Glenn Kelman of Redfin on How Fortune Favors the Bold

October 3, 2017

3:50 pm

Selling your house is considered one of the number one stressors in life. And if you have small children and a full-time job, just go ahead and triple that stress level. Fortunately, companies like Redfin are redefining real estate solutions and streamlining transactions to help people buy and sell homes.

Seattle-based Redfin is a technology-powered real estate brokerage that represents people buying and selling homes. Founded and run by technologists, Redfin has a team of real estate agents who earn a salary and customer-satisfaction bonuses, not commissions. To date, over 10,000 customers have used their service each year.

Heading up this company is Seattle native and CEO Glenn Kelman who has seen a few lines of code in his time. Before Redfin, he cofounded Plumtree Software that was funded by Sequoia Capital, went public in 2002, and was acquired by BEA in 2005. At Redfin, he led the company to IPO status (RDFN) in July 2017, and told the world his goal to be the “Uber and Lyft of real estate,” and give customers more value by measuring their agent’s performance when purchasing a home.

Not only is Glenn active within the company, he can be found offering up the latest advice, news and happenings around Refin on his blog.

At Seattle Startup Week powered by Chase for Business, attendees will be treated to a fireside chat with Glenn on October 4, about Values-Based Leadership. Add it to your calendar here.

We had a chance to catch up with Glenn before his talk. Here’s his take on value-based leadership, life as a chess game and offers some words of wisdom to entrepreneurs.

How has Redfin’s approach disrupted the real estate industry to set it apart from the competition?

Redfin has built its own technology and employed its own agents, so that we can make the whole real estate transaction better and more efficient. This approach is operationally intense, it scales slowly, it limits profit margins, but it lets us pursue a larger market and deliver better service. No one else seems likely to do it, so we believe a combined approach creates a deeper competitive advantage than just building a website or a brokerage alone.

How has values-based leadership contributed to the success of Redfin?

We're in a seasonal, cyclical market. We had to survive the great financial crisis of 2008. If the only premise of Redfin was our financial success, and not our mission to make real estate better for regular people, no one would have lasted this long. Our sense of purpose kept us going through the hard times.

Why are supportive events like Seattle Startup Week important for the local ecosystem?

Seattle has had plenty of big tech companies from Silicon Valley and elsewhere set up shop here. It's easy to make plenty of money just working at Google or Facebook. But it's a lot more fun to start your own company. We should have a lot more startups than we do.

What lessons learned from Plumtree Software have you used as CEO?

I learned from our CEO, John Kunze, to give people room to run, and lots of support. I'm still learning that. I learned in the dot-com crash how fast you're expected to shift from growth to profits. I met a lot of wonderful people who now work at Redfin. And I learned to work very, very hard.

Talk about the importance of having a crazed sense of purpose for your business.

Even when I wasn't sure Redfin would succeed, my wife would always remind me that I should still be proud of what we were trying to do. We all wonder walking home each night whether our work makes a difference. We need to cultivate every day the story of why it does, and make changes in our lives when it doesn't.

Talk about Redfin’s diversity initiatives.

It's really about competing for all the talent the world has to offer. Most companies think of diversity as an initiative to hire more people of color or women. But our first project was to develop the infrastructure for people from all walks of life to succeed at Redfin: training, career ladders, manager check-ins, mentorship. This let us hire people who would have failed elsewhere, but created enormous shareholder value here. This let us scale the organization at a time when others were struggling to bring people on board.

Do you have an analogy that compares the game of Chess to startup life?

I played competitive chess. There's a saying, “long plan, wrong plan.” The tragedy of life at an early-stage startup is that you can't think as long term as you'd like because you're always about to run out of money.

A Chinese grandmaster last year was cut from the national team to make way for younger players. He competed in a tournament against those players, and annihilated them all. The tour de force game involved a sacrifice where he couldn't calculate whether it would actually lead to a win, but he knew that at the very least he could keep his opponent in perpetual check, leading to a draw. He sacrificed the major piece and then later found a way to win the game. The lesson from this is first that fortune favors the bold, and second that you can't always see how something will work out, so you just have to get to the next milestone.

This article is part of a Startup Week content series brought to you by CHASE for BUSINESS. Startup Week is celebration of entrepreneurs in cities around the globe. CHASE for BUSINESS is everything a business needs in one place, from expert advice to valuable products and services. Find business news, stories, insights and expert tips all in one place at Read the rest of our Startup Week series.


Did you like this article?

Get more delivered to your inbox just like it!

Sorry about that. Try these articles instead!

Tishin is a technology journalist and correspondent. She has written for TechCrunch, Demand Studios and Fitness, and has regular network segments on local Phoenix affiliate stations. She holds a Master's degree in Clinical and Sport psychology, and has covered many areas of technology ranging from 3D printing and game development to neurotech and funding for over 15 years.