In a recent episode of Millennial Investing, host Patrick Donnelly sat down with Alan Corey, a self-described "real estate maximalist" and author, to discuss his journey from aspiring comedian to financially independent real estate investor. Corey's story is one of unconventional ambition, disciplined saving, and a deep understanding of leverage in real estate.
Corey began his adult life moving to New York City after college with no connections, living in an illegal sublet in Spanish Harlem for $400 a month – an experience he describes as unknowingly living in "the projects." His initial dream was to be a comedy writer, leading him to perform stand-up for five years while working a tech support job for $48,000 annually. He found a unique way to save money: by being the entertainment instead of paying for it, and by living frugally, often eating ramen noodles and getting discounted bakery items.
Inspired by wealthy individuals in his life who seemed to have control over their time (like basketball coaches who were small business owners and real estate investors), Corey devoured books on personal finance and realized real estate offered a level of control that stocks didn't. He decided to focus solely on real estate. His savings strategy was radical: 50% of his income went into an inaccessible bank account across town, with the ATM card thrown away. His goal was to buy one property a year for five years.
His first purchase at 21, post-9/11, was a $99,600 one-bedroom apartment in Brooklyn. He quickly "house hacked" it by dividing the living room with a heavy curtain and renting it to a friend, covering his entire mortgage. This immediate success solidified his belief in real estate. The next year, with $15,000 saved, he bought a duplex, moving in and renting rooms to five comedians, generating an additional $2,000 in profit—more than his tech support take-home pay.
The 2008 financial crisis, while devastating for many, presented opportunities for Corey. He describes himself as a "deal junkie," and while loans were hard to come by, properties became discounted, and demand for rentals surged. During this period, he partnered with a contractor and a lawyer (his then-girlfriend's father) to flip a mixed-use building in Red Hook, Brooklyn. They bought it for $400,000, invested $200,000 in renovations, and sold it a year later for $1.1 million. The buyer? Barbara Corcoran of Shark Tank fame. This $150,000 profit for a 25-year-old was a pivotal moment, cementing his commitment to real estate and inspiring him to write his first book, *A Million Bucks by 30*.
After losing his tech support job during the crisis, Corey gamified career advancement. His second book, *The Subversive Job Search*, details his strategy: reverse-engineering C-suite job descriptions, acquiring relevant certifications, and rapidly job-hopping to increase his salary, eventually reaching his goal of a $150,000 salary within two and a half years.
Corey later developed his "House Fire" strategy, adapting the traditional FIRE (Financial Independence, Retire Early) movement to real estate. He found the idea of saving 25 times annual expenses in stocks (the 4% rule) daunting. Instead, he proposed buying properties that generate enough cash flow to cover specific monthly expenses. For example, instead of saving $45,000 to cover a $150/month internet bill for life, he'd put $22,500 down on a property that cash-flowed $150/month. This "house for every bill" approach allowed him to achieve financial independence much faster, as rent increases would eventually provide a higher lifestyle, and paid-off "bill-houses" could be reallocated to other expenses. He estimates around five properties are enough to achieve this for most people.
Today, Corey's portfolio includes 18 multifamily doors (quads, triplexes, duplexes) in Atlanta, where he lives, plus partnerships in 350 additional apartment complex doors. He liquidated his high-performing New York City properties, which he bought for cash flow and later sold for multi-million dollar profits (often to celebrities), viewing appreciation as "imaginary lottery tickets" or bonus upside.
Corey is a strong advocate against paying off long-term fixed-rate debt, contrasting with traditional advice like Dave Ramsey's. He argues that a fixed-rate mortgage becomes cheaper over time due to inflation, effectively tripling its purchasing power benefit compared to a dollar earned today. He remains a "real estate maximalist," focusing solely on real estate and resisting diversification into other asset classes, preferring to stay within his circle of competence.
Through House Money Media, a venture with Lauren from Adulting is Easy, Corey now mentors others, providing courses, podcasts, and a Discord community. He aims to be the mentor he never had, guiding first-generation real estate investors and helping them avoid "analysis paralysis" by emphasizing the importance of finding a niche and sticking to it for consistent success.