Why They Cried: Deano

Cause: Ad agency sold to holding company at low multiple

Financial advisors—and he had many—had advised Deano that the market for small, hip advertising boutiques—like the one he owned and was now selling—had been at an all-time peak six months ago, selling at mad cash prices, sometimes at eight or twelve times after-tax profit, but he had not listened. Not that he didn't think they were right. He knew that agencies were selling at a heretofore all-time high. What he did not believe was that this all-time high was a forever and permanent all-time high. He thought it would go higher and then again higher—to twelve, maybe even twenty times after-tax profit—in a dizzying succession of all new all-time highs. That is what he thought, but he was wrong.

When it came time to sell the agency—when the papers came for him to sign—it was a very bad deal. But he did not cry. This was business. He had gambled and he had lost. He signed the papers without a hint of regret and even pried open a case of champagne for his staff and offered a toast to the future.

It was not until much later, at a bar where he had stopped for a nightcap, that he was surprised by a mirror above a urinal and, catching a glimpse of himself and recognizing himself as a man who had just sold an ad agency at a really very poor multiple, that he choked back the first of many tears.    

Tomorrow: "Why They Cried: Jisette"