Craigslist: Craig Newmark - The Forrest Gump of the Internet

with Craig Newmark

Published September 29, 2025
Visit Podcast Website

About This Episode

Guy Raz interviews Craigslist founder Craig Newmark about how a simple email list for San Francisco tech and arts events in 1995 evolved into one of the world's most-used online classified sites. Newmark describes his socially awkward childhood, early work in computer science and the internet, the organic growth and minimalist philosophy behind Craigslist, his decision to hand over leadership to CEO Jim Buckmaster, and his later-life focus on philanthropy in journalism, veterans' support, and animal rescue. They also discuss the disputed impact of Craigslist on newspaper classified revenue and Newmark's belief that he was largely lucky and in the right place at the right time.

Topics Covered

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Craigslist began as Craig Newmark's personal email list sharing San Francisco arts and tech events with friends, then organically expanded into user-posted classifieds for jobs, housing, and more.
  • Newmark never sought to be a CEO, refused investors and banner ads, and intentionally kept Craigslist's design minimal and its monetization limited to categories where users already paid high rates elsewhere.
  • Recognizing his own weaknesses as a manager, Newmark handed the CEO role to Jim Buckmaster in 2000 and focused on customer service while promising not to interfere in management decisions.
  • A shareholder, not Newmark or Buckmaster, sold a significant minority stake in Craigslist to eBay, later leading to conflict when eBay launched a competing classifieds site and lawsuits over governance.
  • Newmark initially believed Craigslist might have helped cause newspapers' decline, but he later accepted research suggesting TV, then Facebook and Google, were far more significant factors.
  • Guided by values learned from Holocaust survivors and a civics teacher, Newmark aims to give away virtually all of his wealth, focusing on trustworthy journalism, support for veterans and military families, and even pigeon rescue.
  • Despite potentially having "elite" levels of money, Newmark says he lives simply, questions how much anyone really needs, and views his success as a combination of daily work and being in the right place at the right time.

Podcast Notes

Introduction and overview of Craigslist and Craig Newmark

Show framing and guest introduction

Guy Raz introduces "How I Built This" as a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.[3:23]
Craig Newmark is introduced as the accidental founder of Craigslist, one of the most popular online classified ad sites in the world.[3:35]

Unconventional nature of the Craigslist business model

Guy imagines a startup pitch: an internet marketplace that ignores design aesthetics, spends nothing on marketing or sales, and whose founder only wants to do customer service.[4:05]
He notes such a pitch would normally be laughed out of the room, yet it accurately describes Craigslist.
Craig never pitched investors because he did not want investors and did not initially set out to build a business.[4:23]
Guy highlights that Craig sees himself as having been in the right place at the right time in San Francisco in 1995 as the internet was taking off.[4:34]

High-level trajectory and scale of Craigslist

Craig created an email list to share informal tech and arts meetups around San Francisco, solving a simple need to let others know about events.[4:53]
The email list grew rapidly, leading Craig to put the postings on a website he called craigslist.org, where people soon wanted to post jobs, apartments, and cars for sale.[5:27]
The site's design was extremely basic and straightforward and has remained largely unchanged for nearly 30 years.
Craig recognized early that he was not a "CEO type" and, about a year after incorporating, handed control to Jim Buckmaster, which Guy describes as a brilliant decision.[5:53]
By 2006, Craigslist had expanded to 190 cities in 35 countries and attracted 10 million monthly visitors with fewer than 50 employees.[5:59]
Guy cites analysts' estimates that in 2024 Craigslist generated around $300 million in revenue, even amidst competition from Facebook Marketplace and others.[6:22]
Guy previews that Craigslist has faced criticism, including blame for the decline of newspaper classified ads, and notes Craig says he never intended to get rich but did and now plans to give most of it away.[6:30]

Craig Newmark's early life, social challenges, and moral influences

Childhood in Morristown, New Jersey

Craig grew up in Morristown, New Jersey; his mother was an accountant and his father, a salesman, died when Craig was 13.[6:45]
Academically he thrived but socially he struggled, particularly after his father's death.[6:54]

