This is a story about fantastic gifts from unexpected people and being vulnerable and putting yourself out there.

I want you to think back to early 2009, and remember where the US economy was, specifically the housing economy. Tough right? As a country, we were trying to power through a crippling mortgage crisis, and in my industry, real estate property management, we were hit especially hard…… well most of us.

I was an Assistant Manager/ trouble shooter in Detroit, MI at that time in history, and also one year into my infant company, Smart Apartment Solutions.   Detroit had one thing going for it, we were used to powering through distressed everything, but that of course is a different story for a different time.

On that snowy January 2009 day, I remember getting an email from my Regional manager Donna saying, “I need you in Naples ASAP!”. 

One of the hardest areas hit in the industry during the mortgage crisis was Naples, FL and our company’s portfolio in Naples, was getting put through the wringer and we were getting dangerously close to losing everything.

I replied back to Donna, got my specific marching orders and boarded a plane to SWFL, with a 6-week mission to locate an elusive housing director at the two (yep two) Ritz Carltons in Naples.  Why was this guy so important? Well… The Ritz Carlton was known to rent 40+ apartments annually to house the Ritz Carlton’s International’s staff members, and my boss wanted me to get those 40 contracts for our two struggling communities.

I landed in FL, got my rental car, hid my suitcase discreetly in the model I would be living in for the next 6 weeks, that would also be an active tour apartment during business hours.

I attended every Chamber, Hispanic Chamber, Beachside Chamber, BNI, apartment association event I could locate, basically if there was a group of people gathering in Naples or Ft Meyers, I was crashing the party.  

In addition to inserting myself into every event I could find, I negotiated with banks, repo people and suppliers not getting paid while covering one of the two properties while the manager was on maternity leave.

I was able to scrape up some funds to try every outreach marketing idea I knew to use on the Ritz Carlton to try to talk to the Housing Director. I tried to go into the hotels, nope, I sent food, and flowers still no.

I didn’t give up.  I kept showing up and started to get recognized at the events I attended, even by a man that is the closest embodiment of Panama Jack and his name is Barry.  Barry is an average stature man, always in beach attire with bright white hair that he gathered into a ponytail at the nape of his neck.  Barry is friendly and laid back like his attire suggests, and he is the owner and face of “Barry’s Paradise Jewelers” in downtown Naples.  

For four weeks of networking I have casually said hi to Barry at every event I attended, and besides me, he was also very active in the Chamber events, but admitted he primarily came for the food and drinks.  I never really talked with Barry, I didn’t see the value he brought to my situation and the properties I represented, I mean what does a jeweler have to do with us?

I only had two weeks left and I was starting to doubt myself, and the chance of making this important connection and getting that contract opportunity for our Naples communities. I was at a “Grand Opening Event” for a golf course the Chamber was holding, and I did something I hadn’t done before, I sat down with Barry and asked him about his business, and what he was trying to accomplish.  

After he was done telling me his fascinating Stories of his high-end jewelry adventures, he turned the tables and asked me why he was seeing me at every event in town…… And I was vulnerable and honest. I shared my goal to locate and talk to the housing guy at the Ritz, and my fear that I was failing and what I thought that would mean for the properties I was trying to help.  Barry smiled, patted my hand, and said, “keep showing up like you have been kid, and no matter what, give it 110% until you get back on that plane.”

We waved good bye and I cried in my rental Ford Focus, we were going to lose the property, I wasted four weeks and had nothing to show for it….. I went back to my model apartment and went to sleep.

The next day I went to the office, fought the battles, and headed to another Chamber event being held in downtown Naples that night.  I didn’t want to go, in fact I sat in the car at the event location and convinced myself. “Stay five minutes, talk to three people have a drink, and bounce.” I felt defeated.

I walked in the room, put on my paper Hello my name is name tag and put on my smile.

There was Paradis Barry! He waved I waved and then he came over and said, “How is it going kid?” “Did you get into the Ritz yet?” I replied, “No not yet, but I’m here and I’m not done yet!  Barry said “that is the spirit, Barry then gently grabbed my arm and guided me to a group of men standing in a circle networking.  Barry tapped a tall man on the shoulder, the man nodded and turned towards me and Barry introduced me to the man….. That man was the International Housing Director at the Ritz Carlton and Barry knew him.

Turns out, fancy guests in fancy hotels like fancy private jewelry shows brought to them, and Barry was that jeweler.

I got my meeting with Mr. Elusive and I got to log this story in the books as a huge success, but not without thanking Paradise Barry! 

 He taught me and hopefully you some important lessons.

  1. You literally never know who people know, and assuming you do is only holding you back
  2. Be kind authentic and vulnerable
  3. And show up each and every time, even when it feels impossible, never give up, you never know who is taking notice of your resilience.

I am and will be forever grateful for beautiful people like Paradise Barry.

Barry and Paradise Jewelers in Naples, FL


Smart Chick Megan