Hey, I recently did an interview with 10 Minute Interviews, and they captured a snapshot of the life of a nerd. They asked about my upbringing as a total nerd, my biggest challenges with craigslist, and what a day in the life looks like… You can read the full interview below.
What was your upbringing like, and how did it shape who you are today?
It’s all a blur, but in retrospect I never had much instinct for social norms or convention. That’s to say I don’t go with the flow, since I had no idea what the flow was.
That combined with a severe literal streak meant that I took stuff like “treat people like you want to be treated” and unfortunately thought that life might normally be fair.
Worse, that resulted in behavior like showing off in class, resulting in a lot of social isolation. I was a total nerd, even wearing a plastic pocket protector and thick black glasses, taped together.
Nowadays, I figure I can help life be less unfair; that ain’t bad.
What were the biggest challenges you faced during the early years of craigslist?
How did you first meet Jim Buckmaster, and was what it about him that convinced you that he was the right person for the job of craigslist CEO?
My biggest challenge was being a little too trusting and a little lazy, taking bad advice.
However, people helped me understand, end of ’99, that as a manager, I suck. Only took a year for me to get it, which is good, by startup standards.
A little earlier I found Jim’s resume on our site, hired him for senior tech work. After realizing my limitations I made him CEO. Among other areas, he’s much tougher-minded than me.
What are your goals with craigconnects?
In the short term, I want to help good people getting stuff done in causes I believe in. That’s in the here-and-now.
While doing so, I hope to learn for the long run, like my work with Veterans Affairs teaches me what might be done to fix Washington.
So in the long term, I want to help everyone connect, using the Net, to make things better fit all, to give everyone a voice.
From your perspective, what are the biggest issues currently plaguing the American political process?
Maybe the biggest issue is hard evidence showing the return on investment of lobbyist dollars for dollar returns in Washington. Sunlight Foundation created the Fixed Fortunes tool, which shows that one dollar invested in lobbying returns $760 in corporate benefits. (This is does not include “dark money” contributions.) Disclaimer: I’m on the board of Sunlight Foundation.
What has been the most rewarding aspect of your work with craigconnects?
I get a lot of feedback that I’m helping get a lot of good get done.
What does a typical day look like for you?
I use my phone to get done what’s awaiting me from last night and from the east coast. Then I do more of that, maybe including writing, on my notebook.
Following that, might be a meeting, say with a charity, followed by the office, more work.
Maybe another meeting, then home, time with the missus, maybe TV or a book, finishing whatever work comes in.
What were your favorite TV shows when you were a child?
I have memories of Captain Kangaroo, Gilligan’s Island, The Man from UNCLE, The Prisoner, The Outer Limits and I’m sure I’m missing a lot.
In your opinion, what are the top three Leonard Cohen songs?
Maybe “Anthem,” “In My Secret Life,” “Democracy,” lots more.
If you could only eat at one San Francisco-area restaurant for the rest of your life, which would you choose?
Maybe Reverie Cafe, since that’s where I see neighborhood friends.
Are you superstitious?
Only for comic purposes.
If you could offer one piece of advice to your 18-year-old self, what would it be?
Listen to people, then listen more. (Keep treating people like you want to be treated, don’t change that.)