Sean Conlon Talks CNBC’s ‘The Deed: Chicago’ and Making It in Real Estate

Sean Conlon

Sean Conlon has been called “the embodiment of the American dream” — a determined immigrant who worked tirelessly at two menial jobs before striking it big. Now a multimillionaire, Conlon is the focus of CNBC’s “The Deed: Chicago.” The reality show features failing real estate projects, investors facing financial ruin, and Conlon, a real estate mogul who invests his own money in the properties (and offers his expertise in real estate) in exchange for a percentage of profits from the properties’ sales.

But, while Conlon now flexes his chops as a real estate expert both on the show and through his business endeavors, he wasn’t always a high-rolling investor. Conlon was raised in Rathangan in County Kildare, Ireland, a small town with 900 people and 17 bars, which he jokes was his first experience with market saturation. But he always knew his future would lead elsewhere.

A diligent reader, Conlon was at the top of his class in school. Despite working several jobs, he was forced to drop out of college for financial reasons. So he moved to England and “applied for 100 jobs, and 99 of them said no” — but Lehman Brothers said yes.

Conlon says he was unsurprised that of all the banks in England, an American bank gave him his start. “Go to America and you can be anything; always I thought that growing up,” Conlon says. “I thought, ‘I’m going to be average in England, so I should go to America.’”

Once in the U.S., Conlon worked as a janitor. Actually, he corrects himself, an “assistant to the janitor, and I sucked at it. I was the worst handyman ever,” he says.

Although his days were filled with janitorial work, he took classes at night to get his real estate license. And with his newfound license, he continued as a janitor while cold-calling potential clients in his free time. “I was always one day away from wanting to give up, but I’d get a little sale and keep going,” he says. “It seemed like a useless talent until it wasn’t.”

Conlon’s business exploded. He focused on Chicago neighborhoods that were at the time just becoming high-end, such as Lakeview near Wrigley Field, and Lincoln Park. At one point in the 1990s, he was one of the top selling agents in North America, partnering with architects, banks and contractors to take people from development of a property all the way through to sale. He even financed a few projects himself.

In 2000, having burned out on the insane work hours and demands of being such a successful agent, he founded a brokerage firm. “Burnout is a risk, because [selling real estate is] such an emotional thing,” Conlon says. “It’s emotional for the seller and for the buyer, and they have a wonderful way of projecting that emotion on you if you care. And most good brokers care.”

He sold, bought back and re-sold again his first brokerage, Sussex & Reilly. Now, he owns Chicago-based CONLON/Christie’s International Real Estate, which does about a billion dollars a year in residential sales and about half a billion dollars in commercial sales.

With numbers like those, Conlon obviously has found financial success. But, he says he doesn’t feel wealthy. “I will always feel poor. I won’t ever think I’ve ‘made it,’ which is probably what makes me, me,” he says. “I will spend two weeks in Malibu, but work out at 5 a.m. and then spend four hours on the phone.”

Conlon still works quite a bit, but he loves to travel and is dedicated to the Conlon Wildlife Fund. “Some day I’m going to buy a boat,” he says. “I said that in 1997 when I was interviewed, so I’m being consistent.”

How does one become a success in real estate? Conlon shares his insight and advice:

Make It Better: What made you such a success in real estate? Did you just get lucky?

Sean Conlon: People wonder why I’m so obsessive at work and why we have double and triple redundancies. I am the least lucky person you’ll meet. If it can go wrong, it will. I have never been lucky. I work incredibly hard. All the clichés become truer as you get older. You get lucky if you’re in the ring. You have to be up and at it.

Why do you think others should consider investing in real estate?

Real estate is an amazing opportunity [in which] most people who consider themselves ordinary can achieve things on an extraordinary scale. By comparison, I am pretty sure that the two of us have a better chance of being hit by the same meteor than creating Facebook. But real estate still is the land of opportunity, just like America.

In regards to real estate development or flipping, what’s your best piece of advice for someone looking to get started?

Trust but verify, meaning contractor costs and costs of materials. On your first flip, assume that your construction costs will double and the amount of time you estimate for completion will double! That is somewhat tongue-in-cheek, but your costs will be way more than you anticipated. Also, be a developer, not a designer. No one cares about your Versace wallpaper!

Can someone be a part-time real estate investor and be successful?

No. To be successful in the industry, like any other, you need to commit 110 percent to the deal. As an investor, no one will treat your money like you will. You need to show up every day!


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Megan Craig has been a journalist for more than a decade, writing and editing stories on a variety of subjects. Most recently, her writing has focused on real estate trends in the Midwest and around the country. She lives in Chicago’s Printers Row neighborhood with her roommate and a few too many cats.