Sean Conlon Reflects on ‘The Deed: Chicago’ Season 2

The Deed: Chicago Season 2 is about to wrap up. Host Sean Conlon shared with Showbiz Cheat Sheet his thoughts on the season and what he hopes to see if the show comes back for a third round. 

Showbiz Cheat Sheet: You mentioned in the last interview there were some “diabolical contractors” in this season. What are the signs of a good contractor?

Sean Conlon | Rob Kim/Getty Images

Sean Conlon: A good contractor is like your mother. They will always tell you what you don’t want to hear and what I mean by that is that a good contractor never over promises and always over delivers. They manage your expectations and that is why the cheapest bid is generally never the best bid.

I’m really proud of this season. All investments worked out, but more importantly, it was a wonderful kaleidoscope of people pursuing their dreams and the peaks and valleys they experienced–just like a snapshot of life condensed into a show.

CS: If there is a season 3 of The Deed Chicago, what do you hope to see in that season?

Sean Conlon NBCUniversal Winter Press Tour |  Michael Tran/FilmMagic
Sean Conlon NBCUniversal Winter Press Tour | Michael Tran/FilmMagic

SC: I haven’t discussed it yet, but I suspect there will be some fantastic stories to be told across this nation of people rebuilding and reinventing themselves. I believe COVID-19 could be viewed as the most ultimate life reset button.

CS: What’s the worst real estate investing advice you ever received? Did you follow the advice? What was the result?

SC: The worst advice I ever received was “Plow full steam ahead and we will figure it out as we go,” for a $75 million hotel deal. Who gave me that advice? Me.

CS: What advice would you give someone who wants to be a real estate entrepreneur?

SC: You better have incredibly thick skin, because you have to be very resilient. I would also say trust and then verify. Whatever somebody tells you, you have to have an element of trust because you’re going to have to work with people. But you should double check the facts. Second, assume it’s going to take twice as long and cost twice as much as you think it will. Third, don’t ever give up. Because the amazing thing about home flipping and life is your world can change. So, no matter how bad a day you’re having, go home, dust off, and come back. It’s the next day again.

Your first two flips, you may break even, you may lose a little bit of money. But if you consider them a lesson and a downpayment on your education, it is one of the few ways still in America normal people can get their foot on the ladder to making a fortune in real estate.

CS: What advice would you give to real estate investors in light of the coronavirus? How can real estate investors carefully navigate this crisis and still earn money?

SC: This will eventually pass but hopefully change a lot of us for the better. A lot of people will panic, and the unfortunate fact of life is that it will present a lot of opportunity for people who are willingly sitting on their hands so they can be ready.

CS: Anything to add?

SC: What an amazing journey it has been. Thanks to everyone who has tuned in and watched The Deed: Chicago. Follow me @realseanconlon on Instagram and Twitter for my next moves.

The season two finale of The Deed: Chicago airs Wednesday, April 8, at 10 p.m. EST on CNBC.

Read more: ‘The Deed: Chicago’: Sean Conlon’s Advice to Fearful Real Estate Investors

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