Flipping Shoes to Flipping Cabins: Rajan Chida’s Journey from Hustle to Hospitality

From reselling sneakers to building luxury cabins — 22-year-old investor Rajan Chida proves that the hustle mindset can grow into something much bigger. In this episode, hosts Alissa Bickar (@consultress) and Andrea Lane (The Fearless Real Estate Investor) sit down with Rajan to hear how a side hustle flipping shoes turned into a thriving short-term rental business.

Rajan shares how he saved his profits from shoe reselling to buy his first investment property near UVA while still in college. One year later, he took on a bigger challenge — developing a luxury wellness retreat in Front Royal, Virginia. He opens up about the highs and lows of building from the ground up, including dealing with county permits, creating viral social media buzz, and learning to navigate relationships with contractors and local officials.

You’ll hear how Rajan’s story highlights the power of persistence, adaptability, and the transferable skills that come from any entrepreneurial venture. Whether you’re a first-time investor or a seasoned pro, this conversation reminds you that every step — even flipping shoes — can prepare you for your next big leap in real estate.

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