A
very Heilbron left his corporate job in 2024 to pursue real estate full-time after building a 14-unit portfolio using the house hacking strategy. This approach involves renting out a portion of your home to offset mortgage costs, making it an inexpensive way to enter the market. Heilbron's experience buying and renting properties began with a duplex in Boston, where he lived downstairs and rented out the upstairs unit, as well as finding a roommate for his second bedroom.

    Heilbron continued scaling his portfolio after moving to Durham in 2021, eventually owning 14 units across various single- and multi-family homes. Working as a real estate agent didn't initially cross his mind, but he decided to get licensed when listing one of his own properties, an Airbnb in Pinehurst, North Carolina.

    Heilbron's rental income allowed him to feel financially prepared to leave his corporate job, with strong reserves covering a year's worth of mortgages and expenses. This enabled him to jump into a new career without pressure or expectations. He now manages a mix of short-term and long-term rentals, finding that the short-term rental business is more lucrative but requires more time and effort.

    Heilbron's Airbnb units stand out due to their unique amenities, such as a cabin and tiny home, which rank high on specific pages on the Airbnb homepage. His strategy involves building properties that fit niche categories and leveraging his Instagram page for listings. Despite working as much as he did in his corporate job, Heilbron finds his current work enjoyable and feels like he's doing his own thing.

    Heilbron's schedule is more flexible now, allowing him to enjoy golfing during the day and taking more vacation days. This year alone, he expects to have 50 days off from work, which he attributes to setting his own schedule as a real estate agent.