Best Retirement Gig Ever

My youngest child is an outdoors-minded kid. Actually, all of my four children love the outdoors, which is rewarding for us all, but this one is ALWAYS outdoors. He’s not had an indoor job since he graduated from college (is that an indoor job?). Like everyone in my family, he loves Maine, especially the little island we live on, Deer Isle, and the charming town of Stonington.

Stonington is a little lobstering town. The town is small and charming, but it also happens to be the largest lobster port in North America (maybe the world?). It’s a rocky coastline and beautifully unspoiled. The year-round population is less than 1,000, but people make the effort to come up here in the summer to see the gorgeous scenery and relax. Even folks from southern Maine (Kennebunk, Portland, etc) come up here and say “oh this is REAL Maine!” I fell in love with this place well over 50 years ago when my parents started coming up here for summers. They ended up moving here full time after retiring. After losing Dad and selling his house, my wife and I bought back in. We got incredibly lucky and found a parcel of land on a small peninsula with 15 acres, on Webb’s Cove, just outside of Stonington. We built a house and it’s got water on both sides of the land and hiking trails all through the woods. We all love it and it’s the family flag firmly planted (figuratively speaking). Frankly it’s dog heaven! My dogs don’t wear a leash much between May and November at least.

So then I started thinking about my own retirement….

My son (youngest, referenced above) decided he wanted to start his own business and asked if I would help. He had become a licensed kayak guide working as a summer job for an outfitter here on the island. The outfitter – Old Quarry Ocean’s Adventures – went out of the business when the owner got tired of it after 20+ years. It was a real loss to the island as people enjoyed going there. Will decided he loved the guiding – being on the water, working with customers, and was interested to learn what it would take to run things on his own. I was finishing up my last IT firm and trying to decide to look for another or not.

Choosing to retire was not as easy a decision as I thought it might be when I thought about it back in the day….it turned out that I liked working. I liked managing people, and leading sales organizations…and it scared me to just stop doing that. I wasn’t going to sit around, play golf and drink beer (much). I knew that I wanted to help some non-profit organizations, and Will’s new company idea represented a new idea. I said yes.

 I suggested we put together a business plan, and a P&L. “Okay Dad, but what’s a P&L?” was his answer. That gives you a sense for where we started. We made a plan and gave the company a name – Osprey’s Echo Sea Kayaking! Ospreys and osprey nests are all around us here on the cove.   We acquired assets (boats, paddles, and other equipment) and developed a plan. In our first year we decided to launch tours from our own property. This was not a strategic decision – it was our only choice. As gorgeous as the kayaking is (i will get to that) there are not many places to launch safely on this island. There’s a town ramp – it gets way too crowded and there’s no parking.  There’s the ‘sand beach’ but launching boats there is frowned upon as sunbathers and swimmers gather there. Our property is on the water, which is good…but it’s very tidal, which presents a problem. Every day, each tour was a new math problem – will we have enough water to launch? and to return? If not, we would have to but the kayaks on the truck and ‘truck’ them to another launch spot.   (well, you can’t live here without a little pickup truck, after all!)

Our first year was good fun and looking back on it we learned a lot. We learned that we need a booking system, rather than pen and paper. We learned that we need to charge customers up front, when they book, or people can cancel at their leisure, leaving us high and dry (so to speak). And we also learned that our property is not ideal for running the business, as beautiful as it is.

Then we got lucky. A small parcel of nearby property came up for sale in 2020. It is an acre, with a small 1-bedroom cabin, and sits on the same cove we are situated on, but it has a ramp, and it also enough water for us to launch even at low tide. We snagged it. It seemed expensive at the time, but it changed everything for the company. We built a couple of kayak racks so we could store all our boats there. Good news, the fellow renting the cabin at the time was an excellent carpenter. Presto – two kayak racks!

We licensed a booking system – PeekPro – which allowed customers to book trips from our (new) website (www.ospreysecho.com). We decided on the culture and ‘vibe’ we wanted, as there are a couple of other kayak companies already on the island. One is led by a very experienced fellow and the other by a not so experienced fellow. They both launch from the town ramp. There were real pluses to being on our own private launch spot. We can launch into the beauty and peace and quiet of Webb Cove, and then make our way to the islands. Those launching from the town ramp will know that it’s crowded, there’s no parking and you launch right into the harbor where the lobster boats are. No prize for guessing which launch spot has more wildlife to see :-).

It is a tribute to the diversity of skills in our family that we got up and running quickly.  Will’s oldest sister Katie is a marketing maven, expert at social media and our social media presence has been outstanding from the start.  His other sister Sarah works for a bank and her sophistication with finances and cash flow comes in real handy for Will. His older brother was in medical school when we started and a bit short on time, but always pitched in with expertise on risk management and provided a lot of muscle when he was in town.

We got up and running at our new launch spot – 35 Big Pond Road in 2022. The little cove is the ‘big pond.’ Somebody’s idea of a joke, i guess. Will is the kayaking expert. I am the business expert – teaching him about customer service from beginning to end, as the way to build a reputation. We make sure that every call is answered. Every single one. We make sure that every email is answered. Every single one.

This is now our fourth season (third season at Big Pond Road) and things go smoothly.  We have a system for taking bookings, greeting customers, getting them into their gear and on the water.  We have a plethora of routes to take, multiple tour options (2-hour, 4-hour, full day, overnight camping, lessons, custom tours) and a post-tour ritual of taking polaroid photos, putting them in our guest book and offering customers a small choice of merchandise if interested (hats, water bottles, coasters, post cards made by Katie).

We didn’t really think about it at the start, but we couldn’t be more fortunate.  The Stonington archipelago is made up of over 70 islands and is considered by many who talk about kayaking online to be the best sea kayaking on the east coast.   The islands provide a sheltered environment for paddling, hosting and seeing wildlife and an almost unbelievable set of scenery.  It’s pretty easy for us to impress visitors to the island.

All in all, it’s not a bad retirement gig 

Published by steinharterm

Former chief commercial officer with global experience in the IT industry and with a current focus on non-profits and family.

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