquisitions accelerate ARR growth
• The credit-based pricing model and consumption dynamics
• How TitanX uses AI to improve outbound performance
• The logic behind raising $27M and taking secondary cash

Joey started in enterprise sales before launching multiple businesses and eventually betting his entire net worth on TitanX. After acquiring the IP in 2023, he shut down a profitable services business to focus fully on SaaS, scaling from zero to $9.7M ARR in under two years.

This episode is for SaaS founders thinking about capital allocation, high-ACV sales, and building defensible data products. It's a practical breakdown of how to scale quickly using acquisition, pricing, and distribution strategy.

Watch this episode on YouTube: https://youtu.be/mxiCodnXo6U?si=zebVllHlOY7UlVqO 

Connect with Joey: https://titanx.io/ 

Connect with Nathan: https://founderpath.com/ 

How do you grow a customer support SaaS to over 1,000 customers and $10M–$25M in ARR in one of the most crowded software categories, without trying to outspend the giants on marketing?

In this episode, Nathan sits down with Grant Stanis, CEO of TeamSupport. The company provides B2B customer support software used by more than 1,000 companies and generates between $10M and $25M in annual recurring revenue. Most customers start around $10,000 per year, but the best accounts expand significantly over time, including enterprise customers paying more than $1M annually.

Customer support software is a brutally competitive market with players like Zendesk and Freshdesk dominating search and advertising. Instead of fighting that battle, TeamSupport focused on referrals, community, and expansion revenue. The core idea is simple: turn support conversations into signals that drive retention, product feedback, and upsells.

You'll learn:

• How TeamSupport grew to $10M–$25M ARR with over 1,000 customers.
• Why most customers start around $10K ACV and expand to $20K–$30K later.
• How one enterprise account grew into a $1M+ annual contract.
• Why they price the product per seat at $79–$99 per user.
• How expansion revenue became a core growth driver.
• Why the company relies heavily on referrals instead of SEO.
• How partnerships and webinars generate qualified pipeline.
• What it's like to lose a top 10 customer and report it to the board.
• How private equity ownership changes the way CEOs run SaaS companies.
• What kind of acquisition offer would realistically trigger a sale.

Grant joined TeamSupport as CEO in 2024 after leading growth at several private equity-backed software companies. The business was founded in 2008 and later acquired by Level Equity in 2018. Today the focus is simple: grow profitably, expand existing customers, and build a durable SaaS business without relying on massive marketing budgets.

If you run a SaaS company selling to support teams, customer success leaders, or mid-market software companies, this episode offers a practical look at how to grow in a crowded category.

Connect with Grant: https://www.teamsupport.com/ 

Connect with Nathan: https://founderpath.com/ 

How do you rebuild a declining cybersecurity company into a $70M revenue platform with ~$25M EBITDA after buying it back for under $10M, while scaling primarily through acquisitions and debt instead of venture capital?

Gary Guseinov is the CEO of Realdefense, a consumer cybersecurity and privacy platform that generates roughly $70M in annual revenue with $20–25M in EBITDA. Gary originally founded the business in 2003 as Cyber Defender, grew it to $70M in revenue, took it public, then later bought the company back in 2017 when it had declined to about $7M ARR.

Today, Realdefense operates as a platform of security and privacy products that monetize partner user bases through software subscriptions, telemetry-driven product offers, and cross-sell expansion. The company has completed six acquisitions since the buyback and now scales growth through a capital-efficient M&A strategy instead of traditional venture capital.

What makes this business interesting is its unconventional growth model. Instead of building new SaaS products from scratch, Realdefense acquires small or declining companies, integrates them into a shared technology and billing stack, and compounds revenue by increasing LTV through cross-product distribution.

You'll learn:

• How Gary bought back his own company for under 1x ARR and rebuilt it through acquisitions.
• The platform strategy Realdefense uses to monetize partner user bases in cybersecurity software.
• Why telemetry-based product triggers outperform traditional advertising monetization.
• The pricing ladder strategy that starts with $20 products and scales customers to hundreds per year.
• How cross-selling security tools like VPN, identity protection, and device optimization increases LTV.
• The debt financing strategy Gary uses instead of giving up equity to venture capital.
• How lenders evaluate SaaS acquisitions using EBITDA multiples.
• Why buying flat or declining software companies can be a scalable growth strategy.
• The operational advantages of integrating multiple software products into a single platform.
• How founder ownership and liquidity decisions change when companies go public.

Gary started his career in direct marketing before launching his first cybersecurity company in 2003 with roughly $50K–$75K of his own capital and an initial $250K raise. After raising significant venture capital and eventually going public, he saw the risks of dilution firsthand. When the business declined under new leadership, he bought it back in 2017 and rebuilt it with a very different capital strategy focused on debt, acquisitions, and ownership preservation.

If you're a SaaS founder thinking about capital efficiency, acquisition-driven growth, or alternative scaling strategies outside of venture capital, this episode is a masterclass in operator-led capital allocation.

