Ben Chester

I started out making $30K a year in New York City and could barely make ends meet. To save money, I secretly moved into my office and rented out my bedroom on Craigslist. That experiment revealed a huge demand for flexible furnished housing — so I scaled it into one of the largest co-living businesses in NYC at the time, with over 700 renters across ~200 units, backed by $5M+ in venture capital. But we expanded too fast, the company collapsed, and I was left personally responsible for more than $120K in debt. I moved into a one-bedroom apartment shared by five people and was forced to get a W2 job to rebuild from scratch. Using creative, repeatable real estate strategies — focused on maximizing leverage, minimizing expenses, and accelerating savings — I slowly started building a new portfolio centered around NYC. One of those purchases ended up being Billy Joel’s former ”Cragston” estate, originally owned by J.P. Morgan — and I was even *paid* to buy it thanks to the techniques I’d learned along the way. In just five years, I built a $6M self-managed real estate portfolio, all while keeping my full-time job — using simple, accessible strategies anyone can replicate!