In the late 1990s, during the height of the dot-com boom, iWon.com emerged as a revolutionary—and wildly extravagant—web portal that paid users cash prizes just for browsing. Founded in 1999 by Jonas Steinman and Bill Daugherty, the company offered daily, weekly, and monthly cash giveaways, including a staggering $10 million prize awarded annually on Tax Day. Users earned entries into prize drawings through simple actions like searching the web, checking email, or reading news—transforming everyday internet use into a high-stakes lottery. Backed by CBS with $70 million in advertising support, iWon.com launched a nationwide marketing campaign featuring prime-time TV spots and the tagline 'Why wouldn't you?' The strategy worked: within a month of launch, the site gained over 3 million unique visitors, growing by 72%. Its business model hinged on attracting massive audiences—'eyeballs'—to sell advertising, betting that gamified engagement would keep users coming back. And it did—for a time. By offering a user-friendly portal with news, weather, search, and free email services, all wrapped in a thrilling incentive structure, iWon.com became a household name for millions of early internet users. Real-life stories, like Gary Kopp winning $1 million just by using the site, fueled its popularity and captured the public imagination. But beneath the flashy headlines and dreamlike promises lay a fragile financial reality. As the dot-com bubble burst in 2000, funding dried up and investor confidence plummeted. iWon.com struggled to sustain its costly prize model without guaranteed ad revenue. In 2001, it acquired Excite.com at a steep discount, rebranding as The Excite Network in an attempt to consolidate power and expand reach. Despite these efforts, profitability remained elusive. In 2004, iWon was acquired by Ask Jeeves for $501 million, later becoming part of IAC/InterActiveCorp. Though the brand lingered for over a decade—as a casual gaming platform and nostalgia-driven portal—it officially shut down in 2016, with its email service closing in 2017. For many longtime users, this marked the end of an era, severing digital identities built around a quirky but beloved piece of internet history. iWon.com stands today as a symbol of the exuberance, innovation, and ultimate reckoning of the dot-com age—a bold experiment in attention economics that proved people will do almost anything for the chance to win.