The Deed: Chicago

How this self-made millionaire went from janitor to real estate mogul, outselling the pros 100-to-1

Sean Conlon was born and raised in the small town of Rathangan in County Kildare, Ireland. His family of seven lived in a modest home of under 1,000 square feet. His parents struggled and, at one point during his childhood, a bank tried to repossess the house.

The experience taught Conlon to value the security of owning a home and perhaps set into motion his future career in real estate.

In 1990, he tells CNBC, he took the $500 he had saved and headed for the U.S. He landed in Chicago, where he took a role as an assistant janitor.

"I was an ordinary person who did some fairly extraordinary things. It's America. You can still do those things." -Sean Conlon, real estate mogul

After a couple of years of cleaning during the day, painting apartments at night and stuffing his earnings in a shoe box for safe keeping, Conlon had saved enough money to buy his first apartment.

"I understood fairly quickly that real estate is a tangible path to wealth," says Conlon, who is now 47 and the star of CNBC's "The Deed: Chicago." "I was an ordinary person who did some fairly extraordinary things. It's America. You can still do those things."

When Conlon started in real estate, the average sales price for a property he closed on was $20,000 or $30,000. But success motivated him.

He says he sold an apartment for $230,000 and the $4,000 commission "was the most money I'd ever made in my life" in one shot. He was bringing in an annual salary of $14,000 at the time.

Conlon started selling real estate at night, and in three years, he was one of the top brokers in North America. There was no secret to his success, he says: "That was through sheer work. I'd like to say I had some brilliant silver bullet. I didn't." He got up at 6:00 a.m., worked his day-job as a janitor and, in that pre-internet age, made cold calls in the real estate office until the wee hours.

Sean Conlon
Photo by Brandon Ancil, CNBC
Sean Conlon

Conlon got a job in a brokerage in 1993 where his hustle again distinguished him.

"I outworked all my competitors. I'd like to say I was smarter than my competitors, but I competed with guys who went to the Ivy League schools and they went to Harvard and Yale and Wharton over the years," he says. "They wanted to go home earlier in the evening. And I got an extra day's work done that night, so I was a day ahead of them the next week, and two days the following week."

Conlon started by picking 1 square mile of a neighborhood and became a master of the zoning laws and lot sizes there. "And then suddenly the circus came to town!" says Conlon. When the zoning laws changed and the Chicago real estate market started to improve, he was prepared. "I dominated. … Your average broker was doing $2 million a year, I was like $100 million to $200 million. So I was in the stratosphere."

In 1996, Conlon became a millionaire. He attributes his success to his hard work, preparation and willingness to move quickly when he saw opportunity. And in 2000, he founded Conlon & Co., a boutique real estate investment firm, and launched Sussex & Reilly, a high-tech real-estate firm he grew to over 300 employees.

Conlon eventually went back to school. He graduated from DePaul University with a Bachelor of Arts last June.

And his success has made him fiercely optimistic about the opportunities in the U.S.

"Kids growing up anywhere in the rest of the world, regardless of what you see in the news today, America still holds a place in most people's hearts and minds as the place where you can be anything," says Conlon. "And I believe after 26, 27 years in this country, it is still a country that rewards hard work. You can really make it here."