Before they were brokers, they rapped and skateboarded

Agents and brokers often don’t start their careers in real estate. 

Teachers and retail workers are typical of those who make career pivots into property. But some brokers — like these five — come to the business from more unusual backgrounds. 

The Rapper

Terrance Harding
Compass’ Terrance Harding

“… don’t let them hold you down, reach for the stars.”

Compass agent Terrance Harding was no struggling rapper when he turned to real estate in 2006. 

He was, and still is, a member of Junior M.A.F.I.A. under the moniker MC Klepto, performing with and mentored by the Notorious B.I.G. in the late ‘90s.

“We were one of the premier hip hop groups,” Harding said. “We had gold records, platinum albums. We toured with a lot of top people. It was a crazy time. We traveled the world. That’s when MTV was big. We did a whole lot.”

By 2006, Harding wanted to get out of his recording contract.

“Everybody in the music industry back then had a totally horrific contract,” he said. “Snoop Dogg says how he wrote all of ‘The Chronic’ and he didn’t get paid. Nobody really knew that. 

“I left the business due to bad contracts. I didn’t know what I was going to do, I could have been a sanitation person, I could have been a postal worker. I had no clue. I happened to see a sign…I saw a sign, I really saw a physical sign, ‘Get your real estate license in one week for $199.’ It was a gig billboard on a building in Brooklyn.”

Harding listened to the sign. He got his license and started working for Mark David in Soho.

“I guess it was rap arrogance, when I first got there, I told them, ‘I’m going to be the top agent within the company within the next year or so,’” he said. “They looked at me like I was crazy. I started in the middle of ‘06, and by the end of ‘07 I was the top agent.”

Harding sees similarities between rapping and real estate.  

“When I became the top agent, everyone started coming at me: Brown Harris, Elliman, Corcoran – like the record labels,” he said. “When an artist makes a hit record, all the record labels start coming at you. The big deals, those are your hit records, the clients are like your fans and it’s all the same thing. 

“I was in heaven, you get to have fun and you get to be successful and do what you got to do. I never thought I would find something that I would like as much as music as well. And I just ran with it.”

The Professional Skateboarder

Tim Gavin
Coldwell Banker’s Tim Gavin

Broker Tim Gavin was 15 when he dropped out of high school to become a professional street skateboarder.

“A lot of sacrifices came into it: school, a formal education,” he said. “But I was lucky. I had a passion at an early age. I was blessed with a passion.”

Gavin, who was born in Boise, Idaho, moved around with his family — his father was in the U.S. Air Force — before falling in love with skateboarding in Phoenix at the age of 8.

He eventually made his way to Hollywood, paying a friend named Dune $200 a month to live under his dining room table.

Gavin met director Spike Jonez in the early ‘90s and began making skateboarding videos. Gavin established several apparel companies that built up $125 million in annual sales by 2011, when he sold them.

Gavin, now 49, says he’d always been interested in interior design. In 2014, he got his real estate license in 2014.

“I remember joining the Keller Williams team, and they asked me, what do you want to sell? Eight million?” he said. “I told them, ‘I’m gonna sell $25 million. That year, I ended up selling $32 million.”

He’s now paired with Donovan Healy at the recently formed Healy Gavin Group.

The Voice of Chicago Sports

Tim Sinclair
@properties’ Tim Sinclair

@properties agent Tim Sinclair is the stadium voice of the Chicago Bulls, Chicago Bears and Chicago Fire, a job he adores.

“It was never in my sights,” he said. “I never would have imagined that’s where I’d land. To me the Chicago Bulls introductions are the best in the history of sports, and I know I’m biased. I guess you could say it’s a dream come true, but I’m too naive to even think that was something to dream about.”

Sinclair is in his fourth season for the Bulls and the Bears and his 10th for the Fire. He’s in his ninth for the University of Illinois basketball team.

He got his start in radio in the Midwest  before landing a job as a public address announcer at the University of Illinois for its Olympic sports — swimming and diving, gymnastics and wrestling. He honed his announcing voice as he went. 

Then, while he was buying a condo in Chicago, his real estate agent asked him if he’d like to be a member of his team. 

