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 Corp. EMC +1.46% Mr. Flynn would cut hair while he and his regularsâincluding local Maytag dealer Rick Capobianco; Ron Danforth, owner of a direct-mail business; and gas-station proprietor Rick Smithsonâtraded news on highflying stocks and mentally tallied their winnings. The next few years weren't so kind to him and millions of other investors. Most of those stocks plummeted. Some companies filed for bankruptcy protection. Mr. Flynn's mixed feelings as the Dow broke through its 2007 record this week is reflective of a collective shrug by investors across the country. Despite the market more than doubling off its lows, the rally has yet to kindle the public imagination. After all, many households have suffered through five years of volatility, only to end up back where they started. Others, like Mr. Flynn, remain so demoralized by the busts of 2000 and 2008 that they have missed the latest boom entirely. Mr. Flynn and other investors also are skeptical about the stock surge at a time when the economy feels so weak for many individuals. Unemployment remains high and home prices remain far below where they stood just five or six years ago. William Flynn, owner of Bill's Barber Shop, saw most of his retirement savings vanish in the stock market and he's not lured by its latest rally. Surveys show that many investors haven't come back to stocks, believing the rally can't last. Other say shares have been artificially propped up by the Federal Reserve's extraordinary stimulus measures. And, while the Dow is back to record levels, the Nasdaq Composite, home to many of the technology stocks in Mr. Flynn's portfolio, including EMC, is still 36% shy of its March 10, 2000 peakâan anniversary that comes on Sunday. Mr. Flynn, 73 years old and a life-long barber, has been clipping hair in his small clapboard barbershop just off Main Street for 15 years and figures he will still be standing at the black swivel chair when the next bust comes. Plans for a retirement in Las Vegas have been put on permanent hold. On Tuesday afternoon, as the Dow climbed to its record close, a handful of customers came and went. Not one mentioned the stock market. The day's big topics: Plans for the local St. Patrick's Day parade and construction up the road that is holding up traffic. A computer in the back room, once ablaze with stock charts and tickers, is now used mainly for the occasional game of Solitaire. His old trading buddies rarely drop by, including Mr. Capobianco, who was once a regular at Bill's, stopping by even if he didn't need a haircut. He was never a convert to the tech mania, he said, though he did buy EMC shares at Mr. Flynn's urging. The 61-year-old moved his appliance store a few miles down the road a little more than a decade ago. He switched barbers, and only sees Mr. Flynn from time to time. For one thing, Mr. Capobianco has had more luck investing. Mr. Capobianco's skepticism of technology stocks meant he lost only about 12% in the bust. Since then, he has bought such stocks as General Electric Co. GE +0.38%and Yum Brands Inc. YUM +0.70%He sold his EMC shares to expanded his Maytag dealership and help pay for his son's college education. Mr. Capobianco is among a growing pool of investors warming up to stocks again. "What I have, I invest," Mr. Capobianco said. "I'm not going to be buying a villa in France or anything, but I'm doing all right." Like Mr. Capobianco, Mr. Smithson managed to get out of most of his stocks before the big bust. He used the money to buy a house. He still pops into Bill's Barber Shop for a trim. "We still talk about stocks now and then, but not like we used to," said Mr. Smithson, who now runs an auto-repair shop. He remains invested in a few tech stocks, like Microsoft Corp. MSFT -0.50%and Marvell Technology Group Ltd., MRVL +3.09%a semiconductor maker. Mr. Danforth, who ran the direct-mail business on Cape Cod, said he lost money in the downturn. But he sold his franchise for a profit and now is living in an exclusive lakeside community in western Massachusetts, where he retired and took up woodworking. Mr. Danforth, age 74, said he feels bad Mr. Flynn can't retire, too. "At that age, you shouldn't have to worry about those things," he said.