ExecuTalks
ExecuTalks
Redfin CEO: Glenn Kelman
Glenn grew up in Bellevue, WA, in a middle-class family. He was the son of an aeronautical engineer and had two brothers, one of which was a twin brother. From a young age, Glenn felt like he didn't fit in with other kids at school because most of them were rich kids that showed off their wealth. His older brother frequently made front-page news in Bellevue, which added to his feeling of difference growing up.
He would then attend the University of California-Berkeley and get his B.A. in English. He made an attempt to write a novel, and after running out of money and hitting a low point in his life, he decided writing a novel wasn't meant for him. He would then go on to meet some brilliant people whom he started a business with (Plumtree Software). That business would eventually be purchased by a large company (BEA) in 2005 after going public and raising $40 million.
Shortly after, he joined Redfin as their CEO and has been there ever since. Redfin is a publicly traded, technology-powered real-estate brokerage now valued at over $1.7 billion, and is revolutionizing the way people are buying and selling homes.
I tried to write a novel one time and girlfriend dumped me cause I didn't have any money. And my roommate came in one day and said, get a job. And I remember going into the bank cause my ATM card would work because I had less than$20. We can't take out$14 with an ATM card.
Speaker 2:Hey, welcome to the executive talks podcast. It's the show that gives you insight to the personal stories of today's top executives. In this episode, you will hear from Glenn Kelman, Redfin CEO, Redfin is a technology powered real estate brokerage that represents both sellers and buyers for small feet. Now valued at over$1.7 billion. You want to make sure to stick around until the end to hear about how Glenn thinks and hear him reflect on what he would tell his younger self. Hey guys. So we initially had this conversation a little over a year ago and at the time we recorded in an open space where there was definitely some background noise. So we pathologize and events, um, for the quality of the audio. So Glen grew up in Bellevue, Washington in a middle class household. His father was an aeronautical engineer and he had a twin brother that he admits, helped develop his competitiveness during his childhood. He felt like he didn't fit in with a lot of the other kids at school because he wasn't raised to advertise or to show off as well. Like a lot of the other kids did. For example, he had a one car that was the crappiest car in the parking lot that he'd split with his twin brother. He also admits that his brother got into a lot of trouble and it amplified his feeling of not fitting in even more. Now this feeling of being different than everyone else was the catalyst for Glen's personal development.
Speaker 1:I was, uh, the son of a, an aeronautical engineer. He founded his own company to create parts for spacious. Most of which blew up. And then my mom had a twin brother, um, my identical twin Wesley. And I think that made me more competitive. We were always sort of racing to the car or trying to eat a slice of pizza first. And then I had an older brother and he was dark or no, a black sheep I think is what you call it. Um, so he got into a lot of trouble and it made front page news and Bellevue. And I think that no, it really did. And I think it affected me because there was just no point in trying to fit in. I felt like we were going to be a different family and that I couldn't be so worried about what other people thought, because if I was, I just wouldn't have survived. So other than that, uh, it was just a goofy, loving family. And I was really lucky because my parents had almost no ambition for me. I think it's hard when you feel that pressure from your parents to be a doctor or a lawyer, uh, to think for yourself. But my parents were just really glad I was there and they let me become whatever I wanted to be. And so it made it easy to become what I am now.
Speaker 2:Interesting. So maybe were there any sort of, um, key events that happened when you were a child? That was like, when you look back, you're like, man, that was painful. And that, and I struggled with
Speaker 1:They're interviewing me like I'm Winston Churchill, like Greg, this was born the age of nine or so that I could tell you. I really did get lucky. I think, I think I just had a chip on my shoulder. I went to Interlake high school, which was full of rich kids and there was a chip on my shoulder. I wasn't one of the rich kids. I had the crappiest car in the parking lot, which I split with my twin brother and I felt like I never fit in. And you just decided you're going to work harder than everybody else. Um, if you're not born with a silver spoon in your mouth and you feel like you just have to hustle, it's this incredible gift. I remember that at one point we were living in this neighborhood where there was a yard of the year competition and my father didn't even own a lawnmower. There was a point at which he was trying to cut the grass with a machete or something like that. And it was just, I was so ashamed, um, that we couldn't be like everybody else and just decided there's no point in trying. And so I think feeling like I had to work harder than everybody else I'm feeling really loved, but also feeling like we were a little bit of a misfit family was just a perfect breeding ground for thinking for myself as an adult, which is just the hardest thing to do.
