So I almost sunk your house… My bad

IMG 0199
 In my defense, Tony chose to use a sailboat as his house. A 40-foot former America’s Cup racing sailboat, at that – valued at a cool $210,000. And then he chose to invite me and a great buddy out on it. Not sure what the worst of those decisions was but on this past summer day, I turned his house upside down… Literally.



I wrote last week about the best and worst jobs I’ve had over the years, and what I learned from some of the stand-outs (there were more than a dozen!!). In writing about my time working as a restauranteur (host) at the Hard Rock Cafe in Maui, an amazing story came to mind… That story is below and, no – I don’t think I’m exaggerating on ‘amazing’ for this one. You be the judge:



Best summer ever…? It’s up there. 


Best summer before 22 (when I met my wife)…? 100%. 


The background


This was the summer after our sophomore years in undergrad and although we were at opposing MAC Conference schools, my buddy Jamal and I kept in touch. Picking up the phone became much easier on my end when a back injury ended my college football career during said sophomore year. And although I accepted a position as a student assistant with the team, the following 3 months were about to be the first summer dedicated entirely to myself since childhood.


The differences this time around were that we:

  • Had freedom of choice and action,
  • Wanted to use the summer to make some cash and have some fun together
  • Had no real responsibilities to class, sports, or parents, AND
  • Were of legal drinking age


We explored every aspect of each of those bullet points above and admittedly focused just a bit too much on the latter. I digress. We weren’t idiots, and there’s a great story in what I’m about to yadda-yadda but for the purposes of getting to sinking my friends house, I’ll just say that Jamal and I decided to spend the summer in Maui, found great jobs working together at the Hard Rock Cafe, and met some great friends along the way! One of those friends (Tony) happened to live on the sailboat that will serve as the setting for my story.


36 Hours until catastrophe


“Guys! We’ve finally got a day off together tomorrow. Let’s take the boat out for a day on the water. Whaddya say?” Tony started it out innocently enough and as Jamal and I digested the offer, we took a second to think, turned toward each other, and answered with a simultaneous…


“WE’RE IN!” 


It wasn’t a particularly difficult question to answer for Jamal and I. There was the prospect of a phenomenal time out on the water with great weather, food, and drinks.


All signs pointed to phenomenal except for these 2 minor details: 


1) We had no idea how to sail.


2) Tony was in his 40s, supposedly married with kids back on the mainland, and living all alone on this boat, “forging a financial path to bring the family out to the island…” He too was working as a Host at the Rock (our slang term for – The Hard Rock), and although we were bringing in bank as 22-year-olds, the salary was “eh…” for someone a little further along in their career path. There was the slight possibility that Tony was a serial killer and although we had speculated that point together, Jamal and I had strength in numbers, youth, and the fact that we were on to his game early (if that was the case…). So we pressed onward toward a joyful Wednesday on the water.


We all worked out the particulars of ales vs. lagers and turkey vs ham by making the decisions any rational 22-year-old males would… “We’ll bring ‘em all!” I mean, if Tony was generous enough to invite us out on this 40-foot gem of a retired racing sailboat (that he lives on), then by-George we were gonna bring some food and brews. It was the right thing to do.


5 Hours until catastrophe

IMG 0195

Jamal and I rolled up to the harbor at 5:30 am, dismounted our gear, met a smiling Tony, and chained our Huffys up to the bike rack before we boarded. “Any destination in mind?” Was Jamal’s casual first probe into whether or not this day would turn out positive.


“I figure we’ll head to (the neighboring island) and see how far we get by mid-day. Then we’ll either hang out for a bit over there or turn back if we’re running out of daylight.” Tony’s reassuring retort was all we needed to hear to drop the guard and decide together that this day would be a glorious one. The only task left now was to pull anchor and set sail.


4 Hours until catastrophe


If you’ve ever been on a boat in the early morning hours before dusk setting out from a western Maui harbor with a guy you vaguely know from work on his old racing sailboat chock full of fairly warm deli meats and near ice cold brews before, then you know that there are 2 things that fit perfectly with the sound of waves and that view… Oh, that view… Jamal said what we were all thinking. “Who want’s a drink?” And at this point, our day started taking shape.


