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The day before Hurricane María made its treacherous landfall in Puerto Rico, Josh Ocasio found himself frantically picking up his last paycheck and packing his life into a single backpack. He knew that anything he couldn’t fit in his bag would likely be gone the next time he came home to Luquillo, a town on the northeast coast of Puerto Rico. But he remained focused on the task at hand: getting to New York City before the hurricane arrived.
A few months prior, Josh had played tour guide to a friend-of-a-friend who was visiting the island from New York with his girlfriend. Despite being a full-time electrical engineering student at the University of Puerto Rico in Bayamón and working as a prep cook at a pizzeria, Josh took time out to show his guests (who he had never met prior to their visit) some of his favorite local haunts and hidden gems.
Fast forward to María’s approach: Josh needed a plan. Hurricane Irma had passed only days before, and he had already spent time and money making preparations for it. Now, the media was comparing María to Hurricane Hugo, which hit in 1989 and was considered one of the worst in the island’s history. Many sources asserted that this new hurricane would be far more devastating than Hugo was. So, naturally, Josh says: “I was petrified. I was so scared, you know? I had spent whatever little money I had on supplies to survive Irma. And then in comes María. Literally a week apart.”
At the time of the storm, Josh was living alone in his childhood home, which he had spent three years refurbishing — redoing everything from its electrical and plumbing to the insulation and flooring. The house was made of concrete, but had an old shingled roof that he knew wouldn’t make it through a Category 5 storm. Lacking the luxury of time and resources, Josh decided to create a GoFundMe page to raise funds for a plane ticket out of the island.
“I wanted to get out of there because I knew I wasn’t going to be able to work, I wasn’t going to be able to go to school, I knew my house wasn’t going to make it,” he says. That’s when the visitors who he’d showed around the island earlier in the year reappeared. He hadn’t spoken with them since they had gone home after their brief vacation. “I got a call from the person I had given a tour to. He said ‘hey Josh, what’s your full name and birthday?’ And like half an hour later, this guy booked a flight to New York for me,” Josh explains, a touch of disbelief still in his voice. “This was two days before María. So I ended up in New York.”
The day he was scheduled to fly out of the island, Josh had his backpack and $120 to his name. When his uncle picked him up to head to the airport, they realized their car was out of gas. Of course, amidst the chaos and panic surrounding the impending storm, there was a long line of cars going into the gas station. Josh barely made his flight: “I had to tell TSA that I hurt my ankle, and they gave me a wheelchair and let me through,” he says, a bit sheepishly. Gotta do what you gotta do.
At that moment, Josh hadn’t given much thought to what the future would hold. All he knew is that he wasn’t sure what, if anything, would be waiting for him at home. The decision to leave was a quick one, but it wasn’t simple. “I had this whole vision for what my life was going to be. I wanted to finish college. And then all of a sudden, in a matter of minutes, I had to come to a conclusion, whether I was gonna stay or go. And I just decided to go,” Josh explains. “I was like, I’m not gonna have a house, first of all. I’m not gonna have a job, second of all. If I don’t have a job, I can’t pay for gas. If I can’t pay for gas, I can’t go to school. And the school was speculating that they wouldn’t have power for six months.”
Upon his arrival at JFK, Josh experienced another dose of bad luck. He knew that he’d need a Metrocard to get around the city, so he immediately purchased an unlimited card at the AirTrain station… only to find out that it was an unlimited AirTrain card, unusable for the subway. “The card looks exactly the same! I spent $45 out of the $120 I had on that.”
Josh’s close friend, Nooklyn agent Leo Heinert (“he’s like my brother”), offered him a place to stay in Ridgewood, Queens. Josh, like many Puerto Ricans, had spent time in New York on and off throughout his upbringing, even living in Staten Island with his mother for a time. Both avid skateboarders, Josh and Leo met while skating in the city and became lifelong friends.