Watch this episode on YouTube: https://youtu.be/ebkYMcJcpg0 

Connect with Gary: https://www.realdefen.se/home/ 

Connect with Nathan: https://founderpath.com/ 

How do you build an AI SaaS company to $1M+ ARR with just a few dozen customers and raise a Series A at a 20x+ revenue multiple while competing against general-purpose AI tools?

Tal Kirschenbaum is the Co-Founder and CEO of Ledge, an AI-native financial close platform helping finance teams automate the month-end close process. Just three years after writing the first line of code, Ledge has reached $1M+ ARR with ~24–36 customers paying roughly $3K per month, while targeting 300% year-over-year growth with a team of ~35 employees.

What makes this story interesting is how narrowly the product is positioned. Instead of building a generic "AI for finance" tool, Ledge focuses on a painful operational workflow: the month-end close process for mid-market and enterprise finance teams. The pricing is not seat-based. Instead, revenue scales with operational complexity — entities, currencies, and integrations — creating a natural ACV expansion motion as customers grow.

You'll learn:

- Why Ledge targets finance teams with 5+ people as the ideal entry point for workflow automation.
- How pricing based on business complexity (entities, currencies, channels) replaces traditional seat-based SaaS pricing.
- The math behind reaching $1M+ ARR with ~24 customers paying ~$3K per month.
- Why focusing on one painful workflow can create a stronger product moat than building a broad AI platform.
- How "glassbox AI" explainability matters for finance and accounting teams dealing with compliance and audits.
- Why selling based on workflow value — not an "AI budget" — reduces churn risk in AI SaaS.
- How enterprise credibility increases ACV over time as new customers pay higher prices than early adopters.
- What raising a Series A at a 20x+ revenue multiple says about early-stage AI SaaS valuations in 2026.
- The internal debate founders face when trading equity dilution for faster growth.
- Why some SaaS companies avoid seat-based pricing when automation actually reduces headcount needs.

Before starting Ledge, Tal led M&A transactions at Meta and worked on new products at Melio, the payments company that later sold to Xero for $2.5B. He left Melio in 2022 to build Ledge, giving up seven-figure unvested equity to pursue the opportunity he saw in financial close automation.

If you're building vertical SaaS, AI infrastructure for finance, or enterprise workflow software, this episode is a masterclass in product focus, pricing strategy, and early enterprise traction. It's also a rare look at how AI SaaS founders think about moats when the platform risk from large models is real.

• Watch this episode on YouTube: https://youtu.be/EGWc23BI7Zw 

• Connect with Tal: https://ledge.co

• Connect with Nathan: https://founderpath.com/ 

How do you turn a failed public ecommerce company into a $5M ARR enterprise SaaS platform serving ~$2M+ contracts — while rebuilding with capital efficiency after bankruptcy and avoiding the growth-at-all-costs playbook?

In this episode, Nathan sits down with Jared Yaman, co-founder of Spresso and former founder of Boxed, the bulk ecommerce company that scaled to $187M in revenue before its IPO and eventual Chapter 11 restructuring. Today, Jared leads Spresso, the enterprise ecommerce software platform spun out of Boxed, now serving roughly 15 enterprise customers worldwide and growing ARR from $2.5M at spinout in 2023 to about $5M in 2025 through large ACV enterprise contracts.

What makes this story interesting is the transition from low-margin ecommerce operations to high-margin enterprise SaaS. Boxed generated hundreds of millions in revenue but operated on ~4–5% contribution margins. Spresso keeps the infrastructure, data, and enterprise relationships — but monetizes them through implementation fees and modular SaaS subscriptions, fundamentally changing the economics.

You'll learn:

- Why scaling revenue without contribution margin destroys optionality, even at $100M+ revenue
- How enterprise implementation fees subsidize onboarding costs and accelerate payback periods
- The pricing structure behind $2M+ enterprise contracts in ecommerce infrastructure
- Why founder-led sales and existing network relationships became the primary GTM channel post-spinout
- How to reposition operational technology into a standalone SaaS category buyers understand
- The debt strategy Spresso uses to keep leverage under 10% of ARR
- Lessons from raising $380M in venture capital and ending with low single-digit founder ownership
- How reducing deployment timelines from 4 months to 4 weeks unlocked enterprise expansion
- Why enterprise SaaS growth favors fewer customers with large ACVs over broad SMB distribution
- The strategic shift from retail unit economics to recurring software margins

Jared previously co-founded Boxed, raising roughly $380M before taking the company public, where founder ownership diluted to about 2.6%. After Boxed filed for Chapter 11 in April 2023, he helped spin out the software platform into Spresso with debt financing support, rebuilding the business around sustainable SaaS economics instead of venture-funded retail growth.

This episode is for founders navigating pivots, operators moving from services or commerce into SaaS, and investors studying capital efficiency in enterprise software. It's a masterclass in restructuring strategy, enterprise pricing, and rebuilding a company around durable margins instead of headline revenue.

Watch this episode on YouTube: https://youtu.be/vslJtgAtjuY 

Connect with Jared: https://www.spresso.ai/ 

Connect with Nathan: FounderPath.com

How do you turn a niche offline sports business into $3M in contracted ARR across 200 locations, while raising $8M and keeping pricing simple on a per-unit basis?

