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 ...
May 21, 2026•25 min•Ep. 2957
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 ...
May 13, 2026•25 min•Ep. 2956
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 t...
May 06, 2026•24 min•Ep. 2955
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 ha...
Apr 29, 2026•18 min•Ep. 2954
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 companie...
Apr 22, 2026•25 min•Ep. 2953
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 customer...
Apr 15, 2026•21 min•Ep. 2952
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 sc...
Apr 08, 2026•18 min•Ep. 2951
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 s...
Apr 01, 2026•23 min•Ep. 2950
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 compa...
Mar 25, 2026•16 min•Ep. 2949
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 ove...
Mar 18, 2026•16 min•Ep. 2948
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 bough...
Mar 14, 2026•24 min•Ep. 2947
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 g...
Mar 05, 2026•27 min•Ep. 2946
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 p...
Feb 26, 2026•28 min•Ep. 2945
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 i...
Feb 18, 2026•25 min•Ep. 2944
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 re...
Feb 12, 2026•23 min•Ep. 2943
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 a...
Feb 04, 2026•30 min•Ep. 2942
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 ...
Jan 29, 2026•23 min•Ep. 2941
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 busines...
Jan 21, 2026•26 min•Ep. 2940
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/mont...
Jan 14, 2026•23 min•Ep. 2939
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. What You'll Learn How Volie scaled from 4 customers to $14...
Jan 07, 2026•24 min•Ep. 2938
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 $3...
Dec 31, 2025•20 min•Ep. 2937
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, a...
Dec 24, 2025•26 min•Ep. 2935
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 surviv...
Dec 17, 2025•25 min•Ep. 2934
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 d...
Dec 10, 2025•36 min•Ep. 2933
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, a...
Dec 03, 2025•28 min•Ep. 2932
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 ...
Nov 26, 2025•27 min•Ep. 2931
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 hi...
Nov 21, 2025•27 min•Ep. 2930
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.
Nov 18, 2025•19 min•Ep. 2929
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...
Aug 08, 2025•28 min•Ep. 2928
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...
Jul 29, 2025•17 min•Ep. 2927
