Clear Eyes & Clear Skies with Clear Sky Lending

Even growing up in South Florida didn’t compare to the clear skies of the Keys. At least, that’s how Oscar Casariego felt when he moved to Key Largo with his parents. He was 20 at the time and excited to build a life for himself in paradise. Oscar saw clearly early on that in order to spend time on the water, he needed to make money on land. So, he started his career by investing in property and developing warehouses to rent the units. Soon after, he met his wife Jennifer, and they started their family.

It was all clear skies for his growing business and growing family until the Great Recession hit. Suddenly, Oscar’s vacancies increased drastically, and the remaining tenants were requesting significant rent reductions. The skies were darkening with no clear solution in sight. For both his sake and that of his tenants, Oscar knew he needed to renegotiate terms with his bank. He went to his bank and sat on the client side of the desk, listening to what he didn’t want to hear. It seemed everything he was told in the past was being contradicted, and the current reality threatened to take all he’d worked hard for. 

“When I sat at the bank’s desk and was told I didn’t have any options, all I could think is, This isn’t right. This isn’t how it’s supposed to be,” Oscar says. “I saw clearly at that moment that I needed to understand what happens on the other side of that desk.” 

Oscar took his disappointment and used it to fuel his new ambition. He was determined to learn everything from the banker’s side to help his land development business not only survive but thrive. His wife then helped him realize he could expand his mission even more. Jennifer Casariego is a real estate agent with LoKation Real Estate and pointed out that he’s not the only one who could benefit from his new pursuit. She and her colleagues had many clients who were turned away from banks because of their unusual situations. That’s when Oscar decided to become a licensed loan originator. He initially worked for a local lender but wanted to do even more. So, he launched Clear Sky Lending in 2016. Jennifer’s cousin, Lissette Romero, joined soon after, and they’ve been expanding ever since.


“We’ve grown so quickly, gaining both agents and clients, because of our out-of-the-box lending,” Lissette explains. “Other lenders go after low-hanging fruit with cookie cutter loans and clients. At Clear Sky Lending, we’ve dug in and formed relationships with banks that offer uncommon lending options. That’s why we can help clients that no other lender can. ”Clear Sky Lending does offer mainstream loan options, like FHA, conventional, VA, and refinancing. However, they also offer a wider range of products, including but not limited to vacant lot, construction, and new and used manufactured home loans.

“I really enjoy helping people buy their dream,” Oscar says, “especially when other lenders basically tell them to stop dreaming.” 

Oscar continues to dream himself. He and his wife work hard in their respective businesses while enjoying as much family time as possible. They spend most of their free time boating with their three children, the eldest of which has become a loan originator herself.

Oscar continues to invest in land development, but his main focus is on expanding Clear Sky Lending to help as many people as possible. He’s continually building his team with local, highly experienced loan originators. “I know what it’s like to sit on the other side of the table. That’s why we offer very personalized service and highly competitive pricing,” Oscar says. “When people go after their dreams, they should only see clear skies.”

–Jerrica Mah is a writer, Army wife, and freelance book editor, who loves to travel with her family.

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