Ben Borton is the Co-Founder of PodPlay Technologies, a vertical SaaS platform powering pickleball and racquet sport venues. What started as internal software for his own ping pong spaces is now a $3M contracted ARR business serving 200 locations and roughly 2,000 courts, with ACVs ranging from $10k–$15k and an $8M Series A completed in 2025.

This business is interesting because it didn't start as software. Ben built PodPlay to solve utilization and operations inside his own physical venues, where courts generated $30 per hour at 70% utilization. The SaaS product is now growing faster than the brick-and-mortar business — proving that real-world operational pain can be the most durable GTM wedge in vertical software.

You'll learn:

— How Ben validated the SaaS by first using it inside a venue doing $100k–$400k in annual revenue

— The exact per-court pricing model and why ACVs land between $10k–$15k for larger operators

— How software-only contracts at $2k–$6k expand into $10k+ hardware-inclusive deals

— Why 70% court utilization at $30/hour created the margin profile to fund early product development

— How founder-led sales drove growth from first external customers in 2023 to $3M contracted ARR

— The GTM motion behind signing 200 locations without a traditional enterprise sales team

— How viral video sharing from players became an organic acquisition channel for physical venues

— Why vertical SaaS embedded in real-world workflows wins over generic booking tools

— How spinning out the software into a separate entity unlocked an $8M Series A

— What operators should consider before raising capital versus compounding through cash flow

Ben's background spans fintech, hedge funds managing $300M AUM, and early-stage investing before launching his own venues in 2020. He opened PingPod during COVID, optimized for utilization and unit economics, and then spun out the internal software into PodPlay once external demand became clear. The capital raise was deliberate: sell 13–18%, accelerate distribution, and double down on category leadership.

This episode is for founders building vertical SaaS, operators sitting on proprietary workflow data, and investors looking for software businesses born out of real revenue. If you're thinking about pricing per unit, founder-led GTM, or when to separate software from services, this is a masterclass in capital-efficient category creation.

• Watch this episode on YouTube: https://www.youtube.com/watch?v=SB8bmy8LylI 

• Connect with Ben: https://podplay.app/ 

• Connect with Nathan: FounderPath.com

How do you build a vertical SaaS company to ~$50M ARR serving 6M homes — after bootstrapping to $5–10M without outside capital — and then 10x with a minority PE round instead of giving up control?

Ben Currin is the CEO of Vantaca, a vertical SaaS platform powering community association management companies. Since launching in 2018, Vantaca has grown to ~500 customers managing 50,000 communities and 6M homes, scaling from low six figures in 2018 to ~$1M in 2019, $5–10M by 2022, and roughly 10x revenue since taking minority investment.

This is not a trendy market. HOA management is fragmented, operationally complex, and historically under-served by modern software. Vantaca didn't win with viral PLG or heavy paid acquisition. They went top-down enterprise, priced per door, embedded payments and treasury, and built the general ledger system of record for an entire industry.

You'll learn:

— How to identify "sneaky big" vertical SaaS markets hiding in unsexy industries.

— Why per-door pricing became the north star metric and expansion lever.

— How to sell top-down into large management companies instead of bottom-up homeowners.

— How Vantaca expanded from pure SaaS into payments, treasury, and vendor monetization.

— What capital efficiency looked like in practice during the first five years.

— The signal that shifted them from capital efficient to capital constrained.

— How to structure a minority PE deal with primary and secondary capital.

— Why retaining majority ownership mattered before a potential 5–10x growth phase.

— How acquiring a YC-backed AI company accelerated product roadmap and attach rates.

— How embedding agentic AI into billing, support, and operations increases platform stickiness.

Ben joined Vantaca in 2018 alongside founder Dave Sawyer, who originally built the software inside his own HOA management business. Neither came from venture-backed SaaS. They bootstrapped for five years, reinvested profits, crossed $1M ARR in year two, reached high single-digit millions by 2022, and only then brought in JMI Equity for a minority investment to accelerate growth. A second minority recap followed, preserving control while funding expansion.

If you're a founder building in vertical SaaS, considering minority growth capital, or thinking about embedding fintech and AI into your core product, this episode is a masterclass in disciplined scaling inside a niche market.

Watch this episode on YouTube: https://www.youtube.com/watch?v=ckRiL_bFK_w 

Connect with Ben: https://www.vantaca.com/ 

Connect with Nathan: FounderPath.com

How do you scale a vertical SaaS platform to $12M ARR while navigating the aggressive valuation overhang of 2021 and a founding team transition. Matt Spiegel is building Lawmatics into a dominant legal CRM by leveraging a serial founder playbook that prioritizes high ARPU and agentic AI over traditional SaaS metrics.

Matt Spiegel is the founder and CEO of Lawmatics, a legal marketing and CRM platform serving over 2,000 law firms. The company currently generates over $1M in monthly revenue with an average ACV of $5,000. After raising $25M in total capital, Matt has maintained roughly 20% ownership while driving the business toward profitability and a potential $240M+ valuation.

