Sean Conlon: Then and Now

Nearly three decades ago a young immigrant janitor, Sean Conlon, rocketed to the top of the Chicago’s real estate market which has now parlayed into a national platform and even his own TV show on CNBC. These days, against the odds, he’s still on top

Twenty-eight years ago, a twenty-something Sean Conlon pushed a mop. He’d just emigrated from Ireland and took a janitorial job, cutting grass, shoveling snow and painting buildings. Within a few short years, through grit and sheer ambition, Sean Conlon clawed himself up becoming Chicago’s most successful real estate agent ever. He sold a jaw-dropping $55 million worth of new construction condos in one year; he had the Jaguar to prove it. 

Sean Conlon’s meteoric rise to the top of Chicagoland’s real estate world launched an auspicious and unexpected career. From janitor to real estate mogul to television star, one thing is clear: Sean Conlon continues to push the envelope, then and now.  

“Daddy, I’m going to go to America and be a millionaire,” Sean Conlon told his father as a child in County Kildare, Ireland. Conlon was one of five children born to a bus driver and dreaming father and a kindergarten teacher mother. He went to college for two years before dropping out, spent a short time at Lehman Brothers, and realized one day that his life wouldn’t change without changing it for himself. He packed a suitcase and headed to America.

“I was a terrible janitor,” Conlon says about his stint as a janitor’s assistant. By day, he shoveled and painted. But soon, by night, he was dabbling in real estate. Within a mind-boggling few years—through caffeine and 100-hour workweeks—Conlon was selling over $200 million annually. He did his homework, entered Chicago’s market at a fortuitous time, and carefully cultivated long-term business relationships. 

Sean Conlon soon launched Sussex & Reilly, a high-tech high-touch, 300-employee brokerage where every employee carried a Blackberry. The group’s sales volume surpassed $1 billion in short order one of the fastest growing high-tech companies in the country.  Conlon subsequently ended up selling this company twice.  Concurrently in 2000, he established Conlon & Co., a boutique real estate investment firm. Conlon founded a $100 million mezzanine fund and a $50 million opportunity fund that acquired distressed property during the bust of 2008-2011. In 2009, he introduced CONLON: A Real Estate Company, and in 2012, CONLON Commercial. The combined brokerage has closed over $4 billion in sales over eight years. In 2016, Sean debuted Conlon Capital, a firm which originated $750 million in commercial real estate mortgages. These days, CONLON is the only real estate affiliate of the renowned Christie’s Auction House in the Chicagoland area. 

As successful as Sean proved himself in real estate, he’s also become a media darling, starting with a prominent article in well-known Chicago Magazine. In the article, author Ted Allen wrote a profile of Sean, "Birth of a Salesman”, highlighting his Cinderella-like rise to the top of real estate. Conlon had struck gold quickly, capturing a curiosity that's continued across venue and media ever since. These days, after regular appearances on CNBC and other networks, he earned the opportunity to star in his own show, “The Deed: Chicago,” which debuted in 2017. Seen nation-wide, Sean mentors and sponsors stressed developers who are in over their heads by bringing his savviness, experience, and resources to save them from financial ruin. 

Just as he transforms derelict properties into sound investments, Conlon has reinvented himself over the years, building a fortune from humble beginnings. He’s become the best in his field, inspired others, and created a national brand. Such radical transformation over three short decades begs the question: What’s next for Sean Conlon?


20th Anniversary of the article "Birth of a Salesman" in Chicago Magazine.

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