Here's Why Craigslist Still Looks the Same After 25+ Years

Craigslist emerged in 1995 to connect strangers through a free, web-based platform that has endured as rivals services like Zillow, Facebook Marketplace, and countless dating apps emerged with advanced features and slick interfaces.

These platforms survive on advertising and subscription revenue. Craigslist, of course, has none of that. Over the years, the OG online marketplace has all but refused to modernize; its mobile app only came out in 2019 after nearly 25 years in business.

Why does the website still look the same after so many decades? That was the main question I had when I sat down for a video call with craigslist founder Craig Newmark, who joined me from the New York City apartment he shares with his wife, Eileen Whelpley.

Newmark stepped down as CEO of craigslist in 2000 after others told him he wasn’t cut out for management, he says. Jim Buckmaster has been at the helm since, though Newmark remains a partial owner. He now works on philanthropy full time, supporting groups like the Coalition Against Online Violence, which helps combat harassment against female journalists. Still, the 69-year-old entrepreneur is a billionaire (or near-billionaire since he’s given away millions).

Our chat yielded much more than expected, from Costco hotdogs to Hello Kitty and his childhood Sunday School lessons. It’s clear that the website is the purest and most enduring expression of Craig Newmark, a humble tech mogul who marches to the beat of his own drum.

PCMag: What’s that behind you? A Wikipedia flag? And what’s in the black frame?
Newmark: Yes, that's Wikipedia. I’m heavily involved with them on my mission to fight disinformation on the internet. And that frame is when I was on the cover of the Costco Connection magazine. That articulates a great deal of what I’m about. My mother used to rave about their hotdogs. They're delicious and highly cost effective. I have very pedestrian tastes, and I’m eclectic. I’m very involved in pigeon rescue, for example.

Is there anything that you splurge on?
Well, I have a new and bigger TV now. And I allow myself to buy as many books as I want. But I have no car. It's more satisfying for me as a nerd to provide for friends and family and to make a difference. For example, Mabel Hsu, who does finances for craigslist and my philanthropic work, loves Hello Kitty for reasons unknown. Up the street from me there’s a store that sells Hello Kitty crap. I think she needs new Hello Kitty clips, so I’ll go there shortly and get her some.

How many people work at craigslist today?
It’s in the 10s - a mix between development, customer service, and accounting. No marketing.

Did your personal financial strategy influence the way you monetized craigslist?
I remember Sunday School, and Mr. and Mrs. Levin - the principal teachers at the Hebrew school at the Jewish community center in Morristown, New Jersey, where I grew up - saying you need to treat people like you want to be treated. And they told me to know when enough is enough. That's central to my philosophy. 

Also, I don’t like banner ads. They slow things down, and they’re often kind of dumb. That’s a decision I made at the end of ‘97. 

Craigslist makes money on listing fees, right? But only on certain types of listings.
Yes, things like job ads, apartment ads, car ads. I don’t have a perfect list in my head.

Since you founded craigslist, so many other sites have been created by people who wanted to make as much money as possible. Did you consciously decide to not participate in that?
Around ‘98, VCs and bankers wanted to throw huge amounts of money at me to do the usual thing. But I decided not to. And again, it’s not altruism. Remember, back to Mr. and Mrs. Levin - you have to know when enough is enough.

To be honest, I find myself resisting the simplicity of your answers. How was it so easy for you to not participate in all that hype?
Well, sometimes you want to do one thing and do it really well. In the computer industry, and maybe everywhere, people get ambitious and screw things up. I figured I started one thing, did it well, and I gave it up when that was the right thing to do. 

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And I mostly am a 1950s-style nerd. Growing up, I wore a plastic pocket protector for real. I had glasses taped together in the middle and marginal social skills.  Even now, I’m only simulating or faking social skills. I am generally oblivious to social cues and signals of prestige and status, so all that doesn’t mean anything to me.

So, this leads me to my main question: Why does the website still look the pretty much the same today as when you founded it? There’s even a new CEO. What’s going on?
Because that serves people better. I've learned that people want stuff that is simple and fast and gets the job done. People don't need fancy stuff. Sometimes you just want to get through the day.

Well, you can still have simplicity with a modern font or a new UI. The definition of simplicity on the web has changed over the years. Is it just that you're making enough money and there's a desire to keep it the way it is?
I'll challenge the premise that the idea of simplicity has changed. The deal is that people still use the site in great numbers. And again, it helps people get something done. It’s fast and easy for people, and that’s a big deal.

And maybe you also don’t care too much about aesthetics (of the website, for example.)
For me as an engineer, simple is beautiful. Functional is beautiful.

How would you feel if craigslist dramatically changed in its appearance or its function?
I'm okay if the spirit is maintained. I like a very simple site with its use and functionality obvious when you look at it. Now maybe there's a better way to do that, that no one has come up with yet. If it's really better, I can't object to that. If it's genuinely better, I will say something. But again, I can't legitimately try to exert serious influence. Jim's boss.

In summary, what is your most concise answer to why craigslist still looks the same today?
People tell me it gets the job done. They want it done. As I like to put it, a nerd’s got to do what a nerd’s got to do.