Best Bet Ever

The Best Bet I Ever Made

I never watched any real estate TV shows growing up. Unless you count MTV Cribs. I needed to make money to stay in New York, so I asked the richest guy I knew if he could help me land a paid internship at Douglas Elliman. He told me to get a job as a “broker” instead and work on rental apartments. So that’s what I did.

I started my career at a medium-sized company. It was small enough that I was able to sit with the president of the company at least once each week and drill him with questions. There was one time where I spent an hour and a half in his office asking him every question that I could come up with. He loved it because it seemed like he genuinely enjoyed criticizing me and telling me that I was terrible at sales. At least at first.

At the end of my first week, I had worked pretty hard and I felt good about myself. The president wanted to bring me down a few notches, so he told me to spend my own money on a NakedApartments account. I remember getting kind of mad at him. I thought: “You just hired me to your company and you want me to spend my own money on advertising? What kind of scam are you running?” But then he told me that the average real estate agent makes $50,000 a year, and to beat that I would have to do things that other people won’ t do. I signed up for an account that day.

Ever since then I’ve seen advertising with my own money as an investment. If I spend $5,000 on advertising and it brings me just one deal for $1 million – the median price point in Manhattan – I’ll make a $30,000 commission. My return on investment is 600%. Even Bernie Madoff couldn’t get me those kind of returns.

In All In, I talked about how things finally clicked when I sold my drum machine for scraps, then made $15,000 that month. The money I earned from selling my drum machine went into real estate advertising. That advertising was what brought me my first success. I had never made that much money that quickly before. I went from dollar beers in the East Village to fancy cocktails that I can’t even pronounce overnight. And it’s all because I bet on myself. Not on the stock markets, not on sports, and definitely not on anyone else.