Sometime in the early ‘90s, during Sean Conlon’s heady days as a rising real estate star in Chicago, he bumped into his old friend Robert Teitel. Conlon had risen in his station considerably since the two had last met — he was driving a shiny new Range Rover down Southport Ave. when he spotted Teitel. “I said, ‘Hey, Bob, what are you doing?’” Conlon recalled. Teitel, now a well-known filmmaker, told Conlon he was working on a movie but had run out of money. So Conlon pulled out his checkbook and wrote his friend a check for $10,000 on the spot. Because that’s what friends do.
Fast forward about 27 years and Conlon — an Irish immigrant whose dizzying success as a real estate broker, owner and entrepreneur has made him a legend in Chicago — is now a reality star, thanks to his old friend.
Back in 2010, Teitel had pitched an idea about real estate to CNBC and reached out to Conlon for advice. That led to an introduction to CNBC Executive Vice President Jim Ackerman, developer of “Deal or No Deal,” “Celebrity Fit Club,” and “The Deed,” among other shows.
Speaking on the phone a week before the second season of “The Deed: Chicago” was about to air, Conlon made it clear he is not pursuing celebrity. “I have no interest in fame,” said Conlon in his thick Irish brogue. “I’ve done enough in life without wanting that. I guess it’s a nice way to pay it forward a little bit. I pretend to be a curmudgeon, but I enjoy helping people.”
Specifically, Conlon’s role on the show involves helping house flippers and developers who’ve either run out of money or who need support and mentoring. Whether they’ve overspent for the neighborhood, miscalculated costs, experienced unwelcome surprises during construction or been bamboozled by contractors, Conlon’s role on “The Deed” is to offer some sage advice — and often, back it up with enough cash to keep the project going. “Home flipping can be an incredible nightmare,” Conlon said. “It’s a wonderful feeling to help get people out of trouble.”
While the days of making easy money flipping homes in Chicago may be behind us, it’s still possible to make it work, Conlon said. “We are late in the cycle right now, so flippers who jump in part-time are going to have problems. The margins are too thin for that,” he said. But still, he added, “There’s no question: Real estate is still the greatest way for an ordinary person to make money in America. Just don’t expect to get rich on your first deal. Consider it a down payment on your education.”
While Conlon still has some skin in the game in Chicago — including Conlon & Co., a modern-day merchant bank he owns in partnership with minority shareholders, former Chicago Mayor Richard Daley and his son Patrick — he is no longer a Chicago resident. Aside from London, Conlon calls Palm Beach home these days. Still, he has thoughts on the strengths and weaknesses of the market in the capital of the Midwest.
“Property taxes are the biggest problem in Chicago, and there’s no clear solution,” Conlon said. “We’re dealing with something that began in the 1920s. They just kicked the can down the road, so there’s a level of uncertainty we have here. Chicago is incredibly undervalued because of that uncertainty. I love Chicago and own a lot of real estate here. It’s an incredible city that sits on a beautiful body of fresh water. We built beautiful buildings here.”
Like anyone who’s built a real estate empire, Conlon has seen his share of losses, especially during the housing crash. “I got hammered in 2008,” he said. “I had lent out a lot of money, and for a long time, there were serious losses. The irony is that I hadn’t borrowed any money.”
But Conlon rolled up his sleeves, doubled down, got a partner and did what he’s always done to make things happen: He relied on the personal ties he had forged over time to help rebuild his fortune.
“My business today is based on relationships I built over a quarter of a century,” he said. “I don’t care how high-tech you are, you’ll always need people. You know the saying, ‘The bank is the guy who will give you an umbrella and ask for it back when it rains.’ I survived the downturn because I had relationships at the banks, and they worked with me.”
As he spoke, Conlon was about to become godfather to Teitel’s son. “My greatest successes in life have come from the people I met and the relationships I have,” he said. “I tell all brokers, ‘Treat everybody as well as you can. Treat everyone as a future relationship, because you will meet each other again and again.’”