Pets.com emerged during the dot-com bubble, a time of wild optimism and reckless investment in internet startups. Founded in 1998 with the backing of Amazon, it quickly became a cultural phenomenon thanks to its iconic sock puppet mascot, which starred in a Super Bowl ad, appeared on national TV, and even floated in the Macy’s Thanksgiving Day Parade. Despite massive marketing spend—over $70 million—the company struggled with a fundamentally flawed business model. Selling heavy items like pet food at a loss, offering free shipping, and facing razor-thin margins made profitability impossible. Sales soared but so did losses, with the company burning through nearly $300 million in just two years. After a disastrous IPO in February 2000, the stock plummeted from $11 to less than 20 cents by November. Pets.com shuttered within 268 days of going public, laying off hundreds and leaving investors devastated. Though seen as a cautionary tale of the dot-com crash, the core idea—selling pet supplies online—proved viable years later with companies like Chewy. Pets.com was simply ahead of its time, lacking the logistics infrastructure and consumer trust that would later make e-commerce successful. Its collapse remains one of the most dramatic, visible failures in tech history, immortalized by its puppet mascot—a symbol of both genius branding and unsustainable growth.