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April 16, 2025 66 mins

Most short-term rental operators hit a wall around 50 units. Scaling beyond that? It’s where quality starts slipping, operations break, and owners walk away.

But not this time.

In this episode, we dive with Steven Chrobak, Owner of Myrtle Beach Destinations, into the playbook of an operator who built a 100+ unit portfolio in under two years — without ever living in the market he manages.

From military precision to guest-first thinking, he shares the systems, mindset, and strategic decisions that set his company up for sustainable scale. Whether you’re at 5 units or 55, this episode will shift how you think about growth, operations, and owner acquisition.


What You’ll Learn:

- How to scale to 100+ STR units without sacrificing guest experience

- Why most operators fail when they hit 50 units — and how to avoid it

- The mindset shift that allowed him to grow fast and stay profitable

- How military leadership principles shaped his approach to operations

- The #1 thing that attracts new homeowners (hint: it’s not sales)

- What to build today if you plan to double your portfolio next year

- Why turning away the wrong units is key to protecting your reputation

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