This business is a case study in the evolution of vertical SaaS and the transition from simple automation to agentic AI. Lawmatics successfully moved from an initial $60 monthly price point to a $400 ARPU by aligning pricing with high-value legal intake data. Matt provides a rare, transparent look at the mechanics of Series A extensions and the decision to forgo all-cash exits in favor of the "bites at the apple" recapitalization model.

You'll learn:
- The specific Google Ads and social spend required to acquire the first 100 B2B customers.
- Why sponsoring practice-area specific conferences is a higher ROI channel than generic trade shows.
- How to manage a $400 monthly ARPU through a value-based pricing strategy.
- The mechanics of a technical co-founder exit after four-year vesting schedules are complete. - Why a 15x revenue multiple in 2021 created a strategic valuation gap for later rounds.
- Tactical execution of Series A extensions to avoid down-rounds in a tight capital market. 
- The shift from "SaaS is dead" to agentic AI products that automate legal intake decisions. 
- Why a 40% equity roll is superior to an all-cash exit for long-term wealth compounding. 
- How to evaluate venture debt offers at 14% interest versus further equity dilution. 
- The data advantage gained from processing 11 million legal intakes to train proprietary models. 
- Why serial founders should prioritize optionality and board alignment on debt aversion.

Matt Spiegel previously founded My Case, a legal practice management platform he scaled to $500k ARR before selling to AppFolio in 2012. After watching that entity eventually reach a $2.5B valuation, he launched Lawmatics in 2017 with a focus on the front-end of the legal lifecycle. His capital strategy shifted from early-stage venture to strategic extensions, ensuring the founding team retained significant upside.

This episode is for B2B SaaS founders and investors managing the transition from growth-at-all-costs to sustainable profitability. It serves as a masterclass on capital efficiency, vertical market dominance, and the reality of scaling a leadership team past the initial founding duo.

Watch this episode on YouTube: [Here]
Connect with Matt: Lawmatics.com 
Connect with Nathan: FounderPath.com

Siddharth Sinha is the co-founder and CEO of Dresma, an AI-powered platform helping global brands create studio-quality e-commerce imagery, videos, and localized content at scale.

Launched in 2020, Dresma helps brands like Puma localize product imagery across markets using AI models, data intelligence, and automated workflows. The company now serves ~28 customers, generates ~$2M ARR, and has grown profitably with a lean team of 31 people.

In this episode, Siddharth explains Dresma's usage-based pricing model, how studio partnerships drive over 50% of revenue, and how the company expanded enterprise customers up to $500K per year—while keeping infrastructure costs and CAC under control.

• How Dresma helps brands localize content globally using AI

• Why usage-based pricing outperformed seat-based or product upsells

• How studio partnerships became a major growth channel

• What percent of revenue goes to LLM credits (and why it works)

• How free tools drive SEO and enterprise lead generation

• Dresma's ABM tech stack (Smartlead, Apollo, Clay + custom tooling)

• How to sell enterprise SaaS with AEs based in India

• How Dresma grew from $1.3M to $2M ARR in 12 months

• What it took to reach profitability after raising a $3M seed round

Before founding Dresma, Siddharth was a serial entrepreneur and Cornell-trained engineer with deep experience in e-commerce content and studio workflows. The company raised a $3M seed round at a $10M post-money valuation in late 2021, backed by early revenue traction and strong domain expertise.

Today, Dresma is profitable, growing steadily, and focused on becoming the end-to-end visual content engine for global e-commerce brands.

If you're a SaaS founder thinking about usage-based pricing, enterprise AI, programmatic SEO, or capital-efficient growth—this episode is a deep, tactical breakdown of what actually works.

Watch this episode on YouTube:

https://www.youtube.com/watch?v=NjSTmVJ_SF0 

Connect with Siddharth:

https://dresma.com

Connect with Nathan:

https://founderpath.com 

How do you grow a nearly $5M ARR SaaS with just 2 sales reps, while staying bootstrapped and capital efficient?

Raf Howery is the founder and CEO of Kukun, a B2B property data platform powering white-labeled tools for banks, fintechs, and insurers. After quitting a $1M/year consulting role, he built Kukun to serve ~25 enterprise clients, each paying $10K–$50K/month. The team now processes ~500,000 property addresses monthly across a growing suite of data-driven products.

What makes this business especially compelling is the dual monetization model: a B2C experience that acts as a PLG wedge, and a B2B monetization layer through usage-based pricing for banks and lenders. Kukun's go-to-market evolved from realtor hand-to-hand distribution to landing multi-product deals with top financial institutions.

