Gail Klein Bentley was on top of the world-actually, way higher than that. The 30-year-old Charlottesville, Virginia, entrepreneur had zoomed out of nowhere to land $1.2 million in angel funding in the fall of 1999, and her Web site, WorkingWeekly.com, was the subject of heavy buzz. It had quickly grown to 60 employees and had a potentially huge customer base because its focus was on the changing workplace-on helping people find meaning and fullfillment in their working lives. How could it fail?
Then one day the bottom fell out. "I had a commitment for $2 million in additional funding. The day they were supposed to put in the money, they withdrew the offer," recalls Bentley. Not good-and the ride became stomach-turning bumpy. "Of course I went to other funders, but nobody else would invest," says Bentley, who served as chair, president and publisher. "I had to lay off all 60 employees. I had never failed in my life. That was just a terrible time."
As we've all seen in the news, Bentley's pain isn't all that unique. Last year, the talk was about the mushrooming number of dotcom millionaires. These days you hear more about all the dotcom disasters. Even big names are among the casualties: Living.com, Boo.com (although Fashionmall.com did buy and reopen it), Pets.com and even ToySmart.com, a onetime Disney subsidiary. But countless lesser-known companies went under, too. Entire Web sites have sprouted to do nothing but maintain death watches on sputtering dotcoms. The upshot is that what had seemed a no-brainer route to riches suddenly looks more like a dead end. But is it? Is dotcomming only for kamikazes determined to flame out? Is there still money to be made online?