Growing from 1 to 250 Rental Properties with Avery Carl


By The Hospitable Team

What if we told you that in just five years, you could scale your short-term rental (STR) business to an impressive 250 properties? Sounds like a wild dream? Well, it’s not at all far from reality! 

During our recent Hospitable Masterclass, Avery Carl, CEO and Founder of The Short Term Shop, unveiled the fascinating story behind her meteoric rise from a single vacation rental to a huge property portfolio. Along the way, Avery provided invaluable guidance to hosts looking to repeat her success, diving into investment tactics, market challenges and expert tips. 

Note down the secret recipe for long-term wealth right now. Watch the recording of our Hospitable Masterclass on YouTube or read on to absorb Avery’s wisdom at your own pace. 

Avery’s Growth Story: Naught to 250 🚀

Avery Carl isn’t your typical short-term rental guru. She believes in the strength of a diverse portfolio, encompassing various investment avenues. In her own words, “I’m not going to tell you that short-term rentals are the one and only way and there’s nothing else worth investing in.” However, she passionately advocates for the special place that STR holds in her growth toolkit.

“The reason I was able to get from zero to 250 so quickly was that five of my first six investments were STRs. So, I was able to kind of use those as a cash flow turbocharger. I could take that and go buy more properties more quickly and scale faster.”

Throughout the Hospitable Masterclass, Avery shared her long-standing strategies for sustained development and successful property acquisitions to help you expand your portfolio.

Many Properties = Remote Hosting 🖥️

With a diverse property portfolio comes wide geography and remote hosting. Avery highlighted the transformative role of technology in streamlining the remote hosting experience.

“You definitely want to be able to check on your property once a year just as a good practice, but the vast majority can’t [permanently] live in the best place to invest in. So you really have to get comfortable with it, knowing that it’s just a mindset shift.”

Gone are the days of manually syncing calendars, missing guest messages and struggling to keep up with cleaning teams across multiple time zones. Avery talked about leveraging platforms like Hospitable to automate essential processes and eliminate time-consuming manual operations — thrive as a remote host and watch your portfolio flourish.

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Assessing Your Investment Opportunities 🔎

With a myriad of factors to consider, Avery shared invaluable insights and practical tips to help you make informed decisions. Here are some challenges you will face along the way: 

  • Investment vs. Lifestyle Assets: Is it simply about generating profit or blending personal enjoyment with rental income?
  • Vacation markets vs. Metropolitan areas: What are the most popular regional vacation destinations? Are those reliant on short-term rentals? And how heavy is the regulation?
  • Thorough examination vs. Online info: Do you contact county or city authorities directly to obtain accurate information or rely on internet sources and anecdotal advice? 

To refine your investment assessment further, Avery introduced the “enemy method.”

“You’re zooming in on the neighborhood of the house that you’re looking at on Airbnb or Vrbo. And you’re looking at comparable properties, that are the same number of bedrooms as yours, trying to figure out where you will fall on that spectrum.”

By analyzing the condition, amenities, and overall appeal of neighboring properties, you can gauge how your investment might perform relative to the potential competitors. Avery’s nuanced comparative approach complements the data-driven analysis, providing a more comprehensive evaluation.

STR Market: What It Was & What It Will Become 📊

When asked about how the STR market has changed over the last five years, Avery stressed the exceptional dynamics of the hospitality industry, both in the US and beyond.  

“Oh, yeah, it’s changed. It’s changed a lot. It kind of used to be like a blue ocean of opportunity… and it kind of still is but you have to be more strategic now.” 

Curious to hear Avery’s past observations and future market projections?
Check out the full Hospitable Masterclass and note down all the trends and investment tips.

Thinking about expanding? Hospitable is here to support a world where short-term hosting is just as carefree as long-term rentals. Get your 14-day free trial now!


Hospitable Masterclasses: STR Tips You Must Know in 2023

We know that being a short-term rental host can be like a game of Tetris… guests, bookings, and cleaning schedules are constantly falling from the sky and you have to fit them all together perfectly. To help our hosts slot everything into place, we organize Hospitable Masterclasses that are jam-packed with inspiration and insight.

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