Sharing His Entrepreneurial Expertise

Article excerpt

Byline: Marie Wilson

The man who co-founded the online dating site OKCupid and now serves as CEO of got his start at a high school better known for turning out scientists and mathematicians than experts in finding love connections.

Sam Yagan, a 1995 graduate of the in Aurora, will be speaking about the importance of a technical education and what it's like to be an entrepreneur. His speech at 7:30 p.m. Monday in Chicago will be before students from his alma mater, many of whom will watch in person, while others will view the speech digitally from their computers.

Yagan, 35, who also co-created the study guide source SparkNotes, is a 15-year veteran of Internet entrepreneurship. He leads a startup accelerator called and has been named to Crain's Chicago Business' "40 Under 40" list.

The Daily Herald caught up with Yagan to ask about entrepreneurship in today's highly digital world. Here is an edited version of the conversation:

Q. What will you discuss during your speech, "The Need for Irrational Entrepreneurship"?

A. I'll be mostly focusing on the decision to become an entrepreneur and how to go about thinking about that decision. People get to entrepreneurship in a bunch of different ways. Entrepreneurship isn't exactly a career, so nobody thinks, "I want to grow up to be an entrepreneur." I want to talk about that decision and what does it mean if you think you want to be an entrepreneur.

Q. What makes a good entrepreneur these days?

A. Certainly one of the driving characteristics that seems to be true of most entrepreneurs is comfort with ambiguity and uncertainty. Things change a lot, and a lot of things are out of your control. You have to roll with the punches and be able to change your entire business without hinging your self-worth on whether you succeed with any one idea. People call it a pivot -- it means my first idea didn't work, but I'm trying the second idea. It means I've started over and that's OK.

Q. Is there a typical career path in entrepreneurship?

A. The defining characteristic of a career is success in one job leads you to the next, there's this ladder. But that's not really the case in entrepreneurship. I've started four successful startups, so when I go to start the next company, I'll have some advantages; I'll be able to hire and raise money more easily. But I still will start with no money, no employees. …