The Self-Made Man: Jim Buckmaster

TSB has talked about Craigslist as a product of self made men before, in that it was built from the ground up by someone with an idea and the willingness to work very hard in service of that idea. That someone, you may recall, was Craigslist founder Craig Newmark, but he’s not the only entrepreneur in the company.

Since 2000, Jim Buckmaster has been the CEO of Craigslist, and he’s every bit the self-starter that Newmark is, which is why he’s this week’s Self Made Man.

Buckmaster started working for Craigslist in 1999, when he applied for a lead programmer job by posting his resume on the site. It didn’t take long for him to start making big improvements to Craigslist, and he was responsible for things like the multi-city architecture, the personals categories, and the flagging system. Those last two items go hand-in-hand most of the time, so it’s good that he rolled them out together.

Before all this happened, Buckmaster was a med school dropout who had trouble finding his feet in the business world. He admitted in a CNN Money interview that he ?kept quitting in the face of adversity until [he] found something [he] loved doing.? It’s rare for men in his position to be so candid about their own failings, but that’s why TSB likes Buckmaster so much. In an industry full of acerbic nerds and trust fund success stories, he’s a breath of fresh air.

As Craigslist’s CEO, Buckmaster makes it a point to practice what he calls the three ironies of ?unbranding, demonetizing, and noncompeting.? His company has no real advertising department, no branding, no HR department, no sales reps; he follows none of the rules for a modern tech company.

Instead, Buckmaster claims that he judges the company’s success by tracking page views to measure site usage, and by how well the users are served by the community he’s built through developing the website and forums. It’s a simple, straightforward pledge to provide something for other people, and it really matters to Buckmaster.

Relatedly, Martin Sorrell described Buckmaster as a ?socialistic anarchist,? and Jerry Falwell called him much worse on Fox News. Many of his business peers think he’s an anti-establishment commie weirdo, possibly because he admires Noam Chomsky and possibly because he’s not a total greedhead looking for short-term gains and not thinking any farther ahead than that.

Here’s Jim Buckmaster speaking to a room of very quiet people about the history of public forums and how they’ve been incorporated into social media.