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Elon Musk tells the story of his early career
Elon recounts building his first startup Zip2 after dropping out of his PhD program at Stanford:
“In 1995 I basically wrote the first — or close to the first — maps, directions, and yellow pages on the Internet. I just wrote that personally and didn’t use a web server (I just read the port directly) because I couldn’t afford one. The original office was on Sherman Avenue in Palo Alto. There was an ISP on the floor below, so I drilled a hole through the floor and ran a LAN cable directly to the ISP. My brother joined me and another co-founder (Greg Kouri who passed away). At the time we couldn’t even afford a place to stay, and the office was $500 per month, so we just slept in the office and showered at the YMCA.”
However, Elon did not intend to start a company at first:
“I tried to get a job at Netscape. I sent my resume into Netscape and nobody responded. Then I tried hanging out in the lobby to see if I could bump into someone but I was too shy to talk to anyone. So I was like, ‘Man this is ridiculous. I’ll just write software myself and see how it goes.’ It wasn’t actually from a standpoint of ‘I want to build a company.’ I just wanted to be part of building the Internet in some way. And since I couldn’t get a job at an Internet company, I had to start an Internet company.”
In 1999, Zip2 was sold to Compaq for $307 million.
After the acquisition, Elon took the $20 million he earned from it and invested it into a new payments company called X, which eventually merged with Peter Thiel’s Confinity to form PayPal.
“I kept the chips on the table,” he recalls. “I got that $20 million check for my share of Zip2. At the time I was living in a house with four housemates and had like $10,000 in the bank. Then this check arrives in the mail and my bank account went to $20,010,000. I had to pay taxes on that, but I ended up putting almost all of that into X.”
In 2002, PayPal was acquired by eBay for $1.5 billion. Elon earned ~$175-180 million from the sale based on his ~11.7% stake. In the subsequent decade, he would keep his chips on the table again and invest it all into Tesla and SpaceX.
Full video: Y Combinator “Elon Musk: Digital Superintelligence, Multiplanetary Life, How to Be Useful“ (Jun 2025)