Portfolio February 10, 2011

The Entrepreneur Questionnaire: Glenn Kelman, CEO of Redfin




Glenn Kelman is the CEO of Redfin, the industry’s first online real estate brokerage — think of it as a cross between Century 21 and E-Trade. Redfin is a Greylock-backed company and it has completed more than $2 billion in home sales with a customer-satisfaction rating of 97%.

Describe your business in 10 words or fewer.

Zappos for Real Estate. It used to be “E-Trade for Real Estate,” but we want to emphasize Redfin’s customer service. Which is awesome by the way.

What is the big idea behind your business? 

For almost everyone in the real estate industry, the agent is the customer. We decided to focus on the consumer instead. This means that we publish data that real estate agents hide, and that we hire and pay our own agents to put customers, not commissions, first.

Why are you excited about the future for this company? 

Our mission — to change the whole real estate game in consumers’ favor — is so obvious and good that everyone can get behind it. And our source of competitive advantage in a $60-billion market is deep and strange: agents and engineers working together to serve customers directly. It makes us feel unstoppable.

Why did you become an entrepreneur? 

I don’t think of myself as an entrepreneur, just as someone lucky enough to be in situations where I could be entrepreneurial. I’ve always looked for those situations, so I could pour myself into them. When I was a kid it was the chess team, Dungeons & Dragons, a TRS-80, debate camp. But then I’d realize it was just a game, and noticed the utter lack of girls, and felt a bit silly. A startup offers the same camaraderie, but in a battle for life and death. It’s sort of like becoming a real fighter-magic user-thief.

What was the most difficult lesson you have learned as an entrepreneur? 

Just to be nice and encouraging to people, always. You can be very driven and still be nice. At my wedding, the people from an earlier startup, Plumtree, asked the folks at Redfin if I’d made anyone cry yet, a question that really embarrassed me. I also remember falling in love with a product idea at Plumtree that was a total flop. When you really believe in something, you’ve stopped thinking about it. You have to keep thinking.

What has surprised you about being an entrepreneur? 

I’ve been surprised at what has made me happy and unhappy. The day of Plumtree’s 2002 IPO wasn’t much of a triumph; my mother sent me a chocolate cake. I was happiest just working on cool stuff & eating Indian take-out in the conference room with all my friends.

What five adjectives would you use to describe yourself? 

Sexy, sexy, modest, sexy, sexy.

What is the best business advice you’ve ever heard? 

Jim Barksdale once told a friend that you don’t have to have the job. This means that you can quit if you don’t like it, or you can be fired too. With all the talk about how hard it is to run a startup, we can forget how lucky we are to be here.

What is your motto? 

Who has a motto?

Which living person do you most admire? 

If you exclude my family? I really admire the fact that whenever Marc Singer gets a call from someone running late, he says he’s running late too. I don’t admit that even when it’s true. Small, unnoticeable acts of generosity are sometimes the most impressive.

What are you passionate about? 

Almost everything is interesting, if you work at it.

What motivates you? 

Not letting down my colleagues.

What was your first paying job? 

Washing dishes for Rax Roast Beef.

What do you like most about being an entrepreneur/CEO? 

Not being able to blame anyone else. We spend our wholes lives campaigning, backseat-driving, second-guessing. But it makes you a better person seeing how things turn out when you do get your way.

What do you like least about being an entrepreneur/CEO? 

The tendency it creates to evaluate people as a means to an end, rather than an end in themselves. If you compared me to my identical twin brother, and heard how carefully he analyzes whether he might have hurt anyone’s feelings in a meeting at the EPA, you’d see how the pressure to hit $100M in less than seven years changes someone.

If you could change one thing about yourself, what would it be?

Sometimes I wish I was less of a maniac, sometimes I wish I was more.

What do you consider your greatest achievement? 

Getting my wife to say I do! And just how the companies I’ve worked at have made people feel.

What is the last book you read? 

A River Runs Through It, which I can’t recommend enough.

What values are important to you as an entrepreneur? 

When asked what rules an artist must follow, Henry James said there were none except this: “be generous, be delicate, and always pursue the prize.” What I like about that advice is its combination of carefulness and impatience.

What advice would you give on how to build a great business? 

To build a great business, you have to do something hard, just to be able to withstand all the competition that will later come your way. And since that usually takes time, you need a mission larger than just making money, otherwise everyone will quit once he has enough money or decides he doesn’t have enough; it’s like trying to tame a lion by starving him, but not so much that he eats you.

“To build a great business, you have to do something hard, just to be able to withstand all the competition that will later come your way.”