'The Deed: Chicago's Sean Conlon Talks Real Estate Lessons Learned and What to Expect From Season 2

• Sean Conlon is an Irish immigrant who came to America with only $500 in his pocket.

• After working as a janitor, Conlon decided to pursue a career in real estate, soon becoming a top-seller while still in his 20s.

• Using his real-life experience and his own money, Conlon helps struggling property investors for his TV show, CNBC's The Deed: Chicago. The second season debuts March 4.

It wouldn't be an exaggeration to say Sean Conlon is the perfect example of the American Dream. Coming to the States with just a few hundred dollars to his name, the now mega successful real estate expert experienced his fair share of mistakes and mishaps while working towards where he is today. With that real-life background, Conlon now uses his time and money to help others who aren't exactly pros at investing in property. His TV show, The Deed: Chicago, premiered in 2017 on CNBC, and saw the 51-year-old guru advising people who were seriously struggling to make projects work. He's now back for a second season, debuting March 4, and is ready to tackle whatever obstacles these people have had thrown at them.

Floor8 spoke to Sean Conlon exclusively all about lessons he's learned over the years, common themes he sees in real estate, and what we can expect from Season 2 of The Deed: Chicago.

This interview has been edited and condensed for clarity.

Floor8: Taking it back to the beginning: Your career path has been incredibly impressive. When you came to America and were deciding what you wanted to do with your life, how did you initially get into real estate?

Sean: You make it sound like I had an abundance of opportunities, I like that. [Laughs]. In hindsight I had zero opportunities, so I got into real estate initially for two reasons. One was a good one, and that was because I was passionate about homes in Ireland. We grew up not rich, and I used to cycle around the block and look at all the wonderful homes, so I had a passion for real estate. And secondly, I was not qualified to do anything else. I was the worst janitor in the world, and I thought boy, everyone has a real estate license, I should get one. With my station wagon and real estate license, what could go wrong?

Floor8: Was there any defining moment when you realized this was your calling?

Sean: Well, really yes, really no. But my first commission check was $350, and three years later I was at the top of the real estate market for North America, so I felt like a rock star in the sense that I had no money, and then quickly had a ton of money. The defining moment was that first sale, but again no one has that unique moment realization in the moment. They look back and realize there were lots of things.

Floor8: Did you ever think you would be at a place in life where you’d have your own TV show? And when you were approached with the idea, were you 100% into it from the start or did it take some convincing to decide this was the right move for you?

Sean: I needed a lot of convincing. I never wanted to be famous. I would be lying if I said I didn’t want to be wealthy, because [with money] you have your freedom. And having grown up in the circumstances I did with my father going broke, I wanted to make sure anyone I cared about wouldn’t have to worry about money again. Television was never on my radar. Never in my wildest dreams did I imagine I'd have a TV show. But did I know at the age of seven or eight that I’d be wildly successful? Yes. That was my plan.

Floor8: What would you say is the biggest risk in investing your own money and time to help struggling house flippers on the show? Is it just the money, or is it your reputation as well, or is it also letting people down?

Sean: Honestly, when I help people, sometimes I come off as a bit of a hardass on TV, but my biggest risk is that I would disappoint them. That’s what made me such a good sales guy, because I always wanted to please people. The most wonderful thing about the show is that I saved everybody on it. I advised them, and they found themselves. When I say I “saved them,” I mean that I helped people to believe in themselves from showing them what their strengths are.

Floor8: Without giving much away about the Season 2 premiere, it looks like you’ll be dealing with a project that’s already over budget. What’s your general advice for people finding themselves in maybe an overwhelming build without all the finances to back it up?

Sean: Firstly, you should try not to get into that situation to begin with. When you plan something, assume it’s going to cost twice as much and it’s going to take twice as long. But if you have dug yourself into that hole, you should take a couple of weeks to press reset and take a breath to figure it all out. You need to start managing your expectations and say, look, this might just be a lesson this time. I don’t have a clear answer, but when you’re that deep, there’s no easy solution.

Floor8: What do you think is the most common mistake people make while house flipping?

Sean: I would say the most common theme I see across house flipping is that people rely on the wrong contractor, and I’m going to tell you right now, you get what you pay for. The second biggest is that everybody watches way too much wonderful design TV, and they want to be architects. I’ve done it, too. You can get so carried away.

Floor8: What are you hoping viewers learn from Season 2 that might not have been explored as much in the first season?

Sean: The lessons are repeated sometimes, but we have dipped our toes into an episode with Airbnb, which is fascinating. That will really be interesting. It’s fabulous because it really opens up a world of income that even, I will tell you, I learned a lesson from. I knew nothing about Airbnb except for what I read, and we went out and met these individuals who make, ballpark figure, close to $1 million for three or four Airbnbs, and I was blown away. That episode is the biggest takeaway this season as far as something new.

Floor8: What would you say is the most rewarding part about helping all of these people with your expertise?

Sean: You know, I suppose in essence, it’s just working with these people we pick—I lend money to people, not projects. I’ve learned that these people I help are usually scared or under pressure, so it’s so rewarding to see how much they grow throughout the episode. I’m pretty self-absorbed because I’m a real estate person [laughs], and I’m shocked by how good I feel helping them, because these are really good people who got screwed over. I realized if you give a good person a chance, often they shine. Wait until you see the people on the show, how they grow and come out of it. It’s really cool. And the thing that I’m most proud of is that it’s authentic. The show is totally real.

New episodes of CNBC’s The Deed: Chicago air every Wednesday at 10 p.m. EST.