Awkward adolescence and social struggles

Craig recalls having friends in grammar school, but as an early teenager he became the academically bright kid eager to show off in class.[7:06]
He lacked the ability to read social cues, so he did not realize how nerdy or off-putting his behavior was.
By high school he was largely isolated, with a few equally nerdy friends who shared interests in science, engineering, and debate.[7:42]
He describes stereotypical nerd attire: thick black glasses taped together, a plaid shirt, and a plastic pocket protector, which he did not realize others found off-putting.[7:46]

Limited support and early psychological intervention

Guy notes that in the 1950s-60s, kids who were different or awkward did not typically receive diagnoses like social anxiety disorder, unlike today.[8:27]
Craig says his public school system in Morristown was good and did send him to the school psychiatrist in sixth grade.[8:39]
The psychiatrist deemed him "salvageable" and provided some help, though Craig says he has little understanding of how that worked.

Spectrum question and socialization

Craig says his only formal intervention was the sixth-grade sessions; later in life he assumed for years he was on the spectrum toward Asperger's.[9:35]
A neighbor who was a specialist told him he was not on the spectrum but was poorly socialized and needed to work on that.[9:43]
He jokes that he can now "fake social skills" for up to about 90 minutes at a time as needed.
He says his social difficulties were and remain a problem, but he has made peace with them and tries to channel them into constructive work.[10:26]

Finding solace in libraries and science fiction

Craig loved being in the library as a kid and credits Morristown with having a great old library.[10:35]
He spent time in the young adult section finding whatever science fiction he could and says he escaped into those books.[10:46]
He notes that reading science fiction written by technologists and engineers is how "we learn to invent the future," although some of it is delusional and some real.[11:10]

Exposure to Holocaust survivors and moral lessons

Craig grew up around many Holocaust survivors in his area; some taught at his Sunday school at his synagogue.[11:33]
He recalls a classmate's mother whose tattooed serial number on her arm was visible; she explained what it meant without being gruesome, making him very aware of the Holocaust.[11:38]
A Jewish newspaper later uncovered that his principal Sunday school teacher, Mr. Levin, had survived by jumping from a speeding train to a death camp and later rescuing his wife and daughter.[12:08]
Craig notes Mr. Levin had an injured finger bent at a bad angle but never explained it.
Mr. and Mrs. Levin strongly influenced Craig, teaching him to treat people the way he wants to be treated, to know when enough is enough, and to take the Ninth Commandment about not lying seriously.[13:07]
Craig says these lessons determined his moral compass to this day.

Education and early career in computer science

Studying computer science and early interest in AI

After high school, Craig attended Case Western Reserve University in Cleveland, studying computer science and graduating around 1975.[13:25]
He was interested in what are now called large language models back in the early 1970s, though that term was not used then.[13:57]
He was influenced by people working on neural networks, which are the basis of large language models, and by the idea of natural language processing as a key to understanding consciousness.
In 1973 he took an AI course where he wrote a theorem prover in Lisp, though he no longer remembers what a theorem prover is.[14:32]
He jokes that Lisp stands for "lots of irritating stupid parentheses," referring to the appearance of Lisp code.

Working at IBM on the Series/1 and PCs

After graduation, Craig joined IBM, working in Boca Raton on a now-forgotten minicomputer called the Series/1.[15:28]
He did software development there and later helped build a Series/1 as a card that could fit inside a PC.[15:52]
He considers it a mistake that he did not get more deeply involved with the IBM PC effort at the time, though he says he got a good education and made the right mistakes.[16:06]

Move to San Francisco and evangelizing the internet at Charles Schwab

Craig spent 17 years at IBM in Boca Raton, Detroit, and Pittsburgh before tiring of the East Coast and wanting a change.[16:23]
He considered Seattle and San Francisco and accepted an offer from Charles Schwab, which moved him to San Francisco.[16:32]
He did good work at Schwab, but says his best work there was volunteer: in 1994 he was one of a few people evangelizing the internet inside the company.[2:16]
He was one of three people saying that the internet was how they would do business.

