Craigslist Founder Craig Newmark | This Past Weekend w/ Theo Von

13 Dec 2024 (5 days ago)
Craigslist Founder Craig Newmark | This Past Weekend w/ Theo Von

Upcoming tour dates and guest introduction

Craig Newmark's early life and personality

  • Craig Newmark attended a comedy and music concert that helped raise funds for veterans and their families, featuring comedians such as Jim Gaffigan, Jerry Seinfeld, and John Stewart, as well as musicians like Nora Jones and Bruce Springsteen (4m51s).
  • Newmark had previously spoken to Springsteen and told him that as a nerd, he didn't know his music, which Springsteen reacted to satisfactorily (5m33s).
  • Newmark describes himself as a nerd who wore a plastic pocket protector, thick black glasses, and had no social skills in high school (6m1s).
  • He claims that he can simulate normal human social behavior but has to work hard on it and can get cranky after a while (6m37s).
  • Newmark is a fan of Leonard Cohen and knows that Cohen spent time at the Chelsea Hotel, where he allegedly spent time with Janis Joplin (7m14s).
  • Newmark has a friend who lived at the Chelsea Hotel during its heyday and knew Cohen and Joplin, but was intimidated by Cohen (7m32s).
  • Newmark's friend is a comedian who was previously a musician and is funnier than Newmark, who acknowledges that he's not as funny as he thinks he is (8m0s).
  • Newmark's friend has given him a few jokes to use, including one about getting older and having trouble getting back up after tying one's shoes (8m38s).

Leonard Cohen and music

  • Leonard Cohen's music was played by Craig's mom when he was a kid, and he vaguely remembered him until he saw the premiere of "I'm Your Man" in 1988, which led him to explore more of Cohen's work, including "First We Take Manhattan" and "We'll Take Berlin". (9m8s)
  • Craig considers Leonard Cohen his favorite musician in an obsessive way and finds his music uplifting, despite being dark, and compares him to a darker version of Anthony Bourdain in music. (9m8s)

Food and the founding of Craigslist

  • Craig's problem is that he finds food too delicious and struggles to stop eating, joking that there should be a stop sign at the bottom of desserts. (10m32s)
  • Craig is the founder of Craigslist, which started as a simple email list in 1993 to give back to the online community that helped him settle in San Francisco by sharing information about cool events, neighborhoods, and restaurants. (11m14s)
  • The email list grew via word of mouth, and Craig started asking for more types of content, such as job postings, apartments for sale, and items for sale, which eventually became the foundation of Craigslist. (13m5s)
  • Craig moved to San Francisco in mid-1993 and was inspired by the spirit of online communities, including Usenet news groups, which were the first big discussion boards, and the idea that people would use the internet to help each other out. (11m39s)
  • Craigslist started as an email list of people in the San Francisco area, initially just a CC list that broke at 240 addresses, prompting the use of a list serve, and was later given the name Craigslist by people around the founder, who explained to him that he had accidentally created a brand (13m27s).
  • The list was initially just for San Francisco events, but it kept growing, and for the first three years, it was just the founder working on it, sending out emails whenever someone had something worthwhile to post, which could be a few times a day (14m8s).
  • The list grew via word of mouth, and no advertising was done, with the founder being careful not to spam anyone (14m29s).

Growth and monetization of Craigslist

  • Early high-value items on the list included job postings, which were considered one of the best things that could be done for someone, as it helped them put food on the table (15m6s).
  • The service was completely free for the first three years, but people who posted jobs wanted the founder to charge them, as they felt they were paying more for job ads elsewhere with fewer results (15m29s).
  • The founder experimented with volunteers and charging for jobs in 1998, but it didn't work, and he had to turn the service into a real company (16m53s).
  • The founder initially ran Craigslist from his home computer, but as it grew, he wrote software to turn emails into web pages, giving him web publishing for free, and later wrote more code to reduce the time it took to manage the site (16m29s).
  • The founder is no longer involved with Craigslist and is retired, but still busy (14m40s).
  • The founder of Craigslist had to create a corporate structure for the company, which included hiring people for coding, customer service, and billing, a process that was scary but necessary (17m16s).
  • At events and parties, the founder would meet with bankers and venture capitalists who wanted him to monetize everything and offered billions, but he didn't need the money and didn't understand why people would do that (17m42s).
  • The founder's decision not to monetize everything was influenced by his Sunday School values, which taught him to know when enough is enough and to treat people like he wanted to be treated (18m3s).
  • Craigslist's philosophy is to monetize only those ads for people who are paying more money for less effective ads, which provides a barrier to entry and some structure to the company (18m21s).
  • The founder found that some people, like apartment brokers in New York City, were making a significant amount of money with questionable ethics, and he wanted to balance giving everyone a break with the need to make a profit (19m5s).

