#235: Craig Newmark — Craigslist

Podcast: Lay of The Land (LS 31 · TOP 5% what is this?)
Episode: #235: Craig Newmark — Craigslist
Pub date: 2026-01-08

Get Podcast Transcript →
powered by Listen411 - fast audio-to-text and summarization

Craig Newmark is the founder of Craigslist and someone whose work has shaped the modern internet as we know it.

Long before Craigslist became one of the most enduring, important, and frequented platforms on the web, long before the internet even connected all of us, Craig was a computer science student here in Cleveland at Case Western Reserve University — tinkering with early programming languages, studying neural networks and AI, and exploring the frontier of software engineering.

The rest is history — an amazing history which we’ll cover in our conversation today, how Craig became the accidental entrepreneur behind one of the most legendary companies of our time, and a driving force of the internet itself. Our conversation spans his path to Silicon Valley, the creation and stewardship of Craigslist, the moral compass that has guided his decision making along the way, his growth as an entrepreneur and leader, the implications and consequences of building one of the largest platforms of all time, and the work he’s now doing to help meliorate the internet and country through his philanthropic initiatives with veterans, journalism, cybersecurity, and lots more.

This was a truly special conversation, and I’m grateful to share it with you today — please enjoy this awesome discussion with Craig Newmark, the founder of Craigslist.

00:00:00 Craig Newmark on Building Craigslist and the Early Internet
00:03:52 From Case Western to Craigslist: Craig Newmark’s Origin Story
00:07:21 Why Craigslist Was an Accidental Startup, Not a Planned Company
00:12:18 How Craigslist Helped Democratize the Internet for Everyday People
00:15:28 The Birth of Craigslist: From Email List to Iconic Website
00:18:31 Monetizing Craigslist Without Selling Out Users or Trust
00:20:23 Turning Down Billions: Craig Newmark’s Moral Compass at Craigslist
00:23:39 Why Craigslist’s Simple Design Beat Venture-Backed Competitors
00:25:50 How Craigslist Survived While Startups Tried to Unbundle It
00:30:22 What Craigslist Taught Craig Newmark About Human Behavior
00:31:58 Balancing Crime Prevention and Civil Liberties on Craigslist
00:36:00 Why Craigslist Became One of the Most Trusted Platforms Online
00:41:12 The Craigslist Design Philosophy: Simple, Fast, and Human
00:44:01 From Craigslist to Philanthropy: Craig Newmark’s Next Chapter
00:55:58 Craig Newmark’s Advice for Founders

-----

LINKS:
https://www.craigslist.org/
https://craignewmarkphilanthropies.org/
https://www.linkedin.com/in/craignewmark/
https://pausetake9.org/

-----

SPONSOR:

Roundstone Insurance

Roundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.

Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.

Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.

Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.

-----

Stay up to date by signing up for Lay of The Land's weekly newsletter — sign up here.

Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/

Follow Lay of The Land on X @podlayoftheland

https://www.jeffreys.page/

The podcast and artwork embedded on this page are from Jeffrey Stern, which is the property of its owner and not affiliated with or endorsed by Listen Notes, Inc.