『From Cold Calls to 20+ Properties: Scaling an STR Business』のカバーアート

From Cold Calls to 20+ Properties: Scaling an STR Business

From Cold Calls to 20+ Properties: Scaling an STR Business

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In this episode of the Short-Term Rental Pros Podcast, co-host Ryan Shapiro sits down with Jackson Sterns, a 24-year-old entrepreneur and short-term rental operator who is building and scaling multiple businesses at the same time. Jackson has grown his STR management business to 17–18 properties, with a goal of reaching 50, while also running a growing boat rental business with seven boats and a subscription-based model. His experience gives him a unique perspective on sales, client acquisition, operations, and what it takes to build systems that can support rapid growth. Ryan and Jackson go behind the scenes of what it really takes to scale a short-term rental management company—from cold calling and acquiring property owners to hiring sales reps, implementing a CRM, and creating automated systems for follow-ups, messaging, remarketing, and guest reviews. They also talk honestly about the challenges that come with growth, including difficult clients, managing a team, knowing when to let clients go, and the constant ups and downs of entrepreneurship. In this episode, you'll learn: • How to acquire new STR management clients • Sales strategies for growing a co-hosting business • How to scale toward 20+ properties • When to hire your first sales representative • Why CRMs and automation become critical as you grow • How to build systems and processes that scale • Lessons from managing difficult clients • How to balance multiple businesses at once • The importance of starting sooner and failing faster • What it takes to build a business with the goal of reaching 50+ properties Whether you're an Airbnb host, co-host, property manager, or entrepreneur looking to grow your STR business, this episode offers a candid look at the sales, systems, and mindset behind scaling a successful short-term rental operation. Save Your Spot! Join Our Lakefront Retreat at Hyco Lake Mastermind: ⁠https://www.investstr.com/lake-front-retreat⁠ Property Management Mastermind: ⁠str-pros.com⁠ Need help buying a property: ⁠investstr.com⁠ Save 25% on BNB Calc. Use our exclusive discount through the link below: ⁠⁠https://bnbcalc.com?fpr=strpros⁠
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