- Know when to get out of the way and not meddle. Early on, Craig hired a great CEO and let him run the company as he saw appropriate. He stayed engaged but tried not to interfere, focusing his efforts on customer service.
He's managed to keep Craigslist at about a 20 person staff. The bigger an organization, the more it's like Dilbert (he worked at IBM before). He made reference to Dunbar's number, or the theoretical limit of about 150 people that can keep a small-company feeling/culture. Beyond this (and probably within this too), people learn to get ahead by just telling their boss what he or she wants to hear. [I'm learning about this same topic in my Leadership, Motivation, and Power class. Will post about it soon!]
In terms of other leaders, he said he admires Ron Conway and Larry Page.
Craig thinks he's not a real entrepreneur and just got lucky. He repeated this a few times. This was neat to hear.
Speaking to a young audience, he encouraged us to take more risks but to develop a broad social network so we can engage enough people when starting new projects or companies.
- Social media is critical, especially for philanthropy. Many people in the philanthropic sector, such as leaders of grassroots organizations, are turning to Craig for help in advising these new organizations on using social media to get their word out. He says social media is key to allowing leaderless organizations to thrive and get input from the community.
He used a funny analogy to "ye olde times" and "social media technology" back in the day. He spoke about the Gutenberg printing press as the original social media technology; Martin Luther was the first to use it for a social revolution. He spoke about the original bloggers (Thomas Payne, John Locke) and the original online forums (religious talks, meetings). Listening to him talk about this was really funny.
In general, he said he wants to bring a voice to the moderates through charitable means and social media. He's been doing a lot to help veterans through IAVA and the Bob Woodruff Foundation.
In terms of social media and the government, he spoke about the Sunlight Foundation which aims to cast light on government activities and find ways to improve them. He says it would be good to cast light on lobbyists and expose the flows of money to the press.
In terms of Wikileaks, Craig acknowledged that diplomats are those that lie for the sake of their country. He has mixed feelings about this: as a nerd, he wants all info to be open, but he also knows that some stuff in government needs to be secret. Maybe just revealing where money goes is all that we need.
Overall, he's in favor of projects like Jumo that aim to connect causes to people and that use social media to involve the community.
- Trust is the new black. With so much user-generated content (UGC) and so many news sources and information, whom you trust becomes critical to curating your reading and learning experience. He wants to get his news from sources that are accountable and use rigorous fact-checking. He says he gets the best news from The Daily Show (unfortunately).
The Daily Show gets away with using comedy while telling the truth, and this is not something new. Oscar Wilde said, "If you want to tell people the truth, make them laugh, or else they will kill you." The only person in the king's court who could tell the king the truth was the court jester.
Craig predicted that in the future we will receive news on pad-like devices and TVs but from trustworthy curators of news, such as our social network and accountable sources.
- Craigslist secret sauce: KISS. Craig described how the website started out as an email list that he ran on Pine (and still uses Pine for) as a hobby. He wanted to just tell his friends about local events and other stuff that meant something to the people around him. His entire marketing was word of mouth (and lots of launch parties in SF).
Their core innovation, he said, was actually listening to users and not web designers, potential investors, marketers, etc. His users wanted a simple, fast, focused, and free site. They spend a lot of their engineering efforts doing just this (for example, writing their own caching code to keep the site fast).
He claims that speed is the reason why the UI remains simple and old-school. He said they do introduce UI changes slowly but want to keep the site fast (they don't have a mobile app because the site works quickly on any phone already). It seems to me like modern server technology could serve up his site quickly even if it had a more complex UI, so I think the real reason for keeping it old-school is the feeling and tradition behind the site and a focus on keeping it simple. Same reason for no use of social media to promote the site. They get about 50 million views a month already; this is plenty for him. They just want to be a classifieds site. Period.
Many people asked why he doesn't monetize the site more, perhaps in order to generate more money for philanthropy that way. He says he's a libertarian primatist and having lots of money to throw around is not always good, like the situation Gates faces. He'd rather help everyone by giving free advertising on his classifieds site for roommates, furniture, cars, etc. and let others use their money as they see best; he does this because it just makes sense to him to do it that way. This was a really interesting perspective on the website; I had never thought about how giving the service for free was philanthropic in its own way.
Overall, I was impressed by his emphasis on just doing what he thought was right, on pleasing his community, keeping his site simple and focused, and using social media and nontraditional mechanisms to promote philanthropy.