the biggest business in the world?” What did the top 1% of people do with their money? Some invested in real estate, I discovered, but the most common answer always led me straight to Wall Street.
Back in the 1990s, the crash of 1987 was still fresh in people's minds. But the market and the economy were on fire, the flames fanned by dot‐com stocks and the rise of the internet. The U.S. economy seemed unstoppable. Cell phones were becoming widely used and telecommunications companies were hot. I consolidated my little horde of candy and fireworks money and bought my first stock: SprintPCS.
For a period of time, the stock did great, but then it collapsed, and I didn't sell it until it was too late. Years later, as fate would have it, my first “real” job during college was working for SprintPCS, selling cell phones at the now‐defunct Circuit City.
After my freshman year at Pace University in Manhattan, I transferred to Florida to escape the high cost of living in New York City. As luck would have it, and thanks to grace from above, that turned out to be a very good move because, back in New York, I would literally walk through the World Trade Center every morning to get to school. I transferred in the summer of 1999 and, had I stayed, I would have been there on 9/11.
To get by, I worked five days a week and I went to school five days a week. I tell people I work with (and my kids) that makes 10 days in a seven‐day week! At first, most people do not believe it, but for most of my 20s, I never had a weekend off, and that's what I did to get ahead.
One day, about a week after I moved to Florida, I was standing at the bank at 4:00 p.m. waiting for a friend to pick me up. The lobby had just closed, so I was forced to wait outside in the hot Florida sun (and I mean hot). A red Corvette pulled up and a beautiful lady hopped out.
“The lobby is closed,” I said.
“I know,” she said, but walked up anyway and knocked on the door. The door opened, she went inside for five minutes, and when she came out she asked me what I did for a living.
I told her I had just moved to Florida and I was studying political science. I asked her what she did and she said she was an executive at SprintPCS. I said, “Wow! What a small world. I own your stock.” She was not expecting that from some random kid waiting for a ride outside a bank. We talked for a little while, and then she asked if I wanted a job at the corporate office. I said sure, we met the following week, and she offered me a position: I was to help increase sales at Circuit City in South Florida. I worked there for the next few years, helped open the first Circuit City in Boca Raton (which later became Barnes & Noble), and my stores became the most profitable in South Florida.
MARKET TUITION
The late 1990s was the era of the dot‐com craze. I pumped money into the market speculating on the euphoria that drove stock prices for internet start‐ups ever higher. They had no earnings, no sales, but all you needed at the time was a “.com” in your name, and people would buy the stock! At one point, on a golden afternoon around the turn of the century, I felt invincible while staring at my brokerage account, proud to have doubled my tiny fortune at such a young age. I've learned that money is all relative. To me, a kid who started with less than nothing, $500 was a lot of money, $5,000 was crazy, and $5,000,000 was a dream. It is amazing how your perspective changes over time.
Then, in March 2000, the dot‐com bubble burst; the market crashed, and I was in a state of shock and disbelief as it imploded over the next two years. I made every mistake under the sun. I did not have a plan to sell if the stock went down, I did not have a clue about risk management or position‐sizing—and thanks to my naivete, I couldn't imagine that stocks could go down so far for so long. I also had no idea that it was possible to actually make money in a bear market. Looking back, I realize I was clueless.
My investment portfolio was bankrupt. But to me, it wasn't just money that I had lost. It was deeper. I lost my Blow Pop profits, my fireworks sales, my cell phone commissions—all the fruits of my early entrepreneurship had evaporated. Essentially, my life's work had disappeared. Gone. All my sacrificed college weekends spent selling cell phones while my friends partied—vanished. It was a gut punch like no other. It was personal. It was emotionally devastating.
On The Street (Wall Street, that is), they call that kind of experience “market tuition”—provided you walk away with some lessons. I knew I wanted to win. I also knew I had no idea what I was doing so I had one job: to learn. Knowing what I don't know became (and still is) one of my biggest strengths.
THE ALLURE OF SPECULATION
Around the same time, my childhood friend Stephen Klein (my business partner in my candy and fireworks ventures) scored a great six‐figure job working at a huge commodities desk in midtown Manhattan as a futures broker. Within a few weeks, he turned $5,000 of his own personal money into over $100,000. As you would imagine, I told him I wanted in. The timing seemed perfect because Stephen's bosses had realized he was conducting personal trades, and they wanted him to stop and focus his attention on his “day job.”
To get around his bosses, we concocted a plan: I would open an account in my name, he would trade it (the same way he had been trading his account), and we would split everything right down the middle, 50/50. My only problem was that I was wiped out from the dot‐com crash, so to ante up, I had to scrape together some dough. I managed to borrow $5,000 from my father, and then I held my breath and jumped in with both feet. I wish I could tell you that I took that $5,000 and turned it into $5 billion, but this story has a completely different ending.
In an ominous sign of things to come, the day before I opened the account, Klein lost $25,000 of his own money in one day—not fun. Our trading account number ended with the digits “69,” so with all the maturity of a couple of recent college graduates, we dubbed it “the infamous 69 account,” and as a testament to our friendship (considering what was about to occur) we still, every now and then, look back on this adventure and laugh.
We filled out the paperwork (at the time we still had to open accounts with paper), and we funded the account on a cold Monday in January. The plan was that Klein would do everything—buy, sell, handle the position sizing, and so on; he'd make all the decisions. Back then, I didn't have access to real‐time quotes, and I could not log in like today and see my statement in real time. Everything was delayed. Essentially, I was flying blind.
At the end of that first day, I called him to ask how we did. Without skipping a beat, he said it was a good day. I asked him how much we made. A little over $8,000 on a $10,000 account, which he added, constituted an 80% return in just one day. “How much do you think we'll make by the end of the year?” I asked. To this day, I can still hear Stephen's voice in my ear, crackling on the other end of my SprintPCS cell phone. It was one of those pivotal moments in my life—one that you just simply never forget. He responded, very casually: “One million dollars.”
I was overcome with joy. Remember, I started with nothing but an insatiable hunger to learn, and for me, at the time, a million dollars was more money than I could fathom making, and it was all happening without me having to lift a finger.
Blinded by emotion, my naive and flawed logic went something like this: Stephen just turned $5,000 into $100,000. Why wouldn't he be able to do it again and then grow $100,000 into $1,000,000? If he could multiply his portfolio 20‐fold in just a few weeks, why wouldn't he be able to multiply it by a measly 10‐fold in a year?
This, by the way, is dumb money thinking. Anyone who knows anything about trading, risk management, or returns knows that while periods of rapid, exponential growth are not unheard of, in the long term such gains are simply not sustainable. The best traders in the world average 20–30% annual returns; realizing 80% gains in one day is not sustainable. I suspect you've guessed where this story is headed.
On Tuesday, the very next day, the market corrected, we lost all our profit, and we were left with our initial investment: the original $10,000, which included the $5,000 I had borrowed from my father. We both wrote it off as “just a bad day,” and didn't think anything