Management and customer service at Craigslist

  • In 1999, the founder turned Craigslist into an actual company and moved it from his house to a commercial strip in San Francisco, and he had to make the hard decision to realize that he was not a good manager (19m41s).
  • As a manager, the founder struggled with hiring and firing, and he eventually promoted someone who was good at those tasks and stepped down to focus on customer service, which he did for around 15 years (20m31s).
  • The founder ended up being a customer service representative at his own company, and he would sometimes handle customer service issues via phone or email, although he tried to avoid answering the phone (21m5s).
  • The founder of Craigslist, Craig Newmark, spent a lot of time doing customer service, which involved responding to emails sent to him at his easily guessable email address, C@craigslist.org (21m25s).
  • Newmark saw that people on the internet are overwhelmingly good, but bad actors get more press because mainstream media emphasizes the bad to generate clicks (21m48s).
  • In the early days of Craigslist, Newmark saw people helping each other out consistently, giving away items they could have sold for cash, such as old computer equipment and baby cribs (22m11s).
  • He also noticed that people would give away moving boxes, which are still useful and often needed by someone nearby (22m50s).
  • Newmark lived with a guy named Kenny, whom he met on Craigslist, and Kenny would use empty boxes to create a playground for his cats (23m7s).

Content moderation and community on Craigslist

  • As Craigslist grew, Newmark saw more questionable content, including people buying and selling drugs using code names, such as "beef jerky" and "brain dander" (24m54s).
  • Newmark acknowledges that content moderation is a tough job, especially for those who are not well-paid and are exposed to questionable content full-time (24m1s).
  • Despite the challenges, Newmark believes that the good on Craigslist outweighs the bad, and he continues to be involved with the site (21m39s).
  • The mainstream press often exaggerates issues and fails to point out that conscientious websites keep digital forensics, which can be used to aid law enforcement, and Craigslist was one such site that cooperated with the police in this manner (25m17s).

Digital forensics and law enforcement

  • Keeping digital forensics requires a balance between fighting crime and protecting the rights of the accused, as outlined in the Bill of Rights and the Constitution (26m2s).
  • The Electronic Frontier Foundation played a crucial role in helping Craigslist navigate this balance, as they are pioneers in standing up for the rights of regular people online (26m31s).
  • To access forensics, law enforcement typically needs a subpoena or search warrant, which is in line with American laws and the Judicial system (27m0s).
  • A good high school history teacher taught the importance of civics and the balance between individual rights and law enforcement, which had a lasting impact (27m21s).

Civics, history, and shift in focus

  • This teacher also took the class to a taping of William F. Buckley Jr.'s show "Firing Line," which introduced the concept of modern American conservatism and influenced libertarianism (27m38s).
  • The experience of navigating the ethics of communication and protecting people's rights while giving them freedoms has been a long-standing concern, dating back over 50 years (28m2s).
  • The focus has shifted from politics to helping people who protect the country, such as veterans, active service members, and their families (28m34s).
  • The current concern is the battles on US soil and systems, which may be a precursor to Space Warfare (28m50s).

Sponsors and cyber security threats

  • Shopify is a popular e-commerce platform that offers a $1 per month trial period, and users can sign up at shopify.com (29m29s).
  • ShipStation is a shipping software that helps businesses achieve their shipping goals, offering automation, simplicity, and scalability, with a free 60-day trial available at shipstation.com using the code "Theo" (30m35s).
  • As an influencer, one may face challenges with fair speech and content moderation, but a greater concern is the threat of foreign adversaries compromising critical infrastructure, such as utilities, water, power, and cars (31m19s).
  • Vault 7 Typhoon is a cyber security threat where Chinese hackers target US critical infrastructure, infiltrating home systems to attack other systems, and compromising programmable controllers that control water and electricity flow (31m54s).
  • These attacks can have severe consequences, including disrupting water and power supplies, swaying elections, and even compromising cars, which are increasingly becoming internet devices (32m16s).
  • The threat is particularly concerning for rural water and electrical systems, which often lack the resources to protect themselves from these types of attacks (32m47s).
  • The potential consequences of such attacks include shutting off water and power supplies, compromising cars, and disrupting traffic, which could have significant impacts on daily life (33m6s).

