The Other Side of Wall Street: The Age of Innocence

Jun 6, 2011

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This chapter is from the book 

Other Side of Wall Street, The: In Business It Pays to Be an Animal, In Life It Pays to Be Yourself

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The Critters Cometh

I used metaphorical representations to represent the stock market—Hoofy the Bull and Boo the Bear—and told both sides of the trading story. There was always a bull case and a bear case, I thought at the time, and the residual grist was what the financial media reported the following morning. It made sense to write through that lens and examine the friction between opinions, which was where I believed true education was found. In time, my readers asked what Hoofy was doing or what Boo was thinking, and they began to assume personalities and perspectives. They resonated—people liked them. It occurred to me that nobody had ever branded the Wall Street bull and bear.

TheStreet.com paid me a salary—$100,000 a year—but it paled in comparison to the money I made running a large fund. For me, writing wasn't about the compensation as much as it was the catharsis, and we never signed a contract because I didn't believe TheStreet.com should own the words "Hoofy" or "Boo." That legal language was industry standard at the time, but it wasn't my primary industry, nor was it my standard.

They didn't press the issue; to them, I was a cash cow that produced content, a man in the trenches who generated page views. I wrote incessantly as I navigated the other side of the technology bubble and chronicled my trades for the world to see. If the stock market was a casino, it felt like I had the dice in my hands for an incredibly long time. TheStreet.com was happy, our investors were happy as we notched double-digit gains, and I was happy, albeit a bit hollow. Profitability was a wonderful distraction from the pain of losing my grandfather, but it didn't fill the void.

Life was good, or so I thought, as I had the toys that society bestows on those with wealth. Forget all the time that elapsed while I sat in front of my screens in an attempt to make money. There would be more dinners with friends, plenty of time to find a bride, and countless hours to relax.

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