Avery Heilbron left the company in 2024 to pursue real estate full-time. Heilbronn, who built a portfolio of 14 homes, started using a strategy called house hacking. He generates cash flow from short-term and long-term rentals. His Airbnb is more lucrative, but takes more time.
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When Business Insider spoke with Avery Heilbron in March 2022, he was in his 20s working on various side hustles and saving more than half of his income to escape the grind of work.
The “FIRE” (financial independence, early retirement) lifestyle didn’t appeal to him as much as the “FIRO” (financial independence, retirement optional) lifestyle.
“I want to get out of my corporate job, but as soon as I do that, I’m like, ‘What do I do next? What projects do I work on?'” he told BI in 2022. I just sit there all day. ”
Heilbron, now 29, quit his day job in March 2024 and answered a question he had two years ago. He wanted to get into real estate, specifically selling houses, “next.”
He had experience in buying and renting real estate. In 2019, he bought a duplex in Boston, where he lived at the time, moved into a two-bedroom downstairs unit and rented an upstairs unit. To maximize his rental income, he found a roommate to fill the second bedroom in his unit. Additionally, his girlfriend has moved into his apartment, meaning three tenants are now paying rent. That was enough to fully cover his monthly mortgage payments, and he was then able to set aside some extra cash to save for his next property.
Heilbron continued to expand his portfolio in North Carolina after purchasing a second property in Boston and moving to Durham in 2021. As of October 2024, he owned 14 units, including a variety of single-family homes and apartment complexes, according to rental agreements and sales documents viewed by BI.
Working as a real estate agent never crossed his mind until he decided to list one of his properties. Airbnb, located in Pinehurst, a small golf paradise in North Carolina, hasn’t been making much money since the coronavirus. Rather than hire an agent, he decided to get a license and try selling it himself.
He enjoyed the process much more than the desk job that often caused him “Sunday dread,” he said. “I really started to get over the corporate world.”
Heilbron left the company in 2024. By: Avery Heilbron
Thanks in large part to rental income, he felt financially ready to escape from a steady paycheck.
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“I wasn’t scared to leave at all, especially since I had the math on my side and I had other income,” he says, adding, “I had solid savings, all with a year’s worth of mortgages.” And what’s more, the cost of one year of my life is probably pretty modest.”
But it allowed him to jump into a new career without any expectations or pressure to perform.
“I knew that if I wanted to work as a real estate agent, I would be perfectly fine with zero sales,” he says. “But so far, I’m close to completely replacing my W2 income. Probably by the end of the year.”
Building Wealth Through Real Estate Investing: From House Hacking to 14 Houses
Heilbron, who was 24 years old when he bought his first home, had to get creative to buy his first two homes.
The strategy he used to buy a duplex is known as “house hacking,” where he rents out part of his home to offset the mortgage. He asserts that this is the “cheapest way to buy property” for anyone looking to get into real estate. The main trade-off is personal space.
It is cost-effective for two main reasons. For one, you are actually living in the property, so you may qualify for an FHA loan. FHA loans are government-backed home loans that allow you to purchase a home with a down payment of just 3.5%. This can significantly reduce initial costs, especially if you live in an expensive market, as Heilbron experienced when he began his investing career.
You can also lower your housing payment. Or, as in Heilbronn’s case, you can eliminate the housing payment entirely and free up cash to buy more property.
By living close to his tenants, he was able to gradually expand to 14 units, including his primary residence, a single-family home in Durham. It has a 750-square-foot detached garage, which he plans to turn into a rental home and eventually offset his current mortgage.
Mr. Heilbron is currently converting a detached garage on the grounds of his main residence into a medium-term rental property. avery heilbron
Heilbronn’s previous side hustles have included personal coaching and creating branded social media content, but he says real estate investing was the main reason he was able to pivot his career.
He manages a mix of short-term and long-term rentals, which has its pros and cons. According to his experience, the short-term rental business is more profitable, but requires more time and effort.
“They’re two completely different things,” he said of the two rental strategies. “Airbnb is definitely more work and not something I would consider a passive activity. I actively think about how to make Airbnb better, checking things like pricing, whereas in the long run I think the tenants There may be some maintenance issues or requests throughout the year.
Short-term rental spaces have also evolved over the past few years, with some hosts struggling in the days when they were known as Airbnbust. It’s harder to make money in 2024 than in 2021, he said: “If you want to buy a normal house and do well, just put furniture in it and don’t go all out. On the other hand. , in 2021, it seemed like you could list anything on Airbnb and it would work.”
His Airbnb units, which include cabins and tiny homes, are popular because they stand out and have unique amenities.
Airbnb’s homepage lists different types of stays. You can click on tabs like “Cabins,” “Tiny Houses,” and “Off-Grid.” Heilbronn’s strategy is to build unique properties that fit into these niche categories and ultimately rank well on specific pages. He’s also garnered attention for his listings on the Instagram page he created for his Airbnb stays.
“I think all of those things have been really helpful, but mainly when people go there, they really love it,” he says, which has led to great reviews from guests.
Heilbron still works as a real estate agent and manages real estate, just as he did when he worked a 9-to-5 job, but says, “I don’t know if what I do is that demanding or demanding.” “It doesn’t really feel like work at all,” he said. Although he works for a real estate company, he says, “I feel like I’m doing my own thing. There’s no particular organization, and I feel like I’m figuring out how to build the business myself.” ”
There are also benefits to setting your own schedule. He enjoys playing golf during the day and taking more vacations.
“This year alone, if we create paid vacation from a corporate perspective, by the end of the year we will have 50 days of vacation, including vacation,” he said. As an agent, he says, “While I’m on vacation, people may ask me questions or write me some offers, so I’m always available, but I love this job, so it doesn’t really feel like work.” .”