Call to action and cyber security initiatives

  • A national call to action is being planned to protect homes and utility companies from potential cyber threats, with the goal of building a network of networks where everyone can protect each other (34m30s).
  • The call to action may upset some people, as it will point out that many utilities are not protected, and some individuals may react negatively to this information (35m9s).
  • A "pause Take N" campaign is being ramped up to educate people on how to identify and respond to suspicious emails that could be phishing attempts (35m25s).
  • A new facility at Vanderbilt University, led by General Paul Nakasone, is being funded to focus on cyber security and defense, with a philosophy of taking active measures against adversaries rather than waiting for them to attack (35m45s).
  • A commitment of $200 million has been made to support veterans, military families, and cyber security initiatives, with over half of the funds already spent (36m24s).
  • The motivation behind this commitment is a sense of patriotism and a desire to give back, rather than altruism, and is based on the idea that when you have enough, you should give back (36m36s).
  • The idea of a law requiring individuals to give back when they have a certain amount of wealth is discussed, but ultimately, it is up to each person to decide what is right for themselves (37m16s).

Capital preservation and philanthropy

  • In the early 1970s, the concept of capital preservation emerged due to high inflation rates, leading people to invest in assets that could safeguard their capital (38m11s).
  • The idea of capital preservation was influenced by libertarian principles, but this philosophy has evolved over time to incorporate a mix of ideologies, including the importance of helping others in need (38m45s).
  • Reading science fiction at a young age had a formative impact on shaping this perspective, emphasizing the importance of being one's brother's or sister's keeper (39m21s).
  • The early years of life can have a lasting impact on an individual's values and actions, with certain experiences and lessons learned during this time remaining influential even in adulthood (39m27s).

Relationships and marriage

  • As Craigslist grew in popularity, it became a platform not only for people to find jobs but also for forming relationships, with some users even going on dates through the site (39m53s).
  • Craig Newmark met his wife in a local cafe, and after working up the courage to approach her, they started talking and eventually began dating (40m26s).
  • Craig Newmark proposed to his wife after about 9 years of dating, asking her permission to change his Facebook relationship status to "engaged" (41m51s).
  • Craig Newmark proposed to his partner online, which he considers a "pretty suave online move," but also acknowledges it might be seen as nerdy (42m10s).
  • Newmark admits to being socially awkward, especially when it comes to talking to women, and that this awkwardness has not changed with age (42m52s).
  • He finds it challenging to ask someone out, even if he's good at talking to them, and often struggles with taking the next step (43m11s).
  • Newmark mentions that misconnections, a feature on Craigslist, can be an effective way for people to connect, and he's encountered couples who got married after meeting through the site (43m27s).
  • The idea for misconnections was conceived by Jim Buckmaster, who was running the company at the time, and Newmark appreciates the understated romanticism of the feature (43m50s).
  • Newmark credits Jim Buckmaster, a good manager, for helping him with the company, and jokes about Buckmaster being a foot taller than him (44m4s).

Early days and simplicity of Craigslist

  • Craigslist was one of the first websites to use the .org domain, which was initially confusing for people, but the site's minimal approach and monetization strategy caught on (44m40s).
  • Newmark doesn't remember the first misconnection or personal ad posted on Craigslist, as he didn't keep records and much of the site's early history is lost (45m13s).
  • The first version of the Craigslist site was launched in mid-to-late 1996, and its minimal style has remained largely unchanged over the years (45m32s).
  • The reason for the site's simplicity is that users prefer a fast, effective, and easy-to-use interface, and Newmark has prioritized this over fancy designs (45m50s).
  • Craigslist is an effective platform that offers a wide range of services, including heavy equipment, biotech, and legal issues, making it easy for users to find what they need quickly, even for those who are not technologically advanced (46m15s).
  • The site's simplicity and lack of big background processes make it fast and user-friendly, allowing tens of millions of people to put food on the table, find jobs, sell things, and advertise their services (46m58s).
  • Craigslist has also shown tens or hundreds of millions of Americans that the internet can be useful and reasonably easy to use, encouraging people who may have been hesitant to get online (47m25s).
  • The site's mission is centered around fairness and treating people with respect, which is an important value (47m42s).
  • Jim Buckmaster took over the company and has done a great job, hiring a tech staff that is better at their jobs than the founder, and recognizing the importance of good customer service (48m11s).
  • The founder chose Jim Buckmaster because he believed in the mission and was good on the technology side, having both management and programming skills (48m15s).

