21 Properties, One Full-Time Job, and a Remote Team: Real Strategies with Jeremy Rosen

In this episode of The Scaling Made Simple Podcast, Jonathan Farber sits down with Jeremy Rosen — a full-time nurse who also manages 21 short-term rental properties. Jeremy breaks down how he successfully balances a demanding job while scaling a thriving STR business, thanks to the power of virtual assistants, strong systems, and smart time management.Jeremy dives deep into the day-to-day operations of managing multiple properties, including his approach to guest communication, pricing strategies, and creating a five-star experience that drives repeat bookings. He shares the tools and tactics he uses to stay organized, the importance of hiring early, and why building a reliable team (both virtual and local) is the key to long-term success.Guest: Jeremy RosenRole: Full-time nurse & short-term rental operatorBased in: San Antonio, TXSTR Portfolio: 21+ propertiesPMS: HospitableCRM Tool: Elite 360Booking Platforms: Airbnb (primary), VRBO, Booking.com (limited), Direct bookings via personal website