Speaker 2:So Glen would go on to attend the university of California at Berkeley and get his BA in English. He initially had ambitions to write his own novel and it took him some time before he realized that that wasn't his calling. At one point, he ran out of money and his girlfriend broke up with him and there was tension between him and his roommates all at once.
Speaker 1:I feel like I could live my life a hundred times over and the other 99 times from the same amount of talent and drive, I would not have the outcome that I have now. I really feel that way. And I think that many successful people want to attribute all of their success to themselves. And it limits your empathy for people who are less successful. It's obviously narcissistic and it's totally destructive. I feel all the time. Like there are a bunch of people at Redfin who might be able to run this company better than I do. And it just makes me try harder every day to be worthy of the honor. And so if you think you're God's gift to leadership, if you think that you're the only one who can run a company or start a company, you probably shouldn't be anywhere near that job. Um, I just think it's easy to let it go to your head. So on that topic, by the way you said in an interview one time with you, you've tried so hard to mess up your life and it makes you like queasy a little bit. What makes you feel like you've tried to mess up your life? Well, I tried to write a novel one time and my girlfriend dumped me cause I didn't have any money. And my roommate came in one day and said get a job. And I remember going into the bank cause my ATM card wouldn't work cause I had less than$20 and we can't take out$14 with an ATM card. Whoa. And I was trying so hard to be unhappy. I didn't enjoy writing a novel. I just thought that somehow that seemed like a good thing to do. And if I had run out of money, I would still be trying to do that. Um, I wanted to become a doctor at one point, this older brother who was the black sheep ended up drinking too much. And we ended up taking him to the hospital every week. And I just really admire the doctors who took care of him when there was no percentage in it. He wasn't going to get better, but they kept trying to help him, even though he was angry that he was going to die. And I thought I should be a good person like that. I should be a doctor. And so I applied to medical school and almost went and I was so relieved that I did not because it isn't a good thing to do, but because I would have been a terrible doctor. So I think I had these notions of what I should be. Uh, there were a war with who I am and I just didn't listen to who I am for a long time. I really liked being in business. I think it's creative. I think it's fun. I think it's exciting. And I think there's a moral way to do it where you can still make the world a better place. Um, but coming from Berkeley and being a little bit of a hippie, it took me a while to find my way. I'm so sorry. I want to go back to the point where you didn't have any money in your girlfriend. Don't do it all. But how, how did that feel at the time? And w w w was where you thought we were going through? Well, I was really lonely and sad. There wasn't a lot to it. I think the most distressing it's part of it. Wasn't anyone's external judgment. It was the deep self knowledge that I wasn't a very good writer. And then I had no business publishing a novel because I didn't have enough to say there are people like Jonathan Safran for who come out of college and they have so much to tell the world. And I did. And so going into your study and trying to put out 2000 words a day before you eat lunch, um, just made me miserable. It meant that I didn't get to eat until three in the afternoon. So I was just trying to do the wrong thing because I'd psych myself out. I convinced myself that this is what I should do and it wasn't what I love doing. And I don't think that you can discover that through any process of ratty assassination. I actually think we just have to try a bunch of different things and I felt so much urgency when I was your age. I thought, Oh my gosh, I'm 23. And I still haven't figured everything out. And now I know people who settle in one group, it's the wrong group, but they say I'm 25. It's too late to change. And they're so miserable and middle aged. And just think you have to try a bunch of different things until you find your thing. And what I had were parents who just said, you are something special. If you don't like this, do something else. Instead of telling me, well, that's just the way life is, you know, you work for a job or you work for a paycheck and you kind of stumbled through. They felt like, no, you should do something you really love. And so I just kept trying until I found it. So you were, at one point you were lonely, you were sad, has been lonely and sad. You guys had it. Yeah. What I'm trying to say is what, how did you pull out of that? What's like, what, how did you pull out of that? Well, you know, evolutionary biologists have tried to understand the value of depression. Not many animals become so depressed. They can't get out of bed in the morning. I guess they don't have a bed, but there's really no reason for it except this, which is that, it's your body's way of saying enough is enough that I am not going to let you continue on this path. If you've known anyone who's been in a horrible relationship or has been writing a dissertation when they no longer believe in it, at some point you just can't go on anymore and realize you have to change. And so I just think that I was miserable doing that and I kept trying to do it. And eventually, um, everything that I had that was joyous to write about just sort of receded from me. And, and that's why so many people who are not willing to stand up writing about depression and, and sad things like that. Cause it's a really, it's a tough life. So one thing you've probably realized by now is that Len has an extremely humble demeanor. Now, before joining Redfin, he co founded a company
Speaker 2:Called Plumtree software, which was eventually acquired by a larger company in 2004 and Glen then later joined Redfin. So four years after Glen had joined Redfin, the great recession that happened in 2008 led to very rough times for lots of companies, including Redfin. Now, Glenn has a very unique approach to handling rough times and his philosophy on leadership doesn't begin during the bad times, by then, it's too late. Glenn says
Speaker 1:Struggling. I know you started red phone was founded in 2004, right. It was founded by David. Yeah. And like any startup, you know, you're trying to keep it afloat, right? Yeah.
