A Look Inside My Private Jet


The $6,330 Promise


When was the last time you had to throw down $6,330 to charter a jet one way to make it to an event you promised you’d be at?


Yes, this happened to me this very week.


2 months ago my wife and I were planning our vacation to Grand Cayman Island, where coincidentally and miraculously, we had landed two events back to back with two different clients between the Westin and the Ritz Carlton, on April 9 and April 11, respectively.  As we were planning our week long trip to scuba and explore the island, working around my speaking schedule while there, we got a call from my office.


“Jason, we have a problem”, said my office manager.


“Yes, I know, I’m still learning how to run a business, I’m sorry”, I replied.


“No, silly, it’s not you, it’s on our end.  We just found out you have a confirmed booking in Marco Island, Florida the same day as you’re supposed to be speaking at your first event in Grand Cayman.”




I cautiously asked, “How did this happen?”


Apparently the person from our office who used to field every call had put April 9 in the 2017 calendar year rather than 2018. The client had just confirmed we were on!


Now, here we were, confirmed and contracted with 2 clients on the same day in 2 different countries, 3.5 flight hours apart.


Asking about commercial flights to connect the events there was no way, all flights out of the US leave to the islands too early.


We then went to the dreaded no man’s land question, “How much would it be to fly privately and charter a private jet?” I bravely asked.


The normal price was $13,000 for a one way from Fort Myers, FL to Grand Cayman, however they had found there was a cheaper option, still a private jet, for $6,330.


“Book it”, I said, confidently, “even if I lose way too much money making it to the next event we have to make it work.”  


Thankfully, the event in Florida would be done by 11 AM, my event in Grand Cayman wasn’t until 6 PM.


Wrapping up my event in Florida on April 9, my incredibly durable and unflappable wife, ran with me to the car as we drove over an hour to the airport and hitched a ride on a shuttle to the private air terminal.  Running into the lobby to announce we had made it in time for our 1:15 PM flight to Grand Cayman, the private jet company had no idea who we were or what plane we were announcing we’d be flying out on.



After much hunting they finally realized it wasn’t in their system, as it was a 3rd party of a 3rd party discount broker and the plane was still coming in from Key West, running late by about an hour or more.


I did my best Zen/Yoga/Buddha impression in trying to remain unfazed, and proceeded to bite off every fingernail as we wondered if we would make it in time.


Sitting in the lobby of the terminal, watching the billionaires land and fly away in their beautiful G5’s and Leer Jets, we anticipated what awaited us, what would our jet look like.


Suddenly, bursting through the door came a weathered, tanned, dirty blond, Harry Dunne of “Dumb & Dumber” doppleganger barreling through the door, shouting, “Hewlett?  Hewlett’s are you in here?”


We were the only ones there.


He shook our hands excitedly and apologized for his tardiness, announcing he is Captain Fletcher, our pilot, and we needed to get out to the plane immediately.


I looked at my wife with the look a man gives only when he’s about to jump off a bridge at a sketchy bungee jump place in the jungle where people have been known to die, and we followed the Captain out to our jet.


Looking around we realized, nope, this is no jet, and nope, this is not good.


Imagine for one moment expecting to see a beautiful jet, and instead realizing you are about to get on a plane you wouldn’t send your mother-in-law on.  3 little windows, little baby wings, propellors, a kind of WWII silver-ish white tint.


Our luxurious private jet


This little puddle jumper plane was so small we had to crawl inside to find our seats as Captain Fletcher began shoving our small carry-on luggage in the back of the tail with all the force of a kid trying to keep the door shut of a closet full of incorrectly folded exploding blankets.


The look my wife gave me was one that only a wife can give a man she knows has just spent more money than he should on something that isn’t good, a look I have grown accustomed to since this past summer when purchasing a new lemon of an RV for our cross country trip because I didn’t know I should have changed the oil in the old RV generator.


Yes, there is a pattern here, folks.