Seeing the early web and finding community in San Francisco

Guy notes that when Craig arrived at Schwab, the World Wide Web was emerging with Mosaic and Netscape browsers, while Schwab still relied heavily on paper-based processes.[17:15]
Craig says the internet realized a vision he had read about in science fiction for decades, and he had already used the early ARPANET in college.[17:44]
At Schwab, he taught brown-bag lunch sessions demonstrating the internet and Usenet, usually logging in via dial-up.[18:13]
In San Francisco he discovered communities of like-minded people through groups such as a virtual reality special interest group at the Exploratorium.[18:58]
From that group he learned of Anon Salon, a monthly fundraiser for Climate Theater, and Joe's Digital Diner, where people ate spaghetti and meatballs while others showed off early multimedia technology.
Craig says this was the kind of community he'd been looking for-people of a like mind in arts and technology.[19:45]
He acknowledges he was still not well socialized but began to change with help from people around him, which he says changed him in good ways.[19:58]

Origins and early growth of the Craigslist email list and site

Starting the email list after leaving Schwab

Around 1995-96, after leaving Charles Schwab, Craig began emailing a small group-about 10 to 12 people-about events involving arts and technology, like Joe's Digital Diner and Anon Salon.[20:45]
Recipients told him about more events, which he shared, and word of mouth led more people to ask to be added to the CC list.[21:06]
Craig had been downsized from Schwab at the beginning of 1995, just as the dot-com boom was starting, and he joined a boutique web design startup while running the mailing list.[21:45]

Expanding content: housing and jobs

As the list grew, Craig realized apartments in San Francisco were getting harder to find, so he invited people to send apartment listings.[22:04]
Others asked him to include job postings, so he began adding those to the list as well.[22:11]
By mid-1995, when the CC list hit about 240 addresses, the email system broke and he had to switch to using a listserv.[22:22]

Naming it "Craigslist" and early community vibe

Craig says he had "caught the vibe of the time" and created a vibe of user-generated content and genuine community.[23:08]
He faced a dilemma with listserv software because it required a list name; as a literal-minded nerd he wanted to call it "San Francisco Events."[23:47]
A friend, Anthony Batt, told him people were already calling the list "Craigslist" and that he had created a brand.[23:56]
Craig accepted the name Craigslist, recognizing it as something distinct with its own identity.
He notes that around this time, a person named Eric Theis offered him the use of his listserv on a real server with an impressive 1.5 megabits of capacity.[23:24]

From side project to company: operations, .org choice, and monetization philosophy

Manually running the early site and automation

Initially, people emailed Craig their ads and he wrote code to turn those emails into classified ads on the website.[30:04]
Whenever a task began taking about an hour a day, he wrote code to reduce it to roughly five minutes.[30:23]
For the first few years it was just Craig handling the work; by the end of 1997 the site reached about 1 million page views per month.[30:33]
Some people from the community volunteered to help run the site, but processes remained partly manual and sometimes slow.[31:51]

Refusal of banner ads and early performance issues

Craig says that around 1997-98, people from Microsoft Sidewalk wanted to put up banner ads on Craigslist.[31:06]
He refused, thinking banner ads were usually stupid and that he didn't need the money because he was doing well enough.[31:16]
In 1998 the site "didn't do very well" with ongoing problems, partly because it was run on a volunteer basis.[31:21]
Ads sometimes took hours or days to appear, and recognizing and fixing technical problems often required technical skills that volunteers didn't always have.

Push to incorporate and become a business

By the end of 1999, people were telling Craig to turn Craigslist into a real company, start charging, and pay salaries.[33:05]
Craigslist incorporated in 1999 as a for-profit business while retaining the craigslist.org domain.[33:29]
Guy notes that many people assume .org domains denote nonprofits, but Craig explains that .org was used then for projects that put community first and embodied user-generated content.[33:21]
They also registered craigslist.com and .net, but kept .org to signal their different philosophy and remind themselves to minimize monetization.