Philanthropy and current focus

  • The founder is now focused on philanthropy, working harder than ever, and is particularly passionate about supporting veterans and their families, as well as independent journalism and active service members (49m15s).
  • One of the organizations the founder supports is Blue Star Families, which helps military families who are relocated frequently and struggle to make ends meet (50m4s).
  • The founder also supports the Bob Woodruff Foundation, which has received $25 million in funding, and is planning a fundraising event with Blue Star Families (50m11s).
  • Craig Newmark has a connection to the New York Comedy Festival through Caroline Hirsch, who used to run Carolines and now runs the festival, which is currently taking place (50m36s).
  • Newmark has never been to the comedy cellar, a comedy club down the street from him, despite it being a popular and often booked venue with limited seating (50m57s).
  • Newmark's focus is on areas where he can do good, including his work in cyber security, which he considers part of the new war (51m32s).
  • Newmark's interest in cyber security came from realizing its importance, particularly in the context of attacks on Craigslist, where hackers would try to disrupt service or steal proprietary information (51m53s).
  • Proprietary information refers to secret information, such as payroll or client lists, which was not a major concern for Craigslist due to its simplicity as a classified site (52m17s).
  • Newmark is now more concerned with the potential for adversaries to use cyber attacks as a form of warfare, such as hacking drones or other internet-connected devices (52m56s).

Cyber security concerns and potential threats

  • The potential consequences of such attacks could be severe, including turning autonomous drones against their owners or causing widespread fires by hacking into internet-connected appliances (53m12s).
  • Newmark notes that even mundane devices, such as hot water heaters and boilers, are becoming internet-connected and vulnerable to hacking (53m49s).
  • The potential for large-scale attacks on internet-connected devices is a concern, as it could overwhelm first responders and cause significant damage (54m22s).
  • Despite these concerns, Newmark believes there is room for optimism and help, as there are already efforts underway to address these issues (54m35s).
  • The idea is to gather funding for people who are good at dealing with various issues, so they can work together with local governments across the country to develop best practices, focusing on making essential services like water and power supplies resilient to natural disasters. (54m40s)
  • The goal is to create systems that can quickly recover from disruptions, and this requires cooperation between different parties, including non-profit organizations and local governments. (54m56s)
  • The use of drones has become a concern, as they can be used for malicious purposes, such as spying on people, and it's essential to address these issues, especially in densely populated areas like Manhattan. (55m36s)
  • In some cities, like New York, there are concerns about contested airspace and the need for law enforcement to use drones, which adds to the complexity of the issue. (56m36s)
  • It's crucial to protect ourselves from potential hacking and cyber threats, and one way to do this is by building networks of volunteers who can work together to address these issues. (56m52s)
  • The idea is to create a sense of community and cooperation, similar to what happened during World War II, where people looked out for each other and worked together to address common challenges. (57m14s)

Content policies and property rights on Craigslist

  • In the context of Craigslist, there were categories that were not allowed on the site, such as gun sales, which was a decision made by the founder based on user feedback and the exercise of property rights. (58m0s)
  • The founder believes in property rights and freedom of choice, and as the owner of the site, he had the right to decide what rules to enforce and what content to allow. (58m22s)
  • Craig Newmark was involved in the decision-making process at Craigslist, but he allowed his team to work out the details, which he considers a bit of good management, although he couldn't consistently deliver good leadership (58m48s).
  • Newmark wants to lead by example, especially when it comes to billionaires with discretionary money who could be doing good things with their wealth, but he feels he lacks the skills to inspire them (59m11s).
  • Craigslist had rules against selling certain items, such as guns, but swords were allowed, and the site also prohibited the sale of illegal items like drugs, although some people tried to skirt around these rules (1h0m1s).
  • Law enforcement agencies have used Craigslist to fight crime, such as identifying stolen items being listed on the site, and the site's operators would provide forensic evidence to the authorities in response to subpoenas or search warrants (1h0m42s).

