• by Michael Kubin , March 20, 2002

What really happened to all those people who jumped off the boring, conventional old-media train and hopped onto the supercharged, sky’s-the-limit dot-com options express? A few — especially those who saw the light early enough — succeeded. They may have seen their net worth erode a bit as the value of their shares dropped, but if they were in before 1995 and out before 2000, you’ll find some of them in Aspen, Palm Beach, and Bali.

Others, especially those late to the feast, might have experienced the exhilaration of rapidly rising options, only to have their balloon cruelly burst by watching their illiquid shares plunging until they were, as applied to the vast majority, ‘under water.’ For every private jet-laden Mark Cuban there are thousands who have been left to arrange their travel via Priceline, three legs from Chicago to Milwaukee.

There are a few, however, who through some mix of good luck and bad timing — or the reverse — were left teetering on the seesaw. Neither a resounding success nor a crashing failure, they continue to believe in the future of the Web, but don’t yet have the Ferraris to show for it.

One especially interesting case is that of a fellow who was way ahead of the curve, heavily involved in the Internet back in the Neanderthal days of the early 90s. He even went so far as to form a group of Internet enthusiasts in 1992, a group whose dedication was so strong they’re still in touch today.

Let’s call this guy Todd (even though he allowed me to use his real name, I wonder if he really knew what he was agreeing to). Using his knowledge of Internet advertising, Todd formed an advertising agency that specialized in the new medium. He and his partners took space in a downtown New York loft, complete with balky elevator, and began gathering clients. ‘Binging’ on clients was more like it, as they soon outgrew their offices and had to take on larger, slicker space. Todd was making speeches, being quoted all over, and generally livin’ la vida Web.

After just a couple of years Todd and his partners got an offer they couldn’t refuse, so they sold their company to a much larger advertising agency. But soon it became apparent to Todd that he wasn’t a big company guy, so he slid out from under his operating duties — though still retaining the title of Chairman.

But the entrepreneurial bug had bitten him hard and soon he was off on another venture, this time creating a keyboard that contained resident buttons, each connecting the user to a function such as travel, flowers, or banking. And each one, of course, represented valuable real estate that could be sold to sponsors. Todd was able to secure some seed money (including his own), hired a staff (including a seasoned CEO), and off they went. In that heady world, the sky was the limit.

But the sky, apparently, had fallen. After a few months of very hard and sincere efforts on the part of the team, Todd’s new venture sputtered, ran out of cash, and bit the dust. Exhausted and fed up with anything Web-related, unable to retire and unwilling to remain idle, Todd decided to apply for a job at…McDonald’s.

Arriving at 4th and Broadway for his interview, Todd filled out the job application. Only one question aroused the attention of the manager: under ‘current employment’ Todd wrote ‘chairman.’ ‘What’s this?’ asked the manager. ‘Just a job I’ve been doing for a while’, answered Todd. ‘Oh,’ said the manager, ‘what’s your waist size?’

For the next six weeks Todd worked behind the counter, taking orders at $6 an hour. His observation: $36 for six hours work turns into $25 after taxes. Not even enough to cover having his laundry done.

Todd has since left McDonald’s and has formed another Web-based venture. Stay tuned.

Michael Kubin is co-CEO of Evaliant, one of the web's leading sources for online ad data.