I can sit here and gloss over my bio. Or, I can tell you the truth. Let’s go with the truth:
Young life: I had a rough but interesting childhood. Born in Chicago, raised old-world catholic. I was the middle of three, with an Italian-born mom and a Brazilian-born dad. My first six grades were spent in an archetypal, pre-Vatican II-era parochial school. Did I mention that it was run by the most psychotic nuns west of Poland?
Grew up doing stints in Italy, Brazil, New Jersey, and Florida. Kicked out of the house on my 18th birthday. Barely graduated high school and didn’t make it past my second year of college.
Notable failures during this period:
Had my car repossessed (despite my efforts to hide it from the repo guys) and got fired from a restaurant job before it even opened. Perhaps my most notable low point was when I found myself scraping asbestos off a school ceiling working for a temp gig. I purposely threw myself off the scaffold to get hurt on the first day. Just so I can get out of there with some workers comp.
Did a navy stint without having to go to the brig, albeit barely. I was stationed on the USS Saratoga and did two deployments in the Med and the Indian Ocean. While I hated military life, it made me realize that I loved the sea and wanted to see more of the world. I should have figured it out another way, though. Thanks to the ridiculously high-noise environment I was exposed to on the ship, I ended up losing most of the hearing in my left ear. And now, I’m cursed with tinnitus for life as some bizarre karmic reward.
I struggled through much of my early 20’s in a hazed, dismal existence blurred by endless partying and fantasies of riches in Florida. Despite the inevitable threat of bankruptcy and foreclosure, I somehow managed to escape to the Caribbean. As if out of some lame Jimmy Buffett song cliche, I worked as a bartender and got into the yacht charter trade around the Virgin Islands.
By 25, I was living an insanely amazing life of sailing, financial solvency, bachelorhood, travel, and adventure. I got married to a Dutch girl I met while backpacking Europe during a summer break, after ditching a crew job in Sardinia. We lived in the Virgin Islands for a year, then moved to Florida. That’s not a typo.
By 33, after a few failed ventures and desperate times, we left Florida for good (and not a moment too soon). My then-wife had graduated with a bullshit liberal arts degree from the University of Florida. Which let me add, served no real purpose and saddled us with $40k of student loans. We made our way to Los Angeles in 1996.
Thanks to a strange combination of luck and incomprehensible levels of hard, stress-laden work, I finally got a break. I managed to build a successful internet company out of nothing over the next five years. Sold out in 2001 after the dot-com bubble and two weeks before 9/11. I ran a couple of other businesses and dabbled in some lucrative real estate investments until 2003.
Then by 40, I declared myself retired. Cashed out totally. Literally sold or gave away everything and bought a 50′ sloop ( named ‘Andiamo’). It was time to make good on a lifelong dream to sail the seas. Seemed like a great plan and a great time to do it.
Six months later, my marriage ended in about the worst way imaginable. I was alone in Mexico with three cats and a boat in shambles. Four months after that, my father died.
Curveballs notwithstanding, I managed to cobble life back together and venture on. I cruised Andiamo around the Western Caribbean between Mexico and Colombia for the next five years, having one adventure after the next. Those ranged from having a shotgun in my face during a Honduras bus holdup, to narrowly escaping death by electrocution while sailing through a most lethal electrical storm.
Don’t worry, there were plenty more good moments.
In late-2008, the global economic crash managed to suck me down with it. Retired life was over less than a mere five years after it started. It was either go back to LA and take a lucrative job at a former colleague’s company or put Andiamo to work. I chose the latter.
Did that for the next four years, with some success. It at least kept me from crawling back to my old life in LA. Things ultimately melted down in 2012 due to a crazy partnership situation. I did manage to come out of the whole situation fairly unscathed, surprisingly enough.
These days I work full-time as a copywriter while traveling the globe as a digital nomad. Having been doing it long before it became a thing, I struggle with the idea of planting roots in one locale. My Italian better half (also a DN) and I often have long discussions about “settling down”. Though we agree that we may eventually have to do it, the nagging question is…