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From his start as a “pugnacious” young exec to recent appearances on reality TV, Kelman has given the real estate community many memorable moments to reflect on as he prepares to leave the industry this week.

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For two decades, Glenn Kelman has been at the helm of real estate tech company and brokerage Redfin.

On Tuesday, he announced that he would be leaving the company to pursue endeavors outside of real estate. His departure comes about six months after Rocket bought Redfin in one of the industry’s most notable recent mergers.

During his many years as a public figure, Kelman has both made enemies and won hearts with his enthusiasm for the company he helped build — and simply for his all-around energy.

As he says goodbye to an industry he helped shape, Inman looked back on some of Kelman’s most memorable moments. It’s not hard to see why Kelman won’t quickly be forgotten.

The 60 Minutes appearance

Screenshot of Glenn Kelman on “60 Minutes” in 2007

In 2007, about two years after starting his career at Redfin, Kelman was featured in a 60 Minutes episode as a young CEO ready to shake up the old guard real estate establishment.

As part of the episode, a crew from 60 Minutes filmed a heated debate at Inman Connect New York between then-Realtor.com executive Allan Dalton and Kelman over commission rates. The atmosphere was tense, and Brad Inman later described the debate as “like the sound of your garbage disposal when a couple of cherry pits rattle around the bottom.”

The moment helped Kelman earn a reputation as a rabble-rouser willing to criticize legacy companies and the status quo.

On taking a stand and taking his place

Glenn Kelman at Inman Connect San Francisco in 2005 (Photo credit: Erik Hersman)

Over the years, Kelman evolved into a gregarious, respectful debate opponent — and noted that his tone has softened, even if his convictions remain as strong as ever.

In 2018, for example, Kelman told then-Inman reporter Patrick Kearns that he regretted being quite so “pugnacious” during the early days of his career. His attitude began to change when, years ago, he had lunch with Matt and Joe Deasy — leaders in Windermere’s East office — who showed him how much they care about consumers too.

“And I just felt, I could imagine them, every time I talked about a traditional real estate agent or a competing brokerage, instead of it being a faceless competitor I imagined those two people who are brilliant and principled,” Kelman said. “And that’s when I began to feel like I could take my place in the industry. I think for a long time I had been just a little crotchety, a little brash and out of line.”

During the same conversation, Kelman added that he struggled between taking a public stand on general political issues versus sticking to topics more closely related to real estate. But either way, the struggle captured Kelman’s early willingness to put his name behind causes he sees as righteous.

“People who are moving, that is a real estate issue, housing and affordability is a real estate issue. Providing the same level of service to white people and black who are trying to buy a home is a real estate issue. And I on all of those issues, I just think that there is a place for us to stand up…”

Becoming a reality TV star

In the fall of 2022, Kelman became the star of Netflix’s Buy My House.

Modeled on Shark Tank, Season 1 also featured Corcoran Group’s Pamela Liebman, NFL linebacker Brandon Copeland and broker Danisha Wrighster. The general premise of the show was that American homeowners could pitch their homes for sale to the real estate “tycoon” stars, in the hopes of making a winning deal.

Over the course of the season, Kelman told Inman, he developed a friendship with Liebman, whom he hadn’t known well previously.

“That was a really fun partnership between me and her because I was often the one hemming and hawing and looking at the numbers,” Kelman recalled, “but she was the one playing the room and observing the emotions of the seller.”

Kelman added that “Pam and I were pretty comfortable with this idea that sometimes it’s going to be competitive, and sometimes we’d work together. Sometimes we split deals if she had a vision for a development.”

An outspoken voice in the industry

Glenn Kelman of Redfin. (Photo credit: AJ Canaria of MoxiWorks)

Kelman’s penchant for speaking out on major issues has, over the years, become one of his signature characteristics — and has set him apart from more reticent business leaders.

In 2021, Kelman and Redfin, alongside Realtor.com, called on other real estate websites to join them in dropping their crime data for listings. They cited fair housing concerns, as well as the varying ways in which people evaluate safety and crime in any given neighborhood.

As racial tensions increased across the U.S. in the late 2010s, Kelman also pledged to hire more agents of color to help address systemic inequality in homebuying.

And more recently, Kelman has championed the National Association of Realtors’ Clear Cooperation Policy. He has argued that it is in consumers’ best interest to see the maximum number of home listings possible, and has framed the rule as a way to avoid a spiral of real estate monopolization.

“No matter how the rules on pocket listings change, Redfin will adhere to those rules, using the same competitive weapons that our competitors use against us,” Kelman wrote in an Inman op-ed prior to NAR releasing its delayed marketing exempt listings option. “Redfin, like the vast majority of brokerages in America, would much prefer that the rules treat listings as a sacred trust, marketing properties to benefit buyers and sellers, and in a way, that’s fair to brokers big and small.”

Email Lillian Dickerson

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