Speaker 2:Yeah. And then few years
Speaker 1:Was later 2008 happens. Yeah. What was going through your head and how did you overcome that? Well, um, first of all, Redfin was hard almost from day one because at the time it really wasn't popular for people who made websites to have a real world business operation. We wanted to hire our own real estate agents and give them healthcare and all of that. And I thought it would be easy to raise money because I've made so much money for Sequoia and the other venture capitalists who were funded our deal. Um, that was just impossible. Almost everybody said now. Yeah. And then in 2008, when the great financial crisis hit, I mean, part of it was a relief because the pain we were going through was being shared by everyone else. And misery loves company. I think because I'd been through 2000 plum tree had been growing very fast and.com bubble burst. I just felt like I knew what to do, which was right away to live, to fight another day, reduce our expenses drastically. We had to do a layoff and the rule there is just to cut once it cut deep, but you don't want to cut 10% of your workforce. And six months later do another 10 because then nobody feels safe. So I just felt like we're going to need to do this. So we need to do it now. So we can pay everyone and really large separates. When we talked about it with our board, there was some thought around waiting and seeing if things got better. Um, but I felt like the people who were working at Redfin, we could pay through the end of the year. And if we waited until the end of the year, there would be almost no severance. And if we let them know, now they can start making other plans, but it was horrible. It was horrible because if you run a startup where you really pride yourself on having a loving culture, some of that just seems like a lie when you have to let people go. Yeah. And now I'm just careful about it. You know, we're growing very fast, but we're not hiring aggressively as we could, because I don't want to let anyone down again. And it's impossible to avoid all risk. We're going to have to take some risks, but just think you have to be more careful about risking people's careers and their lives and all of that. So during that time of struggle or what was it like, you know, how, how did you, how did you motivate your team? Well, I think it's too late. Um, if you wait to talk about the mission of the company, um, the reason you come to work every day, being more than just money, only when the Shataki mushrooms have hit the fan. You can't really start seeing that song. You know, you have to say from the beginning, they're going to be some ups and downs. You know, they've studied families. Um, and there's this narrative that different families have. Some are, we used to be great. And now we fall on hard times. Other are, we were immigrants and every generation does better than the last, but the narrative that's actually best for kids that makes them the most resilient is great for companies too, which is, we've had some ups and downs, but we've always stayed together. And I think even when we were doing reasonably well, we've just always said, there's going to be another hard period. And if you're just jumping on the bandwagon because you want to make a boatload of money. Yeah. That's great. I hope we make some money, but you have to care about what we're really doing here, which is making real estate better for regular people. And so, um, I think you have to kind of stay true to that through the good times and the bad. If you only go to that in the dark times, it just sounds a little disingenuous. So kind of moving on as Ash was telling me that, you know, you commute to work on bike. It's true. And we know that, I thought that was awesome. So I want to know, you know, what, why what's your, what's your philosophy? Well, I think it's awesome. I'm just curious a mentalist. And so, um, some of it is just to avoid pollution. I'm an exercise freak. So it's high yield, you get transportation, but you also exercise. I think the hidden agenda there is that I work in this very seasonal business. So Redfin sales are half in the winter of what they are on the summer. And I came to Seattle after living in California for awhile, uh, from college through my early adult years. And I just thought, Oh my gosh, it's great all the time. And we're not selling any houses. And my wife just said, you need to get outside every single day, no matter what. And it's such a discipline now that even if it's snowing, I will walk my bike to work. And if the snow clear as I get to ride it back home, but I just feel like I know that I need to do this. And I think this is some self knowledge that as an adult, the older you get, the more, you know, the