How to Lose a Lot of Money in Real Estate

Inspiration
July 4, 2024

“There was a drug den in the apartment next door, and a guy got murdered in a botched robbery in the building across the street.”

After a few highly successful deals at a young age, I got overconfident. With the mistaken belief that “I knew enough and couldn’t mess up,” I impulsively bought a fourplex (four residential units under one roof) in an online auction… while on a flight. The first time I saw the very shady property I bought was a week after closing. After a brief, panic-inducing chat with the neighbors, I told my agent to offload it ASAP. It’s the only deal I’ve ever lost money on. How much did I lose? Enough to buy a top-of-the-line Mercedes.

Overconfidence can be very destructive, especially when mixed with a swollen ego and a need to prove yourself. As Victoria Holt said, “If it’s good, it’s wonderful. If it’s bad, it’s experience.” Wiser people than me have said every failure teaches us something. Here’s what I learned from this painful and expensive lesson.

Our ego can be our greatest enemy. I highly recommend Ryan Holiday’s book *Ego is the Enemy*. In real estate, there are many people with a lot of money—and a lot of ego. Sometimes, it shows up as their name on a building, a flashy office in a skyscraper, designer suits, or shiny, expensive watches. Can you think of a few names already? There’s nothing wrong with that; everyone should do what makes them happy. From my experience, some of the wealthiest people I’ve ever met look like the neighbor you just chatted with in the elevator about the milkshake they got using a Dunkin’ Donuts coupon.

Four years ago, I joined a mastermind group of commercial real estate investors from across the U.S. Every quarter, I sit in a room with around 150 of the sharpest real estate minds in America. The conference starts with three days of learning about the market, the economy, tax changes, negotiation techniques, and more. The next two days, each member presents the deals they’re working on, followed by a round of questions and consultations. So, why would people who’ve already “made it” and own assets worth hundreds of millions of dollars take a week away from their families to attend a nine-hour-a-day conference? To learn from others. Bottom line, no matter how good or successful we are, there’s always someone better, and there’s always something new to learn.

A few years ago, I met a Jewish billionaire from Washington, D.C. During our conversation, I asked him about the secret to his success. Without missing a beat, he answered: “My ability to learn from anyone—even a five-year-old girl.”

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