my story

wolf management

While attending the University of Colorado, I took an unorthodox educational route which impacted my business and management career, for decades.  It began when I met Lucas, a one-year old ambassador wolf from Mission: Wolf, a wolf sanctuary and education center. 

So impressed, I eventually lived full time as a volunteer at the sanctuary. Living with wolves and what I learned from them shaped how I would lead and manage hundreds of people for decades to come. 

Tom Popper and ambassador wolf, Lucas

Despite centuries of fear brought about by childhood fairy tales and government eradication programs, wolves are incredibly family oriented, highly intelligent, playful, skillful, and essential to our ecosystem. Even ‘the big, bad wolf’ depends on the group dynamics of the pack and their ability to work as a team to survive. 

Innately shy, especially of humans, it took me months of patience, persistence, learning how to communicate, and giving respect to earn the trust of the sanctuary’s resident wolves. It mattered not, that they relied on me in captivity, I still had to earn their respect. Eventually, they welcomed me into the pack and each day showered me with love, affection, endless play, and the ability to get up close and personal, to learn so much from these incredibly intelligent animals. 

An alpha wolf as a CEO

There are many parallels between an alpha wolf managing his/her pack and how a CEO manages a company. Both are responsible for leading, making tough decisions, and are ultimately responsible for the health and survival of the people or wolves they lead. Both need to understand the strengths and weaknesses within the pack or company and how to utilize those resources for optimal effectiveness. In business, if the leader fails to understand this, it fails to reach its goals. In the wild, the pack starves. 

While the alpha wolf is often the strongest and largest of the pack, ruling with an iron first often spells disaster for the pack. It brings contempt, fear, and disorganization which ultimately threatens the survival of the pack. So much so that overtime, and because it’s essential, the pack will overthrow the alpha wolf and replace him/her with a more competent leader. While a more subtle approach may occur in business, CEO’s can achieve so much more by instilling pride, gaining trust, and earning respect from each employee.  

 

Little did I know that my time with the wolves would impact how I managed teams of people in business and as a President and CEO for 20 years. Being the boss is never enough. A business leader, much like an alpha wolf must be fearless. A leader needs to provide clear and consistent communication, know when to take risks, have a clear vision or plan, and ensure everyone is working together, rather than working apart. But more than just being fearless- it’s about instilling pride, gaining trust, and earning respect from the team.

“Being the alpha wolf isn’t only about being fearless—it’s about instilling pride, gaining trust, and earning respect from the pack.”

Tom Popper at school in Madurai, India

india, where it all began

I’m often asked, how did I become involved in the travel industry. There are two seminal moments, one personal and one professional, which altered the course of my professional career and landed me in travel. The first was during my first international trip, beyond North America, to India. And later my trip to Cuba.

The experience of traveling to India for the first time and being thrust into a completely foreign culture, all while warmly being welcomed into every aspect of people’s lives, made me realize that the world has far more to offer than I had ever imagined. This discovery of different peoples and places was intoxicating. As the people and their communities opened up to my presence and inquisitiveness, I learned to shed my inhibitions, and be confident, if not fearless, and definitely willing to venture far out of my comfort zone. 

By way of a a little story and to provide context to the picture here, one day, I decided to go far off the beaten path. While walking along a footpath through a dense forest, outside the southern city of Madurai, I heard the faint sounds of school children in a classroom. I was surprised since I hadn’t seen any signs of a village or people other than the worn footpath I was on and a few ancient Hindu deities along the way. 

As I got closer to the sounds, I came upon a one room cinder block building and it became clear that I had stumbled upon a little village school. Of course, my curiosity got the best of me, and I had to peek into a window. Startled, the teacher and students immediately saw my face. I thought for sure I was busted. You know, that feeling when the teacher catches you doing something you shouldn’t be doing? As expected, the teacher quickly came around the corner and approached me. 

Much to my surprise and with all manner of excitement, invited me into her classroom to meet her students. As it turns out, she was teaching English when I stumbled upon them. The class looked at me with star struck exuberance. I later learned, they had never seen a westerner before. Before the teacher could finish introducing me, the children leapt from their seats, arms outstretched, running to me offering hugs, squeezes and pure adulation, as if I was a long-lost favorite uncle. The joy I experienced was overwhelming. I had many more similar experiences during that trip, which changed the way I travel, forever. 

Years later, I wondered if other travelers have similar experiences or if the majority of travelers simply miss out, for one reason or another. I thought to myself, that being able to create and share similar moments with others, would be a dream career. Little did I know that this dream was about to come true, after traveling to Cuba. 

cuba, at last

I found my way into the travel industry during my first trip to Cuba, a destination off limits to Americans for 40 years. 

I was greeted with affection from the people I encountered and a genuine warmth and willingness from the Cuban government to work together and bring Americans to Cuba. Shortly after that trip, I left my job as a marketing and sales executive of 10 years, and founded insightCuba, the first company to provide legal travel for Americans.

Tom Popper at the Cuban Association for the Blind, Havana, Cuba

Colleagues and travel industry experts were skeptical of any potential success given the uncertainty of working in Cuba, U.S. sanctions, travel regulations, and the challenge of convincing would be travelers that traveling to Cuba was now legal, after being told for 40 years that it wasn’t.    