For the remaining time up to ‘1 Hour until catastrophe’ all that’s relevant is that we continued with some disproportionate combination of brews and sandwiches, had phenomenal conversation, learned that Tony was in-fact not out to kill us, learned how to sail, got the boat moving at a good clip, and just had an amazing time. It was – to this point – a top 5 day of our Maui summer. And that’s saying something. But here’s when the top-5 day started climbing up to the #1 spot…


3 Hours until catastrophe


There was a fourth weary traveler (we’ll call him Brad – and other than for this portion he is irrelevant to the story) that did not make the initial 5:30 departure so thanks to modern technology he was able to get a text out to us at sea with a new pickup location. As we were out for a good time, Tony had no issue with picking him up at the Lahaina Harbor… Just one of the busiest maritime locations on the island, no big deal. To get our 40-foot vessel’s sails down, power the motor up, and make it to the dock and back would’ve taken hours for experienced sailors. For us, days may have been a better measurement.

With some quick thinking, I spotted a dingy (small rowboat) attached to a moored (tied off to a concrete block on the sea floor) boat near the harbor. In an instant, my feet left the boat and my hands cut through the swell as my freestyle stoke took me to our new neighbor’s abode (the shirt was already off – Maui living). Thankfully, I was able to negotiate a 2-beer price for 20-minutes worth of the rowboat to get into the harbor, pick up Brad, and head back to the origin.


This was going far too well… for far too long…


But I paid that thought no mind as I entered the harbor through the sole open area in between the harbor’s rock border. It was a vibration in my oars followed by an enormously loud ‘HONK!!!’ that were my first two indications of trouble ahead… matey (couldn’t resist). Oh, it was just a 3 story speed passenger ferry that was starting it’s journey to the neighboring island. No big deal…


So I did what any sane man in that situation would do.


I stood up, acted as if I had just been cut-off on the freeway, and proceeded to vigorously wave the 80-foot yacht aside so that I could pass. Their captain responded with HONKS that increased in frequency and volume as our separation quickly evaporated. In a last-ditch effort, I managed to make eye-contact with their captain, point the index (finger) at him as if to say ‘I know you see me, and now you know I know you see me,’ and then like an officer on the roadway flagging down a speeder, I shifted the index to the other side of the harbor entrance and signaled a firm “MOVE ASIDE, sir.”


Maybe it was a desire to eliminate future paperwork, or perhaps he didn’t want to pay to have his hull refinished after running my dingy @$$ over, but in any case the undermanned, outgunned, and inexperienced captain ruled victorious over the harbor entrance’s battlefield on that day when the other captain moved aside and passed. We did not break eye-contact until their boat was at least a few hundred meters out to sea. Tony and Jamal witnessed this entire exchange. Not only did that feat earn me the ability to tell an increasingly exaggerated version of the story to all who would listen for the rest of the summer, but also I got more confident in my naval abilities that day… Just a bit more confident to put it humbly.


1 Hour until catastrophe


Jamal and I were ultra competitive. Like competitive since we were in grade school in any class, sport, game, sprint (he normally won these), weightlifting event (normally got those), trivia, etc… It was clearly abrasive to an outsider but, to us, it was how we lived life. It was a constant of measuring up against one another and having a blast along the way. While we’re pretty mellow at the 32-year-old point in our lives, when we were 22 and on that boat – the competitive juices were backed by liquid courage and they were-a-flowin’.


Not sure who it was but one of us came up with a genius game. We’d head to the bow (that’s the front, for you land-lovers), jump off in mid-sail, scrap like crazy in the water, and see who (if any) could grab on to the rigging in the stern (back, land-lovers…). Have you ever heard that life is all about ‘timing’ …? Well, let me tell you a little about our vessel’s situation at that time. We had gotten both sails up and managed to catch some pretty decent wind.


There were white caps off the bow and as we were headed past the northernmost point on Maui, the Trade Winds were starting to kick in at full-force.


