Christian Toraldo '98 - Destination: Inspiration

“I had this amazing opportunity where I got to meet the Maharaja of Jodhpur, who is basically royalty, and he greeted me in a way that I will never forget. It was one of the warmest, most welcoming greetings that I have ever experienced,” Christian shares. “I’m nobody – just a dude from Baltimore – and the Maharaja greeted me with open arms and congratulated me. It just reminded me that being good and open and loving toward people from all different walks of life all over the planet goes really far.”

Rewind about six years to another meaningful meeting in a place far less grand. It’s the winter of 2010, and the United States economy is recovering from the Great Recession. Banks are back on the rise, and a young Christian is planning on riding the wave of imminent economic growth all the way to Wall Street, where he has a job waiting for him following his spring graduation from Columbia Business School.

Christian and his friends are on a winter break ski trip in Vail, Colorado, when he bumps into a friend and former employer. The friend, Exclusive Resorts founder Brent Handler, reveals that he had been planning on calling Christian that weekend with an idea for a new, subscription-model luxury hospitality business. Sitting in the corner of a dingy ski town bar, the two shout over loud music about Brent’s vision and its potential for success. After a few follow-up discussions, Christian would turn down the job at the bank and begin building a business from the ground up with his new partners.

Today, their Denver-based company, called Inspirato, manages about $1 billion of luxury residential real estate assets around the world. It has over 550 employees and 17,000 members, who each pay an initial membership fee and annual dues in order to have access to Inspirato’s portfolio of vacation properties.

“Inspirato has grown so quickly because we have democratized the way that people can approach staying in luxury homes,” Christian explains. Rather than following the common model of luxury clubs or luxury fractional properties, which requires members or owners to pay exorbitant fees for access to a single property, Inspirato offers its members more reasonable prices and destination flexibility. “We thought, wouldn’t it be better to have access to a billion dollars of real estate, hundreds of luxury homes around the world, all managed and controlled by Inspirato, and you could join at a fraction of the cost of owning a house?”

Christian’s main responsibility within the company is acquiring real estate worldwide to add to Inspirato’s portfolio, which currently includes locations in the United States, South America, Mexico and Central America, Europe, the Caribbean and Bahamas, Canada, Australia, Asia and the Pacific, and Africa. Previously, Christian served as the global head of sales, building, training, and leading an 85-person sales team across North America.

In each of his roles, Christian has had to rely heavily on contacts within his network to help him establish business relationships in the international market. “It’s an amazing business opportunity when you realize that the world is actually pretty small,” he says.

For Christian, those relationships are key. They are not only necessary for getting his foot in the proverbial door of acquisition negotiations, but they are also intricately knit into every aspect of Inspirato’s business model.

“In Mexico, everything is based on relationships,” he explains. “People will not do a deal with you until you sit across the table from them and talk to them. That’s one of the cultural differences that I loved because at the end of the day, you end up forging these really longstanding relationships. When the deal is founded on personal connection and trust, you have a much stronger and more fortified business relationship.”

When building relationships across cultural barriers, it helps that Christian is fluent in Spanish and has a working proficiency in Italian. However, he says the most important aspects of his approach involve proving he is a capable negotiator, presenting himself in the right way, standing behind his brand, and holding true to his word. “Those are all values that came from the institutions I first learned from,” he says. “And, Saint Joe was at the very center of that. The education at Mount Saint Joseph translates very quickly outside of Baltimore, outside of Maryland, outside of the United States – it crosses borders.”

With those tenants in mind, Christian trained his sales team to approach each potential client as a new relationship. “We have access to the most wonderful and beautiful moments of people’s lives,” he muses. “In fact, in many ways, we help create them. When people go on vacation and celebrate a 50th birthday, a graduation, the birth of a child, a marriage, Inspirato is woven into the tapestry of that life experience.” And, that is exactly what they are selling – experience.

As Christian sees it, travel is a gift. It is brilliantly transformative, and his company creates the opportunity for people to experience that. “At the very heart of the human condition is a desire to understand our existence,” he says. “Think about how great people feel when they travel. Think about how exhilarating it is and how they think differently and how the future becomes brighter. There’s this instant hope and this reconnection with the people they love. Creating and building a brand around all those emotions is one of the most exciting parts of my career.”

Just as Christian was awestruck by the compassion shown to him in Jodhpur, he hopes his clients will also return from their vacations feeling a sense of purpose and wonder, refreshed by the new lens through which their travel experience allowed them to see the world.

Inspirato, after all, is Italian for “inspired.”

Read more stories about Gaels abroad in the Summer 2019 issue of The Mount magazine.