The end of my walk across Cuba

This is part i / iv of telling my Cuba story. We’re establishing the DNA of SlingShot — your personal concierge for reward travel. Our mission is to empower more people to see more places by making it way easier to travel for free.


Writing in my journal — first days in Havana.

In August 2014, I quit my cushy San Francisco startup job to ride a bicycle from Seattle to the Florida Keys. Before setting off, I told myself and others that, should money and motivation remain at the end of my journey, I planned to find a boat headed to Cuba.

The bicycle tour was truly epic — across Washington, through Idaho and over the rugged mountains of Montana, Wyoming and Colorado, till the dry, flat plains of Oklahoma, Texas, and Louisiana.

Then, upon reaching New Orleans in late November, a series of deeply personal, powerful, spiritual moments were set in motion by a sudden realization: I no longer felt safe riding my bicycle in the Southeast USA. This area is sadly well-known as a dangerous place for cyclists. Without going into detail, these events led me to quit my bike trip ~800 miles short of Key West.

I felt my identity, shattered. I was no longer the intrepid bicycle adventurer. Instead, I was just some idiot who had quit a six figure role at one of the hottest tech companies in the world only to then …. quit my journey, just a stone’s throw from the finish line.

What followed can only be described as crisis. I borrowed a friend’s car, drove into the woods, and spent two manic, sleepless days and nights wondering what could possibly come next. Lost.

And then — December 17th — the announcement of the dramatic, long overdue reconciliation between the United States and Cuba, brokered in large part by Pope Francis — a truly great man. My earlier plan resurfaced — purpose, once again.

Less than 3 hours after this news broke on December 17th, 2014, I visited the New Orleans State Department Office. I told the woman behind the heavy glass panel a story; with announcements of the diplomatic breakthrough playing on a nearby TV, I shared that I’d met a British girl on Bourbon St, and needed a passport to track her down in London. “Consider yourself expedited”, the agent said.

Only a few weeks later, I landed in Havana, Cuba.

Stay tuned for part II / IV.

  • Dan

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