advertisement CEO: 'You have to be willing to fail'

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 Illinois Mathematics and Science Academy 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 TechStars Chicago 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. You still start at square one even though you have some advantages. It's not a slam dunk the second time. It's still very unclear what it means to be a career entrepreneur.

Q. What did you learn about entrepreneurship during your time at IMSA?

A. You have to be willing to fail. In that regard, IMSA does challenge students. It happens to a lot of students in college — they really get tested for the first time. But being in an environment that's so experimental and such a lab by itself, almost by nature failure is going to happen more at IMSA than at other schools that are much more structured and traditional. Just because you fail doesn't mean you're a failure and that came out at IMSA.

Q. How does your startup accelerator, TechStars Chicago, assist budding entrepreneurs?

A. In the '90s when I got my start, what you really needed to succeed was cash. Nobody knew what they were doing, but they raised as much money as they could so they could learn on the job. There were not experts and mentors to go to because it was so early in the evolution of digital startups.

Cash is relatively easy to come by now, so what really differentiates successful startups is whether you have access to the brainpower and the mentorship of people who have been there and done that. TechStars Chicago basically brings together this army of mentors, this army of experience and we unleash it onto the select startups that make the class.

Q. Have you ever worked with other IMSA students?

A. We have a great partnership with IMSA. We always take our high school intern from IMSA. The most amazing thing for the interns is the immersion. The IMSA experience is itself immersive. But in the internship, they're sitting alongside 10 startups, seeing 150 mentors come in through the doors throughout the summer and getting to interact.

Q. What should high school students with big ideas do to set themselves up for careers in online entrepreneurship?

A. The biggest thing is to get a technical education. I've always been on the business side of my startups, but I studied enough computer science and engineering to know how the tech side of the operation works. Even if you want to be on the business side of a digital startup, you will make yourself so much better and more useful if you understand the tech side. And if you want to be an entrepreneur and you want to build things, just start building.

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