Richard Dempsey | Baseball Players and Bull Holes

February 02, 2022   |   Podcast

Senior Advisor, Richard Dempsey talks on his journey into real estate and how he's landed multiple large cash transactions.

The “Commercial Real Estate King'', Richard Dempsey holds the potential to become a successful future broker if he should so choose. He has seen it all from large cash transactions to low-grade scammers and frauds. In this episode, Richard outlines his experience within the industry along with some of the more “interesting” transactions that he has come across.

Below is an excerpt from the interview. Listen above for the full podcast.


How did you get into real estate? I was a state certified general staff appraiser for an agricultural lender. Then, after 13 years, they decided they didn't not need the staff any longer. They called the entire staff and it was a shock to all of us. It did turn out to be a very good thing, because Dean [Saunders] and I both had independent friends who recommended we talk.

I started with Dean in 2000. So it was very cool how we were put together. It was providential. Some people would say.

What was your first large transaction? It was 1200 acres in Indian River County. It was a large patch of track used for cows and the buyer was looking for a site to develop for duck hunting. This was well suited to that. When we showed it to him, he pretty much offered full price. Turns out, it was the former owner of the New England Patriots.

How do people afford these large transactions? One of the things I have learned in this business that's surprising to me is how much cash there is out there. My largest transaction to date was a cash deal. It was the shortest closing I've ever been involved with. The seller signed one document and that was it, we were done. I would say that probably 80% of my transactions are cash. Very few are financed.

Vetting your prospects. That's a very difficult thing to do. Fortunately with technology, it's a lot easier today than it was when I first started. There have been plenty of crazy people throughout our career. Vetting people is so very difficult because in each case, they have a level of credibility. So you just have to do the best you can.

My most recent example was another 109 acres in North Lakeland. It was through another realtor whose prospective buyer shows up in a Maserati. That gives the illusion of having money. While we were showing, the other agent said that the prospective buyer and her boyfriend had just called them off of Zillow. 

The prospect was a cash buyer and wanted to close as soon as the paperwork was done. I began to think this was a total waste of time.

Apparently, she's taken advantage of a couple other realtors in town on large acreage tracts. Then we find out that just before she came out to us, she had been released from probation for fraud.

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Richard Dempsey
Richard is a proud Central Florida native. Raised in Lakeland Florida, Richard would obtain a fond admiration for the Sunshine State’s natural beauty along with a bright-eyed vision into its future. He holds a strong reverence for the state’s fascinating history along with the mul...