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- #16 - Rajan Chida: Social Media, Selling Shoes, and Building Real Estate
#16 - Rajan Chida: Social Media, Selling Shoes, and Building Real Estate

Great careers are made with good people, and better questions.
This week I spoke with Rajan Chida, a 2025 UVA alumni who’s now Building Royal Oak Retreat (short term luxury rentals in Virginia) and blowing up on social media with over 300K instagram followers.
The Rundown:
COLD OPEN: Selling shoes to building real estate
TURNING POINT: Finding a work life balance
STEAL THIS: How do you do it?
INDUSTRY INSIDER: Social media runs on storytelling
IF I WERE YOU: Find someone smart and tag along
COLD OPEN
How Did You Get Your Start?
When I was 17, I saw a Gary Vee video about flipping garage sale finds on eBay. Once I got my license, I started flipping shoes.
Then COVID hit, and with all that free time I was either gaming with friends or selling shoes. I did well in high school, but since I couldn’t have a car my first year at UVA, I had to pause the business.
Once I got a car, I rented an office unit in McIntire Plaza, filled it with inventory, and ran the business for the next two years. Every Sunday I’d wake up at 8am, drive to Northern Virginia to source shoes for eight hours (eventually getting local suppliers), and make it back to UVA in time for Monday classes.
On my 21st birthday, I met a UVA grad real estate agent who helped me buy my first investment property in Charlottesville — my first dip into real estate.
I went deeper after reconnecting with my friend Renzo, who had been interning at a development firm. He pitched me on an idea inspired by Live Oak Lake, a seven-cabin retreat in Waco, TX, that sold for $7M.
He had his eye on a 2.5-acre plot in rural Virginia. After some due diligence and thought, I said, “fuck it, let’s do it.”
TURNING POINT
What’s A Challenge You Faced Early On?
For me it was balance. At UVA, I always felt like I let something slip when I could've avoided it.
Second year I was selling shoes a lot and didn’t go out as much. Third year I went out a lot and let the shoe business fall a bit.
Then I started this land development and I and my grades dropped a bit.
Finding that balance — and keeping it — is something I’m still working on.
STEAL THIS
What’s A Question You Love To Ask Yourself?
My favorite question to ask someone is “How do you do it?”
In real estate, there’s so many ways to skin the cat, and everyone took a different approach in their success.
There’s always something to learn from people who’ve done well in the same field, and asking them how they did it uncovers that.
INDUSTRY INSIDER
What Do People Misunderstand About Social Media?
The social media game is changing. It’s all about storytelling.
Whoever tells you it's not and you can do some catchy hook or magic thing to grow an audience is lying to you.
If you’re trying to build a community and you want to go deep with them, you have to tell a story.
When I first started with shoes, I didn't know where I wanted to go with it but I knew I wanted to make it like a TV series.
My first series was hitting a certain number on eBay. Now it's the journey to build luxury cabins.
IF I WERE YOU
Do You Have Any Advice For Students?
If you want to do something, find another person that's done it, and tag along behind them.
My real estate agent had 9 properties before I met him. I tagged along with him and bought my first property.
On social media, I was lucky enough to meet a UVA alum who runs one of the highest performing short term rental companies in Virginia, and tagged along with him. Now he’s helping us build our property.
You don't have to be the smartest one in the room. You just got to know smart people and tag along.
CLOSING TIME
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