This article is part of The Poynter 50, a series reflecting on 50 moments and people that shaped journalism over the past half-century — and continue to influence its future. As Poynter celebrates its 50th anniversary, we examine how the media landscape has evolved and what it means for the next era of news.

The decline of newspaper print classifieds and the ripple effects that gutted newsrooms began, by many accounts, in 1995. That’s when Craig Newmark invented Craigslist, the homely but oh-so-successful site that matches buyers and sellers, mostly for free, with only a few listings carrying a modest charge.

Did Craigslist drive the downfall of print classifieds?

“I’ve always wondered about that,” Newmark said in a Zoom interview July 1. “I think it had an effect.”

But portraying him and the list as torpedoing an otherwise great business model is way overblown, he still believes. Citing an influential essay by Thomas Baekdal, Newmark contends that the root of newspapers’ trouble was the loss of readers.

“TV hit hard. … (And) l’m like the folks on ‘CSI,’ I follow the evidence. That goes back at least to the ’60s.”

Bad in itself, the loss also took away newspapers’ dominant share of local audiences and ability to charge premium classified ad rates. The slide in circulation looks even worse, Baekdal pointed out, when compared to continued increases in the number of households over the years.

Still, Craigslist came to symbolize the shift. Dozens of other vertical digital sites cropped up, before and after, all offering a deadly competitive pairing of an effective and much cheaper service than newspaper classifieds. Even if Craigslist was just one of many, though, it was arguably Newmark who put a face on the massive disruption.

Here in six short chapters is the tale of Craigslist’s rise to a business generating hundreds of millions of dollars a year, how Newmark has used that fortune and how newspapers, slow to adapt, failed to respond effectively to the digital shift. It’s based on information already on record, supplemented by analysis and color from my interview with Newmark.

Chapter 1: The early years

When Newmark launched Craigslist, he was in his early 40s with two decades of experience as a computer engineer, including a long stint at IBM, later consulting at large firms like Charles Schwab.

He wasn’t a media mogul or startup evangelist. He was, by his own admission, a socially awkward nerd. (“Nerd” appears in the one-sentence mission statement for his foundation.) That sensibility shaped what would become Craigslist.

Craig Newmark in a cubicle in an undated photo. (Courtesy: Craig Newmark)

Newmark said he was more comfortable replying to user emails from a distance. For a decade and a half, he called himself a customer service representative, not CEO.

Craig’s definition of his role is revealing. He saw himself as a builder of a simple tool that created a community of users. Toppling the news industry business model was not the point at all.

Chapter 2: Accidental entrepreneur?

Craiglist’s beginnings are a twice-told story. At first, it was literally a list for Newmark’s circle of friends about interesting goings-on in the San Francisco Bay area. Soon, Newmark added swaps and free ads for things like furniture and refrigerators. Before long, he expanded to other big cities and began generating income by charging for job and real estate listings, turning the hobby into a business.

But Newmark didn’t want to run a company. “I’m a terrible manager,” he said. “I’m just not emotionally suited to making tough decisions.”

As growth took off over the first five years, he continued as owner but hired fellow programmer Jim Buckmaster and quickly promoted him to CEO — a position he still holds today.

Programming and Craigslist CEO Jim Buckmaster, left, and Craig Newmark in an undated photo. (Courtesy: Craig Newmark)

Buckmaster, an off-and-on graduate student for 10 years at the University of Michigan who occasionally contributed haikus to the Craigslist site, is as unconventional as Newmark. His official bio notes that he has been called a democratic socialist and a communist. He and Newmark are neither, he wrote, but rather the kind of capitalists who are not fully focused on maximizing profit.

That ethos defined the company. Newmark and Buckmaster rebuffed ideas for expansion — like adding user reviews — because it would make Craigslist easier to game and harder to moderate. (Review sites like Yelp and Airbnb have turned out to have exactly that challenge.)

Calling Craigslist an accidental smash, as Newmark often does, is not all wrong. But neither has the business managed itself.

In the first 15 years, growth was fast and uninterrupted. Newmark started with a mostly volunteer staff but quickly transitioned to paid employees. Craigslist now claims a presence in more than 700 cities and 70 countries, though it is still U.S.-focused. Competitors like Oodle and Kijiji jumped up, then newer ones like Minjari and OfferUp. The tech giants also got in the game. Ebay bought a minority stake in the company from a former employee in the mid-2000s. Partnering possibilities did not pan out, lawsuits ensued, and Craigslist ultimately bought back the shares.

Craigslist dealt with other challenges, including — haltingly but ultimately successfully — instances of abuse and crime, finally shutting down the erotic service category of the site. The business hardly flinched.

The plain and unchanging list site had a loyal customer base. Both Newmark and Buckmaster are resolutely tight-lipped on Craigslist’s finances and other business details. Newmark told me, as he has told many interviewers, that outsider estimates of revenues and profits have in common that they are wrong. He declines to provide the correct numbers or even a range, but the enormous combined volume of Craigslist with fewer than 100 employees points to wildly high profits.

