Scaling Short-Term Rentals in Europe: Regulation, Operations, and Surviving Covid, with Ben Painter

Scaling short-term rentals in Europe without funding is an operational grind that forces you to learn fast, fix mistakes in real time, and build resilience the hard way.In this episode of Minute by MÎNUT, host Nils Mattisson sits down with Ben Painter (award-winning CEO) to unpack how he grew Dromor from his dining room table in 2017 into a 1,500-unit operation without raising external capital. Along the way, Ben navigated regulation and Covid, built a remote-first team, and learned what it really takes to scale an operationally heavy business in this industry.  They dive into the early “fail upwards” years, why selling is often easier than operations, the brutal reality of retaining properties, and what the next wave of regulation and industry professionalisation means for operators across Europe.  Chapters01:07 Show intro01:37 Meet Ben Painter02:08 Drummer’s story: from 1 listing to 1,500 units06:49 What founders underestimate about scaling07:38 Selling vs building: which is harder for founders09:13 The early mistake: sales first, operations later12:35 Why Ben hired sales and focused on ops15:32 Bootstrapping vs raising money: what it changed17:14 The hardest phase: Covid and the brutal drop18:55 The pivot: isolation accommodation and rapid recovery22:17 Resilience, leadership, and getting “beaten up” as a founder26:03 Where founders get stuck when scaling to 100+ units27:30 Regulation and barriers to entry in Europe29:23 Professionalisation: corporates buying up smaller operators31:28 Why bigger isn’t always better for guest ratings34:16 What operators still aren’t preparing for38:17 If Ben started again: what he’d do differently40:29 The craziest thing that happened while scaling42:47 Final thoughts and wrap