Making Your Own Berkeley Way

Running and cycling. Both are fitting leisure activities for Phi Beta Kappa Cal graduate Glenn Kelman ’93, who operates at warp speed. Now the busy CEO of Redfin, an online real estate brokerage, Glenn chose Cal because “it was the best public university in the world, my best friend in high school attended, it had good physics and engineering programs, and it was affordable at the time.”

His dad wanted to be a physicist, and wanted his son to be one, too. Though a self-described math kid, Glenn couldn’t decide between physics and comparative lit when Cal called to clarify which major he intended. The response he received changed him forever. “She said I would be the first, but I could do it all. I’d never had an adult tell me this. She took me out of the box,” recalls Glenn.

As a reporter for the Daily Cal, Glenn covered Berkeley events similar to the LA race riots. “I was a scared kid. The whole town was getting torn apart. I was trying to call in my story on a pay phone and people were hitting the glass. Berkeley was a wild, exciting, scary place. You had to make your own way.”

Berkeley introduced Glenn to the legacy of Mario Savio and the Free Speech Movement. “Outside Sather Gate, there [were] arguments with a stadium of people,” he recalls. “Berkeley was a gladiator academy for discourse—a lesson in how to talk about race and gender.”

Ultimately, Glenn’s destiny wasn’t medicine or literature. Enter the Stanford Technology Group (STG). “Three Stanford people telling three Berkeley people what to do. It was fun. I was surrounded by all these nerdy, ridiculous, and very smart people. I felt at home,” describes Glenn.

Meeting Kirill Sheynkman M.B.A. ’94 liberated him. “I was already a contrarian. Kirill had always done what he wanted, he was excited by ideas,” says Glenn. Inspired by Kirill’s notion that “it was better to fail at the ‘big thing’ that you were excited about than succeed at something that bored you,” Glenn co-founded Plumtree Software, an industry-changing software company.

When Glenn was pulled back to Seattle to help care for his brother, he found leaving Plumtree heart-wrenching. “I wanted the next thing to have a deeper calling. The pitch that worked on me at STG—its pure creativity, ‘out of nothing you make something, and it runs on when you’re not there’”—was the notion that would become Redfin. “Real estate was an area where [one] could make the world a better place,” Glenn explains.

Today, Seattle is home. Glenn attributes his evolving moral consciousness to his wife Sylvia’s influence. He credits her with making him more empathic, more emotionally centered. “Sylvia wanted to make sure the company has a moral mission, and that the way we treat each other is to be kind. That is always good advice. Just remember and appreciate people.”

Redfin, described by one reporter as “a rabid squirrel,” is the fastest growing online real estate brokerage in the country. When asked about his own growth as a CEO, Glenn says, “Most entrepreneurs are driven to the point of being miserable, but most leaders are a consistent positive force. It has been hard to be both.” Glenn is most proud of his “colleagues who have developed into dazzling leaders, within Redfin or in other walks of life. Your legacy is almost always other people, not products.”

Glenn’s advice for current Cal students: “Give yourself as many choices as you can. Most people don’t have a dream to follow. I did a bunch of things. Don’t keep at one thing in the early days. Work hard, because when you work hard you have more options. And don’t marry the wrong person, or choose the wrong career.”

He has no doubts about Cal or what he hopes for the future. “I want my kids to go to Cal. I want them to learn a little toughness. Berkeley taught me that. I love Berkeley.”