Freemium SaaS: 18 Months to 10 Customers Then Liftoff

Jon Fagg spent 18 months struggling to get 10 paying customers. Then he introduced a freemium SaaS model, and within six months, Skedda had more signups than they had managed in the previous two years combined. In this episode, Jon reveals how Skedda grew from a side project that three part-time co-founders built across time zones into a bootstrapped 7-figure business with 4,000 paying customers. He explains why the freemium SaaS approach - combined with one focused SEO project - replaced every other channel they tried, including handwritten letters in the mail. The freemium model unlocked free trial conversion at scale. Skedda replaced confusing pricing tiers with a generous SaaS free tier plus one $49 paid plan. That simplicity, combined with vertical-specific landing pages for SEO, created a freemium SaaS flywheel where word of mouth matched organic search as a growth driver. Key Lessons 🎯 Freemium SaaS creates volume that unlocks word-of-mouth: Skedda's free tier drove signups, usage, and feedback that eventually made word-of-mouth as powerful as SEO - all without paid marketing spend. 🔄 Simplify pricing to one freemium SaaS tier plus one paid plan: Skedda replaced confusing alliterative pricing tiers with a generous free plan and a single $49 premium option, making the decision obvious for users. 🚀 One SEO project can replace paid marketing entirely: Jon restructured Skedda's site with vertical-specific landing pages in a single focused effort, and organic search became the primary customer acquisition channel for years. 📉 18 months of failure does not mean the idea is wrong: Skedda's founders tried handwritten letters and various outreach tactics for 18 months before freemium SaaS and SEO unlocked growth - persistence mattered more than tactics. 💰 Bootstrapped freemium SaaS can reach 7-figure ARR without funding: Skedda grew to 4,000 paying customers and multiple seven figures with a team of 15, proving this model can scale without venture capital. Chapters Introduction Jon's motivation: building things with interesting people What Skedda does: space management software Why Skedda exists: flexible scheduling across verticals Customer range: from farmers to Harvard and Mercedes-Benz Business size: 4,000 paying customers and 7-figure ARR Origin story: running a sports facility in Melbourne Recruiting an engineer doing his PhD in Germany Building the MVP and first product iteration 18 months to find the first 10 customers Trying handwritten letters and other failed tactics Introducing the freemium SaaS model and simplifying pricing The SEO project that changed everything Why SEO became the biggest growth driver What held them back from freemium sooner The avalanche effect after launching freemium How COVID accelerated enterprise adoption In-person founder retreats for strategic decisions Lightning Round Wrap Up Resources Full show notes: https://saasclub.io/296 Join 5,000+ SaaS founders: https://saasclub.io/email