Real Estate Deal Analysis & Advice

Best Deal Ever Show #21: One Deal, $7M Profit With Sean Conlon

Expertise: Real Estate Investing Basics, Landlording & Rental Properties, Real Estate News & Commentary, Mortgages & Creative Financing, Real Estate Wholesaling, Personal Development, Flipping Houses, Business Management, Real Estate Deal Analysis & Advice
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Chicago downtown skyline at twilight with highway and traffic.

Today we chat with Sean Conlon, and it’s easily one of the most fascinating interviews I’ve had the pleasure of hosting.

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Born in Ireland, Sean made his way to the U.S. and began as a janitor in Chicago with the philosophy of "I have no option but to succeed." In 1993 at 23 years old, Sean was a janitor by day but at night he would go into the office to begin cold calling, which is how he got his start in real estate.

By 27, Sean became one of the top real estate agents in Chicago within his niche by becoming an expert of an area, growing his network, and finding single-family homes that could be torn down and replaced with four-unit buildings (which was not done yet in the areas around Wrigley field).

Now Sean focuses on connecting families and institutions to global real estate operating companies. Currently, he represents groups looking to build all over Europe, introducing his clients to the networks they need overseas.

Chicago Investor’s Best Deal Ever

After finding a property in the local listing book, Sean stumbled across a beautiful retail building on a corner in Lincoln Park (with 16 apartments above it!) that he was determined to buy.

Each morning while drinking his coffee across the street, he realized that the foot traffic was special. He decided he would hunt down the owner and make every effort to buy the property. The owner eventually succumbed to Sean’s persistence and sold him the building for $2.9 million.

Related: Best Deal Ever Show #20: $6.5M Purchase with Zero Out of Pocket

At first, some might’ve thought Sean overpaid, but his vision for what used to be a Western boot store was to replace it with a Ralph Lauren shop. After putting in $300,000 to clean it up, Sean did in fact realize his vision of convincing Ralph Lauren to move into his space. A year later, Sean sold the space for $10.4 million.

Sean emphasized that it wasn’t any magic or special education that helped him succeed. It was him trusting his own intuition and being an expert in the area that helped him find his deals. Listen to the full interview in the video above to hear more about this in depth!

strip mall with clothing storefront in view

Closing Thoughts

In the beginning of the interview, Sean explained that the secret to his success was truly becoming an expert of the area and connecting with local builders and developers, sourcing properties for them, showing which were available, and pointing out the fine details that would ultimately benefit them in the long run (like which lot had more room to build an additional unit).

Related: Best Deal Ever Show #19: Hidden Profits in Extra Acreage

Sean’s closing thoughts surrounded how important it is to never become overconfident. When the market crashed in 2008, what allowed Sean to recover was getting his hands dirty, doing what was necessary to recover assets, and being willing to go back to the humble beginnings.

One quote that has been pivotal to his success and is now a favorite of mine was: “You can’t tell champion by the way he behaves when he’s winning, but you can tell a champion by the way he behaves when he’s knocked down.”

Be sure to listen to the whole interview in the video above to hear Sean’s inspiring storytelling, wisdom, and experience. You won’t be disappointed.


What was your best deal ever? 

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Ken Corsini G+ is the host of the Deal Farm Podcast (on iTunes) and has 10 years of full-time real estate investing experience...
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