In the year 2000 – when I first came across it — Craigslist was an earnest site providing a deceptively simple service — free classified ads online—  that was extremely useful to most everyone. Today, Craigslist is the 9th most popular website in the United States. As much as it is loved, it is also vilified. Some blame Craigslist for newspapers’ lost profits and decimation of  the revenue model for news. If only it were that simple.  If Craigslist hadn’t brought free classifieds online,  some other web service  would have. Personally, I credit Craig Newmark and Craigslist for setting a kind and gentle tone for the  Internet. For him the Internet has always been about social change.

Today Craig can be found on Twitter with nearly 39,000 followers, Facebook with more than 120,000 and on his CraigConnects site. He converses constantly with his followers, chatting about the birds and other wildlife he sees on his deck in San Francisco’s beautiful Cole Valley.  Craig’s current focus focus is on craigconnects, which he says is his “initiative to link up everyone on the planet using the Internet to bear witness to good efforts and encourage the same behavior in others.”

He will be speaking at 11 a.m. today at Chicago’s TechWeek at Merchandise Mart.

Q. Do you see the pressure from social media to change the culture of businesses as leading to lasting change or a new type of organization? What would that organization look like?

A. I do see that in large organizations, those with 150 or more people or more, that’s the Dunbar number. Currently, to get ahead in a large hierarchy, you tell your boss what he or she wants to hear, and then she or he tells her or his boss what they want to hear. That means that real company knowledge and possible improvements never make it to the top. However, social media tech can be used by line workers to combine knowledge and improve business businesses. In such situations, the boss has to back this up, and that often proves difficult.

I’m currently seeing the Department of Veterans Affairs using such methods to better serve vets and also provide better return for the taxpayer dollar.

Q. 435 Digital is all about increasing the capacity of smaller and local businesses to operate efficiently online to reach their customers and grow their businesses. What kind of tools do you see developing as an alternative to traditional advertising for local business? What other services do you see emerging?

A. I like the use of social media, where friends can help friends make better product choices, and that includes Twitter, Foursquare, Google+, Facebook, etc. Also, importantly, there are user review systems, like Amazon or Consumer Reports, which help.

The big problem is that sometimes such systems can be gamed, that’s already a problem. I feel that that might only be fixed with lots of reviewers, constant vigilance, and networks of fact-checking.

Q. You like to say trust is the new black, what are your thoughts for how local businesses can best translate the trust they have built on the ground into trust online? Services like Yelp might be part of the answer, but what else do you see?

A. I’d say that organizations just need to be straight with people in all presences, offline and online. Maximum transparency is good, within obvious limits.  (There’s always stuff you can’t talk about, like customer private info.)

It helps to speak in plain language, and to get to the point, and then stop.

Q. You recently successfully launched a veteran’s initiative through craigconnects, and community building is another area that you plan to encourage under craigconnects.  How do you plan to use the tools of the social web to encourage us to take more responsibility for our communities and neighborhoods.  What new tools are you excited about?

A. We’re still planning that, but probably soon two areas:

  • networks of factchecking so that we can get trustworthy, reliable info.
  • use of nonprofit rating services to help us select good nonprofits to help and how to find bogus ones to avoid.  We’re working with GuideStar, charity Navigator, and