The Biggest Opportunity in Short-Term Rentals (Ep415)

The Biggest Opportunity in Short-Term Rentals (Ep415)

In a recent interview with Skift CEO Rafat Ali, Brian Chesky predicted a near-future revolution in travel. A revolution that presents a big opportunity for short-term rental hosts.

As more companies offer employees the option to work remotely, Chesky believes people will take advantage of the flexibility to travel. And this will increase demand for STRs, especially in secondary markets.

On this episode of Get Paid for Your Pad, Eric and I sit down to discuss the biggest opportunity we see right now in short-term rentals, describing how we’re finding older vacation homes in drive-to destinations and converting them into unique, modern STR experiences.

We explain how the STR landscape has changed in the last 18 months and why we’re focusing our investments in secondary markets a few hours’ drive from urban centers.

Listen in for insight on the benefit of investing in real estate for Airbnbs and learn how to upgrade an older STR property—without losing sight of what makes the local area special! 

Topics Covered

Our key takeaways from the recent Brian Chesky interview

  • People won’t go back to working in offices full-time
  • Affords much more flexibility to travel

The opportunity for STR hosts in this revolution of travel

  • Find older vacation homes in secondary markets
  • Convert into unique, modern STR experiences

Why we’re investing in properties in secondary markets

  • Financial decisions shaped by experience of COVID
  • People want to travel AND live there (can sell later)

What short-term rental guests will need moving forward

  • Fast internet, workspace for remote office
  • Option to disconnect and be in nature

Our approach to upgrading older STR properties

  • Improve experience (e.g.: smart locks, guidebook)
  • Highlight what makes local area special

The benefit of investing in real estate for STRs

  • Ownership affords opportunity to build wealth
  • Money in properties as hedge against inflation

How the Get Paid for Your Pad podcast is changing

  • Mondays focus on small hosts (Airbnb 101)
  • Wednesdays about managing STR business at scale
  • Fridays we share journey building hospitality brand


Brian Chesky: Travel Revolution 

Remote Work at Buffer 


The Psychology of Money: Timeless Lessons on Wealth, Greed and Happiness by Morgan Housel

Strawberry Creek Village 



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