Why I left Wall Street to launch a Cuba travel business
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.
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 wellbeing 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.
Along came Cuba.
On the last day of my first semester as a Harvard MBA, December 17, 2014, President Obama announced the normalization of diplomatic relations with Cuba. I went to Havana that summer for my “internship” and discovered that Cuba was an infinitely fascinating frontier, a rich tapestry of raw and authentic experiences. Cultural vibrancy emanated from every corner of Havana, while the business environment was nascent and tumultuous.
The hot summer of 2015 led to a vision forward. With no prior connection to Cuba, no Spanish speaking ability, no industry experience, no clients, no partners, no investors, no market research and no business relationships, I started an experiential travel business called CUBA CANDELA.
If this sounds like it’s shaping up to be a glamorous story of self-discovery, let’s get real right now. The entrepreneurial journey took me from being well-adjusted and self-confident to anxious and terrified.
Our first trip for 137 Harvard students produced several disheartening complaints that I took personally. It was an unexpected setback, but the trip did lead to a crucial pivot. We moved away from large university groups and instead focused on private custom arrangements for individuals (couples and families), where service quality could be executed with a higher degree of reliability and where intimate contact with locals would create a more enriching experience.
The next eighteen months were brutal.
Plagued by self-doubt, half of me wanted to fail so that I could return to stability and a regular paycheck. I was torn apart by ambition on one hand and pride on the other. I discovered that my identity relied on being the guy who had made the leap from state university undergrad to New York City investment professional. I wasn’t ready to give that up, and it turned out to be one of the hardest steps on my journey as an entrepreneur—risking who I am. I suffered an identity crisis. To be an entrepreneur is to not just face challenges but to face death itself, death of the enterprise that is you.
I was intensely lonely—disconnected from friends and family due to my relocation to Miami and frequent trips to Cuba—while bootstrapping as the sole founder and watching a meager savings account click closer toward zero every day. The only way out was to work through it.
No days off. No hours off.
I pushed and pushed and pushed, as hard as possible. As the 100-hour weeks, sleepless nights and bottomless cups of coffee stacked up, my health began to suffer symptoms of chronic stress and physical exhaustion, yet another challenge to overcome.
Then the State Department issued a Level 4 (“Do Not Travel”) warning for Cuba, creating a perception that travel to Cuba was as dangerous as travel to countries like Syria, Iraq, and Afghanistan, despite Cuba being widely recognized as very safe to visit. About the same time, Hurricane Irma was called “total devastation” by the news media. To top it all off, President Trump released new travel rules that claimed to “cancel” the “Cuba deal,” another blow to public perception. The industry crashed. My business suffered significant cancellations. Was this it? Time to give up? Did I still have a business?
I was all in, and it seemed I had been dealt a losing hand.
Some of the hardest questions crept back: Why am I doing this? Who am I? What did I give up? Does every entrepreneur go through this?
I kept breathing.
Failure was not an option. I knew in my heart that as chaotic as the world around me seemed, my belief in this path could not be shaken. A purpose had taken hold of me. Still, the stress was unsustainable. I had poured everything into the business and my reserves were depleted. I needed a new framework. Sheer will was no longer viable, though it had allowed me to move fast and retain full ownership of the company.
Since my exploration of external experiences no longer provided answers, the time came to explore the internal experience. I discovered that most of my stress came from within, from self-imposed pressures, personal insecurities, and unrealistic expectations. My fears and anxieties were generated by my mind.
To rejuvenate and mitigate these stressors, I developed a wellness practice of meditation, visualization, neurofeedback, coaching, therapy, diet and exercise. Slowly, a reservoir of inner peace began to emerge, providing insulation from the entrepreneurial roller coaster and leading to dramatic sleep improvements. At times, I could even laugh at the stress and bring instant relief with an optimistic mindset.
I focused on enjoying the process. This diffused my anxiety about “make or break” outcomes and redirected my competitive nature toward a healthier goal, one less dependent on expectations of financial success and status. I valued the experience of being an entrepreneur and the courage to have taken the leap as sufficient compensation amidst uncertainty. I focused on simply being myself as much as possible.
None of these changes happened over night. They all required substantial effort and training to change embedded behavior patterns and belief systems, especially those that had served me well in the past. The accumulation of incremental benefits eventually turned into paradigm shifts. With renewing focus and enthusiasm, I doubled down. I kept pushing, but I pushed smarter. I kept investing in the company even though we were losing money.
New achievements began to pour in.
Suddenly, every month seemed to outdo the last. Our uncompromising adherence to U.S. law and ethical treatment of local partners, our painstaking attention to detail on the client experience—a great challenge to maintain initially, became a compelling value proposition.
We accomplished one “first” after the next, bringing exceptional service to the Cuba travel market. Our guests, which now included celebrities, high profile individuals and prestigious corporate groups, called their experiences “five-star plus,” “fabulous,” “perfect,” “unforgettable” and “the trip of a lifetime.”
We became the premier provider of private custom tours for couples and families based on a survey of industry-wide client reviews.
