Sequoia backed WhatsApp before mobile messaging economics looked obvious. A small early venture bet gained exposure to a product that scaled with almost no marketing and was later acquired by Facebook for a transaction valued in the tens of billions.
Andreessen Horowitz put $100 million into GitHub after the company had already grown profitably without outside capital. The bet recognized that developer collaboration could become network infrastructure for the software economy.
Facebook spent tens of millions redesigning servers and data-center infrastructure, then gave the designs away through Open Compute. The counterintuitive investment lowered its own costs while helping create an open hardware ecosystem.
Facebook's Instagram purchase looked extravagant in 2012, but it bought a fast-growing mobile network at exactly the moment Facebook needed to prove it could win beyond the desktop.
HP bought Autonomy to accelerate a shift toward higher-margin software, but within a year recorded an $8.8 billion impairment. The deal became a case study in acquisition pricing, diligence, governance, and post-merger strategic overreach.
Microsoft paid $8.5 billion for Skype to strengthen communications across consumer and enterprise products. The technology and user base mattered, but the standalone brand ultimately disappeared into Microsoft's broader Teams strategy.