The Remarkable SaaS Podcast

The Remarkable SaaS Podcast is a run of conversations between Ton Dobbe and software founders, and one simple question sits underneath them: what made this product something customers would miss? Episodes open on the same premise. Most SaaS companies, the opening argues, fail because they never became a must-have to the right customer, not because the technology was bad. The titles show how that premise gets tested. Each founder is framed around a single decision that cut against the obvious move: '#399 – How Louis Hoch rejected the obvious customers—and grew when rivals collapsed', '#398 – How Scott Reynolds bet on depth over breadth and built a position that sticks', '#396 – Why Hewitt Tomlin reversed course at $10M'. Dobbe's questions keep pulling each story back toward the lesson. In the Louis Hoch episode, he casts the guest's company as a kind of anti-Stripe built on relationships and asks whether that is part of the differentiation. The answer is candid. Picking up the phone and treating customers' money like your own should not be competitive advantages, the guest says, but in that industry they are. The guest also admits to liking Stripe partly because it keeps prices high, which leaves room to offer a discount. Other conversations turn on shifts inside the founder. Dean Mathews describes a workplace culture that once made him not want a team at all, and the mental flip that turned team building into what he calls his passion. In the Hewitt Tomlin episode, early users are valued for information rather than revenue. As outsiders to the athletic department, the team learned from those customers what outcomes they wanted, who the other stakeholders were and how their job performance was judged. Scott Reynolds looks back over ten years of work on building-code compliance and sketches three eras of tooling: a unified database, then language models that answer complex code questions, and now an agentic phase in which software can do some of the work for the customer. Dobbe introduces Ken Rapp's story as a path from a cracked guitar to a ten-year mission, and that path includes why a first attempt built on IoT sensors was wrong. Rapp's central observation concerns the moment after purchase. The customer gets the product home, the emotional connection to the company drops, and something like buyer's remorse sets in. The episode titled '#400 - What 99 CEOs wish they'd known sooner' widens the lens. In it, Richard White, who was in the very first batch of Y Combinator, says the most successful operators he watched trusted their own gut early, before they seemed to have any right to. His example is Superhuman insisting on 30-minute onboardings with every customer, a choice he suspects almost any VC would have advised against. Episodes close with a request for a rating or review and a plug for Dobbe's daily email, Espresso with Ton. The show suits someone whose SaaS product works but is not yet pulling customers in, and who wants other founders' specific decisions rather than general advice.