The Best Asymmetric Bet of the Year Is Upon Us

The Best Asymmetric Bet of the Year Is Upon Us

Bankruptcy was staring me in the face.

I lost my career, my family, my self-respect, and for a brief moment, I even lost my will to live.

It was a dark time in my life. And it forever changed the way I viewed risk and reward.

It all started with the first big payday of my life…

I began buying beaten-down junk bonds in 1990 when I was 19.

Before the year was out, my junk bond trade had netted me over $250,000. That’s about a half-million dollars in today’s money.

The year before, I had made just $8,000, or a bit more than $15,000 in today’s money.

During the mid-1990s, I was making money hand-over-fist in technology stocks – including $54,000 in a single day.

By then, I was 22 and making a fortune. And I let the money make me an arrogant jackass. A few years later, I’d lost it all.

You see, I made a terrible mistake…

Instead of taking small bets on high-risk, high-reward ideas, I was taking massive stakes in these types of trades.

When the 1997 Asian financial crisis rolled around, I’d built up a substantial portfolio. But I stuck around too long and got too greedy.

And when the market went against me, I made bigger and riskier bets. I lost all perspective and was investing for my ego… Not my bank account.

Within three weeks, I lost everything I’d made – and more. I went from wealthy to poor in less than a month. And ultimately, I was compelled to file for personal bankruptcy.

It mentally destroyed me… My wife and I separated. I ended up renting a room from a friend in Queens… And lived on a wafer-thin mattress for nearly a year-and-a-half.

One day, I remember sitting in this tiny room on a tiny mattress and saying, “You know what? My story can’t end like this.”

And at that moment, I started thinking about where I had gone wrong… What I should have done differently… And how I could make my life better.

The Lesson I Learned to Get Rich Again