Adam: Thanks again for taking the time to share your story and your advice. First things first, though, I am sure readers would love to learn more about you. What is something about you that would surprise people?
Craig: This is maybe not such a surprise, but for reasons unknown, I love birds. They visit my wife and me at home. Just moments ago, a couple of different kinds of hawks and hummingbirds flew by, maybe ten feet away.
Adam: craigslist is one of the most successful and iconic websites of all time. Can you walk through your vision for the site, how you executed on it and share a couple of interesting stories from your time leading craigslist?
Craig: In 1995, I started emailing friends and colleagues lists of arts and tech events happening around San Francisco. Many people had helped to let me know what was going on in the city when I first moved there, so I wanted to return the favor. Then, the project began to grow, and people started calling it “Craig’s List,” hence the name now.
When I officially turned craigslist into a company, I monetized it minimally. My goal was never to become rich, just to help people put food on the table, help get a table, and help to find a roof under which to put that table. I figure that “doing well by doing good” is a really good business model.
Adam: What failures, setbacks or challenges have been most instrumental to your growth as a leader?
Craig: Well, early on at craigslist, the people around me let me know that I wasn’t the best person to help the company grow. And, they told me about Founder’s Syndrome, which is when someone who’s started a company doesn’t know when to let go to allow that company to reach its potential. So, I figured I’d learn from other people’s mistakes, and I passed on the reins to Jim Buckmaster. In the end, that’s really what’s allowed me to commit so deeply to philanthropy. I’ve taken my goal of serving the public interest, which is what led me to start craigslist in the first place, and applied that to a number of causes that I’m really passionate about, including trustworthy journalism, voter protection, women in tech, and veterans and military families.
Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?
Craig: One quality is knowing your limitations and then surrounding yourself with smart people who can help to fill in those gaps. No one is good at everything. As a philanthropist, there’s a lot I don’t know. So, I find people who are doing good work in the areas I care about and then provide funds and other support, like lending my voice, and get out of the way to let them do their jobs. It makes much more of an impact than trying to go at it alone.
Even more important is making sure that you build a diverse and inclusive team so that many identities, backgrounds, and viewpoints are represented. If news organizations, for example, incorporate a wide range of voices into their reporting, the stories they produce are more accurate and fair. Relatedly, as a leader, if you employ and otherwise work with people from all sorts of backgrounds, you’re more likely to come up with innovative ideas because inclusivity generates a real melding of minds.
Adam: What is the single best piece of advice you have ever received?
Craig: When I was a kid, growing up in Morristown, New Jersey, my Sunday School teachers, Mr. and Mrs. Levin, taught me two things that really stuck with me. The first is to know when enough is enough, as in recognizing when you have enough money to be comfortable and to support the people you care about and then stopping there. The second is the Golden Rule: treat others as you want to be treated. Their advice has affected basically everything I’ve done in my adult life, from deciding to monetize craigslist minimally to getting really serious about philanthropy. I’m very privileged to have earned enough to give substantial funding to initiatives and organizations that I’m passionate about, and I do what I can to support the people who fight to uphold the values that America was founded on: fairness, opportunity, and respect.
Adam: What is one thing everyone should be doing to pay it forward?
Craig: All of us should treat others as we want to be treated, plain and simple. That means being inclusive and respectful of people of diverse backgrounds and viewpoints. It also means standing with people who don’t get much of a break.
That’s why I’m so dedicated to strengthening trust in news and promoting voting rights. America aspires to achieve fairness, opportunity, and respect for all, but there are a lot of bad actors who are trying really hard to suppress the news and the vote. To counter these measures, there are many great organizations that support trustworthy journalism and voting rights.
This is especially timely because the U.S. midterm elections are fast approaching, and we need trustworthy journalism to report on election results and policies that uphold the right to vote. But, this is work we should always actively be undertaking. Our democracy depends on it.
Adam: What are some of the key lessons you have learned from your time and involvement in the nonprofit world? In what ways have and haven’t you been able to apply the skill set that led to historic success in business to the social causes you care about?
Craig: Through my philanthropic work, I have seen first-hand that there many smart and dedicated people behind initiatives that are doing meaningful work to tackle society’s most pressing problems, from voter suppression to fake news. It’s because of them that I remain optimistic about our collective future, despite the real severity of these times.
Adam: Is there anything else you would like to share?
Craig: Those who do well in this world should give back to their communities. I see my role as one that connects and funds people who are doing good work well, enabling them to do what they do best and then getting out of the way. My goal is to amplify and multiply the voices of the grassroots so that we can maximize social impact from the bottom up. I encourage others who have benefited from the many opportunities afforded by our country to give back. It’s the right thing to do.