Another thing… We were at least 2 miles offshore. And if my calculations are correct, I would’ve lasted about 30 minutes in the water before my dehydrated state would severely cramp up. At that point, we would’ve had ourselves a bonafide situation. So, in returning to our game – it was important that either, A) one of us caught ahold of the rigging, or B) Tony would manage to get the 40-foot boat out of the wind and turned around to pick us back up… But what did we care, this game was exhilarating!


You may be thinking that Tony was pretty upset with our shenanigans… False you would be. He chose one of us to cheer on during each round and actually steered away from re-capture if you weren’t his prized horse during that round’s playing. He even jumped into the rotation after a while.


Life went along for what seemed like hours as we shuffled through all the possible 1-on-1 combinations that 3 players would yield. 


And when Tony and Jamal were up to play, it was my turn to take the helm and keep our boat on And when Tony and Jamal were up to play, it was my turn to take the helm and keep our boat on course (and upright). Tony gave me a crash-course before my first go of it and after my first maritime 30 or so minutes as captain of the Pacific’s finest sailing vessel (go ahead, I’ll hear your argument…), my confidence was at an all-time high. Some may say – perhaps a little too high.


30 Seconds until catastrophe


Jamal and Tony were back toweling off near me at the helm for this next sequence. You see, I took notice that if I would steer the boat in such a way that caught a little more wind, our speed would also increase. This, in turn, made the game more challenging. And, I’d be lying if I didn’t admit to loving the higher-volume splash that would result as we cut through the white-caps at an increased rate… Small things in life… So, I’d turn the wheel slightly. We’d pick up speed. My two counterparts were gearing up for another round, so I wanted to increase the difficulty to Madden-Level (that’s as high as it gets if you’ve never played the NFL video game) before they jumped in. Turn the wheel a little more. Little more speed. “I can get a little more out of this wind,” I thought to myself as I twisted that wheel just a slight bit more, and in that instant, terror leaped from those white-capped waters and grabbed ahold of my soul. I had managed to put our sail at a near-90-degree angle into the wind, and the force of our lead weighted keel was finally dwarfed by the insurmountable force of the Pacific Trade Winds. In a split second, our mainsail slapped the waves with a “THWACK!!!” and the giant lead weight that is designed to keep our boat upright rose above the sea…


Tony was sitting directly across from me when this all went down and his face said it all: “Oh my God.”


My house is about to be at the bottom of the Pacific. Wait, we’re 2 miles offshore. HOLD UP, there goes our sandwiches… WAIT!!!! There goes the beer cooler. NOOO!!” In an escalating look of panic, my eyes oscillated between both voyagers as they looked back at me wondering, waiting, to see if the boat would flip a full 180, or if the keel would return to its rightful location below sea level. That instant felt like the fourth quarter of a modern college football championship game (soooo many commercials. “It’s about the kids!” They say… Right. I digress). Our collective fate was suspended in air during that moment as none of us truly had any idea whether we’d be stranded at sea, drifting toward Tahiti, and probably left for dead… Or not.



Tune in next week to see if I survived…



Jk, jk. The boat righted itself after the 5 worst seconds of my life, to that point, and as we sat down on the benches that had just been our ceilings, Tony’s voice cut the silence. “Damn. I did not want to have to swim 2 miles for my next beer. Mike, I think you’ve earned the job of fishing those coolers out of the water… We’ll wait.”



Reader’s input


Thanks for reading through to the end!


I’d love to know – do you enjoy stories like this or would you prefer I stick to more ‘traditional’ posts?


Any ridiculous stories you’d like to share with the readers? Feel free to let us know in the comments below!



Thanks for reading!


– I’d love it if you would subscribe to MikedUp Blog’s FREE newsletter and/or share this post with a friend.
I’m glad you’re here. Thanks again and talk soon!


– Mike
Join Over 2,100 Other Team Members!
Learn valuable skills to build wealth, achieve a higher level of fitness, boost your business' profits, and more...  All in support of a healthier YOU!
By signing up you agree to receive regular emails with exclusive content, deals, and more! Unsubscribe at any time - and it is my honor to NOT SPAM your inbox (I promise)

You may also like