“I’ve always been interested in home design, planning and space and how it makes people feel,” he said. He even studied architecture in college. “Five or six times in the last 20 years I’ve thought about getting into real estate because I think I’d do a good job. I’m personable, I enjoy space and how it makes people feel.”

So when his agent asked, he jumped at the opportunity.

“Once my super busy sports season was over, I said, ‘Let’s do this,’” he said.

Sinclair says his real estate career is going well. He’s been at it six months, and he’s made a couple of sales while keeping up work in Chicago sports.

“The market is not great for anyone,” he said. “I feel great about it, but ultimately the real estate world is going to be somewhat seasonal because of seasonal sports. This week I’ve got seven events in eight days. That involves a lot of time and travel and all kinds of stuff. I love what I’ve been able to do so far.”

The Former Journalist

Sandy Edrys
Keller Williams’ Sandy Edry

Keller Williams agent Sandy Edry’s last stint as a journalist was for the print edition at Newsweek in 2006. Deep in debt and divorced, he decided it was time for a change.

“I saw the proverbial writing on the wall for print media,” he said. “There were constant buyouts or layoffs, and by that point, I was a little disillusioned with the industry.”

He thought he might write a book, but apartment hunting captured his interest.

“You can’t live in New York without being fascinated with real estate. It’s our version of porn. I said I will try it for six months. Worst comes to worst, if I hate it I will have a great article or book to write about the seamy underside of Manhattan real estate. That was my expectation. Once I got in, the weirdest thing happened, I actually fell in love with it.”

Edry says there are two major transferable skills between journalists and real estate agents.

“As journalists, we’re storytellers, so when I walk into an apartment or a new development or whatever else I’ll be working on, that’s just where my mind goes,” he said. “I look for what is the story of this property that is going to make it appealing to the next buyer. That takes me down some unique spots.”

Second, he knows how to ask the right, open-ended questions.

“Real agents love the line — which I find demeaning to our industry — ‘Buyers are liars,’” he said. 

Edry says he tells his agents that the worst day of their career will be when they’ve worked with buyers for months and then get a call that they’ve gone with another apartment two neighborhoods over.

“That’s just a lack of asking the right questions,” he said. “What’s their true motivation? Why do they want to be in that specific area? If I know that, the type of social life they’re looking for, then yes, I am going to show them what they want. 

“But after they’ve seen that stuff, I’ll tell them, ‘I know you wanted to be here, I heard you want to be in this neighborhood because it’s got great activities for kids, but have we gotten further enough in our relationship where you trust me to check one apartment I want you to see?’ 

“More often than not it opens up more opportunities and areas to explore with them. They feel closer because I get them. I understand them at a deeper level than they thought.”

The Rock Singer


Brown Harris Stevens agent Amelia Gewirtz has been writing music and lyrics since she was a child.

When she was in elementary school, her cantor invited her to be on his rock ‘n roll records. Gewirtz majored in art at LaGuardia High School and was in a couple of bands, including one that passed up the chance to open for The Ramones.

“We never rehearsed, we actually turned that down,” she said. “Not the smartest thing we ever did.”

While her artist friends were waiting tables, Gewirtz tried real estate.

“It was a naive thing, but in my first two weeks, I sold two apartments,” she said. “I’m a very big believer that positive thinking brings positive results.”

Gewirtz also stuck with music, forming Amelia’s Dream, recording several albums with songs that have appeared in televisions shows like “Dog the Bounty Hunter” and movies like “Wishmaster 4.”

“I named it Amelia’s Dream because I had turned down so many opportunities,” she said. “Even when I was 14, RCA wanted to meet me and I didn’t go. Just insanity that I did that. So Amelia’s Dream just to keep my eye on the prize.”

Gewirtz says the band got as far as it could go without “being everywhere.”

“One of the things that made me shift more toward real estate is we had 20 songs on Disney Channel. It was my lyrics, my voice, co-writing, my husband’s music — and we got a check for $362.” 

Her skill in the arts  —  she’s also a deft watercolor artist — are particularly helpful in real estate, as she provides free staging for sellers, and her songs have helped sellers move their properties.

She has “channeled” a special song just for the seller of a particular property, like one at 35 West 82nd Street.

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