The Road More Salty

Original Post on The Salty Way                   

                                   Two roads diverged by the sea, and I—

                                             I took the one more salty,

                                     And that has made all the difference.

Climbing the ladder to that higher salary never seemed worth it. 2 days off a week, 2 weeks off a year, for 20-30 years...

Those numbers don’t add up for me.

I’ve worked a seasonal gig in Montauk New York, lifeguarding for the state and working a bar for close to a decade. The state set me up with a campsite by the beach, just needed a tent or trailer and its rent free living. You can bank decent money in a few months and that was enough to help get through the winter. Things were always pretty thin by springtime.

During college I did a semester abroad in Australia with a side trip to Fiji, went with a friend I played rugby with to his home in Argentina, and took a few trips to Puerto Rico. I worked a bar to support this growing addiction. Surf and travel were the only things that motivated me to make more money.

I graduated college with a degree in history and secondary education. I could teach middle or high school social studies. I was in it for the summers off and ridiculous vacation time but knew halfway through student teaching that I had no interest in being a teacher.

After graduation I booked a one way ticket to Panama. Didn’t know how far north in Central America I wanted to go or how long it would take me to get there. You need proof that you plan on leaving the country so before I flew in, I made a fake reservation for a return flight through a travel agency. I ended up surfing and traveling for 4 months and flying out of Mexico.

I knew I didn’t want to teach or start in on a real career. I had my summer jobs but that alone wouldn’t cut it. I asked everyone I met in Central America that was traveling for longer stretches of time what job allowed them the flexibility for extended travel.
The job that kept popping up was yacht work.
Deckhands and stewardesses servicing multi-million dollar boats in exotic locations. Solid money, all expenses paid and some boats even pay for return flights anywhere in the world for your 1-3 month break. Sounded like an answer.

Ft. Lauderdale in the winter and a handful of spots in Mediterranean during the summer are the largest yachting hubs in the world. The most boats, the most jobs, the most competition. Some guy working at a hostel in Nicaragua turned me onto yachting in South East Asia. Not as many boats, not as much competition, a good place to get your foot in the door and SERIOUSLY cut living expenses while you do.

Went to Phuket Thailand, did my requirement courses and learned to sail for half the price of what it would cost in the states. Walked the docks looking for a job, picked up daywork on random boats and eventually got a full time gig on a 112 ft private motor yacht. M/Y Happy Days.

 M/Y Happy Days

 Left that boat after a month when an opportunity came up on a 100 ft custom built charter sailing yacht. S/Y Asia was half the pay but twice the adventure. We ran 1-3 week charter trips back to back for 4 months straight in the Mergui Archipelago in Myanmar (Burma), the Andaman Islands in India and spots throughout Thailand. 15 hour days for 4 months without a day off unless you include the 2 weeks I was hospitalized with a bad infection in my leg. 

S/Y Asia

After that charter season I left the boat, went to Indonesia and surfed Bali/Sumbawa for a month then went back to Montauk.

Left Montuak in the fall and moved with my girlfriend to Ft. Lauderdale looking for another yacht job. I didn't want to take a charter job spending crazy periods of time at sea so when I came across a position as a property manager/caretaker for an estate in Boca Raton I took it. I detailed their cars, boat, rv, maintained the property and took care of anything they needed. Pretty much chores with high expectations in a really nice house.
Did that for a season then went back to my summer gigs but when I did something didn’t sit right.

REAL ESTATE INVESTING had infected my brain. RENTAL PROPERTIES. Buy it right and you have a property that will produce relatively passive cash flow each month AND build wealth paying down the mortgage with the tenant’s money PLUS potential equity gains. Buy enough of these and you have a consistent income and solid savings in equity building up that allows the flexibility to live life on your own terms. FINANCIAL FREEDOM. I became obsessed. I read everything I could get my hands on and listened to hours and hours of podcasts and audiobooks.

I went back down to south Florida in the fall of 2015, got my old job back and jumped into real estate investing head first.