I hear America singing. The songs are “Nobody Knows The Troubles I’ve Seen,” “It’s Only Money” and sometimes, “Hard Times Come Again No More.”
America is not yet ready for “Happy Days Are Here Again” or “Cheer Up! Good Times Are Comin’” or “We’re In The Money” because no one believes that happy days are here again or that good times are coming. And most Americans are not in the money, either.

But Americans are enterprising souls and I fully expect that someone will cover all those old Depression songs like “Brother, Can You Spare A Dime” or “Long As You’ve Got Your Health” or “If I Ever Get a Job Again.” They’re timeless, if you think about it. And timely, too.

When the stock market rollercoastered from a high of 14,164 to a low of 7,449 in roughly a year’s time, I was not alarmed. What, me worry?

The 778-point drop in the Dow Jones Industrial Average on September 29, 2008 put many on their knees, but not me. The worst single-day point drop in the history of investment in recorded time! A $1.4 trillion dollar loss! Even when Lehman Brothers, the 158-year-old investment giant, collapsed, and friends were putting everything in the mattress, I was calm.

When Linens-N-Things went bye-bye, I thought, “What’s the big deal?” Linens I can get elsewhere. Ditto, things. Office Depot was next. Then Sharper Image. Not a problem. My image is sharp enough.

Then Legg Mason’s Svengali Bill Miller— the man who tamed the S&P— lost his magic touch and it looked like his next stop might be selling the ShamWow on cable TV. “It’s like a chamois, a towel, a sponge. Works wet or dry. It takes up cola, wine and pet stains. You’ll say wow every time!”

Next up, the Big Three auto giants panhandling on Capitol Hill. Even that did not bother me.

But I have to admit I was a bit startled late last year when I got a letter from the guy who used to clean my gutters. He was writing with an investment opportunity of a lifetime. He was writing because he felt “compelled to share a tremendously valuable discovery.” He’d found something bigger than Microsoft. And he had not forgotten me! The guy who used to clean my gutters was now Warren Buffet! That’s when I got scared. That’s when I knew the end was near. I fully expected to see the Four Horsemen of the Apocalypse galloping down Club Road.

Truth be told, this guy was a phlegmatic gutterista. His staff of experts was hard to round up. I’m not fussy about who cleans my gutters. Normally, the first aerialist to get here when they need cleaning who can climb the ladder to the third floor gets the job. But the guy who used to clean my gutters once forgot my gutters and we had a freak ice storm and a gutter fell off my house and cost a lot of money to replace. That’s when he became “the guy who used to clean my gutters.”

Gutters are like the economy. You go along day after day and only notice when they back up in a storm. Or peel off the side of the house and cold-cock the UPS man. One day the gutters look fine. Two weeks later they’re sagging. We take them for granted. Like the economy. We sort of think someone else is watching the gutters. But there is no Securities and Exchange Commission for gutters. You are on your own.

And then came the gutter man’s letter inviting me to share in the investment opportunity of a lifetime. He didn’t explain what the opportunity was. Perhaps it was alchemy— pig iron into gold. That would set the commodities market on edge. Perhaps he’d transformed tap water into Chateauneuf-du-Pape? Perhaps he’d found the elixir of life or the seven cities of Cibola? He did hint that his invitation was akin to Bill Gates coming to see me before Microsoft was launched and asking me to invest in his idea of putting PCs in every household.
Bill Gates! Microsoft! PCs in every household! We’re in the money! Happy Days are here again. “You’ll say wow every time!”

Alas, I did not jump at the gutter man’s offer. Timing is everything and this one-in-a-million chance of a lifetime arrived when most Americans were looking for a-chance-of-a-lifeline. And it was just too vague for me. I know the doormen on The Block used to say, “you gotta pay to see the girls dance.” But this was not a time when I needed more risk in my life. And I’ve seen the girls dance. I took a pass. Let others become fabulously wealthy, thank you.

But I liked the guy’s style. I like a man of vision, a man willing to take risks. The world was falling apart but this guy was thinking big, recalling Oscar Wilde, who once mused: “We are all in the gutter, but some of us are looking at the stars.”

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