Courtesy of Avery Heilbron
When Business Insider spoke with Avery Heilbron in March 2022, the 20-something was working various side hustles and saving more than half of his income to escape the corporate grind.
The "FIRE" (financial independence, retire early) lifestyle didn't appeal to him as much as the "FIRO" (financial independence, retire optional) one.
"I want to get out of the corporate gig but as soon as I do that, it becomes, 'What's the next thing? What projects am I going to be doing?'" he told BI in 2022. "Because I can't just sit around all day."
Heilbron, now 29, quit his day job in March 2024 — and answered the questions he was asking two years ago. He wanted "the next thing" to be real estate, specifically, selling homes.
He had experience buying and renting properties. In 2019, he purchased a duplex in Boston, where he was living at the time, moved into the two-bedroom downstairs unit, and rented the upstairs unit. To maximize rental income, he found a roommate to fill the second bedroom in his unit. Plus, his girlfriend moved into his room, meaning he had three tenants paying rent. It was enough to cover his entire monthly mortgage payment and then some, which freed up extra cash to save for his next property.
Heilbron bought a second property in Boston and, when he moved to Durham in 2021, continued scaling his portfolio in North Carolina. According to lease agreements and sale documents viewed by BI, he owned 14 units across a variety of single- and multi-family homes as of October 2024.
Working as a real-estate agent didn't cross his mind until he decided to list one of his own properties: an Airbnb in a small North Carolina golf haven called Pinehurst that wasn't bringing in as much revenue post-Covid. Rather than hire an agent, he decided to get his license and have a go at selling it himself.
He enjoyed the process a lot more than his desk job, which frequently triggered "the Sunday scaries," he said. "I started getting really over the corporate world."
Courtesy of Avery Heilbron
Mostly thanks to his rental income, he felt financially prepared to walk away from a steady paycheck.
"It was not really that scary at all to leave, especially because I had the math on my side and the other income on my side," he said, adding that he had "strong reserves — a year's worth of mortgages for everything, plus a year's worth of expenses for my life. It's probably pretty conservative."
But it allowed him to jump into a new career with zero expectations or pressure to perform.
"I knew that if I wanted to do the real-estate agent stuff I could make zero sales and still be totally fine," he said. "But up to this point, I've come close to completely replacing my W2 income — maybe by the end of the year."
Heilbron, who was 24 when he bought his first home, had to get creative to notch his first two units.
The strategy he used to afford his duplex is known as "house hacking," which involves renting out a portion of your home to offset your mortgage. He's adamant that it's "the most inexpensive way to buy real estate" for someone looking to get their foot in the door — the main tradeoff being personal space.
It's cost-effective for two main reasons. One, since you're actually living in the property, you may qualify for an FHA loan, which is a government-backed mortgage that allows people to buy a home with down payments as low as 3.5%. That can significantly lower your upfront costs, especially if you live in a pricey market like Heilbron did when he started his investing career.
It can also lower your housing payment — or, like in Heilbron's case, completely eliminate it and free up cash to buy more property.
Living in proximity to tenants is what allowed him to gradually expand to 14 units, which includes his primary residence, a single-family home in Durham. It has a 750-square-foot detached garage that he's converting into a rental that will eventually help offset his current mortgage.
Avery Heilbron
Heilbron's past side hustles have included personal coaching and creating branded social media content, but he says his real estate investments are the primary reason he was able to pivot careers.
He manages a mixture of short-term and long-term rentals, which come with their pros and cons. In his experience, the short-term rental business is more lucrative but requires more time and effort.
"They're two completely different things," he said of the two rental strategies. "The Airbnb is definitely more work, definitely not what I would consider a passive activity. You're actively thinking about it — how to make it better — and checking pricing and all that stuff, whereas the long-term you just sign a tenant and might have a couple of maintenance issues or requests throughout the year."
The short-term rental space has also evolved over the past couple of years and some hosts have struggled during an era coined 'Airbnbust.' It's harder to make money in 2024 than it was in 2021, he said: "If you were to just buy a regular house and wanted it to work out well, it might be a little bit more difficult if you just throw furniture in there and don't give it your all. Whereas in 2021, you could kind of just put anything up on Airbnb and it seemed to do well."
His Airbnb units, which include a cabin and tiny home, do well because they stand out and offer unique amenities.
The Airbnb homepage features different types of stays; you can click on tabs like "cabins," "tiny homes," and "off-the-grid." Heilbron's strategy is to build unique properties that fit under these niche categories and eventually rank high on those specific pages. He also gets eyeballs on his listings from the Instagram page he's created for his Airbnb stays.
"I think all of those things have been really helpful, but mainly when people go there, they really like it," he said, which leads to excellent reviews from guests.
While Heilbron still works about as much as a real-estate agent and managing his properties as he did when he had a 9-to-5, "it doesn't really feel like anything I'm doing is that much work or hard work at all," he said. He works for a real estate agency, but "it feels like I'm doing my own thing. There's not really any structure, so you're sort of figuring out how you want to build the business yourself."
Setting his own schedule has its perks, too. He enjoys golfing during the middle of the day and taking more vacation days.
"This year alone, if you did it from a corporate world perspective with PTO days, I'll have by the end of the year, with holidays, 50 days off from work," he said. As an agent, "sometimes on vacation, people have questions or have written a few offers so you are still available at any point, but it just doesn't really feel like work because I like doing it."
