From $450K to $9M ARR in 5 Years: Club Caddie's Vertical SaaS Playbook

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 What you'll learn:  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.

Sid Bendre and his co-founders at Oleve built a $6 million ARR mobile app empire with just 6 people, generating $500,000 monthly revenue and 10-30% profit margins from their education apps Quizzard and Unstuck. Their first TikTok video exploded to 2.3 million views overnight, converting to 10,000 users instantly, and they've since scaled to 4 million total downloads by running 6-7 A/B tests simultaneously and building AI agents that automatically find app store arbitrage opportunities. In this episode, Sid reveals their exact "milk the alpha" playbook for building million-dollar apps in any market, including their viral TikTok formula, paywall testing strategies, and how they're using AI agents to replace entire marketing teams.

Romain Torres bootstrapped ARCads.ai from zero to $6 million ARR in just 16 months with only 5 employees, achieving an extraordinary $1.2 million in revenue per employee while staying completely profitable. He launched in January 2024, hit $5,000 MRR in his first week, crossed $1 million ARR by June 2024, and recently added $1 million in new ARR in a single month between April and May 2025. His secret weapon is an arsenal of over 100 AI agents built in Gumloop that automate everything from competitor research to content creation, allowing his tiny team to serve 4,000+ customers and compete with much larger organizations. In this episode, Romain screen-shares his actual Gumloop dashboard and reveals exactly how he built AI agents that scrape competitor ads, automatically rewrite copy, and send daily Slack alerts with replication opportunities—plus his three-channel growth strategy that's driving $500,000+ in monthly recurring revenue.

Ricardo Ghekiere bootstrapped BetterPic.io from $3,000 to $270,000 monthly revenue in just 12 months, building a $3.2M revenue AI headshot empire with 13 people and zero churn using a one-time purchase model. His affiliate program converts at 12% (versus the industry standard of 0.5-1%) with just 7 top performers driving $77,000 monthly revenue, while generating $230,000 revenue per employee. In this episode, Ricardo screen-shares his actual affiliate dashboard and revenue metrics, revealing his 7-channel growth system that compounds SEO, affiliates, and free tools to capture 500 daily leads from a hidden page most competitors can't find.

Jake Mor is the founder of Superwall (superwall.com), a mobile app paywall platform that generates $3.6 million ARR with just 12 employees by powering over 100 million paywall views monthly for 3,000 customers. His company processes $25-50 million in customer revenue each month and has built over 4,000 custom paywalls while facilitating 4-5 million new user conversions monthly across their customer base. Jake reveals his exact hybrid PLG-to-enterprise strategy that starts customers at $200-300 monthly on self-serve plans then graduates them to $1,000-1,500 negotiated enterprise deals, plus his AI demand scoring system that delivers 20-30% revenue lifts overnight for apps generating $5-10 million MRR. In this episode, Jake breaks down how 2 lines of code became a $3.6 million business, his white-glove onboarding process that takes over customer paywalls for 4 weeks to prove value, and the failed experiment database that helps customers avoid costly mistakes while achieving conversion rates of 20-30%.