Running Lean Through the Dot-Com Bust

What if the founder of one of the internet’s most enduring brands… never wanted to run a company?

In 1995, Craig Newmark was a 42-year-old computer programmer in San Francisco who simply wanted to share local tech meetups with friends. He started an email list that became Craigslist—a website that reshaped how we find jobs, apartments, and community.

In this conversation, Craig opens up about how not having a grand vision (or a taste for power) led to one of the most popular platforms in the world. With fewer than 50 employees, Craigslist still generates hundreds of millions in revenue—while looking like a website frozen in 1996.

This is the story of an “accidental entrepreneur” who built a global brand by being in the right place at the right time—and why he now calls himself the Forrest Gump of the Internet.

In this episode, you’ll learn:

• Why keeping things simple is often the smartest design choice.
• How knowing your weaknesses can be the ultimate superpower.
• Why community beats marketing every time.
• How to monetize minimally—and still build a wildly profitable company.
• Why luck and timing matter more than you might think.

Timestamps:

• 07:10 Craig’s childhood struggles with social situations—and how local Holocaust survivors shaped his worldview
• 16:15 Discovering the early internet and becoming an “evangelist” at Charles Schwab
• 20:07 The simple email list that broke at 240 addresses—and became “Craig’s List”
• 29:16 Why Craig refused banner ads and said no to early monetization
• 35:00 Handing the CEO role to Jim Buckmaster—and how that decision led to Craigslist’s success
• 49:44 eBay buys a stake in Craigslist, then launches a competitor—sparking a messy legal battle
• 53:46 Was Craigslist really responsible for killing newspaper classifieds? Craig reveals his opinion
• 58:08 Why Craig gave hundreds of millions of dollars to support journalism, veterans, and… pigeons
• 1:03:10 Craig on money, meaning, and why billionaires are often miserable

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This episode was produced by Chris Maccini with music composed by Ramtin Arablouei.

It was edited by Kevin Leahy with research by Sam Paulson. 

Our engineers were Patrick Murray, Maggie Luthar and Robert Rodriguez.

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