By JONATHAN CHENG
DENNIS, Mass.—As the stock market roared higher in the spring of 2000, Bill's Barber Shop was the place in town for a $10 haircut and a hot stock tip.
More than a decade later, Bill's shop is still standing. But it is $15 for a trim. And stock-market talk now is taboo.
So it was a special exception Tuesday afternoon, when William Flynn turned the TV briefly to the financial news and watched the Dow Jones Industrial Average notch a record closing high. After watching in a stoic silence, he switched the channel back to "Dr. Phil" and swept up hair clippings.
Mr. Flynn has been through two booms and busts in the 13 years since his investing travails were first chronicled in The Wall Street Journal. In those days, Bill's Barber Shop was a hub of stock-market fever. Mr. Flynn, a hefty former high-school hockey star with a handlebar mustache, was hot on technology stocks, with a special passion for data-storage company EMC Corp. EMC +1.46%
The next few years weren't so kind to him and millions of other investors. Most of those