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10 Leadership Lessons from the CEO of Redfin

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Buying a house as an investment or as a place where your family is going to live is as big of a purchase as many people will ever make in their lives. Seattle-based Redfin set out 15 years ago to create a combination tech company and a real estate brokerage to make the industry work better for customers and agents. The technology-powered real-estate company generated $1.9 billion in revenue in 2021 — a 10x increase from 2015. Since launching in 2006, it has saved customers more than $1 billion in commissions. Despite a volatile housing market, it currently boasts 53 million average monthly users on the website and app, serves more than 100 markets across the US and Canada and employs more than 6,000 people.

Related: Free Webinar | September 13: How To Build A Billion-Dollar Business

For my latest episode of entrepreneur‘s Leadership Lessons series, I had the opportunity to speak with Redfin CEO Glenn Kelman. Before joining the company in 2005, he was a co-founder of Plumtree Software. In his seven years at Plumtree, he at different times led engineering, marketing, product management and business development; he also was responsible for financing and general operations in Plumtree’s early days. Before that, Kelman was one of the first handful of employees at Stanford Technology Group, a startup that was acquired by IBM.

“I started as a web expert, not a real estate expert,” Kelman said during our conversation. “I had no idea how to build such a large organization, but along the way, we’ve learned a lot of valuable lessons. It’s been a wild ride.”

The Seattle-raised leader is one of the most authentic, energetic and unflinchingly honest CEOs I have ever met. He graciously shared 10 valuable leadership lessons with me during our hour-long talk:

1. Business can be a force for good.

Kelman describes himself as an “ex-hippie from UC Berkeley” who thought business was a force of evil as he set out to better the world post-college. How do you improve the world without some kind of business interaction? “That dichotomy made me miserable for the first decade of my professional life,” Kelman admits. But he soon realized that business is only as good or bad as the people who drive it. “An enterprise can give people a common sense of purpose, a sense of belonging and a way to express their ideas and abilities. Most important, we need the industry and commerce of humanity to solve the world’s problems.”

Related: How This Tech Leader Found Her Voice and Took the Reins of a Major Company

2. Find a support group that knows your value and continually pushes you to realize it.

Kelman’s friends and family never gave up on him. “I was always encouraged and told that if this doesn’t work, I can try something else. It’s never too late to find something you really believe in.”

3. A leader’s path isn’t always in a straight line.

Kelman says he’s thankful for his post-college years of searching for his dream job, including writing a novel and considering a medical career, as these experiences helped develop him into the person he is today.

4. Not everyone has to be Steve Jobs. Just be yourself.

When a friend told Kelman, “You are not Steve Jobs,” he took it as an insult that he wasn’t as brilliant, creative and innovative as his hero. But after taking a step back from the statement, Kelman understood that what his friend really meant was, “Only a genius can be a genius. But any leader can be respectful and kind.”

5. Focus on what customers need and want versus trying to please Wall Street.

Investors have fickle demands. Trying to please Wall Street can tie a leader into knots. The best bet is to tell investors who you are, how you are going to make your customers happy and how that will lead to profitability. “It takes a mature person to be a good leader, because the hardest business problems are often not technical, but rather questions of the soul and heart,” Kelman says.

Related: ‘Everyone’s Got a Story of How the Healthcare System Has Fallen Short.’ This Founder Is on a Mission to Change That.

6. A CEO should love their company more than anyone else.

“If someone was more ambitious for the company, or believed in our mission more than I did, how could I possibly be better qualified than that person to run the company?” Kelman asked me. If self-interest and the biggest paycheck led to you running the company you are running, there will be friction down the line.

7. Don’t let your level of self-esteem ride up and down with the ebb and flow of your finances.

There are always going to be times when war chests are full and other times when cupboards are bare. Your job is to get out of bed and bring the future to life, whatever the current standings.

8. Get enough sleep.

Remembering and tending consistently to the bottom-line fact that you’re a human and that you need things like proper sleep, exercise and time with family and friends will make you the best person you can be and — by extension — the best leader you can be.

Related: What Has This 100-Year-Old Business Done to Ensure Its Longevity? Its CEO Follows These 7 Leadership Principles.

9. We all want to be the smartest person in the room, but the best and most valuable trait for a leader is to be humble.

“That’s a skill that’s accessible to all of us,” Kelman says. “It’s one where you can get an ‘A’ for effort. If you let other people flower, you will build a much larger and more successful organization.”

10. A CEO should be the “great exhilarator.”

Writer Robert Louis Stevenson’s wife compared life with him to having lunch on a volcano, but she married him anyway because he was the great exhilarator, Kelman says. “A CEO’s employees will stick with a great leader for the same reason. You can’t be volatile as a CEO, but you can be — and have to be — emotional when the emotions are big and good. You have to make the people you lead feel something big and good.”

For more from my time with Kelman, watch the full webinar here. The growing collection of episodes from our series gives readers access to the best practices of successful CEOs from the biggest brands, including Wayfair, Foot Locker, Heineken, Headspace, Zoom, Chipotle, Warby Parker and ZipRecruiter.

Related: The CEO of Wayfair Has Helped Revolutionize Digital Shopping for 20 Years. Here’s How He Handles Rocky Economic Conditions.

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