For some reason we entered the little plane, propellors and all, as Captain Fletcher crawled past us on hands and knees, squished himself into the cockpit, and announced, “Well, let’s go!”


Fear is a word often used too casually.  Such as, “I have a fear of scary movies”, or “I fear swimming in a dark lake”, or “I fear we may not have adjoining rooms in this hotel for you and your children.”


But you know fear when the jet you thought you chartered turns out to be a puddle jumping, solo captain flying, Disney ride gone bad baby propellor airplane, and as you rattle down the runway feel the need to text your life insurance guy to make sure the premiums are up to date.  I sent my Mom all the passwords to our bank accounts so she would be ready to inherit our children.


That’s fear.


As my wife squeezed my hand with her head uncontrollably shaking in her seat, we were the equivalent of a Jamaican bobsled team going down the cement track practice round for the first terrifying time, I tried to summon all the courage a man can while holding my GoPro in an attempt to document this amazing experience, as the plane careened down the runway in it’s mission to get off the ground, we screamed as we took off.


Bouncing from cloud to cloud, we were a pinball machine in the sky, as the wings flailed as steadily as Bambi’s first time walking on ice.  Hanging on for dear life, while simultaneously searching for something to throw up in, we smelled the waft of a banana as our pilot cracked one open and casually ate the fruit as if he were sitting on a beachfront chair.


3 and a half hours of terror and holding in our bathroom needs, my wife and I did our best to keep our composure.


At some point it dawned on me that, if the captain were to pass out or have a heart attack, we would die as well, since I’m not sure how to land a plane.  I mean, I have a hard time putting air in the tires.


The whole flight wasn’t terrible.  I tried to calm down by writing in my journal and it reads like a calligrapher charting a richter scale, or perhaps just my heart rate on a screen in the hospital I would soon be in.


The pilot yelled out only once during the flight: “CUBA!”  I thought that meant we were going down.


Yes, we were flying right over Havana, and I realized Barry Manilow was right, we were in the hottest spot north of Havana…in a prop plane just a few thousand feet above.


As we rounded the bend and landed without incident in Grand Cayman, it is rare for a person to get on the ground and kiss pavement, but we did, and we texted the kids that we had made it.  The text only cost $45 with our international data plan.  Much cheaper than the flight though.


Handing the Captain a tip of gratitude for not letting us die, he grabbed and hugged me and said, “Anytime you need a ride buddy, let me know!”  And he hopped back in the plane and flew away to Key West.  I watched him take off and swear I saw a banana peel fly out the airplane window.


My wife and I raced to the hotel, changed and ran to the beach where I gave a barefooted in the sand presentation of The Promise speech as the sun set and ocean waves crashed beside us, speaking to the top 50 sales people, and spouses, of a wonderful company.  I was referred by my friend and legendary speaker, Connie Podesta.  Grateful we had made it work.  We got there just in time.  It was a miracle.


It was the $6,330 Promise.


But next time, I promised my wife, we will spring for the $13,000 private jet option if we really need to do this kind of thing again.  She just laughed and threw her head back, as we walked hand in hand along the beach just grateful to be alive.


The photo we sent our kids, terrified we may not be coming home, before boarding our private jet


Video message sent to my JHE newsletter subscribers about the adventure:


~ jason

Jason Hewlett, CSP (Certified Speaking Professional), CPAE Speaker Hall of Fame, Keynote Speaker for the largest corporate events in the world. His primary message, The Promise, is essential for Leadership, Management, Sales, Marketing, Direct-Sales Companies, and is a combination of engagement and entertainment meets inspiration.  Jason has even received standing ovations from IT guys.  He has been acknowledged as life-changing by Conference Attendees, C-Level Executives and Hollywood Elite.  jasonhewlett.com

Please click here to learn about how Jason Hewlett, Speaker Hall of Fame, introduces the opportunity for you, or someone you love, to have the gift of learning how to create a Career From the Stage and begin moving toward fulfilling a lifelong dream as a full-time speaker, performer, or entertainer.



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