In early 1995, Craig Newmark was a newcomer to San Francisco sending a manually typed email list of local tech events to a handful of acquaintances. Inspired by the community spirit of the Well, MindVox, and Usenet, he assumed people wanted parties. Instead, subscribers asked for job postings, then more categories, then a website. By June 1995 he had installed Majordomo to automate subscriptions, and craigslist.org followed when users demanded a web interface.

This episode traces how that list became a company earning an estimated $1 billion a year with a staff of around 50, a plain text design, and almost no ads. It covers the abandoned List Foundation nonprofit plan, incorporation as a for-profit in 1999, and the arrival of Jim Buckmaster, who rose from lead programmer to CEO within 2000. It also examines the eBay lawsuit, crime on the platform, and the laws that forced Craigslist to close whole sections.

• Revenue came from charging businesses, starting with a $25 fee for job posts in cities like New York and Los Angeles, while individual listings stayed free.
• eBay bought a 25 percent stake from a former employee in 2004, then sued in 2008 claiming Newmark and Buckmaster diluted its interest by more than 10 percent.
• Craigslist countersued, accusing eBay of using its board seat to gather confidential information for its rival service Kijiji. eBay sold its stake back in June 2015.
• On September 4, 2010, Craigslist shut its US adult services section, giving up an estimated $44 million in revenue for that year.
• After FOSTA and SESTA carved an exception into Section 230 protections in 2018, Craigslist closed its entire US personals section rather than risk liability.