Best of Bootstrapping: Gesture CEO Jim Alvarez Bootstraps to $10 Million

Jim has bootstrapped a $10M company by providing a software solution to the charity auction management problem. Interesting journey.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Jim Alvarez: I was born and raised in the south side of Chicago. I went to college at the Indiana University.

Sramana Mitra: What did you study?

Jim Alvarez: I was a marketing major.

Sramana Mitra: When did you graduate college?

Jim Alvarez: I graduated in 1998.

Sramana Mitra: What happened after that?

Jim Alvarez: My dad is an attorney. My whole life, I wanted to be an attorney and work with my dad. He has a small firm in Indiana. That was my career path. In my junior year at Indiana, I wanted to learn about the stock market and understand how it works. I had the opportunity to be a clerk for a trader down at the Chicago Board of Options Exchange. I agreed to work for free during my junior year.

While I was there, I met a gentleman by the name of Brian Novack. As I was filling out my housing applications for law school, Brian called me up and said, “How about I give you a million dollars to trade? Whatever you make, you get to keep half. If you lose it all, you lose it all.” I knew that was probably the right thing to do. It was a pretty amazing opportunity.

Sramana Mitra: Why were you getting this opportunity? What was it about you that got people betting?

Jim Alvarez: I was just a junior in college so I didn’t really know what they saw in me, but they saw something. I don’t know. I have a lot of drive. Instead of going to law school, I ended up trading. I did that for five years. I was a partner with Brian for most of that time. I was fortunate, I made quite a bit of money.

In 2003, right when computers were starting to come out, I had a choice of being a trader from a computer screen. The technology was starting to get stronger in that time frame. I could see the writing on the wall. I was either going to be a screen trader or something else. In 2003, I decided to do something else. That’s when I started my second company. My first company was a golf club company.

Sramana Mitra: As in you were an e-commerce site selling golf clubs?

Jim Alvarez: Yes, I invented a putter called Hammy. I put most of the money I made trading into this company and I had it manufactured in China. It was sold in all the major retailers.

Our conversation continues here.

This segment is a part in the series : Best of Bootstrapping