Skip to main content

Meet the 25-Year-Old Who Buys Crappy Real Estate and Builds Cool Companies

Meet Connor Gross — an entrepreneur in his mid-twenties who is currently focused on building a portfolio of self-storage units across the state of Texas.

Connor graduated from Northeastern University in 2020.  As a part of a co-op program at Northeastern, he was able to spend a semester building his first start-up, Cardly, with his co-founder Giovanni, which was a snazzy looking credit card holder that attaches to the back of your iPhone.

After selling the start-up in early 2020, Connor began learning about real estate investing.  While the idea of investing in a short-term rental was attractive, in Connor’s mind, being responsible for a place where folks actually lived or vacationed was a bit too much of a headache.  So, he decided to start with self-storage. 

Tune in to an energetic, idea-producing conversation where Connor and I discuss:

  • How he convinced the host of a luxury Airbnb villa in Bali to let him stay in their home for free
  • How he founded, built, and sold his first e-commerce company
  • Why you’re never too young or too old to start your entrepreneurial journey
  • Connor’s hot takes on the future of travel and hospitality after living out of a suitcase for 2 years and traveling to more than 30 countries. 

This episode of Behind the Stays is brought to you by our friends at Touch Stay

Touch Stay enables hosts to build beautiful, digital guidebooks in a matter of minutes…
And enhances the guest experience by packaging your recommendations for coffee, wine bars, artisan bakeries, and Michelin star restaurants in a single online location. 
Guests can access everything through a simple link — and yes, it works WITHOUT a wifi connection. 
Touch Stay allows you to customize your guidebook to match your brand — pick the colors, fonts, and images that best align with your STR. 
Learn more about a plethora of other features they have, and start your free trail at in, Behind the Stays).
If you liked this episode, you’re going to love some of our other recent conversations:
How She Built an Insta-Famous Airbnb — The Story Behind the Cozy Rock Cabin.
She Left Her Law Career to Become a Hospitality Entrepreneur — Meet the Creator of Field and Lake
How They’re Building Canada’s Premier Luxury Treehouse Company

About the Show

Behind the Stays is brought to you twice a week by Sponstayneous — a free, biweekly newsletter that brings subscribers the best last-minute deals and upcoming steals on Airbnb.  
You can subscribe, for free, at

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.