PayPal
Online payment system. Confinity (Peter Thiel + Max Levchin) + X.com (Elon Musk) merged 1999. eBay acquired in 2002 for $1.5B → spun off 2015. "PayPal Mafia": founders went on to start YouTube, LinkedIn, Yelp, Tesla, SpaceX.
Drove e-commerce payments 2002–2015. Later competition from Stripe (more developer-friendly for SaaS), Square (Block), Adyen (enterprise), Wise (international), Klarna/Afterpay (BNPL). Acquisitions: Venmo (2013, P2P payments for US millennials), Honey (2020, shopping coupons), iZettle (2018, EU POS). Recent CEO changes (Dan Schulman → Alex Chriss 2023) → strategy shift toward AI + ad business. Valuation has dropped dramatically from the 2021 peak.