Giving Away Half-a-Billion Dollars w/ Craigslist founder, Craig Newmark

from Reasonably Happy with Paul Ollinger · host Paul Ollinger

If you had hundreds of millions of dollars, how would you use it? Craigslist founder Craig Newmark faces this exact “problem”—and he’s working hard to give his fortune away to nonprofits tackling some of society’s most urgent challenges. In this week’s episode, Craig and I discuss the early days of Craigslist, its radical “revenue-minimization” strategy, and how its simple tools changed the classified ads game in the late ’90s. He told me how Sunday school values shaped his approach to business, why he demoted himself to customer service rep, and what he learned by hiring a CEO to run the company he built. Our conversation explores the art of giving money away strategically: from supporting veterans and military families to investing in cybersecurity and protecting democracy. We also get personal - talking favorite TV shows, the pros and cons of AI, and the big question: how much is enough? Listen now.Read Paul’s Substack here⁠: https://words.paulollinger.com/Learn more about Craig’s philanthropic endeavors ⁠here⁠: https://craignewmarkphilanthropies.org/Please rate, review, and share this great episode! Get full access to Reasonably Happy at words.paulollinger.com/subscribe

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This episode is 41 minutes long.

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This episode was published on September 17, 2025.

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