US Constitution, Craigslist's impact, and personal anecdotes

  • The US Constitution and Bill of Rights provide checks and balances that protect citizens' rights, and the founders of the country did a good job of establishing these principles, which still stand today (1h1m30s).
  • Craigslist has become a part of history and has been used for various purposes, including dating, with some people having successful relationships and experiences through the site (1h1m57s).
  • Craigslist was a platform where people started marriages after meeting through the site's dating section, with some users even getting married after posting ads looking to meet someone, and the founder has been invited to a number of weddings as a result (1h3m6s).
  • The founder has a dispensation from attending certain family events and ceremonies, which his relatives are aware of and respect (1h3m26s).

Valor Recovery and Craig Newmark's financial decisions

  • A program called Valor Recovery, founded by Steve, helps men overcome porn abuse and sexual compulsivity by providing tools and coaching for a healthier sex life (1h4m26s).
  • Valor Recovery's coaches are in long-term recovery and serve as partners, mentors, and spiritual guides to help men transcend problematic behaviors (1h4m59s).
  • The founder of Craigslist, Craig Newmark, has not sold the company, but instead gave a portion of equity to someone who later sold it to eBay, only for Craigslist to buy it back (1h5m41s).
  • Craig Newmark created a 501c4 foundation and put his equity in it, which generates dividends and sales that he uses to fund various projects (1h6m12s).
  • Craig Newmark estimates he has 5 to 20 years to give away his money and has a rough idea of how much he can donate each year based on the foundation's earnings (1h6m30s).
  • At 72 years old, Craig Newmark is concerned that he may not have enough time to conduct due diligence on all the projects he wants to fund, joking that he may have to come back and haunt people to ensure his wishes are carried out (1h6m45s).
  • Craig Newmark no longer owns equity in Craigslist, as the company was transferred into a 501c4 foundation, with other people owning parts of the company, and he uses the majority of his wealth for charity (1h7m26s).
  • Newmark's decision not to follow the usual Silicon Valley path of selling the company and accumulating wealth means he would have been worth $11 billion, according to an economist's analysis, but he doesn't know what he would do with that amount of money (1h8m7s).
  • Newmark values being sensible and altruistic, believing in having enough to be comfortable and indulge family and friends, and then giving away the rest, as he thinks the future is unpredictable and there are people who need help (1h9m0s).
  • Newmark's approach to wealth is influenced by his upbringing and values, and he tries to maintain a balance by being frugal and doing things for himself, which helps him stay grounded and avoid the negative side effects of having too much money (1h11m12s).
  • Other tech companies have been explicit in their dislike for Craigslist's model of doing well by doing good, but Newmark stands by his approach and believes it's fair to prioritize what he aims for (1h10m0s).
  • Newmark has met many rich people who are not happy, and he thinks having too much money can be a trap that leads to being surrounded by yes-men and becoming insulated from the needs of regular people, causing damage (1h10m29s).
  • To keep himself balanced, Newmark tries to maintain a sense of humility and connection to the needs of others, and he prioritizes using his wealth to make a positive impact (1h10m56s).

Personal life and art

  • Craig Newmark prefers taking the subway over driving a car, but occasionally attends fancy dinners and treats himself to good food, which he believes can also be found at a lower cost and with more fun (1h11m26s).
  • He wouldn't mind having a smaller house, but his wife's large family, with 20 nephews and nieces, is a consideration, and he has learned to control his language around them (1h12m6s).
  • When his relatives' children are allowed to watch HBO, he is allowed to use a saltier language (1h12m41s).
  • Craig Newmark bought some autographed prints by Leonard Cohen, who was not only a musician but also an artist, and regrets not participating more in an auction of Cohen's letters and other items (1h13m12s).
  • He owns black and white prints by Cohen and has considered buying more art pieces, including a painting he saw in Tanzania 15 years ago, which he wishes he had purchased despite the cost (1h13m42s).
  • His wife, an art major, has made the biggest investment in art for their house, often finding affordable pieces at auctions, and has also developed a hobby of getting free upgrades while flying (1h14m57s).

