‘I’m Using My Thrifting Side Hustle Money To Create a Real Estate Portfolio’

College life is usually reserved for classes and campus parties, but for a University of Virginia student, his Sundays are set aside for shopping.

Rajan Chidambaram spends most of his Sundays waking up at 8 a.m. to make a two-hour trek to go thrifting. The college senior has been looking for bargains since he was a junior in high school.

He focuses his sales on shoes and has sold more than 7,500 pairs through his eBay store.

With the money he has made, he’s been able to invest $150,000 into real estate, including a townhome in Charlottesville, VA.

His recent investment is a Shenandoah Valley property that he would like to develop into luxury cabins to rent out on Airbnb.

He explains to his college newspaper that workers have broken ground on the construction project. It’s 2.5 acres in Front Royal, VA, that he and his high school friend and business partner Renzo Sanio bought for $37,000.

UVA Today explains the cabin community the men are developing is called Royal Oak Retreat. It’s being modeled after Live Oak Lake in Waco, TX.

Live Oak Lake founder Isaac French “bought land and built seven cabins for $2.3 million,” Chidambaram told UVA Today. “And in 18 months, he was able to sell those cabins for $7 million. We’re running his playbook to a T.”

The vision to create a real estate empire

Chidambaram shares updates on his real estate venture with his 44,100 Instagram followers.

Chidambaram pinned a post in December 2024 showing what he and Sanio would like to do with their land. He shared a sketch of how the land would be divided into four lots.

Recently, the real estate entrepreneurs broke ground on the 2.5 acres they bought to create the luxury short-term rentals. Each plot is about a half-acre with a conventional septic tank.

He showed how heavy machinery has been brought in to clear the site of trees and rocks. While they plan to turn the felled trees into mulch, they’re still trying to figure out what to do with the big rocks that need to be hauled away.

It will be many months before their vision comes to life, but Chidambaram noted that he and Sanio are “Just 2 college students with a dream.”

“You don’t need to be spectacular to do spectacular things,” Chidambaram said. “At UVA, I see kids who are so much smarter than me and if they just went for it, they could do so much better than anything I could do.”

Short-term rental rules

For people who are considering renting out property for short-term stays, it’s best to check the rules and regulations within your town or city.

Homeowners are usually required to pay a fee for a permit to register the property. For example, in Front Royal, VA, where Chidambaram is building, the town has a “special use permit” request form that all property owners must fill out. It comes with a $400 application fee.

Other cities may limit the number of permits given out. Charleston, SC, has short-term rental rules divided into categories. San Francisco imposes hefty tourist taxes, and Las Vegas bans special events such as bachelor/bachelorette parties, birthday parties, and weddings from taking place at the rental.