Carlos Rodriguez Sr. was ready to do anything to fund his real estate-focused hospitality career beyond Costa Rica, even selling his children's toys.

Rodriguez, founder, chairman and chief executive of Driftwood Capital, did just that to build his first U.S. hotel, a six-storey Holiday Inn near the airport in Miami in 1996.

"We sold everything to move [to the United States] and get our first hotel," said Rodriguez.

Since then, he has expanded Coral Gables, Florida-based Driftwood Capital into a business with 80 hotels in the United States and more than 3 billion U.S. dollars in hospitality assets under management. His investors come from 34 countries, with about half the capital from the United States.

Rodriguez's real estate career started after his stint as an investment banker on Wall Street was upended by the death of his older brother Augusto. His father and brother had built the Aurola Holiday Inn in San José, Costa Rica, but his brother died in 1986, just shortly after the hotel opened.

So his father asked him to return home after 18 months in New York so he could help run the family business.

"There was a Latin America debt crisis, and unfortunately, when he died, the hotel was in trouble," said the Driftwood Capital founder. "I was working in investment banking in my dream job. But my father asked, 'Carlos, can you come and help me?' How do you say 'no' to your dad? You can't."

He learned the hotel business as quickly as he could, even returning to the U.S. to take some courses at Cornell University. He operated that Holiday Inn for a decade and the hotel business grew on him.

"I didn't enjoy the operations side as much as real estate, structuring deals, buildings, hotels," Rodriguez said. "I adapted the hotel business to my background."

The family business, including the San José hotel, continued to expand in Costa Rica with the purchase of a second hotel, but not as fast as Rodriguez wanted. Rodriguez didn't want to compete with his family, so he moved stateside to Miami to start his own hotel company.

"I found it easier to do business in the States versus Latin America. It was easier to raise the money, borrow the money and more liquid to sell hotels," said Rodriguez.

Through the downturn in travel from 9/11 to partnering with Lehman Brothers, a relationship that almost destroyed his company during the financial crisis, Rodriguez learned how to create a capital structure that didn't leave him depending on one investor.

Eventually, he created his first fund with his son Carlos Jr. and David Buddemeyer, who had launched Driftwood Hospitality Management with former Lehman Brothers executives.

Driftwood now has four divisions focused on acquisitions, development, lending and the management company with about 110 employees, not counting the 5,000 workers at the hotel level.

As he looks back to that first hotel in Miami, Rodriguez remembers being down to his last US$500 before he cashed his first US$10,000 dividend. He has learned that every test or setback in his career has made him stronger.

"My mantra from day one" has been to "always keep a good close relationship with your bankers," he said. "The other thing is to keep your investors informed whether it is good or bad."

Rodriguez said if he does expand beyond the United States, Canada would be Driftwood Capital's logical next step because both countries have a strong rule of law with more liquid markets for acquisitions.

"I have been asked to go internationally, but to do it right, you need a whole infrastructure, which is costly," he said, adding that would equate to a launch with about eight hotels in a country like Canada.

Rodriguez said mentoring is one of his goals as a leader, and that includes his son Carlos Jr., who helped him found Driftwood Capital.

"If something happened to me today, Carlos could take over without batting an eye," said Rodriquez, laughing that there is no lingering anger over the sold toys.

Everyone in commercial real estate had to start somewhere. CoStar's First Job column explores where careers began.