eBay

Founded in 1995 by Pierre Omidyar, eBay began as a digital garage sale where you could snag a Beanie Baby or a vintage lava lamp with the same ease as you might acquire an antique typewriter—or so they claimed. Now an e-commerce juggernaut, eBay is famed for turning online auctions into a cultural phenomenon and, inevitably, a treasure trove of questionable purchases. It rocketed to fame in the early 2000s with IPO fanfare and has since become synonymous with eccentric collectibles and an alarming number of “rare” action figures. Valued in the tens of billions, it’s achieved a few shiny awards but not without its fair share of blemishes, including scandals involving counterfeit goods and fraudulent sellers. The company’s biggest gambles included trying to pivot from auctions to a fixed-price model—a move akin to swapping your vintage car for a sleek, but ultimately soulless, sedan. Today, it’s overseen by CEO Jamie Iannone, whose task is to navigate eBay through a landscape now crowded with competitors eager to offer the same kind of dubious bargains. If eBay were a person, it would be that eccentric uncle who collects everything but never quite lets go of the past.