You'll learn:

—How Raf uses white-label distribution to monetize banks and fintechs

—Why bundling multiple products improves ACV and deal velocity

—How product-led growth drives enterprise adoption through homeowners

—What pricing bands based on address volume look like in practice

—How to build an enterprise SaaS with just 2 quota-carrying reps

—Why realtors were the original GTM channel, and how they unlocked enterprise

—How Raf kept control by raising only $7M in pre-2022 convertible notes

—Why usage is tied to seasonality, and how Kukun hedges that risk

—The real CAC math behind serving 20–25 enterprise accounts

—How PLG and founder-led sales work together in regulated markets

—Why current mortgage dynamics are boosting home improvement software

—How Raf positioned Kukun as the "post-transaction" engagement layer for banks

Before founding Kukun, Raf spent over a decade in management consulting, advising Fortune 500 clients at Capgemini. He walked away from a $1M/year role to build a capital-efficient SaaS company, investing $1M of his own money and raising only private capital. For the first several years, he focused entirely on product and data before scaling sales.

If you're a SaaS founder thinking about bootstrapping, pricing usage-based products, or selling into regulated industries—this is a masterclass in control, distribution, and enterprise monetization.

Watch this episode on YouTube:

https://www.youtube.com/watch?v=sm22u4w_-pk 

Connect with Raf:

https://mykukun.com/

Connect with Nathan:

https://founderpath.com/

How do you scale a digital document tool to $15M ARR with 28,000 customers—without raising a dollar of VC?

Gabriel Ciordas did it by going deep on SEO, mastering self-serve onboarding, and closing six-figure enterprise contracts—all while owning 100% of the business.

Gabriel Ciordas is the founder and CEO of Flipsnack, a digital magazine and brochure platform. Since launching in 2011, he's grown the company to $15M in ARR, with 28,000 paying customers and a pricing range that spans from $16/month self-serve plans to $200,000/year enterprise deals.

Flipsnack operates in a surprisingly large and overlooked market: digital collateral for internal and external business communications. The company's strength lies in a dual-motion GTM strategy—self-serve for the long tail, and custom pricing for enterprise accounts. Despite a small sales team, the business is expanding into high-ACV deals thanks to its early SEO moat and product simplicity.

You'll learn:

— How Flipsnack converts 160,000+ monthly SEO clicks into paying users

— Why their template library drives $3M/year in equivalent ad traffic

— How they price from $16/month to $200K/year based on use case

— Why only 3 team members manage their SEO playbook

— How to transition from PLG to sales-led without abandoning self-serve

— Why they pulled—and are now reintroducing—a freemium tier

— The real ROI of in-house paid ads vs. influencer marketing

— How to identify and upsell high-ACV users from low-touch channels

— Why they're opening sales offices in Japan, Korea, Portugal, and Switzerland

— How accessibility and AI are shaping their product roadmap

— Why Gabriel took $2.5M in debt capital but stayed 100% bootstrapped

— What founders miss when they underestimate the enterprise sales cycle

Gabriel started Flipsnack in Romania in 2011 after years of building companies since 1999. He bootstrapped the business from the ground up, scaling it with organic demand and SEO discipline. Even after raising $2.5M in non-dilutive capital from Founderpath, he remains the sole owner.

If you're a SaaS founder navigating freemium vs. enterprise pricing, PLG vs. sales-led GTM, or simply want to scale efficiently without venture capital, this episode is a masterclass in strategic growth and capital discipline.

Connect with Gabriel:

https://www.flipsnack.com/

Connect with Nathan:

https://founderpath.com/ 

Volie quietly hit $1.2M in monthly revenue ($14M+ per year) selling BDC communication software to car dealerships — fully bootstrapped. In this episode, Scott Davis (President & Co-Founder) breaks down how Volie scaled from 4 customers in 2017 to powering 2,000 dealership rooftops across 300 store groups, all while maintaining a 16% profit margin and retaining ~85% ownership — plus whether he'd take $70M cash for 60% of the business.

• How Volie scaled from 4 customers to $14M/year without raising capital

• Why selling into car dealerships is a powerful (and overlooked) SaaS niche

• How Volie prices dealerships and store groups to reach $1.2M MRR

• The economics behind a profitable, quota-carrying sales team

• How Scott thinks about AI, growth, and a potential $70M acquisition offer

Sabari Nair, co-founder and CEO of Skillveri, joins Nathan to break down how he's scaling a VR-powered vocational training platform to $1.5M ARR today, serving 100+ schools in the U.S., with $350K enterprise contracts — and why he believes immersive training plus SaaS pricing is the future of skilled labor education.

In this episode, Sabari explains how Skillveri combines VR software subscriptions, hardware add-ons, and a reseller-led GTM motion to win in a category traditionally dominated by $30K+ one-time simulation vendors.

You'll learn:

— How Skillveri sells VR training software starting at $4K/year per school

— Why their largest customer pays $350K annually (and how they plan to reach $1M contracts)

— The SaaS + hardware hybrid model driving 60% recurring revenue

— Why schools (not industry) are the wedge into a massive skills market

— How reseller partnerships replaced direct sales across the U.S.

