Craig Newmark founded Craigslist as a hobby in 1995. The site is one of the most popular destinations on the Internet and Craig’s way of seeing things is still much part of how the web company operates.

Craig was very kind to answer our questions about his current role at Craigslist, lessons learned from past work experiences, controversies, customer service, design, and more.

Please check out his very interesting blog and follow him on Twitter.

1. Every month, Craigslist gets 20 billion page views, 40 million new classified ads, and 50 million people looking to buy stuff, meet others, and get a job. What would you have done differently from 1995 to 1999, if you had known what your hobby was going to become?

I wouldn’t have done anything differently overall, but would have listened more to the lawyers and my own instincts.

2. In what ways (positive and negative) did your previous professional experiences help shape the culture of Craigslist?

I learned how important customer service is, and how largeness in organizations leads to dysfunction. For example, in a hierarchy, you get ahead by telling your boss what he or she wants to hear; then he or she tells his or her boss what they want to hear.

3. Craigslist is largely based on trust. Do you often wake up and wonder how your site continues to deliver what it offers despite the controversies and criticisms?

 Not a problem, unfair controversies and criticisms just strengthen us, and increase community support and traffic.

4. You Twitter bio and business card say “Customer Service Rep.” What exactly does that mean and how has that role changed since Jim Buckmaster took the role of CEO in 2000?

I do forums moderation and ad hoc abuse cases. It’s gone down to half time these days.

5. Craigslist exists primarily as a “.org” web site. What statement is the company trying to make through this?

We’re a community service and a business, doing well by doing good. Policy decisions are driven by the community.

6. Much of the revenue that Craigslist generates comes from job postings. The pricing strategy seems to be quite different from that of Monster and CareerBuilder. How do you keep your price per ads so low and why would people choose you over competitors?

Jim runs the company very efficiently, and we’re very effective.

7. Wired magazine once asked about what your “touchy-feely corporate mantra” was and you answered “give people a break”. What kind of break do you think people need in the current economic downturn?

Considering our ethos, can’t think of anything new given the downturn.

8. You have been known to support organizations and efforts that improve the life of others. If you could change something such as health care in the United States, what would you focus on?

I’d focus on helping the people doing the real heavy lifting, like I’m helping Consumer Reports/Consumers Union lead in health care reform.  Also, helping the Iraq and Afghanistan Veterans of America to get fair treatment for vets.

9. There are many nations that don’t have much freedom of speech. What do you think about web sites that try to ignite citizen journalism through the web and SMS in such countries?

I like the idea of them a lot, not sure if any have figured out how to get real traction.

10. What are your views on transparency online and how does it differ for bloggers, politicians, and corporations?

I feel we should be as transparent as possible, limited by normal personal privacy concerns and legitimate trade or state secrets.

11. You care more about usability than design and Craigslist is a testament to that. Would Craigslist do a major re-design to please users if the web continues to evolve (imagine that we somehow get to Web 5.0 and no one remembers Geocities anymore)?

If people in our community want a redesign, we do it. So far, there’s essentially no interest.

13. Star Trek is one of your movie favorites, you wrote computer code for many years, and you’ve also denied your own existence a few times. Do you consider yourself a nerd and if so, would you also consider yourself to be a “social nerd”?

I’m very much a nerd, working hard to overcome some dysfunction. Not sure what a “social nerd” is…???

14. What advice would you give to anyone who works in an IT department who dreams of starting a web company?

Make sure you’re addressing a real need.

Pay attention to media strategy.

Treat people like you want to be treated.