“The Deed: Chicago” Star Sean Conlon Shares His Insider Guide To The Windy City

Sean Conlon Photo Credit: Conlon & Co.

On “The Deed: Chicago”, multi-millionaire mogul Sean Conlon signs on to help struggling small-time Chicago developers avoid disaster. Flipping may be a fast track to the American dream, but it’s a high-stakes gamble to take these troubled projects to payday. Profits can quickly turn to dust, but with a partner like Conlon, lives and fortunes can change with just one deal. Here, Conlon shares how you can make that deal, how he made the American dream happen for himself (he started his career as a janitor!) and how he has made a name for himself as one of the most prolific sellers of residential real estate in the country, as well as his favorite spots to eat, drink, relax and be merry in the Windy City in advance of his show’s March 4 premiere.

Sean ConlonPhoto Credit: Jeff Schear/CNBC

Walk us through the series and your role within the series.

I essentially give struggling developers a lifeline, investing his money, time, and expertise to help them revive their floundering projects. I roll up my sleeves and share in their frustrations and their accomplishments while working as a team to ensure they don’t lose their money (or mine!).

How did this come to be? Did CNBC approach you?

It actually goes all the way back to 1990 when I became friends with Bob Teitel. In 1994, he told me that he was trying to do a movie, and he’d giving up because he was $10,000 short. I wrote him a check for $5,000 or $7,000. I got my money back, he made movies, and in 2010 he was working on something at CNBC and said: “Why don’t you be my adviser.” Eventually CNBC wanted a real estate show.

Have the businesses you showcase on “The Deed: Chicago” been saved from financial ruin?

A lot were never thinking they’d be able to break even when I met them and many were able to thrive as a result of the show and our work together.

What are the most important business strategies you’ve learned over the course of your career that can help real estate moguls in the making succeed?

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!

Sean ConlonPhoto Credit: Robin Marchant/CNBC

You started your career as a janitor. Let’s talk about the in-between then and now. How did you push yourself to make it to where you are today? Did you get lucky? Was it seriously all perseverance and hard work?

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. In 2008, my company Conlon & Co. was part of a larger fund that had provided mezzanine equity for over $1.2BN in real estate construction all over North America… Let me tell you something, when they tell you leaders are inspired by mountaintops and matured by valleys; I spent four years in the valley of death. Fortunately, my partners and I were able to rescue of all of the investors and my capital on the construction projects which was unheard during that time. I survived it and it taught me a valuable lesson, that if you get up every day invariably the sun will rise and that one needs to always prepare for the worst possible outcome and then hope and work for the best!

When did you realize that there was a full-time career in flipping, and how did you become good at it?

I taught myself everything about a neighborhood and one day I saw a guy building three apartments to rent, and I asked him if I could sell them as condos. He said they’d never sell. Well, I sold them in one week and I thought: “What if we could tear loads of buildings, build condos instead and sell them.” I walked up and down the streets and put contracts under people’s doors offering to buy buildings for teardowns. I sold thousands of properties between 1993 and 1999 — probably $100 million to $200 million a year.

Is the Chicago real estate hot at the moment? Is it a good time to buy or no? If so, where are the hottest areas?

Prices continue to move in a positive direction and Chicago is witnessing more residential tower construction than any other U.S. city when it comes to construction cranes. Midwest cities, like Chicago, will continue to be a hotbed for millennials so it remains a great city for investing, particularly around the West Loop.

What do you think is the true secret to your success?

I work hard, I prepare and I have a willingness to move quickly when I see an opportunity.

Sean ConlonPhoto Credit: Robin Marchant/CNBC

How long have you been in Chicago: Since the 90s.

What is your favorite neighborhood: Gold Coast, especially in the summer. I also love Lincoln Park, off of Armitage Ave.

Occupation: Founding Partner at Conlon & Co.

Favorite Restaurant: Gibsons in Gold Coast, the end table outside is the best people watching in the world, during that time of year.

Best Sushi: Shine Sushi is my go-to take out place.

Best Steakhouse: Chicago Cut has the best steak in the city and its run by a Dubliner.

Best place for a romantic date: Bistro Zinc – French Bistro that just closed, but I was friends for a very long time with the owners.

Best Lunch: My lunch usually consists of a piece of salmon in my office between meetings but if I am meeting someone, I like Gibson’s Italia, especially with the retractable roof in the summertime.

Best Dessert: I avoid desserts at all costs now! The pounds don’t come off as easily as they once did

Best Sunday brunch: LuxBar

Best place for a power business meeting: Brisk walk in the park through Lincoln Park Zoo. It tends to really put the business meeting in perspective.

If you have out of town guests, which hotel would you recommend: The Talbott Hotel on Delaware Place, one of the best boutique hotels in Chicago that I own with Sterling Bay.

Favorite shopping venue/boutique: Nordstrom

Favorite place to buy jewelry/watches: I’ve worn the same Breitling watch for 25 years so not much help in this department.

Best Spa: The Spa at Trump Chicago

Favorite Charity Event: After School Matters Gala founded by former Chicago First Lady Maggie Daley

Favorite Cultural Event: Of course Chicago is known for it’s massive St. Patrick’s Day Celebration in March but the Irish American Heritage Festival in July is one I highly recommend.

Favorite Cultural Institution: Chicago Cultural Center is one of my favorites. Not to mention it’s brilliant architecture with one of the largest Tiffany domes in the world.

Best Gym/Athletic Facility: Nothing beats an old fashion run along Lake Michigan. No matter what time of the year, it is always beautiful and helps clear my head.

Best Massage: Urban Oasis

Best Limousine/Driving Service: Limousine service give us better deal

Best Museum/Exhibit: The Art Institute of Chicago. One only has to travel around the world once to realize it has one of the most amazing collections, particularly for impressionists. I am an avid art collector.

Favorite historic/legendary place to see or explore: I tend to love graveyards and Chicago has some amazing ones with incredibly well known people. One in particular I love is Graceland Cemetery on Clark Street. Charles Dickens youngest brother is buried there.

All-around favorite spot in Chicago: I love to sit by the lake behind the golf course off Addison Street. I sit there in the summer after long runs and watch boats come and go.

Describe Chicago in three words: Muscular, American & Bold

Best Aspect of Chicago: Chicago is still the most authentic American city but the perfect product of every immigrants’ dreams that came before us.

Sean ConlonPhoto Credit: Jeff Schear/CNBC