Cowboy Ventures
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Cowboy Ventures

Announcing Cowboy Ventures’ Investment in Getaway: Investments with a View

By: Jillian, Aileen & Allegra

We’re thrilled to partner with the amazing team at Getaway, an innovative tech-enabled platform for investing in real estate.

Generations of Americans have built wealth through investing in real estate. But, soaring home prices and rising interest rates have made the potential financial returns from real estate inaccessible to millions of would-be investors. This has been especially true for one of the highest yielding (and most enjoyable) asset classes, historically accessible to only 4% of people: vacation rentals.

At Cowboy Ventures, we’re excited about fintech solutions that democratize access and make things more efficient, understandable, and engaging. That’s why we invested (in addition to Getaway’s fantastic team) in Getaway, launched today with their first investment offerings in 🌵Scottsdale and 🏖Miami — and 🌴Palm Beach soon to come.

Getaway is creating a new model of ownership that empowers a much broader population to invest in vacation properties, a $3.6T asset class that has historically delivered top-rate financial returns. Through Getaway, investors can own a fractional share of a property with as little as a $1,000 investment.

As investors,, Getaway members:

✅ Earn monthly cash flow from the property’s rental income

✅ Earn their share of the profits when the property is sold

✅ Invest in a longer term asset with a different return profile than volatile public markets

✅ Benefit from VIP members-only rates for stays at any of Getaway’s properties

❌Forgo the heavy lifting of finding, managing, and operating a property — that’s Getaway’s job.

When we met co-founders Ali and Amr, we were blown away by their passion, expertise, and vision for the future of real estate. They met at Bungalow, a residential real-estate platform company where Ali led marketing, growth, biz ops and real estate, and Amr led product and design. As real estate lovers and experts in the single family rental space, they both wanted the financial benefit of property ownership, but couldn’t afford the high entry ticket prices, nor the time to find and maintain a property — and they knew many of Bunaglow’s renters had similar frustrations. In building Getaway, they have created the opportunity to make investing in and enjoying vacation rentals accessible — while providing strong rental income and long term property returns.

We are thrilled to back this incredible team alongside friends at XYZ and Night Ventures, and an amazing group of angels including operators from Robinhood, Ramp, Plaid, Pipe, Masterclass, Divvy, and more.

If you’re someone who has long hoped to own real estate, wants to add diversity to your investment portfolio, scrolls through property listings thinking “one day”, or obsesses over your Airbnb wishlists, take a look at Getaway. And send us your travel bucket list — the Getaway team plans to build out a portfolio of properties in the highest returning markets, and in places their members dream about vacationing in.

As for us, you can catch us soon at The Western, Getaway’s dreamy Scottsdale property for our next 🤠offsite.

PS Getaway is also hiring! Check out open roles here.

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Cowboy Ventures

A seed-stage focused technology fund backing exceptional founders.