Parking lots: they occupy more than a quarter of urban land, and yet remain one of real estate’s most overlooked assets. With most lots still managed by pen, paper, and guesswork, millions in revenue is left untapped. Meanwhile, parking is a daily headache for most Americans—endless circling, confusing signs, and clunky payment machines.
AirGarage was born from firsthand frustration. As college students, Jonathon, Chelsea, and Scott faced the challenges of campus parking everyday. Their first idea was straightforward: connect students with nearby homeowners open to renting out their unused driveways. But, as they dug deeper, talking to property owners and surveying the landscape of underused lots, their ambitions grew. AirGarage now handles all aspects of operating parking facilities while boosting revenue for owners through technology, including dynamic pricing, license plate recognition, and online marketing .
Today, AirGarage manages over 300 locations in 38 states and has processed more than 10 million parking sessions. With a vision to bring all real estate online and AI-optimized, AirGarage is poised to transform not just parking, but the way cities and owners unlock the value of every square foot.
Here’s more about Jonathon, Chelsea, and Scott, answering Headline’s Founder Q&A.
What is your drink of choice?
Scott: Espresso.
Chelsea: Diet Coke.
Jonathan: Black coffee.
What’s on your desk right now?
Chelsea: AirGarage coffee mugs and every color pen.
Jonathon: Parking tickets.
What business question do you hate the most?
Scott: Are you going to replace your entire team with AI now?
Who was the last person you called or texted?
Scott: “My mom; it’s snowing in Texas!”
Jonathan: My best friend, Michael, from New York City.
Chelsea: “It was these two - asking where they are!”
What would your last meal be?
Chelsea: Joyride Pizza in San Francisco.
Scott: Farmhouse Thai in San Francisco.
Jonathan: Waffle House’s all-star special.
What about being a founder has most surprised you?
Chelsea: Being your own boss is just a vehicle to have lots of bosses. Customers, investors, even ourselves.
Jonathan: I appreciate the rewarding aspect of building a team and seeing them grow. I didn't think about that when we started. For instance, it’s been awesome to see Bryan, our VP of Ops, excel and move up the ladder for six years.
What is your unofficial catchphrase?
Chelsea: If you aren’t cringing about who you were six months ago, you aren’t growing.