Craigslist founder Craig Newmark built one of the internet’s most recognizable companies. Now he is directing much of his wealth toward philanthropy.

In this conversation with Quanda Allen and Meredith Hanley, Craig talks about his approach to charitable giving, cybersecurity, scam prevention, trustworthy journalism, veterans and military families, women and girls in technology—and even pigeon rescue. But beneath the range of causes is a remarkably consistent philosophy: find capable people, do your homework, give them meaningful resources, and try not to make their work harder.

Craig also talks candidly about charitable gifts that did not work as expected, why prestigious organizations are not automatically effective ones, and why donors should be willing to change course when evidence tells them something is not working.

The conversation explores wealth, the Giving Pledge, philanthropic responsibility, trust-based giving, simplicity, due diligence, and the question every donor eventually confronts: How much is enough?