Founder Guidance

Craig Newmark

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.

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.

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.

Read why Craig Newmark calls himself the “Forrest Gump of the internet.”—JH

      

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Growing Your Business

Caraa

While many brands are locking into the World Cup, women’s accessories brand Caraa is looking forward to the 2028 Summer Olympics as part of its growth strategy.

Co-founder and CEO Aaron Luo, a lifelong fencer, is banking on a passion project to spur growth for the over 10-year-old brand, which has revealed a partnership with USA Fencing in the lead-up to the Los Angeles Summer Games. The partnership kicked off with a capsule collection incorporating fencing motifs and styles for Caraa’s premium bags, and 100% of the proceeds will be donated to the USA Fencing Foundation.

“The idea is that we wanted to learn from the community, hear the feedback, and then iterate from there,” Luo said about the ongoing partnership. “This will be one of the few [products] that we hope to launch before the Olympics, during the Olympics, and, of course, after the Olympics.”

Connecting with the community

As the US fencing network is relatively small compared to other sports participating in the Olympics—according to USA Fencing, it had just over 45,000 registered members as of August 2025—Luo is leveraging his connection to the community for the partnership. He hopes the collections appeal to both fencing enthusiasts and sports fans more broadly.

“Because this is something that we care [about], because we want to give back to the community, we want to really give [customers] something that’s really cool,” he said. “The end product ends up being something that is special, and that’s something that we learn from the design standpoint that we’re going to translate more into other designs that we’re going to do.”

Read more about Caraa’s Olympic connection.—LI

      

How CFOs (and boards) can tackle executive burnout (CFO Brew)

There are tactful ways to broach this sensitive subject, former Overstock CEO says.

Anthropic’s latest agent wants to be your new employee (HR Brew)

Claude Tag expands Anthropic’s Slack integrations, allowing it to take over tasks and communicate across a channel.

Data pros share their non-negotiable governance standards (IT Brew)

And how to enforce them.

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Stat: $500 million. That’s the amount that B Capital—the global VC firm founded by Howard Morgan, Eduardo Saverin, and Raj Ganguly—is looking to invest in seed and Series A companies with its new Ascent Fund III. (the Wall Street Journal)

Quote: “Also, if you’re a solo founder, is that because you chose to be or because you’re terrible to work with? Or is your idea bad? There becomes a signaling thing to investors and even customers, like, ‘Why is this person alone?’”—Todd Hall, assistant professor of business at the University of Kansas, explaining a new academic paper he co-wrote examining the promises and pitfalls between starting with co-founders and flying solo (the University of Kansas)

Read: JPMorgan is growing its team of bankers focusing M&A deals for companies valued between $100 million and $500 million. The bank is staffing up in this area due to an uptick in succession planning events for small-cap companies founded by baby boomers looking to retire. (the Wall Street Journal)

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