Craigslist

Craigslist, the internet’s digital garage sale, was founded in 1995 by Craig Newmark in San Francisco, a man who turned a humble email list into a sprawling virtual flea market where everything from free kittens to job offers and dubious second-hand furniture is up for grabs. Known for its minimalistic design and notorious lack of glamour, Craigslist has become the go-to for everything that doesn’t fit neatly into a glossy app or a highfalutin marketplace—think DIY bro ads and the odd scam. Its defining moment was perhaps surviving the digital ad revolution by clinging stubbornly to its free classifieds model, dodging the need for a tech makeover like a dodgy car dealer evading emissions tests. Despite its current valuation hovering around the $3 billion mark, Craigslist has been embroiled in more scandals than a reality TV show, including issues with criminal activity facilitated through its personals section, leading to numerous legal battles. The leadership remains as elusive as the site's interface, with Newmark still the face behind the screen, steering this chaotic bazaar through both boom times and scandalous scandals. In sum, Craigslist is the rough-around-the-edges digital marketplace where you’re just as likely to find a great deal as you are to stumble into a world of trouble.