Developing the revenue model and minimal monetization

Craig says their pricing model, largely unchanged today, involved charging for job ads, some real estate listings, and a few other categories while keeping most postings free.[35:04]
He says the community itself articulated the core philosophy: charge people who already pay more for less effective ads elsewhere.[4:53]
For example, charge employers posting job listings, not people posting resumes.
Charge apartment owners or homeowners renting out places, not people seeking housing.
He emphasizes that Craigslist avoided "gentrification" by monetizing minimally and focusing on community service.[4:05]
Craig mentions that in about 2000 they briefly tried a little marketing, such as job ads in HR magazines, but only for about a month.[35:54]

Leadership transition and Craig's focus on customer service

Hiring Jim Buckmaster and recognizing management weaknesses

Toward the end of 1999 Craig hired Jim Buckmaster to take over technology, so Craig was no longer needed for technical work.[34:44]
Craig served as CEO while also acting as a customer service representative during the first year as a company.[35:47]
He candidly says, "as a manager, I suck," citing difficulty making tough decisions, including hiring and firing, and lacking boldness of vision for expansion.[35:29]
He was not emotionally inclined to lead from the top down and was not bold enough to push into new categories and national expansion.

Making Jim CEO and Craig's non-interference pact

In November 2000, Craig made Jim Buckmaster CEO after realizing Jim would not "suck" in the ways he did as a manager.[35:52]
Craig promised Jim he would not interfere with his work and would leave him alone to do the job.[35:44]
Craig credits Jim with having tactical skills, socialization, and an intuitive understanding of community needs, and says Jim has maintained and amplified the Craigslist vibe for about 25 years.[35:35]
Craig shifted to being a heavy customer service rep for about 15 years and explicitly did not take any management role.[4:05]
He says he has no influence or decision-making capability in management matters and that Jim must be left alone to make key decisions.[4:23]

Philosophy of not giving "notes" and focusing on strengths

Craig compares management meddling to Hollywood producers giving directors "notes," which he says are usually a bad idea.[4:23]
He describes himself as someone who rarely gives notes or their equivalent; instead, he focuses on what he does well, such as building and supporting networks.[5:10]

Craigslist's lean model through the dot-com bust and beyond

Surviving without outside investors

In the early 2000s, as the dot-com bubble burst and tech companies collapsed, Craigslist remained strong largely because it had never taken outside investors.[47:55]

Lean operations and unknown profit figures

Guy observes that Craigslist had low overhead and high margins compared to many businesses.[48:24]
Craig credits Jim for running a lean operation and says they are known for that.[48:28]
Craig notes that no one outside the company knows how much profit Craigslist makes; he says people fabricate numbers for articles, and if someone tells you how much Craigslist makes, you might want to disregard it.[48:51]

Small team size relative to revenue estimates

Craig says that the last time he asked, the company had around 40 employees, though he is not current on the exact number.[49:04]
Guy notes that even if revenue estimates are far lower than reported, making, for example, $50 million with 40 employees would still be a very healthy company.[49:38]
Craig reiterates that Jim does a great job running the company and adds that he has committed all of his personal byproduct from the company to charity.[49:57]

Lack of early competitors

Guy finds it remarkable that in the first three to five years, as Craigslist was bringing in tens of millions of dollars, there were no credible competitors.[50:27]
Craig explains that venture capitalists and bankers at the time were funding opportunities promising very large, multi-billion-dollar returns, whereas classifieds offered substantial but smaller amounts of money.[51:05]

eBay's minority stake, conflict, and legal resolution

How eBay bought into Craigslist

Guy says that in 2004 eBay, already a giant company, approached Craigslist about an acquisition and ended up buying a 28% minority stake for $32 million.[51:13]
Craig clarifies that he and Jim did not decide to sell equity; rather, he had previously given large chunks of equity to several people, and one shareholder who did not share the community mission wanted to sell.[51:51]
Because eBay told Craig and Jim that they shared Craigslist's community mission and vibe, they were convinced and authorized that shareholder to sell his equity to eBay.[51:57]
Guy notes that eBay gained a board seat through the purchase, giving it access to confidential company information.[52:48]

Launch of Kijiji and Craigslist's response

In 2007 eBay launched a competing classifieds site, Kijiji.[53:21]
Craig says he was not overjoyed but tried not to dwell on it, focusing instead on his own responsibilities and listening to Jim and legal counsel.[53:01]
He says he did not view eBay's site as a real competitor because it lacked Craigslist's vibe and mission.[54:10]
Craigslist's lawyers and leadership decided to dilute eBay's share so that eBay would lose its board seat, partly because they did not want a competitor with access to inside information.[52:48]
This angered eBay, which sued Craigslist; Craigslist countersued, and the conflict was not fully resolved until 2015.[53:01]
Guy notes that in 2015, as eBay spun out brands like PayPal, it agreed to sell its Craigslist shares back to Craigslist.[55:02]

