Sean Conlon Talks ‘The Deed: Chicago’ And The Importance Of Cultivating Relationships

THE DEED -- Riverdale, IL -- Pictured: Sean Conlon -- (Photo by: Tasos Katopodis/CNBC)
The Deed: Chicago returns for its second season as multi-millionaire mogul Sean Conlon guides and aids developers in their respective projects. Flipping an investment property for a profit can, at times, be a promethean task, but Conlon’s business acumen should help these folks find greener pastures. During my chat with Conlon, he talked about the keys to his success and why he will always remain loyal to the Windy City.

THE DEED — Chicago — Pictured: (l-r) Sean Conlon, Bryan Sonn — (Photo by: Jeff Schear/CNBC)
Is turning 50 just a number (Conlon turned 50 last year)?

It’s interesting because I never thought about turning 50. Life goes in a blink of an eye. It’s not something I celebrated big. Quite interestingly, I threw a fundraiser for Joe Biden with Jim Chanos, who’s a regular on CNBC and he’s one of the greatest hedge fund managers in America. He’s the guy who broke Enron. So that’s what I did on my 50th birthday.

It’s a number at this stage. It’s been an amazing half a century. My life has been a fairytale and sometimes a Brothers Grimm fairytale with all the ugly bits but it’s a number.

THE DEED — Chicago — Pictured: (l-r) Mark Ainley, Sean Conlon, Bryan Sonn — (Photo by: Jeff Schear/CNBC)


The Deed Chicago, deals with properties and investments, but the a big part of the show’s focus is on your relationships with these people people.

It always is about people. What did 50 tell me? Fifty told me that relationships are even more important than I ever imagined. It is easy to make money short term and sometimes you will win short term. The most success I’ve seen in the last couple of years has come from relationships I’ve had for over a quarter of a century in business. You can’t underestimate it.

Even on the show, I was willing to do more for people I genuinely liked and trusted. There is a couple of people, but there is one person in particular – after the show, I lent her money for her to figure some stuff out on a handshake. And she paid me religiously every month and came to the office with the money.

The thing I realized at 50 is people are absolutely the most important thing in the world. You can have your high tech, which of course we all embrace, but there are always people involved. We are involved in everything. So yes, relationships are by far the most important thing ever. Period.

Can you talk about the keys to your success? Is part of it that you won’t be outworked?

I would say absolutely. I was famous, infamous, whatever the world should be for outworking everybody. But I had to. I might have been the smartest kid in high school, nobody knew I was like a duck. I was really (showing strength) on the surface but I was paddling furiously underneath. It was the same sports – I was good in sports but no one knew how hard I tried and practiced on my own.

I think there is no silver bullet to success. It is hard work. But then the other magic that people miss is consistency. And complacency is a great thing to touch on. We all get complacent. I nearly went down in 2009 and not because I got lazy, but I got complacent and I wasn’t watching and I didn’t know where things were. So consistency of behavior is such a key to success. So I am incredibly consistent in everything I do. Hard work and consistency is a recipe for success. 

You have invested a lot of your life in Chicago, what is it about this city that continues to pull you in and invest in that area?

A couple of things. Chicago is where my dream happened. Chicago is a very rural, American city. It’s kind of muscular. If you were to cast a city as a character, Chicago would be that tough, wise-cracking, American detective. I love its Americanism.

That being said, it is a wonderful melting pot of all the immigrants who came before me and will come after me. It’s everything that’s great about America. I have a loyalty to Chicago, because it gave me a huge opportunity. I would also be lying if I didn’t mention that Chicago is a huge center of influence. The amount of wealth that emanates out of Chicago around the world is unbelievable. It punches way above its weight in a lot of ways. As they say, she is the girl that brought me to the dance. I do live in Palm Beach now. I do live in London. I have lived in Malibu, but I still go back to check and make sure she’s okay.

A new season of The Deed: Chicago premieres tonight on CNBC (10 pm et).