Redfin CEO Glenn Kelman

Redfin CEO Glenn Kelman is known for his colorfulerudite and oftentimes controversial remarks when it comes to startups, business and entrepreneurship. And so it was with some anticipation that I attended Kelman’s talk Monday night at the Get a Real Job Fair in Seattle.

Kelman joked that he had a really juicy keynote in store until he saw me in the audience with my camera and recorder, noting that his goal was to become  “less interesting” so he didn’t appear in the pages of GeekWire anymore.

Well, sorry Glenn.

What did Kelman, who previously co-founded Plumtree Software, have to say? Well, his remarks centered around the importance of thinking big; why tech giants like and Microsoft don’t serve as entrepreneurial “gladiator academies;” and what time travelers would say if they returned to this period.

Here are some excerpts from his talk.

On why big technology companies aren’t the best breeding ground for startups:

“I often hear people say that ‘I am going to learn how to build software at Microsoft or Google or Amazon,’ and those people are amazing at building software. The best software companies in the world are here in Seattle, operating at massive scale. But I actually don’t think they are gladiator academies for you to really learn to build your own company. One of the proudest accomplishments we’ve had at Redfin is not the people we’ve kept, but the people we’ve lost….”

On why most startup companies fail:

“Most people I know think of reasons that they can’t do it on their own. They say: ‘I need to get an MBA. I need to learn this. I need to learn that.’ And, I’ve got to tell you, you are wrong. Most people who start companies fail because their idea is terrible.  That’s why the fail. And it’s usually the only reason. The only other possible reason is that they are not willing to work really hard…. Most people who are idea people don’t really want to work that hard. If you can be both, you are the ultimate warrior.”

On why entrepreneurs should think big and fail often:

“Most people are going to try to convince you to do some small, stinky little niche. Don’t do it, baby! If you go with a big idea, it gives you lots of room to move, and you’ve got an aspirational message that you can use to hire other people. You can make all sorts of mistakes. Whereas if you choose a little niche, you’ve got to nail it, you’ve got to be perfect. What I love about Redfin is that it is a biggest idea in this room. We have screwed up in so many different ways, and we are still making so much money…. Even someone like me can run it.”

On how startups “ruin” your life for the better:

“Once you do (a startup), you are ruined. Ruined, because you will always need the action. It is such a rush to be given that much power and to have that many brilliant people around you, and almost none of the bullshit. Almost none of the bullshit. So, I wouldn’t wait, especially now that there are all of these places you can go. It is sort of like applying to college, if you apply to TechStars or Y Combinator or TheFunded’s Founder Institute, they just take you through a program. So, you have three months or four months to figure things out. So, I’d take it, because most people don’t realize that this is an historical aberration. The period we are in now where a 23-year-old woman can walk into a venture capitalist’s office and get $5 million for an idea. People are going to look back on it, and if they could come back in a time machine and they could only ask us one question: That would be the question: How did someone with only an idea get $5 million for it? I still don’t know. But I promise you this, it won’t last. In five years, it will be over, in 15 years it will be over. I don’t know when it will end. I don’t know how to do anything else. So, I’d make the most of it. You should work at a startup to learn the skills because you are not going to learn them anywhere else, and once you’ve got them down you should go start your own thing. As soon as you have your idea, don’t let anyone talk you out of it. And don’t force yourself to do it before you have a idea. I know a lot of great entrepreneurs with bad ideas, and it just doesn’t matter how good they are.”

Previously on GeekWire: Why it’s so gosh-darned hard to find tech talent: Thoughts from 8 startup veterans

[Editor’s note: GeekWire served as a media partner of the Get a Real Job Fair]

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  • Chris McCoy

    Love these thoughts.

  • Bryan Starbuck

    I think Glenn’s comments are spot on.  Sounds like it was a great talk.

  • Matt

    We are excited to be a new start up in the real estate space right now. And scared too!

  • @CascadeRam

    >>The period we are in now where a 23-year-old woman can walk into a venture capitalist’s office and get $5 million for an idea

    How many 23-year-old women have walked into a VC’s office and got $5 million for an “idea” ?

    For that matter, regardless of age (and even gender), how many people have accomplished this ?

    • Steve Chayer

      Right on for being astute enough to catch this statement. Seriously!

  • Ben Reierson

    I enjoyed this talk very much and I agree with most of Glenn’s points. However, I think saying that most startups fail because they have terrible ideas is a gross oversimplification at best. I would be interested in Glenn’s thoughts on experiences like this:

    I think we’ve all seen great ideas fail several times before they succeed. In fact, most truly innovative ideas spend time in a failure loop before the right set of people, circumstances, and technology enable them. 

    • jordanmitchell

       Ditto … great points from Glen all around, and I enjoyed his perspective. But I suspect it comes down to the definition of “terrible ideas”. Market timing for instance is another huge reason why startups fail, regardless of how good the idea is … which speaks to his other point about picking a larger not-too-niche market which you can pivot within.

  • Mitch Stokely

    Agree with everything that was said….but add one extra concept. Failure rates are abnormally high and making money in IT is till darn hard. MySpace stayed in the red even though it appeared to be successful. And a lot of web companies stay in the red for years. Its a crowded space. Energy and Utility stocks the past 10 years have averaged 10% on Wall Street….technology has a negative return over 10 years. Thats says something. Its not easy and not just about good ideas and working hard. We said that in 1999 before the dotbomb era. Its true today. Search and advertising and software today is one giant popularity contest….the one with the most eyeballs wins. Its not a good a business model. We need a new Web model or search model before it changes….until then, a handful of companies will maintain near monopolies and its not going to change.

  • GreatCon

    I’m confused. Plumtree was an atypical old-school success. Now he’s an expert? He hasn’t been an idea guy, just someone enjoying preaching about something he actually may not have as much experience doing. I rarely hear about Redfin plans or objectives that are tangible. Oh, and after accepting tens of millions in investment, Redfin is hardly the “cash strapped, idea fused” company it once might have been. The amazing thing is he keeps convincing VC’s to burn money, while harboring no concept of exit for them.

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