instruction manual, uh, to make yourself happy. You know, these are the things that I need to do to put myself in a productive place where I can be a good parent where I can be a good, uh, colleague and friend to people here at work. Um, and so that's just one of my set ups. There's so many times when some strive me crazy at work, and I don't want to walk in to my house feeling that way at the time. I've a time trial that Capitol Hill, I feel a lot better. Awesome. So what would you say are maybe your top three, you know, habits to stay happy free for yourself, maybe, you know, translate to the audience watching, or I have probably three or four. Um, number one is getting outside and exercising. Number two is I just make a list of the things that I want to get done. And then it really makes me happy crossing those things off. I think you have to kind of break things up into little pieces and get them done. I have an incredible family. I love my wife and my children. And it's hard to imagine that you can be happy if you don't love your spouse. I know people who are in marriages that are okay, and I just think you can never be a 10. You can only be a six or seven or eight. So if you guys aren't married yet, just be really careful about the choice, most important choice. That's the, I'm actually in the process of homemade. Like I'm ready to get married, but I'm kind of scared. Aren't you worried your girlfriend's going to watch this video?
Speaker 3:Maybe we'll edit it out. I don't know.
Speaker 1:That would be hard for me to hear about Dave. Awesome. So what are y'all, we're having a good time. We're talking to you. If you were to choose me, if you were to, if you were to want to learn more about a different executive in Seattle, who would that? Uh, well, I mean, I think everybody's favorite CEO right now is Jeff basis.
Speaker 3:Third one third, one in a row. Now
Speaker 1:Get it sorta like your, is your favorite quarterback?
Speaker 3:[inaudible]
Speaker 1:The gold standard. Um, could be what's the Wilsonville seal? No, I know, but Russell Wilson would be a little more unconventional, whereas Jeff Bezos. So please. Um, so I think that's the obvious candidate. I admired Jim Senegal because he's, he founded Costco. Um, and he's just tough as nails on expenses. He wants to told me this story about how the Kirkland private label Reese's peanut butter cup got redesigned from one shade of orange to another. And I said, which shade did you like better? You said, no, it's just a waste of money. And what I really admire about him the most is that I think he has 1% of Costco. They did one round of financing maybe. Well, um, and so he gave most of that company to the employees and I met them when I first came here. Um, and that was when Walmart was just running up the score against Costco. And so it was hard to believe what he and the CFO were saying, which was just that they treat their employees terribly. It makes you feel terrible when you walk in the store, that brand isn't going to endure. Um, and now, you know, you go into Costco, you see people pushing carts around who have a pen that say they've been there since 2011. And you know, that's a good company. It's one of the only retailers that's effectively competed against Amazon. And I think it's because they put other people first, um, and they weren't lining their own pockets. And right now that's a real crisis for tech. There's a lot of people in tech who are just cashing it. Yeah. So you've heard of you think you told me about the Zillow Zillow. Oh no. Yeah. I was just going to ask you, uh, what are your thoughts on Zillow's new ventures sure. And purchasing homes, then, you know, how do you know, what are your plans? Well, but that business about 18 months for Zillow. And I think we're probably more measured about it because you're borrowing money to buy houses. Cause you think you're smarter than everybody else. And you could end up owning a thousand properties in Phoenix that you just can't sell. Right. And so Zillow certainly aware of that. And there are other companies like Opendoor and they're aware of it. It's sort of the first time that tech has used artificial intelligence or machine learning to really take a massive bet like that with our own money. Um, so I just think, be careful, be careful. Um, there's certainly people who need that liquidity who need to be able to sell their house and stuff, but, um, you can just wind up upside down on a lot of houses. Great. Cool. I'm going to switch gears just a little bit. Okay. It's called simple, rapid fire. But before that, I just wanted to say that last night I was watching your Ted X talk in 2013 and you guys have gone through the archives when you're talking about Hudson's pure software, there's only 12% of pure