Craigslist's unique approach and Wikipedia

  • Craigslist was considered the stepchild of the tech industry, as it was a basic, peer-to-peer platform that allowed people to connect with their neighbors and offer services, which was different from the expensive and fancy approaches of other companies (1h15m26s).
  • The site's founder prefers the ungentrified nature of Craigslist and notes that not everything has to be expensive or fancy (1h16m5s).
  • Wikipedia is considered an ungentrified site, where facts go to live, and is the most important site, as it allows people to write and edit articles, giving them power to determine how people think of things and write history (1h16m14s).
  • However, Wikipedia's system is imperfect, and some information may be incorrect, but it can be corrected with good citations and evidence (1h17m12s).
  • The founder notes that newspapers often don't correct themselves, especially not in a big way, but Wikipedia allows for corrections to be made (1h17m8s).
  • The founder is working with Wikipedia's local chapter in New York to give classes on Wikipedia for beginners and has not yet attended a class to learn how to edit articles (1h16m30s).
  • The founder believes that the system is imperfect but better than anything else that has been tried, and things do get fixed, even if it takes time (1h17m44s).
  • The founder disagrees with the idea that some newspapers don't want to correct their mistakes, even when presented with evidence, and instead want to shape history (1h18m11s).

AI and customer service

  • The founder worries about the alteration of information on the web, especially with the use of AI, which can produce wrong information if trained on compromised data (1h18m48s).
  • The founder hopes that good AI can replace or supplement search but is concerned about the potential for AI to produce incorrect information (1h19m4s).
  • There is hope for AI doing customer service if it's done with commitment and done right, as it can be more effective than human customer service in some cases, especially when human representatives are not knowledgeable or well-trained (1h19m36s).
  • The goal is to have an AI system that is responsive, provides good information, and can escalate issues to a human representative if necessary (1h20m37s).
  • Craigslist makes money by running very lean and minimally charging for services, which is enough to sustain the company without needing to produce great results for venture capitalists (1h20m59s).
  • The company's financial independence allows it to avoid the pressure of going public and seeking large returns for investors (1h21m20s).
  • The founder is happy with the current results and is not concerned about the future, despite its uncertainties (1h21m34s).

Independent journalism and support for service members

  • The importance of independent journalism is emphasized, as a free and trustworthy press is necessary to keep a republic alive (1h23m5s).
  • The media system is currently fractured, and efforts are being made to support trustworthy sources, such as the journalism school at the City University of New York and Wikipedia (1h23m26s).
  • The founder is trying to focus on areas where he can help Americans defend the country, despite feeling confused and paralyzed by the current state of the media (1h23m48s).
  • Craig Newmark's goal is to help service members, active or veteran, and their families, who have given up a lot for the country and are not treated right, by doing something about it (1h23m54s).
  • He also wants to help with cyber warfare, which needs attention from everyone, not just the government, and people need to harden their systems to prevent being targeted (1h24m12s).
  • Compromised systems, such as cars or home appliances, could cause significant problems, even if only 1% of them are affected (1h24m47s).

Personal reflections and future goals

  • Craig Newmark does not consider himself a real businessman, and his success has been a happy accident of being in the right place at the right time with the right attitude (1h25m2s).
  • He tries to follow the golden rule and bring people together, which he learned from Sunday school (1h25m22s).
  • Craig Newmark's parents have passed away, but he knows they would be proud of his contributions, and his high school history teacher was also proud of his accomplishments (1h25m33s).
  • He still keeps in touch with his teachers, who work hard for little pay, and values their long-term impact (1h26m8s).
  • One of Craig Newmark's current goals is to make cyber security a household word that everyone takes seriously (1h26m39s).
  • Personally, he has a humorous goal of making the same joke to his dentist every time he visits (1h26m47s).
  • He also wants to share the importance of taking cyber security seriously and encourages people to take action (1h27m10s).
  • The goal is to help one person in need by being of service, which involves learning and acknowledging one's strengths and weaknesses. (1h27m53s)
  • Craig Newmark recognizes that customer relations is a strong suit of his, but managing is not, which is why he sought help in that area. (1h28m5s)
  • Craig Newmark has been married for 12 years and together with his wife for 20 years, and he is better at remembering their dates than she is. (1h28m19s)

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