Olds (Part 1)


I still remember the first time I sailed a boat by myself. I was about eight or nine years old and my older brother Jachin wouldn’t let the boat heel over. I was with my cousin Caleb who was on my side and wanted to tip, so we mutinied.

On a close pass by the little beach in front of our cabin my brother gave up the ship and jumped off. I had sailed in the past but hadn’t been in command of the vessel before, as this plan of me as captain wouldn’t have been agreed upon under normal circumstances. We did lots of fast passes of the shore as we were waved in. My brother wasn’t the only one who didn’t agree with my sailing style. But emboldened by Caleb, who I looked up to as a fellow want-to-be bad boy, we sailed off into the lake.

               I don’t recall how the trip ended, if I was in trouble with my parents or not. But one thing is clear in my memory from that day through the end of high school: I lived for the windy days, but sailed most every day of the summer regardless.

               My father was a camp director and we were all camp brats. We spent our summers in the mosquito swarmed paradise of Camp du Nord, in Northern Minnesota, on Lake Burntside near Ely, Minnesota. The camp was often donated boats, many of which I’m sure I was never told about, and they were auctioned off at fundraisers I was vaguely aware of. But some were pressed into service at the camp and were usually in some form of disrepair in those early years.

               When I was ten two big events took place in my summer life. The Chrysler 14 and two other distressed vessels were retired and new boats were donated. A used but in great shape Holder 14 named ‘Tiddley’ (which was the flagship of the fleet and my father figured it would be the director’s boat to be used by staff) and two brand new Johnson Mini-Scows (to be the camper boats). I think my Dad thought if I had the Holder to sail I would leave the Mini-Scows alone, but that only worked to a degree.

               This is when I discovered just what a tub that Chrysler had been and just how far I could go on a swift little boat. Burntside is a beautiful lake that has many islands and bays, crystal clear water and is relatively sparsely populated. The lake and the boat were the perfect place for adventure.

               In my head I can recount many adventures, but there are two that come to mind as harrowing events. The first was probably the second year we had Tiddley. I was protective of it and was able to do so by being an ever present captain for anyone who wanted to sail.

               I slept in a small a room about ten feet from the water, with my two brothers. The room would have been small for one person but we managed to fit a bunk bed and a single bed in too with a small walkway between. I then estimated the best position on the lake for the boat to be moored so I could keep an eye on it during the frequent overnight storms. I dove and carried the cinder blocks in short dives, running along the bottom of the lake in about ten feet of water. In an afternoon I had them all moved, tied back together, and put the Tiddley back on the empty bleach bottle that was the mooring buoy.              

               So when the storms would come I could lay in bed looking out the window and with every flash of lightning see the boat being buffeted by the storm. My great fear was the boat breaking free and bashing all night on the rocks near the house. The bay we were on was over a mile across and when the wind whipped up the waves could get high enough to really bash the boat around.

               One night when I was probably eleven, and I was woken by a violent thunderstorm. The boat was there in a flash of lighting with distant thunder and I fell back asleep. I woke a short time later as the rain was pounding on the thin roof right above my head. Another violent flash with the thunder right on top of it and the boat was gone. I was gone too, out the door in just my shorts. The wind took the boat north and it wasn’t far away. I had woken up just in time as the wind pushed the boat quickly towards a rocky outcropping called Peace Point. There was a rock foot path along the shore to the point and I knew it by memory- dashing over the wet stones in the dark. Off of Peace Point were many large rocks submerged with giant holes between them. It was very treacherous ground and I knew it was no place to try and fend off a boat. So I scrambled over the rocks into the lake to swim to meet the boat as it blew toward the point. The waves were really kicking up but I managed to get over the wet rocks and crashing waves and met boat before it hit the shore.

Scrambling aboard, I flipped the center board and rudder down, which in those high winds was enough to get some control over the boat. I turned it away from the point and towards the beach beyond. The whole time I was doing this lightning was hitting the lake. Once the course was corrected I flipped the center board and rudder back up and abandoned ship. I figured I’d have a better chance on shore then next to an aluminum pole and just in case the boat missed the beach I wasn’t ready for getting blown into what felt like an electric maelstrom.

The boat hit the beach and I was there waiting for it. I tried to pull it up the beach but once it had stopped moving the waves quickly filled it with water. I opened the drain but it wasn’t clearing the cock pit fast enough that it was far too heavy for me to pull all the way out of the water. I got it as far up the beach I could but the waves were still hitting it when I gave up and went home. Having broken about every swimming rule there was at camp, I retired to sleep and figured it would be fine in the morning.

However, it was not fine. After I had retired the waves had turned it sideways and eventually flipped it on its side, at which point the mast broke off. I was devastated. I could have fought longer and harder maybe and now my boat was ruined.

Luckily for me there were plenty of people around who took pity on me. I can’t recall how I must have been to observe, but I felt like a good friend had been killed and I had let it happen. Knowing more about boat repair now, it was in fact a fairly simple job to bend the mast step back into shape and reattach it. But, to me at that age, it was the benevolent act of an angle who went by the name Scott and was the maintenance manager at camp. 

Derek Rupe - to be continued



First Post (New)


I’m writing this blog as a bit of a personal history project, a bit to promote my company, and of course primarily as an exercise in narcissism.

Currently I’m sitting at home, on my sailboat berthed in New London harbor. My wife Grace is at work as a middle school science teacher. About a year ago I quit my middle management job in low finance to start my own company called Captineer. At Captineer our primary service is converting sailboats to electric auxiliary power. In later posts I hope to lay out the whole story of how we got here but for this introduction I’ll try and stay current.

Currently the wind is whistling through the rigging, a sailboat nearby has its halyard clanging off the mast in the wind. If I pay attention I can feel the waves and hear them hitting the haul in little smacks and gurgles. 

Right now I’m stressed about business. I need more customers but I don’t know how to find them. I need to find more effective marketing for my very limited budget. I’m also a little worried about my wife currently being the primary bread winner, as all the money generated by my efforts is being put back into the business without yet seeing the returns. But when I’m not busy I feel guilty, and so I’m worried I’m inventing tasks to keep busy because I don’t know what to do.

Right now I’m stressed about living on our boat for the whole winter in New England. I think discussion of life aboard will be the primary subject of this blog in the near future. Grace and I live on a Tripp 37 with our cat Kitniss.

Right now I’m happy that I have the opportunity to follow my dreams. However, there is still that little voice in the back of my head that tells me that getting what you want in life might not be a good thing. I’m doing what I’ve always wanted to do, but what if it doesn’t work out? Dreams are sometimes best as dreams, because then it’s always something that could be. Whereas reality is dirty and sometimes ugly and when you mix it with your dreams you can lose them in it.   

Right now I’m happy because I still have my dream, but I’m stressed because it’s been harder than I thought it would be to sell people on a superior product.

But I’m mostly happy because I have a great life, a great wife to share it with, and pretty good cat who usually comes when she’s called, but not if she doesn’t feel like it.

Thanks for checking this blog out, and please share it around if you’re the sharing type.

10/31/16 – Derek Rupe