— The commission structure that motivates resellers without killing margins

— Why in-person demos beat cold pitches for immersive tech

— How VR + mixed reality creates objective skill grading (welding, painting, more)

— The COVID pivot that forced a full reset — and buying out investors at a discount

— Why Sabari turned down a $4M all-cash acquisition offer

— The roadmap to $10M ARR by expanding to 2,000+ schools

Sabari started the company in 2012 building hardware, pivoted hard into software during the pandemic, bought out early investors in 2021, and rebuilt the business into a capital-efficient SaaS with hardware upsells. Today, Skillveri runs on a lean team, supports Meta Quest and Pico headsets, and is redefining how skilled trades are taught globally.

Whether you're a B2B SaaS founder, hardware-plus-software operator, investor exploring edtech, or operator designing reseller GTM motions, this episode is a masterclass in enterprise pricing, channel strategy, and scaling immersive technology without burning cash.

Connect with Sabari:

Skillveri.com

Connect with Nathan:

FounderPath.com

In this episode, we sit down with Andrew Fennell, founder of Standout CV, to unpack how he built and scaled a resume-builder SaaS to over 18 million organic visitors, $30K MRR, and $1M+ in lifetime revenue — without venture funding.

Andrew walks through his SEO-first go-to-market strategy, pricing evolution, churn reduction, and the exact content and link-building tactics that helped him win in an ultra-competitive space. This episode is a masterclass in bootstrapped SaaS growth, monetization, and acquisition efficiency.
_________________________________________________________________________________

• How a recruitment background led to a SaaS opportunity

• Transitioning from services to scalable software

• Bootstrapping vs. raising capital

• Why one-time payments killed LTV

• Switching to subscriptions to unlock recurring revenue

• Using low-friction paid trials to boost conversion

• SEO as the core go-to-market motion

• Why content beats ads in crowded markets

• Building trust before monetization

• Creating linkable assets journalists actually cite

• Digital PR vs. guest posting

• Programmatic SEO pitfalls and content pruning

• Reducing churn in naturally short-term SaaS use cases

• Running a high-margin SaaS with a small team

• Positioning a bootstrapped business for acquisition

_________________________________________________________________________________

Andrew started Standout CV as a freelance CV-writing service, evolved it into a content-driven traffic engine, and eventually built a subscription SaaS now generating consistent monthly revenue. Today, he's also advising other SaaS companies on SEO while exploring acquisition offers for the business.

Whether you're a bootstrapped SaaS founder, B2B operator, or investor evaluating SEO-driven businesses, this episode is a masterclass in organic acquisition, monetization, and building real leverage without venture capital.

Connect with Andrew:

Standout-CV.com

Connect with Nathan:

FounderPath.com 

Vlad Malanin, MD, PhD and co-founder of SpeedSize, shares how he scaled an AI-powered media optimization SaaS from $400K to $6M ARR with just 25 employees. SpeedSize helps enterprise and mid-market brands deliver high-quality images and video without sacrificing site performance, serving over 200 global customers.

In this episode, Vlad breaks down SpeedSize's capital-efficient growth strategy, enterprise pricing model, partnership-led GTM motion, and the hard founder decisions required to survive near-zero runway during wartime—while maintaining low churn, strong expansion revenue, and founder control.

• Founder background

  • Surgeon turned AI scientist and CTO

  • Forbes Technology Council member

  • Ukrainian-Israeli founding team navigating geopolitical risk

• Company overview

  • AI-powered image and video compression for rich media websites

  • Focus on preserving visual quality while improving load speed

  • Core customers: fashion, apparel, marketplaces, travel, jewelry

• Revenue & growth

  • $400K ARR in 2022

  • ~$1.5M ARR in 2023

  • ~$3M ARR in 2024

  • ~$6M ARR today

  • 200+ paying customers

  • Low churn with strong net revenue expansion

• Pricing & ACV

  • Annual contracts only

  • Pricing based on:

    • Data transferred (GB)

    • Number of original assets / SKUs

  • ACV ranges:

    • $10K–$20K (lower mid-market)

    • $50K–$100K (mid-market)

    • Low seven figures (enterprise)

  • Multiple customers paying $100K+ annually

• GTM & acquisition

  • Minimal reliance on paid ads

  • Partnership-led growth strategy:

    • AWS Premium Partner

    • IBM Cloud partnerships

    • Agency referrals

  • Focus on cloud providers lacking native media optimization

• Sales motion

  • Land-and-expand strategy

  • Customers grow usage as they adopt richer media (video, animations)

  • Enterprise-focused negotiations vs self-serve SMB motion

• Team & operations

  • Team downsized from 50 to ~25 for efficiency

  • ~70% engineers

  • High revenue per employee

  • Cash-flow controlled with variable spend levers

• Capital & fundraising

  • ~$5M total raised (2022–2023)

  • Founders retain 70%+ ownership

  • Pre-Series A

  • Lessons learned from VC-driven spending pressure

• Crisis management

  • Two months of runway during 2023 war escalation

  • Cash dropped below $300K

  • Founders cut their own salaries first

  • Focused on survival, efficiency, and customer retention

• Transitioning from medicine to AI SaaS

• Building during war and geopolitical uncertainty

• Making survival-first leadership decisions

• Structuring enterprise SaaS pricing by usage

• Designing ACV tiers from $10K to seven figures

• Using land-and-expand to drive ARR growth

• Why SpeedSize prioritized partnerships over outbound sales

• How AWS and IBM partnerships actually work

• The realities of enterprise marketplace distribution

• Why low churn matters more than hypergrowth

• Enabling customer expansion through product value

• Avoiding paid ads in favor of scalable channels

• Downsizing teams without killing momentum

• Managing cashflow with variable spend

• Staying capital-efficient while retaining founder control

This episode is a must-watch for SaaS founders, operators, and investors interested in pricing, GTM strategy, retention, capital efficiency, and real founder resilience.

