Why I left Wall Street to launch a Cuba travel business

Why I left Wall Street to launch a Cuba travel business

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And how I endured Trump’s travel policy, a hurricane and an identity crisis

by Chad Olin | Founder & CEO

Who knew that building a business in an emerging market would be such a gut-wrenching experience? Yet, as a 30-year old Harvard Business School graduate, I set out to pursue my dream of launching a socially conscious travel company.

Havana, Cuba | 2017 || by Danielle Levitt

Throughout my twenties, travel was my passion.

When I began my career in investment banking, I planned to work for two years, then take a break and travel the world. But after a few months on the job, common sense prevailed and I went to work in private equity. Moving up professionally seemed the logical next step, not chasing some vague dream to see the world.

Vacations never seemed long enough to quench my thirst to explore. Believing that “dense” experiences were the key to living life to the fullest, I still sought to expand myself. Dense experiences are enriching, time-bending, transformative “firsts”—often a local adventure in a foreign land. They totally immerse you, so that one impactful day can stay with you forever, while three routine years can fade in the blink of an eye.

When I applied and was accepted to Harvard’s MBA program, with the semester to begin in four months, I saw a chance to travel extensively for the first time. I left my job and set out on a solo backpacking adventure. Booking a one-way flight to Thailand and a hotel room for the first two nights was my only itinerary. The rest would be spontaneous. I was thrilled to be plunging into the unknown and excited to connect with whatever I might discover.

The next four months felt like a year.

I trekked to base camp at Mount Everest, lived in a tree house in Cambodia, meditated 100 hours in Nepal, interacted with pilgrims in Tibet, crashed a motorbike in Thailand, and camped on desert dunes in India. Along the way I met locals and explorers from all walks of life, and was surprisingly inspired by their humanity, the personal connections we made and the stories we shared.

One night in the desert, I saw four shooting stars and felt a compelling wish for the well being of others. A desire to deviate from my career path began to absorb me. I began to feel fulfillment in creating experiences and moments of personal growth for others.

I seriously considered skipping Harvard Business School and staying in Asia for the next twenty years. With money I had saved from working in finance, I could “retire” at the tender age of 28 and live in a small shack on the beach. Weighed against the cost of tuition, I could survive there for decades.

But dropping out and sitting on a beach was not the answer. Raised in a family of musicians and artists, I still felt a deep desire to create and to give back, along with an insatiable hunger to continuously improve and invest in myself. Just as experiences were the pinnacle of personal growth, I felt impact entrepreneurship was the pinnacle of professional growth.

I went home and enrolled at Harvard. I would use the time there to decide what was next—continue in a secure career or launch my own business. Approaching my thirties, it was now or never. Deep down, I wasn’t sure I had the guts. I was scared.

Read more at Cuba Candela

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