What happened? I connected to a purpose.
Cuba inspired me to trust in a purpose, an opportunity to make an impact, to show the world there is more that unites us than divides us. My mission was to share this worldview, through transformative travel in the unlikeliest of places, a country that had been off-limits for decades. My own personal experiences in Cuba were the final catalyst.
Experiences in Cuba shaped my worldview.
Early on, I met a local artist named Fernando, one of Havana’s most charismatic characters. Together we explored a neighborhood far from the tourist crowds. It seemed like a society from another world. Stepping into the living room of a Cuban family home, I felt out of place, and I felt alive. There was something about the way Fernando leaned up against the counter, went right into the fridge and began joking with the family. He had known these people his entire life. Almost immediately, I felt at ease, and in the next moment, as we were invited to sit down for coffee, I felt totally relaxed and welcomed. This was my first experience with cubaneo, the essence of being Cuban, which means to always feel at home, even in the home of a complete stranger. Sharing what we had in common, in the unlikeliest of places, was the most meaningful travel experience of my life.
Minutes later, I was on the building’s stunning rooftop taking pictures that don’t exist in any guide book or photo blog. I stopped at a local studio to hear the graffiti artist describe Cuba’s emerging art scene. I visited an abandoned theatre nestled among dense local housing, a small unmarked door the only clue to its existence. The grand space had been fit for an opera, reminiscent of the grandeur of colonial Spain. Then, another local home to witness a tribute to the deities of the Yoruba religion. Next a local flower shop. A salsa band practice. A local market. An antiques dealer. The cultural vibrancy was overflowing with energy, like Times Square at rush hour, except the complete opposite. Then another secret rooftop. With the sun setting on architectural gems, the rumba band hit full swing, Cuba Libres were passed around and I stepped right into beat without a trace of hesitation. Had it only been two hours? I lost track of time and each moment of the experience took me further from this world and into the next. It was my first experience of the vibe of Cuba. I was blown away.
Then there was the time I met Alexis, a chef, painter and art director from the Cuban cinema. He never kept recipes, insisting that cooking is an art form, and that the artist must work from true inspiration not a formula. Making his own condiments from scratch, scouring local markets for the best organic ingredients, never making the same dish twice, Alexis exuded his passion with every breath. His kitchen looked too authentic to be real. It felt like a movie set, but it was real. The open-air kitchen crossed into a covered terrace with pots and pans hanging outside on a curving wall. Chairs beckoned invitingly nearby. Jars of fragrant spices ringed the counter while trays of freshly chopped food awaited my eager participation in the interactive cooking experience. Every single ounce that went into the dish was magnified by the personality and charisma of the chef.
The tastes were divine. The freshly squeezed juice of cucumber, parsley, lime, celery, mint and ginger was otherworldly. Alexis invited me to participate in his next project, a live cooking performance. A stirring emotion would be chosen by the audience, say love, or even hate, and he would craft a dish that captures that emotion through his ingredients and cooking techniques. It was my first experience of the depth of artistic vibrancy in Cuba.
After dinner, I jumped into a meticulously restored 1950s Chevy Bel Air, and we sped off to Havana’s best nightclub for front-row seats to a 14-piece salsa band with indescribable raw energy. They had just returned from a sold-out international tour to play for an intimate hometown crowd. It was true artistry with soul, up close and personal.
I will never forget my encounter with one of Cuba’s most famous jazz musicians. As I walked up to his local home, I saw the tall, colonial, pastel-colored door was already flung open, and I noticed that nearly every home on the block appeared to be expecting guests. Dodging street life—fruit vendors, children chasing a ball, grandmothers passing by arm-in-arm, hearty laughter, neighbors shouting greetings to fourth-floor open windows—I could feel the warm embrace of the community, far from tourist crowds and cruise ships. Inside, a jaw-dropping performance by the acclaimed young pianist, accompanied by an old timer on acoustic double bass, gave me chills.
Hearing the pianist speak about his family and the inspiration for his music was an experience. As we said our goodbyes, he handed me an unreleased recording just submitted to the Latin Grammys. In almost any other country, this man might live far from the people of his community. In Cuba, he lived right here, his door flung wide open.
The Cuban culture and the authentic experience of that culture are unlike anything I’ve seen on planet earth. More than the energy, the Caribbean sensations, and the digital detox, it is the remarkable people, the moments of being present, and the extraordinary public safety that create an environment for bonding with loved ones, deep conversations on shared values and personal growth.
I just had to share this with the world.
What about the name CUBA CANDELA?
In Spanish, candela means “flame” or “candle,” and in Cuba it is a slang term used to describe something with energy, passion and charisma—just how I feel about Cuba. Candela evokes my mission to illuminate the undiscovered. And, it represents the burning flame of experiential travel, which has the power to bring us all closer together.
My mission at CUBA CANDELA is to make a 360-degree impact. Each one of our private custom tours directly supports more than thirty Cuban entrepreneurs, providing additional meaning and depth to the experience. Yes, you can still travel to Cuba!