Romain Torres is the founder of ArcAds.ai, an AI-powered video ad platform that helps marketers create and scale ad creatives with zero production overhead. In just 20 months, he scaled the company from $5K to over $10M in ARR—completely bootstrapped.

In this episode, Romain shares how he validated demand without even having a dashboard, the growth playbook that drove viral traction, and the three channels fueling ArcAds' revenue engine today: paid ads, sales, and influencer marketing. He also dives into usage-based pricing, churn recovery, and what's next for the company.

Notes:

• Growth Levers

  • Reached $10M ARR in under 2 years

  • From $5K to $64K MRR in 1 month after a viral tweet

  • Paid ads, influencer virality, and enterprise sales are main levers

• GTM Strategy

  • Started with direct outreach and manual fulfillment

  • Product-led motion with a transition into high-touch enterprise sales

  • Events and conferences (Affiliate World, App Growth Summit) for pipeline

• Revenue & Pricing

  • Usage-based pricing (number of generated ads, actors, etc.)

  • Highest ACV in the six figures

  • Profitably bootstrapped despite heavy infrastructure/API costs

• Churn & Retention

  • Early churn spike due to product breaking after viral growth

  • Rebuilt platform in one month post-refunds

  • Retention improved with onboarding and product stability

• Scaling Operations

  • 8-person lean team managing 210+ live ads

  • Internal use of ArcAds platform to generate their own creatives

  • Strong rev-per-employee metrics

• Data & Tech Stack

  • Sits on top of GenAI models from OpenAI, Google, ByteDance

  • Auto-selects best model per prompt based on use case

  • Internal feedback loops using ad performance data to improve UX and features

• Founder Insight

  • Tested market fit without a product UI

  • Hired sales after passing $5M ARR

  • SEO and enterprise sales are next big focus areas

Founder Story

• How Romain validated the idea with no product

• Why ArcAds went viral and what broke

• Bootstrapping vs VC-backed strategy

Pricing & Revenue

• Usage-based monetization and six-figure ACVs

• Profit margins despite high API costs

• Leveraging viral growth to fund product rebuild

GTM & Outbound

• Transition from product-led to outbound sales

• Scaling via events, outreach, and Twitter content

• Building a two-person sales team to close big brands

SEO & AEO

• Organic strategy and plans for future growth

• Why they've done no SEO so far—and why that's changing

• How content virality and influencer posts fueled spikes

Acquisition & Scaling

• Managing churn during hypergrowth

• Operating a multi-million ARR business with 8 people

• Systems for testing, tracking, and scaling 200+ ad creatives

Golf course SaaS founder Jason Pearsall shares how Club Caddie scaled from $450K to $9M ARR in 5 years, sold to Constellation Software (CSI), and keeps growing with 600+ golf courses paying ~$15K ACV. If you're building vertical B2B SaaS, this is a masterclass in niche focus, capital efficiency, and smart deal-making.

Jason breaks down why he built an end-to-end ERP for golf courses, how he used data-driven outbound, review sites, SEO and "answer engine optimization" (AEO) to win market share, and what really happened during his CSI acquisition and long-term earnout. We cover pricing, ACV targets, GTM channels, fundraising vs. selling, and how to design a growth engine when your entire ICP is just 15,000 accounts.

In this episode, Club Caddie founder & CEO Jason Pearsall breaks down how he:

• Built a vertical SaaS ERP for golf courses after buying and operating his own club

• Scaled Club Caddie from $450K to $9M ARR in 5 years with ~600 customers and ~$15K ACV

• Raised just $600K before being acquired by Constellation Software (CSI)

• Structured a long-term earnout instead of a flashy headline multiple

• Used data-led outbound, review sites (Capterra, G2), SEO, and AEO (answer engine optimization) to win in a niche

• Built a target list of every golf course, including who runs it, what software they use, and when contracts expire

• Turned multi-course operator deals into 50–100 account wins from a single sale

• Organized his BDR + AE team to touch every account on a consistent cadence
  
  

Founder story & capital strategy

• How Jason went from golf course operator to SaaS founder

• Why he raised only $600K seed and then chose CSI over closing a full Series A

• How he thought about risk, fatigue, and opportunity cost when deciding to sell
  
  

Revenue, pricing & margins

• How Club Caddie reached $9M+ in ARR with 600+ customers

• Why they target $15,000+ ACV / ARPO per golf course

• How complex, multi-venue golf facilities drive higher contract values
  
  