Craigslist and the decline of newspaper classifieds

Context: collapse of newspaper classified revenues

Guy explains that classified ad revenue for newspapers peaked in 2000 at an estimated $20 billion, then fell by 70-80% over the subsequent years.[55:42]
As revenue collapsed, many in the media focused attention on Craigslist and online advertising as contributing factors to the decline of local newspapers.[55:59]

Craig's evolving view on Craigslist's impact

Craig says that in the past, he felt Craigslist had a substantial effect on newspaper survival.[56:36]
He later spoke to industry analysts like Ken Doctor and Rasmus Nielsen, who told him it was ridiculous to think Craigslist had such a big effect and argued that newspapers' problems dated back to the 1950s and 60s.[56:54]
They pointed to TV news replacing display ads and affecting revenues long before the internet.
Craig says that until 2018 no one had run the numbers; then researcher Thomas Bechdel published work showing a continuous straight-line decline for newspapers starting in the 1960s.[57:39]
Bechdel's research indicated that around 2008 Facebook and Google began taking significant advertising revenue, and that trend has continued.
Bechdel told Craig that if Craig believed Craigslist had that big an effect, he was deluding himself and that TV news, followed by Facebook and Google, were the main causes.[58:34]
Craig expresses frustration that journalists writing about this rarely consult the research and instead start from a preconceived conclusion about Craigslist's culpability.[58:34]
Craig confirms that until 2018 he had considered the possibility that Craigslist significantly harmed newspapers, but the data changed his view.[58:34]
He adds that there was never any reason a newspaper could not have built what he built, since the coding he did was fairly simple for a good programmer.[59:20]

Philanthropy, journalism, veterans, and personal values

Motivation for supporting journalism

Guy suggests that Craig's heavy support for journalism might be a form of penance or guilt, but Craig says that would be false.[1:00:35]
Craig credits his high school U.S. history and civics teacher, Anton Shulsky, with teaching him about due process, the Bill of Rights, and the importance of a trustworthy press.[1:00:46]
Shulsky told them that a trustworthy press is the immune system of democracy and protects the country.[1:01:03]
Craig says he has put a couple hundred million dollars into supporting the press.[1:01:12]
His current press focus is on the CUNY Journalism School, which offers opportunity to people who have had little, and on Wikipedia, which he calls "where facts go to live."[1:01:34]

Attitudes toward wealth and how much is enough

Craig notes that others have pointed out he may have "elite" levels of money, but he says he has the tastes and attitudes of a peasant.[1:01:57]
He says his Sunday school values stressed balance: living comfortably, helping family live comfortably, and then asking how much you really need before giving the rest away.[1:04:54]
He states he does not need homes around the world or a private jet and observes that while some billionaires are not miserable, "the majority are miserable."[1:05:25]

Plan to give away most of his money

Craig has publicly said he wants to give virtually all his money away and is asked how he will manage that, given the practical complexity of philanthropy.[1:05:38]
He says he now has it in motion, planning 5 to 20 years out, with a good foundation for decision-making.[1:06:00]
He acknowledges his own limited social skills and thus built networks of people who are strong in topic areas he cares about, funding them to continue their work.[1:06:32]
He jokes that if all the money is not given away before he dies, he will exercise due diligence via a combination of seance and haunting people.[1:08:59]

Focus areas: veterans, military families, and birds

Craig feels strongly that society should support veterans who have sacrificed to protect others.[1:06:57]
He supports the Bob Woodruff Foundation, which runs the Got Your Six Network, a collection of nonprofits that help veterans.[1:07:06]
He also backs Blue Star Families, which runs networks of chapters and outposts helping military families get what they need to live okay and support service members.[1:07:20]
Craig says he loves birds and has a sense of humor, and he supports pigeon rescue groups such as the Wild Bird Fund on New York's Upper West Side and Palomacy in the Bay Area.[1:07:58]

Honoring early moral influences

Craig notes that Mr. and Mrs. Levin, his Sunday school teachers at the Jewish Community Center in Morristown, had never been honored until he did something to recognize them there.[1:08:14]
His honoring of them included funds to restore a Torah that had been damaged in the Holocaust.[1:08:32]