As president I took our company from obscurity to becoming a well-known pioneer in a rapidly quickly growing destination throughout the travel industry. I became an expert on U.S. regulations as well as U.S.-Cuba relations, much out of necessity, and was sought-after by the media to talk about a country that the U.S. knew little about. See my In the News page for some of my media coverage.

Over the next 20 years, I grew the company, continued to innovate, and defied expectations in a politically charged climate.  We brought thousands of Americans to Cuba each year to experience their amazing culture that had been unaffected by westernization. We introduced the first Americans to the Havana International Jazz Festival. 

We became the first company to promote the Havana Marathon in the U.S, received the first cruise license, secured numerous strategic partnerships, and led a lobbying effort which avoided the cessation of legal travel to Cuba for Americans. 

We also sent the largest numbers of Americans to Cuba in half a century, and received numerous awards including the Conde Nast Traveler Top Specialist Award for six consecutive years, the Hospitality Sales and Marketing Association International (HSMAI) award for marketing and public relations three times, and Tripadvisors Travelers’ Choice Award.

In 2019, insightCuba was acquired by global tour operator, Friendly Planet, where I stayed on as president of insightCuba and was also appointed CEO, for Friendly Planet.

In 2021, I formed 82° WEST CONSULTANTS, to help businesses explore and execute a market entry strategy into Cuba across many sectors of the Cuban economy. 

SUCCESS STORIES δ AWARDS

launched & positioned brand as market leader

Positioned insightCuba as the leader in the Cuba travel marketplace, and secured the largest B-C market share for six years.  

Conde Nast Traveler Top Specialist Award 2020

SIX time Condé nast traveler award winner

Earned Condé Nast Traveler’s, Worlds Top Travel Specialist Award, for six consecutive years.

Public relations expert

Dominated as a public relations expert and spokesperson regarding the travel industry, U.S.-Cuba relations, and regulatory issues. I’ve been featured and interviewed in 100’s of media outlets and been a contributor on CNN, NBC, CBS, and NPR.

Tripadvsor Travelers' Choice 2020

sale of insightcuba

Orchestrated the sale of insightCuba to global tour operator, Friendly Planet Travel, Inc., to cement their position in the Cuba market.  

international relations & trade expert

Established and advanced relationships at top levels within the Cuban government cementing trust and business access for the company and the U.S. market.

HSMAI Adrian Award

successfully lobbied u.s. dept of the treasury

Successfully lobbied the U.S. Department of the Treasury with Congressional leaders and a high-profile media campaign to restore industry licensing.

award-wining integrated marketing strategy

Led the largest integrated marketing strategy in the industry inclusive of SEM, email marketing, SEO, social media, text marketing, lead generation, public relations, CRM management, and sales automation.

Lux Life Travel Award

Achieved 1 billion media impressions in single quarter

Achieved 1 billion media impressions in a single quarter, the largest in the travel industry, through the execution of an international public relations campaign surrounding a brand relaunch with live and prerecorded coverage in the U.S. and Cuba.

increased b2b revenue by 150%
over 3-years

Increased B2B revenue by 150% through the execution of a 3-year trade strategy including the procurement of preferred supplier contracts and the creation of a dedicated B2B business development team.

Conde Nast Traveler Top Editor's Pick

proprietary sales training program & protocol

Drove sales growth, increased sales efficiency, and provided industry-leading customer service through the creation of a proprietary sales and customer service sales training program and protocol.

increased customer engagement through Sales automation

Increased customer sales engagement by 25% through the creation and execution of a sales automation strategy using personalized drip marketing emails, SMS texting, and CRM lead scoring.

digital transformation strategy

Achieved significant increases in ROI and operational efficiencies through a multiyear, companywide digital transformation initiative, including real time booking automation, CRM integration, sales and lead attribution, data analytics, and sales intelligence.

opened new sales channles

Increased sales revenue by as much as 15% and reduced cost of goods by 5% by opening new sales channels through marketing partnerships within and outside the travel space. Also resulted in increased awareness.

launch of call center in Panama

Realized a 10% payroll reduction and other operational savings by opening a sales and customer service call center in Panama City, Panama.

crisis management

Shepherded insightCuba through numerous economic and political crises. Retrenched the company, remained profitable, and remobilized to return to growth.

secured authorization for U.S. travel agencies

Secured the ability for all U.S. travel agencies to legally sell Cuba travel products without licensing from the U.S. Department of the Treasury, paving the way for the larger industry to enter the marketplace.

Sales Coaching & Certification Program

Improved sales performance, sales training and customer service by developing numerous sales coaching and certification programs.

official travel provider for havana marathon

Procured first-ever rights as the Official Travel Provider for the Havana Marathon which positioned us as the go to source for bookings and race information. Resulted in sending the largest delegation of U.S. runners in the race’s history.

Secured cruise authorization to Cuba

Secured authorization from the U.S. Department of the Treasury to allow for Americans to legally cruise to Cuba for the first time in history. 

feature in the new yorker magazine

After President Obama’s détente with Cuba, my story as president of insightCuba was featured in The New Yorker Magazine.

first U.S. lead media event in havana

Organized and moderated the first U.S. lead media event in Havana for the first time since 1959 with over 150 participants from the media as well as U.S. travel industry leaders.

Awarded first sports license for Havana Marathon

Obtained licensing from the U.S. Treasury to permit U.S. runners to legally run in the Havana Marathon for the first time in the race’s history.