Zip2 — Musk’s first company

In November 1995, 24-year-old Elon Musk co-founded Zip2 with his brother Kimbal and Greg Kouri, after deferring a Stanford PhD to join the internet boom. Zip2 built online city guides and searchable business directories — essentially an internet "yellow pages" with maps and directions — and licensed the software to newspapers including The New York Times and Hearst so they could put their classifieds and local listings online.

In the early days the company ran lean: Musk reportedly coded through the night, slept in the office, and showered at the local YMCA. The bet was that newspapers needed a bridge to the web, and Zip2 became that bridge.

In February 1999 Compaq acquired Zip2 for $307 million in cash — then one of the largest sums ever paid for an internet company. Musk received roughly $22 million for his stake, capital he immediately rolled into his next venture, the online bank X.com.