Reflections on luck, work, Craigslist's future, and legacy

Craigslist's future and competition

Guy lists modern competitors like Facebook Marketplace and Nextdoor and asks whether it matters what happens to Craigslist in 50 years.[1:09:35]
Craig says their orientation is different: the key question is whether Craigslist serves the community and maintains a genuine community vibe.[1:09:37]
He says he wants Craigslist to survive and thrive and thinks about its future, but if a community service fails in its mission, maybe it's time for it to go.[1:09:52]

Forrest Gump analogy and role of luck

Craig calls himself "the Forrest Gump of the internet," saying all his success has to do with accidentally being in the right place at the right time and accidentally making the right decisions.[1:10:06]
Guy notes that Craigslist became a cool brand and then a default place people still go for things like secondhand skis.[1:09:57]
Craig says he has worked every day for the last 30 years; some days are lighter than others, but he keeps working with a sense of purpose.[1:10:32]
He says he doesn't know how to assign proportions between luck and hard work, but he keeps plugging away while trying to maintain his values.[1:10:20]

Views on design, growth, and "enough"

Guy remarks that Craigslist's design looks like going back to 1999 and that it has never tried to win design awards.[1:11:05]
Craig emphasizes that their focus has been serving community needs rather than chasing aesthetic trends or aggressive growth strategies.[4:12]
He reiterates his principle of deciding how much is enough and then practicing what you preach by giving away the surplus.[1:10:54]

Closing anecdotes and Best of Craigslist

Guy notes that aside from being a marketplace where you can find almost anything, Craigslist hosts bizarre and humorous ads on a "Best of Craigslist" page.[1:11:18]
He mentions examples like "This is a long shot, but any chance I can get my rock back," "Haunted tie puppet available for sale," and "I need someone to retrieve a hidden obelisk."[1:11:38]
Guy encourages listeners to check out the Best of Craigslist and then gives production credits for the episode.[1:11:43]

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Knowing your own strengths and weaknesses and being willing to step aside when someone else is better suited to lead can dramatically improve an organization's long-term health.

Reflection Questions:

  • Where in my work or life am I holding onto a leadership role that someone else might be better suited to fill?
  • How could clearly mapping my strengths and weaknesses change the way I allocate responsibilities on my team?
  • What is one concrete responsibility I could delegate this month to someone whose skills are a better match than mine?
2

Building simple, community-focused products and monetizing them minimally can create durable value without compromising trust or overcomplicating operations.

Reflection Questions:

  • What aspects of my product or service could be simplified without reducing its core value to the people who use it?
  • How might a "minimal monetization" mindset change the way I price or promote what I offer?
  • Where could I shift focus from short-term revenue maximization toward strengthening long-term community trust?
3

Data and careful research are essential for correcting narratives-especially when you may be blamed or credited for trends that actually have other causes.

Reflection Questions:

  • In what areas of my work or industry am I accepting conventional wisdom without having looked at the underlying evidence?
  • How could I incorporate more rigorous research or outside expertise before drawing conclusions about what's helping or hurting my business?
  • What is one strongly held belief I have about my field that I could test by seeking out data or academic studies this week?
4

Defining "how much is enough" for yourself can guide healthier decisions about money, lifestyle, and the role of giving in your life.

Reflection Questions:

  • If I wrote down my own definition of "enough" in terms of income, lifestyle, and possessions, what would it look like?
  • How might my daily choices change if I believed I already had enough and treated extra resources as fuel for helping others?
  • What is one small financial or lifestyle adjustment I could make this year to bring my actions closer to my stated values?
5

You can amplify your impact by building networks of people who are strong where you are weak, rather than trying to become an expert in every area you care about.

Reflection Questions:

  • Which causes or domains do I care deeply about but lack the expertise to navigate well on my own?
  • How could I start identifying and building relationships with trusted experts or organizations in those areas?
  • What is one concrete step I can take this quarter to participate in or support an existing network instead of trying to create everything from scratch?

Episode Summary - Notes by Hayden

Craigslist: Craig Newmark - The Forrest Gump of the Internet
0:00 0:00