Business professor Clayton Christensen’s influential book, “The Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail,” was published in 1997. The timing means that Newmark could not have been following Christensen’s theories when he hit on his basic design and strategy for the list. (Newmark confirmed that he did not find out about Christensen’s work until much later.)

Still, Craigslist has been cited as a near-perfect example of the kind of disruption that Christensen identified: Take a lucrative, long-established product line (in this case, newspaper classifieds) with a huge base of satisfied users. Bring in a challenger with a much cheaper alternative that’s “good enough” for most users, and rapid substitution will follow.

Craigslist was not only “good enough,” but in important ways better. Its short headlines easily opened to longer sales pitches. The seller of a car, for instance, could include photos and had plenty of space to tout attractive features. Newspaper classifieds, in contrast, were often a jumble of abbreviations, trimmed to save on costly per-line pricing.

Chapter 3: A flat-footed newspaper response

In 1995, Tony Ridder became CEO of Knight-Ridder, then the nation’s preeminent collection of regional newspapers. At a company retreat that year, an editor asked Ridder what kept him up at night. The editor and the audience expected a ringing endorsement of the importance of newspapers’ editorial mission. Instead, Ridder replied, “electronic classifieds.” An audible gasp followed. In hindsight, his answer was prescient.

By the early 2000s, newspaper executives had a dawning awareness of the business challenge from Craigslist and similar sites. They took minimal action to meet it.

As concern grew, the Newspaper Association of America, the industry’s trade group, commissioned a study by premier consulting firm McKinsey and invited Goldman Sachs to present at its annual meeting. Both came to the unsurprising conclusion that, unless the industry could quickly mount strong countermeasures, print advertising was cooked.

The association’s executives and members thought that the advice was alarmist. The biggest response was that three big companies — Knight-Ridder, Tribune and Gannett — bought a copycat of Monster called CareerBuilder.

Christensen’s book’s theory of disruption intended to shock vulnerable incumbent firms, like newspapers, into action. Conversely, he wrote that at some point, it may be just too late to respond effectively. By the time newspapers acted, online classifieds had a full head of steam.

Newspaper executives can be faulted for keeping their heads in the sand, hoping the golden goose of print classifieds could stay viable. Competing with disruptors typically requires the hard choice of cannibalizing a top revenue and profit generator. An approach that sometimes works is forming a small band of innovators working separately on the challenge and not bound by company culture — so-called skunkworks.

That said, what would a winning response have been? It’s far from obvious. To combat Craigslist’s general listings, some advocated that newspapers offer a separate set of free ads for small things like used appliances or pets. Would that really have pulled away Craigslist’s growing band of  users? Besides, newspapers were struggling with the big question of how to invent an audience-friendly digital news report and balance that with print.

By 2010, 70% of the newspaper industry’s print classified business was gone. Reliable statistics are no longer kept, but the trend continued over the last 15 years. What used to be a fat section of job listings in Sunday print editions may now be just a few columns. Other main categories — real estate, auto and retail — are way down, too.

Newspapers continue to do well only with paid obituaries and legal notices, though the latter is now also under threat by digital startups.

Chapter 4: Keeping it simple

On June 24, the final clue on “Jeopardy” read:

WEBSITES

A 2006 WSJ article described this website as having “row after row of blue…hyperlinks and nary another color or graphic in sight.”

The answer, of course: What is Craigslist?

Craigslist became famous for its radical simplicity, and it remains that way. Redesigns were one of the many embellishments Newmark and Buckmaster avoided.

They also rejected banner and other display ads, potentially a monetizing bonanza but also a source of clutter. Nor did the executives see any need for news content.

Both have said that they paid relatively little attention to competitors. “Competition is always a distraction,” Newmark told me. His time was better spent, he said, “providing great customer service.”

Now in his 70s and with Craigslist celebrating its 30th birthday, Newmark is in a reflective mood. He has started recording a short oral history on the early years of Craigslist, with plans to do more.

Craigslist’s pages have changed remarkably little in the 30 years the site has existed. (Screenshot/Craigslist)

In our interview, Newmark said that he thinks his greatest contribution to Craigslist was creating and sustaining a “vibe.” No frills. No unnecessary changes. Measuring success by tracking how often established customers returned and new ones were added. Word-of-mouth marketing — no big dollar ad campaigns like those favored by Monster and GoDaddy.

Walter Isaacson has written a series of long biographies about serial innovators — among them Benjamin Franklin, Steve Jobs and, most recently, Elon Musk. All are restless spirits, eager to move on from one success to the next thing. Many of the Big Tech companies, even as the founders departed, have found ways to build important adjacent lines of business to the original: Gmail, Chrome and Google Maps.

That’s not Newmark. Rather, he is a practitioner of doing one thing very well and sticking to it.

Perhaps it is partly a cultivated image, but the simplicity theme spills into his private life, too. No yacht, no fast cars. He has a comfortable but not mansion-like residence in Greenwich Village and another in San Francisco.

