Craigslist founder Craig Newmark on becoming an 'accidental entrepreneur'

Craig Newmark has a lot of titles. His most famous is founder of Craigslist, the online classified ads marketplace Newmark began in the mid-1990s. Originally its CEO, Newmark stepped aside from leadership and served as a customer service rep before retiring from the company in 2018. Today, he focuses on philanthropy, journalism initiatives, and fighting online scams.

Newmark describes himself as socially awkward and told Founder Brew he was outsourcing his social skills to the Count from Sesame Street—a more charismatic celebrity “spokespuppet”—in a new anti-scam campaign that the two appear in together.

“I’m at best an accidental entrepreneur,” said Newmark of the eponymous brand worth billions.

In a conversation with Founder Brew, Newmark unpacks Craigslist and his personal brand, stepping aside as CEO, and why he sees customer service as a profit center.

This interview has been edited for length and clarity.

Craigslist isn’t just your company—it’s your name. How did having your personal reputation tied to the business shape the decisions you made early on?

In the middle of ‘95 when I had to give it a name because I had to move to a listserv, I was just going to call it San Francisco Events…Then people told me that they were already calling it Craigslist—that I had created a brand inadvertently. They explained to me what a brand is. They were right, because from the very beginning I took it personally.

When did you realize you weren’t the right person to lead Craigslist anymore—and what made you step aside?

I realized that I was bad about making tough decisions, like hiring and firing. I really sucked at that, and people around me nudged me into finding someone who would be a much better CEO than I was. That was Jim [Buckmaster, current CEO of Craigslist]. They were right.

I really didn’t want to do it, and I wasn’t comfortable in the spokesman role. I wasn’t bad at it, but I wasn’t good at it either. I had to give up coding because I hired a whole bunch of people better than me at it, but I realized I could go into full-time customer service, which is part of treating people like I want to be treated. I was a great customer service rep for around 15 years, until we had hired people who were as good as me or better. At that point I started thinking the nonprofit world could use some help building community, and I could help with funding.

You left a lot of money on the table by Silicon Valley standards. Was that a conscious trade-off?

This was a conscious decision when I had to turn Craigslist from my hobby into an actual company, in early ’99.

VCs and bankers told me they wanted to throw billions at me to do the usual thing and heavily monetize…I’m thinking, “I can already see that I’d make enough to live well and to help my family live well, so I’ll minimize my monetization,” and I built that into the DNA of the company. Jim has maintained that, and that’s worked pretty well.

Why do you consider yourself an accidental entrepreneur?

I started something, committed to it. I was accidentally in the right time, right place, no planning. This all makes me like the Forrest Gump of the internet, no planning at all. Now I would be smarter, but that would represent 31 years worth of learning.

What do marketplace founders consistently underestimate?

They underestimate the need for audience development that is building a market, because we’re all responsible for getting people to pay attention to what you’re doing. That’s true in straight business; that’s a big deal in journalism because people are always responsible for breaking through all the noise, particularly if someone is trying to flood the zone with bullshit.

What’s a piece of startup advice you wish people would stop giving?

The advice that I hear relatively quietly is giving up good customer service, because it’s only a cost center. I think good customer service is a profit center, even if it’s hard to measure.

Founders should act as customer service reps, at least part-time. They should always be listening to their customers, and part of the customer service rep’s job should be to document customer concerns such that they really are seen by the founder.