62. Filling the Gap: Last-Minute Bookings, OTA Strategy, and Focusing on What’s Working in Your STR Business

In this episode of STR Like the Best, I sit down with Alex Alioto, Co-Founder and Head of Growth at Whimstay, an OTA built specifically to fill your last-minute and gap-night inventory.

We break down why relying solely on Airbnb is like owning a stock portfolio with just one stock, how to think strategically about OTA distribution, and why last-minute travelers aren’t just bargain hunters—they’re a fast-growing segment that can boost your weekday occupancy.

Alex shares practical tips on integrating with Whimstay, avoiding the “race to the bottom” on pricing, and meeting the needs of the next-gen traveler (21–35 year olds booking 8–10 trips a year). We also talk about the importance of focusing on what is working in your business, and the role gratitude and key relationships play in the journey.

Whether you’re looking to maximize revenue, diversify your booking channels, or simply reframe your mindset as an operator, this episode delivers both tactical strategies and a reminder to enjoy the people you meet along the way.

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod

Apply to work with Michael: https://strlikethebest.com/applypod

Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb