INVESTMENT TIPS

In the early 2000s most everybody in the real estate biz was not hitting the long ball. But what was better? My late father, who was a stock broker for about six months in the 1950s, taught me the stock market was legalized gambling. John Bogle, former chairman of the Vanguard Group, said, “The investor in America sits at the bottom of the food chain.” You have to be lucky twice with stocks: when you buy and when you sell. In March 2009 the New York Times business-page headline was “Are We There Yet?” There meant the stock market’s bottom.

In March 2009 the price/earnings ratio was at its lowest in more than 20 years: 13. (Shiller trailing 10-year figure.) The worldwide P/E was even lower, down to 10. It was a good time to invest, but scary.

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My Uncle Lou and Uncle Al drove a truck, delivering wholesale items to stores. They sold me a carton of baseball cards — 24 packs — at a deep discount. I immediately ripped open all the packs. I was 9. This investment was my first speculation. I got a lot of Humberto Robinsons (a nobody, an Indians relief pitcher) and no Mickey Mantles. Maybe my uncles were teaching me dollar-cost averaging: better to buy a pack a week (dollar-cost averaging) than go all in.

Am I ready to jump into the stock market again? No, I’m not scared enough yet.

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