The day of our interview, Newmark excused himself briefly. A mirror was being delivered that he and his wife planned to hang on a door.

“Back when I worked for IBM, I wore a suit and tie every day,” he said. “(Now) it’s three times a year, but I want to be able to get it right.”

Chapter 5: A third career — philanthropy

Newmark retains the largest ownership share of Craigslist. But, by 2015, he stepped away from even a loosely defined role in running the company. His focus turned to giving his fortune away. Characteristically, he does it differently than most.

Rather than building a large staff of grant officers and other corporate apparatus of foundations, Newmark has kept his operation lean. The how-to-apply section of Craig Newmark Philanthropies reads, in part, “CNP operates in a manner generously described as ‘unique,’ evolving as needed, trying to avoid the slowness and red tape elsewhere.” As a guide to grantmakers, he continues, “Less is more. Please balance an informal approach with brevity and specificity as you can throughout. Heavily polished presentations and lots of attachments will only slow things down.”

His philanthropy focuses on three main areas: cybersecurity, trustworthy journalism, and support for military families and veterans. With much smaller grants, he supports pigeon rescue. Like him, Newmark has explained, pigeons are unglamorous but engaging once you know them.

Newmark has a longstanding passion for pigeons, which he has described as “the underdog” and “possibly our successor species.” (Courtesy: Craig Newmark)

In journalism, he tilts, but not exclusively, to education and thought leadership. He gave $20 million to endow the journalism school that bears his name at CUNY, along with big grants to Columbia and Harvard.

Newmark is Poynter’s largest donor, having provided $6 million for ethics work, including endowing the Craig Newmark Center for Ethics and Leadership, chaired by Kelly McBride, who is also NPR’s Public Editor. (This story was reported and edited independently of the ethics center.)

In speeches and articles, Newmark invariably says the spur for his support is a belief that “trustworthy journalism is the immune system of democracy.” He often attributes the thought to a favorite high school civics teacher. As best I can tell from a few searches, the aphorism did not originate from someone else. Newmark is the one who popularized it. He confirmed that he “blurted it out” in an interview with writer James Fallows.

A Wikipedia pennant is visible in the background of his Zoom screen. In our conversation, Newmark praised the well-established digital upstart and its largely volunteer editing corps. “Somehow it works,” he said. One of his current funding projects, “Wiki editing for beginners,” aims to train more contributors to sustain the quality of the free digital encyclopedia. He also feels a kinship with co-founder Jimmy Wales. Wikipedia is needed now more than ever, Newmark said, to combat misinformation.

According to the most recent IRS Form 990, Craig Newmark Philanthropies gave $43 million in grants in 2023. Newmark regularly replenishes the foundation with personal contributions and has no plans to make it permanent. His goal, he says, is to give away nearly all of his money in the next few years.

Chapter 6: An assessment

One of the most detailed estimates of Craigslist’s finances — which Newmark insists are inaccurate, remember — came from Peter Zollman, whose AIM Group has studied and consulted on the classified business for 25 years. In a 2019 report, Zollman estimated that Craigslist had its best year in 2018, with revenues of nearly $1 billion and a profit margin of more than 80%.

Zollman’s methodology involved researchers counting paid ads on 62 of Craigslist’s hundreds of sites, and multiplying those by the posted rates. Even with rock-bottom prices, he reasoned, Craigslist’s earnings mounted fast.

If you accept Newmark’s contention that all estimates, Zollman’s included, are way off, and the report errs on the high side, Craigslist is still an extraordinarily lucrative business. Though Zollman thinks revenues have fallen in recent years as competitors finally disrupt the disruptor, the company has fewer than 100 employees and throws off a lot of money.

Zollman’s report (in which I am quoted) backs Newmark’s argument that he’s been unfairly scapegoated for the decline of newspapers. American newspapers stumbled while several well-managed counterparts in places like Scandinavia found ways to prosper, he argued. “Craigslist has often been blamed for killing newspapers,” Zollman wrote, “but that’s a gross canard. It just isn’t true.”

Providing confirmation, I found a deep-dive New York Times article from 1999 headlined, “HELP WANTED; Newspapers Seek Cyberpartners To Fight On-Line Ads.” Examples of killer competitors included Monster, Hotjobs, <a href="http://Realtor.com" rel="nofollow">Realtor.com</a> and many others. Craigslist appears nowhere in the story.

The bottom line on Newmark and newspapers echoes a much-cited line from “The Man Who Shot Liberty Valance.” In the 1962 Western, U.S Senator Ranse Stoddard (Jimmy Stewart) built his legend on a shootout with Liberty Valance, a feared outlaw. But it was actually a gruff rancher (John Wayne) who fired the fatal shot. A local newspaper editor knew the truth, but said nothing. “When the legend becomes fact,” he explained, “print the legend.”

Newmark deserves full credit for busting out of obscurity with originality and persistence. He’s a symbol of the digital disruption newspapers have struggled to navigate. But he didn’t shoot Liberty Valance.