An 8 a.m. wakeup call is followed by a two-hour drive and an exhaustive search through upward of 10 thrift stores across Northern Virginia.
It’s all in a Sunday’s work for one University of Virginia student entrepreneur.
Rajan Chidambaram’s weekends rarely reflect those of a typical college student, and that’s OK. Chidambaram prefers this life.
“I need it to be part of me,” he said, “because I have so much fun doing it.”
Chidambaram is a few months shy of receiving his bachelor’s degree from the McIntire School of Commerce, but his success story begins before he arrived on Grounds. He’s been a hustler since his junior year of high school when, after watching a Gary Vaynerchuk YouTube video, he was inspired to sell items from his own home – clothing, electronics or random trinkets that could carry value in the online marketplace.
By his senior year, the Herndon native found his niche – shoes – and, four years later, he’s up to more than 7,500 sales through his eBay store, “TheChida.” He’s invested about $150,000 in profits into other ventures along the way, including a townhome in Charlottesville – where he’s the landlord – and, most recently, property in the Shenandoah Valley that he’s working to develop into luxury cabins for Airbnb rentals.
[♪ upbeat song plays ♪]
Rajan Chidambaram speaks: I’ve sold over 7,000 pairs of shoes since I’ve been in college and here’s how that’s going to translate into managing short-term rental cabins that I’m building in the mountains.
As corny as it sounds, you got to put the customer first. Selling shoes for over four years, I’ve maintained 100% positive feedback because I’m providing a quality product and I resolve any issues that buyers have immediately.
For the cabins, it’s got to be the same. That means clean check-ins, fast responses and making sure every guest feels taken care of.
Five-star reviews are everything in this business and you got to maintain a damn near perfect reputation.
Next is making sure you have a perfect listing. In my shoe business, I always rank at the top of search on eBay because I had top-tier photos and I optimize all the titles.
Again, same for the cabins. We’re going to have to pay up for the most professionally staged photos and we got to optimize our listings to rank higher in search.
Next, I want to avoid automating anything until I actually understand what I’m automating. In the shoe business, I manually did most of our operations first before I went out to look to automate anything.
For example, I manually listed shoes for a long time so I knew what a perfect listing would look like. That made it a lot easier to automate because I knew exactly what the listing needed to look like to be successful.
I want to do the same thing when managing the short-term rental. I want to be super hands on in managing the rental and do things manually when I can at the start.
For example, I think it’ll be super beneficial if I manually communicate who stays at the cabin in the beginning. I really want to understand what a good check-in, check-out and feedback system looks like.
Once I think I understand the processes enough, I’ll go ahead and automate it.
I know selling shoes and managing short-term rentals are two completely different things, I still think there are core concepts that apply to both.
Follow to watch us build something beautiful.
The lifeblood of Chidambaram’s business, though, fills the 10-by-19-foot office unit he rents in Charlottesville’s McIntire Plaza. Floor-to-ceiling shelves are packed with pre-owned shoes, and Goodwill bags with the next supply are spread across the ground.
All products of his weekend treks.
Since the start of his second year at UVA, Chidambaram has mostly kept to the same Sunday routine of rising early to tour a variety of bargain, secondhand shops near his hometown. He’d typically return to Charlottesville that evening with a car full of footwear and food.
“I love my mom, God bless her soul,” Chidambaram said. “She’d always cook me meals and put them in coolers for me to take back. That was every single Sunday.”

Chidambaram photographs a pair of Under Armour basketball shoes before he posts them for sale on eBay. Chidambaram has made more than 7,500 sales through the online marketplace since his junior year of high school. (Photo by Matt Riley, University Communications)
Properly fueled, Chidambaram gets to work on reselling the shoes. He cleans them, photographs them, prices them accordingly and takes detail in marketing them.
“The key to a good sale,” he said, “is a good price, but also having really crisp pictures and good keywords. You get 80 characters in an eBay title and I try to use every single one. I’ve learned to throw in as many keywords as I can – like ‘athletic running shoes’ – because it increases the chances of a sale.”
From Air Jordan basketball shoes to Puma golf spikes to Cole Haan loafers, TheChida offers a wide range of selections. Chidambaram said his best find came from a thrift store in Manassas, where he landed three pairs of rare Kobe Bryant-line Nikes – Kobe 6 Protros – for $10 each, which he then flipped for $250 a pop.
Not every trip north involves a wild adventure, as he’s developed relationships with a few bulk suppliers who can sell to Chidambaram directly.
“My market is mostly everyday wear,” he said. “It’s shoes that I can buy for $5 in bulk and then sell for $25. I think that’s the easiest market to scale because that market will always be there.”
While selling shoes remains Chidambaram’s baby, he’s passionate about the construction of his next project.
Ground broke last week on the 2.5 acres in Front Royal that he and his business partner and high school friend, Renzo Sanio, a Virginia Tech student, purchased for $37,000.
[♪ jazzy song plays ♪]
Rajan Chidambaram speaks: Me and my boy bought 2.5 acres of mountain land to develop into luxury cabins, and today, we just broke ground on our project.
Right now, we have people just clearing the site of rocks and trees.
Our 2.5 acres are subdivided into four different plots. It’s divided by this road right here. Six hours ago, you could not even walk through this road at all because it was covered in bushes and branches.
But now it’s clear and it’s set up to be a gravel road.
We eventually want to build four units on our four plots. But we’re starting by building one on this plot just to see if we can execute it correctly.
It’s definitely exciting breaking ground, but I know there’s going to be so many roadblocks in our project.
I’m going to be documenting it all, so you guys know what to do – follow me.
The developing cabin community is called Royal Oak Retreat and is being modeled after Live Oak Lake, a similar space in Waco, Texas, that comes with a story Chidambaram has studied religiously.
“(Live Oak Lake founder Isaac French) bought land and built seven cabins for $2.3 million,” Chidambaram said. “And in 18 months, he was able to sell those cabins for $7 million. We’re running his playbook to a T.”
This includes documenting the build of their project to a large social media following. Chidambaram’s updates are shared mostly through his Instagram account, which has nearly 42,000 followers.