iWon.com

» see iwon.com as it lived, on the wayback machine

~ the obituary ~

iWon launched in October 1999, the product of Bill Daugherty and Jonas Steinman, two Harvard Business School friends who had been arguing over lunch about what the McDonald's Monopoly promotion taught about user behavior. Their answer was a search portal where every click bought you a sweepstakes ticket. CBS came in with roughly seventy million in advertising and promotion in exchange for the majority of the company.

The prize structure was the whole product. Ten thousand dollars a day. Thirty thousand-dollar prizes a week. One million a month. Ten million on tax day. The page itself was a generic late-90s portal, headlines from CBS properties, a search box, a horoscope, weather, a game grid. The reason to use it instead of yahoo was the lottery wallpapered over every interaction.

iWon's whole peak was the american sweepstakes-portal moment, a thing that did not happen in turkey. there was no localized iwon for ttnet users, no turkish-tax-day-prize variant, no equivalent in arabesk culture. i first read about it years later in fortune magazine archives. it sits in the part of late-90s us web culture that needed a US bank account and a US tax filing date to even play.

~ the case file ~

~ the climb ~

By late 1999 iWon had three million unique visitors. By summer 2000 it was inside the top twenty-five US web properties by reach, ahead of some legacy newspapers and behind only the obvious portals. The model worked because the prize structure was cheap relative to the advertising. Ten million on tax day, given the math of audience growth, paid for itself.

The acquisition spree started in early 2001 when iWon bought Excite at a firesale price during the at-home collapse. By 2002 it ran under the holding company Interactive Search Holdings, alongside My Way and other walked-out brands.

~ the actual end ~

Ask Jeeves bought Interactive Search Holdings on 6 May 2004 for about 501 million dollars, mostly in stock. iWon was now a sub-brand inside Ask. IAC bought Ask later that year. The prize structure shrank, then shrank again, then quietly went away. The site stayed online as a Yahoo-Bing search frontend with a sweepstakes coupon page for another decade.

It went dark for good on 6 January 2016. The companion iwon-branded email service hung on until 2 October 2017 before that too closed.

~ the long tail ~

The thing iWon proved is that a meaningful chunk of search traffic will choose the worse engine if the worse engine pays. The whole modern paid-to-search category, the Bing Rewards points, the Honey browser plugin, the Brave BAT model, all of them point back to the iWon thesis. The thing iWon did not survive was the same thing that killed every late-90s portal, which is that google's clean white search page beat every walled-in destination that hoped you would stay around.

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