History Is Doomed

A Cautionary Tale For Techies: The Downfall of a Dotcom Millionaire

When the party ends badly.

2 dot com A Cautionary Tale For Techies: The Downfall of a Dotcom Millionaire

On Sunday the Times published the melancholy and disturbing tale of former dot-com millionaire Jennifer Sultan, who is sitting at Rikers Island, facing the prospect of years in prison.

Jennifer Sultan’s name is not familiar to anyone in tech today, but at one time she and her boyfriend Adam Cohen were sitting atop a small, forward-looking, valuable startup called Live Online. Ms. Sultan and Mr. Cohen sold Live Online in 2000 for $70 million. They rented a house in the Hamptons. They bought a big loft not far from Fifth Avenue.  But that was 12 years ago. Now? The Times reports:

Now, a little more than a decade later, Ms. Sultan is bankrupt and sitting in a jail cell, unable to pull together $85,000 for bail. If convicted, she faces 15 years to life in prison on charges of selling prescription painkillers to an undercover police officer and of trying to sell a .357 Magnum to the man accused of being the ringleader.

Her life has in some ways followed the arc of her times, with even more extreme swings.

Times writer Russ Buettner notes that Jennifer Sultan “rode the euphoria of the late-1990s” tech boom to cashing in at 25, but that bubble burst in an epic way and her apparent good fortune went along with it. She and Mr. Cohen tried out new tech ventures but they ended in fractured business relationships. The couple attempted to maintain their lifestyle, but bills began to mount and eventually they were faced with foreclosures, evictions and bankruptcy. Business associates told the Times they were behaving “strangely.”

The Times also reported that Mr. Cohen told a judge in bankruptcy court the couple lived “like animals” unable to “provide for ourselves.” Now that Ms. Sultan is in jail, she and Mr. Cohen also face contempt charges in bankruptcy court, where they have to represent themselves, as their attorneys quit.

The entire story may read like a big bucket of cold, dirty water on everyone TED-Talking their way to the party now, but it’s doubtful anyone will take note. That is until their own millions start to wear thin.

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