So for the last two winters of college I managed a ski shop at one of the local ski hills. I assumed that I would do that again that fall. But I stopped in at the local outdoor gear store called the Trailhead and I applied for a job.

It turns out that one of my professors from the University of Virginia who used to live in Missoula was friends with the owner. When I first moved there I had brought a handwritten letter that said: “this is a good guy, hire him.”

I thought I would work for a few months and then get a teaching job. But I want to stay in Missoula, but with the university cranking out science teachers left and right, it was very competitive and there was no demand.

The owner of the trailhead asked me what I would plan to do. I told him I didn’t know but that I had been paid more for managing the ski shop. He offered me the job as manager of the store, and I said OK.

I worked at that store off-and-on for twenty years.

Something that I forgot to mention that was probably one of the most valuable things was my friends at the University of Virginia who turned me on to skiing and backpacking and climbing. Somewhere along the line I went to the meeting of the outdoor club. I guess I had on big hiking boots and a shirt that said “I hiked the grand canyon.”

The next thing you know I was elected president of the outdoor club. I think it was only because of the way I was dressed; I don’t know. I was the head of the club for three years and I made it from a club that didn’t do anything into a club that did everything.

I organized stuff and I got to go for free. That was the beginning of a good thing for me. I learned that I could provide a service that others were afraid of, but would pay for. Most people want to be guided or led. But I’m an “I’ll organize it, you pay for it,” kind of guy.

That experience worked very well for running this outdoor store. After three or four years I realized that I hated being a manager. I was good at it but I didn’t like it. I was stuck between the guy who makes all the decisions and the people who ask all the questions. The guy in the middle doesn’t do well, so I quit.

We were at a trade show in Reno, Nevada. My wife-to-be had been venturing into sailing in a few places, including Flathead Lake in western Montana. We had sailed in the San Juan Islands, and the Florida keys. My buddies used to work at these various sailboat-building places in the Tampa Florida area.

I had been on many trips with these guys. I’m a Florida boy, pure and simple, and I missed the ocean. Bequia became interested in it, too.

We would go up to our friend Steve and Deborah Buckley’s place on Flathead Lake and just looked out at the water. I remember sitting one day on a deck overlooking the lake and what we used to call the gulf of Montana. We had sailed that morning on a friend’s small boat. We looked at one another and said: “why don’t we sell everything and buy a boat and just sail away?”

Everybody says it, but we did it.

We answered an ad in the back of a magazine for crew on a boat in the Caribbean. It was a 43ft. Endeavor, and we had just chartered a 38ft. Endeavor for a week or ten days. We scared the crap of ourselves but we survived.

We exchanged letters back and forth with the fellow who ran the advertisement, and he suggested that we meet. I took that to mean “I can’t go, so I should buy a ticket, and Bequia should fly to Milwaukee.”

So she did. We were living in Reno at the time. She called me and told me we had the job.

So this meant living on a sailboat in the Caribbean for the year. The owner and his wife would come down and live aboard for two weeks, and the boat would be ours for four or five weeks. We didn’t get paid, but they covered our expenses while we were on board.

So we were sea gypsies. We got on the phone and started calling everyone we knew And telling them that we would be at such-and such port on such-and such date, and to come on down!

So lots of friends came down and sailed with us. We married some of our friends on the boat! I’m the captain, and I could marry them! This was in St. Lucia, and they did the real-life would be all it easy on shore.

But we had a great time. We decorated the boat with an archway of palm fronds, flowers everywhere.

But what became of us during that year, was that everyone had such a great time two things happened. The year two the day after we left I asked Bequia to marry me. I figured that if we could live no more than 43ft. apart from one another for the year in the Caribbean, then we could get along anywhere.

The other thing that happened was that our friends said that they had so much fun that they wanted to do it again. To me this was just like college. People wanted me to organize and plan and they would pay for it.

So I started looking around in Cruising World magazine and I found a boat to lease for eight weeks out of Saint Martin’s. I had never seen the boat before in my life but I started marketing and sold six trips.

We showed up the night before in a place we never seen on a boat we’d never been aboard. The next day our guest showed up and we all went sailing!

That worked out really well. Everyone had a great time. We didn’t lose any money.

The next year I was looking in the back of Cruising World magazine, a nice on two different boats for sale in a partnership arrangement. They both happen to be in the British Virgin Islands.

I called the guy who taught me to sail and we both flew down to the BVI’s and looked at both of these boats and test-sale them. I ended up buying a one-quarter share in one of the boats and started selling trips. It was a Gulf Star 44. We ran that business for eight years.

Bequia and I ran a business called Island Passages Shared Sailing Adventures.

We ran a highbrow and a lowbrow option. For a lot of money, we would take care of everything. We downplayed this option. The other option was more economical for everyone, and we didn’t have to work so much as a shared adventure. We would keep people out of trouble, but we would all shop together, cooked together, do dishes, bartend. We had a great time doing it this way, and we didn’t have to work so much.

After all, we weren’t doing this business for money, we were doing it for the lifestyle of living way beyond our means. I always like to live well… beyond my means!

Eventually we sold our share of that boat to one of the other owners. After that, we least a boat in the British Virgin Islands for six or eight weeks and did it again. We skipped a year, then at least a boat back in the Grenadines. For the last two winters we haven’t been back. We’ve been coming here to Todos Santos.

Nothing’s happening right now, because I go surfing every day, but La Paz is calling my name. There are lots of boats there, and plenty of people would want to rent them. Boats are black holes in the water that you pour money into.

Eventually, we may find a boat to use. Most of our customers have been sailing with us for many years. They tell us anywhere you want to go just let us know where and when, and we will be there.

I have a 100 ton master’s license from the United States coast guard. That meant a lot to me to get that. Bequia is a dive master.