GTM, outbound and channel mix

• Why vertical SaaS is a data game when your entire ICP is ~15,000 accounts

• How his team touches every golf course every quarter, across multiple contacts

• The role of Google Ads, review platforms, trade shows, and word of mouth

• How they use multi-course operator consolidation as a growth multiplier
  
  

SEO & "Answer Engine Optimization" (AEO)

• Why traditional SEO became a priority post-acquisition

• How they implemented schema.org and structured data to win AEO

• How to intentionally show up when buyers ask ChatGPT and other answer engines for "best golf management software"
  
  

Acquisition & long-term upside

• Why Constellation Software was the right home for Club Caddie

• How a small cash component + long earnout can still be a huge win

• What Jason wishes he knew earlier about enjoying the journey, not just the outcome
  
  

If you're a B2B SaaS founder, investor, or operator building in a niche vertical, this episode gives you concrete tactics for pricing, GTM, data strategy, AEO, and selling your company without killing long-term upside.

Callum Mckeefery built Reviews.io from scratch with his wife—no funding, no equity dilution, and no fluff. In this episode, he shares how they scaled to $12M ARR, outpaced VC-backed competitors, and exited for $82M in an all-cash deal.

He breaks down the exact viral loop that created SEO-fueled growth, how they hit $240K revenue per employee, and why he chose not to give employees equity—but still made many millionaires. Callum also opens up about the emotional driver behind the exit: his son's rare genetic condition, and the cutting-edge research he's now funding.

Finally, Callum talks about his new SaaS startup, Partner.io, where he's rebuilding from zero with the same gritty playbook.

In this episode, you'll learn:

• How to engineer viral loops in B2B SaaS

• Why small ACV doesn't mean slow growth

• How to win against VC-backed competition without fundraising

• The emotional side of selling a company

• Tactical breakdown: SEO, paid ads, and partnerships as growth levers

• Post-exit reflections and the pitfalls of private equity buyers

• What he's building next at Partner.io

Perfect for: SaaS founders, B2B operators, bootstrappers, PE firms, and investors looking for real, gritty founder stories with no BS.

How do you scale a consumer AI company to 100,000+ paying customers… without raising VC and while staying profitable?

Ricardo, founder of DreamStories.ai, joins Nathan to break down how he built an AI-powered personalized children's book studio that's already done $3M+ in lifetime sales, with average order value around $60 — and why most people misunderstand how to scale paid acquisition for an AI startup.

You'll learn:

— How he used Facebook ads to profitably acquire 100,000+ customers
— Why his CAC target equals his AOV (and why that works)
— The onboarding funnel that converts like magic (and why it's intentionally stupid-simple)
— How DreamStories runs 4+ A/B tests at all times
— The tech stack powering the company (Shopify, PostHog, Looks)
— Why he chose kids' books as the wedge into a much bigger AI content vision
— How parents create episodic "reverse books" that drive repeat purchases
— His seed fundraising strategy (less than $1M raised) and why he avoids the "VC money pit"
— Why personalization + paid ads is the most underpriced arbitrage right now

Ricardo previously helped scale Spotify (joined in 2009), built and exited multiple companies, and now leads a 7-person team building the next generation of personalized storytelling.

Whether you're a SaaS founder, investor, or operator looking for the next scalable AI business model, this is a masterclass in paid acquisition, funnel design, and consumer AI monetization.

Connect with Ricardo:
DreamStories.ai

Connect with Nathan:
Founderpath.com

Lemlist revenue has passed $40M revenue with strong profit margins as CEO Charles Tenot breaks down their $25M Claap acquisition and Lemlist's path to $100M revenue by 2028. He explains how Claap reached $2M ARR with a 7-person team and why Lemlist used a mix of cash, vendor loans, and convertible bonds to structure the deal.

Ry Walker, serial entrepreneur and founder of Tembo.io, walked away from his first company, Astronomer.io (yes the Coldplay one) during their $213 million Series C in 2022. The company was doing tens of millions in revenue.

Now, he's building Tembo.io, an AI developer teammate that's already processing 1,000+ merged pull requests for 200 organizations just 2 months after pivoting. He previously co-founded Astronomer in 2015, which has raised $380-390 million total and is now estimated at $80-100 million ARR, but took a rare secondary exit in 2022 to return to his true passion: early-stage building.

In this episode, Ry reveals how he went from zero to 30 paying customers in 60 days, why he believes AI agents will 10x the software development market, and his strategy to land million-dollar Fortune 50 contracts by letting non-technical teams create pull requests without bothering their developers.

Bassem Handy, CEO of Briq.com, survived the VC apocalypse by firing 215 humans and replacing them with robots, growing from burning $1M/month to hitting $25M ARR with just 135 employees.

After raising $50M including a peak-bubble Tiger Global round, he took a flat $150M valuation in 2024 and used his own robot technology to automate 80% of his sales team, achieving the lowest customer acquisition costs in company history.

In this episode, he reveals exactly how he got 600 companies to pay him $2,000-$5,000/month for robots that process 2.6 million automation minutes monthly, and his plan to double revenue without hiring a single human.