software companies, fortune 500 and pure software usually, or I mean, you know how now if your software companies are actually, they're like, there are real. So I forget what you call them, which is in that you had, but it was a lot of pure software companies that have actually ventured into the real world, got Google's job camera on top of a car using Google maps to build a self driving car. That's exciting to me. You've got Amazon buying whole foods. You've got Netflix house of cards. You they're, they're not just an algorithm for recommending movies. They're hiring Kevin Spacey and other actors to movies. And so I just think that tech is going into the real world and changing the real world and exciting ways. And that seemed a little bit revolutionary back when everybody just wanted to make Instagram 13 people build an app and a billion people download it. Now you've got Snapchat, which is one of the last really pure media companies. And there's a question about whether it can compete at half a billion, monthly active users or half a billion. And so I think that more entrepreneurs are just going into the real world and doing really cool things. And technology is going to be part of that, but it's not the only party. Right. Eating. Yeah. All right. Now in terms of rapid fire. Okay. So in your opinion, what is the most important life skill? The ability? Well, at least it is for me because it's so easy to be a stuck up CEO. I think you live in this little fortress inside your brain where your child suddenly trying to defend what you did and other people are trying to help you. They're trying to tell you how to get better and you can't hear them because it's easy to get stuck up. It's easy to feel defensive. And I dunno, it just, there's so many virtues that are impossible to reach, right? Like I wish I were the worried or the Steve jobs was, I wish I had the brain of Jeff Bass. I was, I can't do those things, but anybody can be humble. And so that would be, I think the hallmark of our culture is that we're not going to be arrogant. We're just going to work hard and listen carefully and try to learn from what I've got to say. You're like, I've never met somebody that's so successful as chiefs so much and downplay myself. That much shows how humble you are. Oh, well, I'm kind of stuck up.
Speaker 3:[inaudible]
Speaker 1:That's interesting. So let's imagine you're a new addition to the crayon box. What color would you be and why? Well, my instinctive reaction is pink, uh, and it's because my youngest son loves pink and he just went to the playground and figured out that he's not supposed to love paint. And I've been on the warpath and said, it's totally fine. Um, so I feel like I need to embrace that. There. You're gonna say red
Speaker 3:[inaudible]
Speaker 1:How many books, but I don't know if this kind of like how many books have you read so far this year? 10, probably 10, um, favorites. I love Pachinko. It's this novel about a Korean family, over many generations in Japan. It turns out that lots of Koreans immigrated to Japan. He couldn't really prosper. There was sort of a racist society. And I don't know, it just, it's a tear jerker. It's uplifting. All the people are somehow good. She sees the good in everyone and it helps me see the good in people. Um, that's my fav, I wish there was some like business reason. I liked it, but I didn't like it.
Speaker 3:Okay. What advice that you would give to 15 year old glib?
Speaker 1:Just don't settle. I think you can settle for the wrong girlfriend or boyfriend. You can settle for a job that you don't really love. Um, it takes confidence to say, I think I can do better. I'm going to keep trying to break up with your job to break up with, whatever's making you unhappy to try to really go for a little bit of joy, a little bit of passion, a little bit of excitement. Um, but mostly I would say it's going to be all right. Um, I felt like the stakes were cataclysmic about which school I went to about what my first job was. And you can fix almost anything if you're willing to just say, wait, I don't want to do that. I'm gonna try something else. Um, that's probably what I had said. Don't show the last one is a quote you live by. I don't really have one. I know that there's supposed to be some maximum that I looked back, but I don't really have one. One of my favorites is, um, is from Ezra pound. Um, but I don't know that I live by it every day, but here it is. Um, he says that the fault lies all in the knock, them all in the defense that falter
Speaker 3:Thank you for tuning into this episode. If you enjoyed listening, please subscribe on Spotify or Apple podcasts and please leave a review so that we can better serve you. Take care, dream big, and we'll see you next Monday.