Not Easily Classified

As told to AMY ZIPKIN at New York Times

I WAS at Virginia Tech and was thinking about being an engineer, but then I decided I didn't like engineering and switched to pre-med. I applied to the University of Michigan for sentimental reasons. I was born in Ann Arbor, still had a lot of relatives there, and the program had a good reputation. I was accepted.

I remember liking gross anatomy and embryology my first year, but in the second year pharmacology was like memorizing the white pages of the phone book.

About a year and a half into medical school I started having doubts. Medical school didn't seem particularly stimulating, but since my student loans, between undergraduate school and medical school, were between $50,000 and $100,000, it wasn't clear if I left medical school how I was going to pay that back.

I took a leave of absence and began auditing classes in the classics at the University of Michigan. I was leery of taking on additional loans. And when the deadline rolled around to return to medical school, I took another leave of absence and continued to audit classes. The medical school wouldn't allow a leave for a third year, so I left.

I worked in survey research at the university and often took at least one class for credit so I would have gym access and infirmary access and could live in student co-op housing. One winter I lived in an informal housing arrangement. We decided we would spend the winter with no heat. Winter starts in Ann Arbor in November and runs until April. At night the indoor temperatures would dip into the 30's. Daytime, the temperatures would climb to the 50's. We didn't use heating per se, but we did use electricity, using a stove and oven for cooking and turning on lights. I wore a hat and light gloves around the house. I made my own mittens out of old purses from a thrift store. I was also making my own bread and grinding my own soybeans to make tofu. I kept my costs low because I was paying off student loans.

I backed into computers as a way to make a living. Originally I was computer-phobic. By the early 90's I had worked my way up the computing chain from data entry to programming. I was working on a data archive called the Inter-University Consortium for Political and Social Research, which had 450 members. A colleague showed me the World Wide Web on an early Mosaic browser. It was a religious experience being shown the Web for the first time. I was so absorbed that I didn't get out of my chair from 5 p.m. to 8 a.m. the next day. I thought this was something special. Not only could I be a user of this but I could create it myself. Over the next year and a half I created a Web interface for the consortium's archives so researchers at member institutions could access the data themselves.

I was 33 and had never made more than $15,000 a year. That winter in Ann Arbor had been particularly bleak. There were eight days when the temperature never rose above zero. I sent out my résumé on the Internet, and all the responses I got were from Silicon Valley. Some were offering air fare. I had been to San Francisco once, when I was 15.

I took a job just north of San Jose and moved out there not knowing a soul. I had never owned a car. In Ann Arbor I took my bike everyplace. In California I took the bus, but there was very little provision for mass transit.

After two or three years I moved to San Francisco and still commuted two and a half hours each way. The train let me off 12 miles from the office, and then I'd take two buses. Finally, during the dot-com boom, I got a job in San Francisco. That company didn't have a very long life.

In late 1999, I posted my résumé on Craigslist.org. Craig Newmark, the founder, saw my résumé. He was looking for a programmer at the time. I took the job over a better-paying one, and became president and chief executive a year later. Craigslist was different in my eyes from other companies.