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Dream Big, Win Big

Posted on: Wednesday, May 14th, 2014

Published  | By LifeInNaples

The American dream is personified in its success stories. One of those is the story of Juan Carlos Castilla. He came to America in 2002 from Peru after graduating from Catholic University Santa Maria having studied economic science. Despite an impressive professional degree he obtained at the age of 22 and an early desire to become a diplomat in Peru, Castilla wanted to come to America.

And for Castilla, the American dream would not be paved with gold, but with roof tile and shingles. Today he owns one of the most respected roofing companies in town, Castilla Roofing. The American dream was an epic journey for Castilla. He arrived in The States on a tourist visa – landing in Miami with less than $100 in his pocket. The
first paychecks he received he used to pay back the money he owed for his visa and travel expenses. For a long time, Castilla had no shelter, no food – he looked for odd jobs riding his bike going door to door asking for work. In the beginning he lived in Ft. Myers, often having to sleep outside in the elements.

“Every night I searched for food and I lived in an abandoned house – that was my shelter,” he says. Southwest Florida nights can get cold too, and in coldest days of
winter he could barely move his fingers.

Juan Carlos Castilla

After a few nights sleeping in the abandoned house every little noise would wake him.

“I began doing roofing work and whatever I did, I had to do it right because I was so hungry – and when I found that job in a roofing company I promised myself I would never be hungry again,” says Castilla. “When I was in those years with no money I survived on crackers and instant soup – and I didn’t speak the language so coming
here was like moving to China with $70 in your pocket; it was hard but it was an adventure.”

Castilla credits his resurrection with a family of strangers. “One night, this big guy with a huge cigar knocked on the door of that abandoned house and I freaked out – living on the street you had to run from bad people who wanted to hurt you or had to do with drugs, but you also had to run from police because they don’t want you
to sleep on the streets. Half my body was out of the window but the man said, ‘It’s a really cold night’ and he brought a blanket for me. He told me, ‘I’ve been seeing you coming here every night on your bike, sleeping in this house’.

The stranger had a mechanic shop in Ft. Myers and the next morning, Castilla went to see him.

“I said, ‘Sir, you helped me last night – thank you’, and his wife had prepared a hot meal for me – I started crying when she gave me the food and I ate it so quickly,” says Castilla. “I told them I had no money to pay them, but I asked them to let me wash the dishes and they were so kind, they wouldn’t even let me do that.”

Juan Castilla and Son

Castilla insisted on washing the man’s cars and he helped cleaning the shop to pay for the food the man and his family provided. Eventually he found a job in a labor company and finally had enough money to afford a little tiny room.

“I moved up quickly and learned fast, so they made me a crew leader in the company, and then at his next company in Naples I made supervisor,” says Castilla. After that in Dec. 2006 I formed Castilla Roofing and in 2007 welcomed my first customer.”

Castilla drove around knocking on doors of homeowners who had roof problems to get business. ‘I noticed you have a broken tile – can I fix it for you?’ Castilla would say.
“Some of the people were happy to see me and others would threaten to call police and tell me to leave,” Castilla says, laughing. But he went everywhere, traveling all over for Florida looking for work, a journey that would help him build a reputation and name as a trustworthy, hardworking individual.

Castilla always wanted to be his own man, so rather than work for contractors, he preferred working directly with homeowners, a model that worked for him and still does.

His experience with some contractors shaped the way he treats his own employees. He was once doing stucco work and some of the days worked in excess of 16 hours – yet the man only paid him $50 – and that was after taxes.

“That’s why I believe in treating people as well as possible, with justice and fairness because I was there and I know how hard it is,” says Castilla.

“My motto is work hard, be honest and try to do the right thing because when you work hard, dreams can come true.”

Castilla Roofing does a lot of commercial work and works closely with boards of directors of homeowners associations – most of the company’s work is on big projects, for example one recent project encompassed 25 large buildings.

The Castilla family works as a team, with Juan Carlos working closely with his brother Ramon Castilla who as operations manager is charged with managing all the safety and field operations for Castilla Roofing. The sons credit their father Oscar Castilla for his role as principal business advisor in the company. Both Ramon
and Oscar served in the Peruvian Army.

Castilla is a proponent of charitable work and he is often invited to speak to young people. Last time he went to Peru he spoke to a group about motivation, following dreams and goals and how to accomplish them.

But perhaps his biggest influence now is on his 18-month old son Marcelo Castilla. Castilla says his son is the joy of his life and the biggest reason he pushes himself. “I want to give him the best life ever, provide for him and treat him with love and respect, because while anything can work if you have respect, if you don’t have that nothing is going to work,” he says.

For the future of Castilla Roofing, Castilla has lofty goals. He wants to the most successful roofing company in Southwest Florida and open branches of Castilla Roofing in more places. His motivation is more than just making money – Castilla takes pride in providing work to others who need it.

“Before I was so focused on being somebody in life and growing in my professional life and that was my focus, to grow the company,” he says. “But my son has made me understand that family is the most important thing.”

For more information on Castilla Roofing, visit or call 800.578.0035.









 Read the May 2014 edition of Life In Naples

Read the May 2014 edition of Life In Naples




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