Sean Conlon interview: The Deed Chicago returns for season 2

Sean Conlon never intended to become famous. He certainly didn’t want to be a TV star. But thanks to The Deed: Chicago, he’s become both.

The CNBC series features Conlon as he puts his own money on the line to help struggling real estate investors in Chicago. But with his investment comes a first-hand crash course in this high-stakes world of flipping houses and potentially changing lives. It’s a masterclass in business, and there are some life lessons to be learned as well.

The Deed: Chicago season 2 starts Wednesday and presents even tougher challenges for Sean. He spoke to me ahead of the premiere to discuss what he’s learned from the show so far, what audiences can expect from the new episodes, and how he took the long way around to becoming a TV personality. His story is as fascinating as any of the ones on his series, and he’s someone we can all learn a lot from.

Get to know Sean Conlon better in our interview below, then make sure you tune into The Deed: Chicago season 2 at 10:00 p.m. tonight on CNBC! You can also find my preview of the first episode here.

Brittany Frederick: What interested you in starring in a TV show and adding The Deed: Chicago to your already expansive portfolio?

Sean Conlon: No interest whatsoever. But in essence, in 1990, I was an assistant janitor in a building in Chicago, and a very bad one. And there was a fellow in the building who was very, very funny, and to this day, he’s one of my best friends and I’m godfather to his son. But he nicknamed me Subtitle, because he said I didn’t speak English. Which is wonderful. Fast forward to ’93, ’94, he raised money for a movie he wanted to make, and he told a story.

He’s walking on the street and he sees a Range Rover coming, and he’s like, “Only politicians and the Windsors have Range Rovers. And who gets out of the Range Rover? Subtitle.” Which is his nickname for me. And I’m like, “Oh my god, what are you doing?” And he’s like, “What are you doing?” And he thought I was dealing drugs or something. I’m like, “No, no, I’m a real estate guy now.” And so, I wrote him a check for $7,000 or something like that, and he went out and made all these movies.

He was pitching a show to CNBC in 2009 or 10, and he’s like, “Sean, I really need you to come as my advisor. It’s a real estate reality business-y thing.” And I said, “I’ll come along,” and by the end of the interview, the guy running CNBC said, “We’d like to do a show with you.” And I’m like, “I can’t, because you need somebody to pretend they’re a real estate mogul,” and in 2009 I was trying not to go broke.

But they kept coming back and were like, “Look, we really would love to do something with you, and you really have a great story, great energy.” And around 2014, they called me [and] I said, “Fine, I’ll come in again and have a chat,” and I did it.

And it’s been a wonderful experience, but I have no interest in being famous or well known for television. But I do love the fact it’s real. It’s authentic, and I lend all my own money, and everything you see on the show is real.

BF: You had some incredible challenges in the first season that were intense for any real estate TV series. What kinds of projects do you take on in season 2?

SC: We had some really interesting situations. We had a wonderful gentleman who hired a guy who had nicknamed himself “The Rottweiler.” The Rottweiler got paid upfront as an advisor, but never really spent any time on the property, and was not responsible for finishing it or anything. It was the most unbelievable thing ever.

He was getting paid for, I don’t know what. He was an independent advisor, who got paid a basic contractor’s fee just because. Because he convinced the poor guy that he should pay him upfront for everything. So I had to deal with that. Myself and The Rottweiler, let’s just say we won’t be going out to dinner anytime soon.

I’ll give you another cool example. We had two young guys doing a home flip, and I was really hard on the younger guy because he seemed…well, I found out he was really shy, but initially, I misread him. And I normally read people, I give them a really hard time. He’s so good [that] I hired him after the show. He’s working on hundred million dollar deals now. From a $500,000 home flip last year, he now works for the Merchant Bank, and he’s in a senior position already because he’s so good. That’s a cool end to the story, isn’t it?

BF: Real estate always depends on the market. So what are some of the considerations you have in Chicago real estate that we might not see in other cities?

SC: Chicago struggles with uncertainty. This is a world-class city, but because there’s such issues with what’s going to happen with the tax and the pension issues, there’s uncertainty. But like everything in the world, all real estate is local. There are markets in Chicago that are absolutely on fire. But if there’s one thing to be worried about, uncertainty is bad for any sort of market. And we’re just not sure what’s going to happen in Chicago with the new property taxes. That’s it, the uncertainty. The dream’s still alive, though.

BF: The unique thing with The Deed: Chicago is that you have a sister series, with Sidney Torres and his version of The Deed in New Orleans. Have you two ever met or compared notes?

SC: We actually have. We’re very different, which is great. We have very different styles. I think he’s very creative. Quite fabulously, I was in the Bahamas this year, and I ran into him. So it’s cool. We have a good relationship. We just go about things very differently, which I think is complementary. And our shows are very different; they are two separate shows, even though it seems somewhat similar. But I love what he does. I think he’s a real creative.

BF: How do you manage filming The Deed: Chicago while staying on top of your own businesses?

SC: I would hate to sound like I’m bragging now, because people do sometimes, but I wake up at 5:00 a.m. Look, I’m incredibly passionate about what I do. I have the most incredible life balance. I travel the world. I live in London, I live in Palm Beach. I do a lot of really cool things. With my Merchant Bank, I find super high network families across the globe in crazy, interesting deals, which is off the charts cool stuff.

I get up at 5:00 a.m. and I’m still going at midnight, but it’s a choice right now. It really is. I used to work that hard to make it. But I also will go fly fish in the mountains of British Columbia, or I went on a tiger safari through the jungles of India and disappeared for ten days, and I’ll go up the Nile this year. I take a boat along the Italian coast for two weeks and stuff. So I really do have a good work/life balance.

But I am very focused. When it seems like I have a hundred things going on, I stay in my lane. One lesson I learned [was], prior to 2008, I was involved in island gap wells, and technology, and gold mines in Mexico. Then I realized I knew nothing about any of them. Now I’m very focused. I sit at the intersection of capital and people. And I connect both in the real estate space, which is 80% of my business. That I do really well.

I can connect the dots across the world. If somebody’s doing something in Kenya, I know who they need to talk to. I have a group that did 50,000 student housing units in America, and when they decided to go to Europe, they hired me. And every city they went to, I had somebody to plug them in at the absolute top. So that’s kind of what I do.

BF: Now that you’ve become a more public personality because of The Deed: Chicago, is there anything you want people to know about you? Or that you’d want them to learn from the show specifically?

SC: I didn’t do the show to be famous. It has been incredibly educational for me, and I love that. I never imagined it would be. I think there’s a real comfort in not wanting to be famous and having a TV show. It’s a real luxury. And I was never a big believer in using different parts of your brain for different things, but it turns out you do.

I really enjoy being creative. And I realize that human nature is somewhat the same across the board, and there are tendencies to watch. So I guess I’ve learned an awful lot about myself on the show. And I’ve learned even more about people, because just when you think you know everything about people, they go and surprise you and do something else strange.

I’ve learned a lot from the show, and I honestly think if people watch it, it’s so authentic and real. And I’m not pitching it, but if I wasn’t on the show, I’d watch the show, because there is so much to be learned from it. And while it’s not as pretty as some of the other real estate shows – not to talk criticism about them, because they’re all great – but it’s so real. It really does have real wins in the end, too. It just allows us to roll our sleeves up and get stuck in. This is real life. It’s as real as you’ll get. If you want a real, real estate television show, this is it.

The Deed: Chicago season 2 premieres tonight at 10:00 p.m. ET (PT viewers should check your local listings) on CNBC. For a preview of the first episode, click here.

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