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Jason Fried


VIDEO: The Men

VIDEO: The Women

SLIDESHOW: Behind the Scenes at the Photo Shoot

GALLERY: Singles 2008

34 years old // Cofounder of the Web-based-software company 37signals // Raised in Deerfield; lives in Wicker Park 

I used to hate learning things, even in college.* I thought I knew everything in my 20s. Maybe I'm a late bloomer, but I find so many things fascinating these days, like gardening. I sit in front of the computer all day designing stuff in the ether, so it's nice to touch the earth, to get dirty and dig around. // I've worked since I was 13. My first job was bagging groceries. You had to look at everything and figure out how it all fit together. I still think about that. // Software is way too complicated—too bloated and slow, trying to do too much stuff. I'd rather execute the basics beautifully.  // Jeff Bezos** has the biggest laugh on the planet. It's so contagious. I can't help but crack up. // I've never understood why people make things so difficult. Then again, the one thing a date should know about me is that I'm a contradictory contrarian. 

* As a finance major at the University of Arizona.  ** 37signals has turned down all investment inquiries, save one: The Amazon.com founder's Bezos Expeditions holds a minority stake in the company. Fried says the deal was brokered specifically for access to Bezos.

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