Rebound: Life After Divorce & Addiction

by Matthew Andrews

“Maybe you’re right,” I admitted. “I can’t seem to get over feeling shitty about being a cheat, which causes me to do all kinds of insanely stupid things to cover up the past. I just keep making the same mistake over again in the present.”

“Bingo! Let’s go help some sick mother fuckers who have a hell of a lot more to worry about than you do,” Frank yelled as he got up to pay the bill and slapped me on the back.

By the week of Thanksgiving 1999, two years after making our original investment, my Internet company was selling more stock to the public in a secondary offering. The insiders agreed to sell a small percentage of our holdings. That week I was on a retreat in Vermont, staying at a bed and breakfast with just one phone line. I huddled in an upstairs hallway, the phone receiver pinned to my sweaty ear as I listened to music, on hold for the secondary pricing call. My right leg jumped uncontrollably, causing the old wooden chair supporting my large frame to creak noisily.

Finally, I heard a series of clicks as the founders, the rest of the board, and various advisors joined the call. When I heard the price—over one hundred times our cost basis—all the twitching and huffing stopped. I couldn’t believe that in three business days several million dollars would be wired to me. I still owned stock worth, on paper, many multiples of that number.

In the weeks that followed, greed and fear dominated my life. The market capitalization of my little turn-around project was over a billion dollars. I wanted to sell every last share of my stock immediately, but was restricted from doing so by the initial public offering “lock-up.” Buyers of an IPO want reassurance that faint-hearted insiders aren’t going to dump their shares and tank the stock. So insiders are forced to legally bind themselves to a six month waiting period as a precondition of any IPO. I still had several more months to wait until my remaining shares would not become freely tradable, which made me tremendously nervous. Many a hedge fund trader had made a killing by shorting a stock like ours. I was sure that our stock would take a massive hit the day it finally became liquid, it was just a matter of how massive.