Initially, Josh planned to stay in the States for two or three months and then return home. But as soon as he received word from the island about the state of his house, he knew this wouldn’t be as temporary as he’d hoped. “My plan was to get any job, save, come back and rebuild, and then go back to school,” Josh says. “After the hurricane, my cousin who also lived in Luquillo went to my house and saw that the roof basically flew off. My cousin gave the news to my aunt, who was the only person on the island I could reach in the days after the hurricane, and she told me what happened.” He pauses before continuing, “I put my heart, my soul, into that house. And I lost it all during that hurricane.”
Within days of being in NYC, Josh landed a job in Coney Island. But it required a three hour daily commute and the pay wasn’t great, making him question it and consider other options. “I was like, at this rate I’m never gonna be able to build my house. And Leo had been telling me to get into real estate for a while. So I finally listened. All of a sudden, I was like what do I have to lose? I lost everything already, you know?” Josh says. “So I got licensed, Leo introduced me to Noble [Novitzki at Nooklyn], and he hired me.”
Discovering an unlikely career in real estate
With no prior real estate experience, and frankly, little interest in the industry, Josh dug up the willpower to double down, learn, and see what could come of it. Now, less than a year later, he says, “I love real estate. Nooklyn and real estate have changed my life forever. I love my job. And that’s why I don’t mind spending endless hours in the office, working late nights at home, or showing apartments all over.”
This transition wasn’t as breezy as it sounds, though. A solid support system was vital when Josh was starting out as an agent. “When I met Noble, I didn’t even have a bank account. You have to pay $50 to get your [real estate license] pocket card. And I only had $60 to my name at that point. So Noble just said don’t worry about it and used his card,” Josh recounts. “He has no idea how much he helped me by paying that $50. I wouldn’t have had money to eat after that.”
At the time, Josh wasn’t only new to real estate — he was new to Brooklyn. “Even though I’d lived in New York before, Brooklyn was a mystery to me. I’m like Bushwick, what is that?” he says, chuckling. Instead of succumbing to the overwhelm, though, Josh spent hours in the office studying Google Maps, learning the ins and outs of real estate listings, asking questions, and seeking guidance from agents he noticed were doing well. “I remember being in the office until three, four, five in the morning. Pulling all nighters, doing my homework. I developed a system — I gotta do X in order to get Y.” With this work ethic and step-by-step mentality in place, Josh started to realize he was actually really good at the work. Even better, he realized how much he enjoyed it and welcomed new challenges as part of the game.
“At first, I didn’t know what to even say to clients. But then I started thinking of myself as a client — just a person looking for an apartment. That’s how I figured it out,” Josh says. “Even though I didn’t have an apartment or house myself, I felt a lot of joy in helping other people find a home. But I was kind of jealous finding people apartments, when I couldn’t even get myself one.”
His talent for the job and work ethic didn’t go unnoticed. One day, out of the blue, Josh received a phone call from a number he didn’t recognize. Turns out, it was Nooklyn CEO Harley Courts. “I was like oh sh-t, the CEO is calling, my Puerto Rican a-s is getting fired,” Josh laughs. “But instead, he asked if I wanted to work on a project in East New York. I was like wait a minute, I’m not getting fired? Sure, whatever! And he made me the listing agent.”
When he mentioned the project and the building location to other agents, he got some negative responses — but that only fueled Josh to put in even more effort and prove them wrong. “People were like ‘dude, you’re going to waste your time.’ But I saw it as an opportunity, so I worked hard on it. At first I doubted myself, but eventually I made it work. Now the landlords love me and we leased all 51 units.”
Many of Josh’s peers at Nooklyn admire his work ethic and fearlessness when it comes to exploring new opportunities and facing large learning curves. I ask him how he developed such perseverance and he replies, “Skateboarding. There’s a lot of trial and error in skateboarding,” he says. “I’m not afraid of failing, ’cause I know you gotta fail in order to get back up and succeed. That’s my mindset with everything now. I’ll keep going and going and going until something works. I become obsessive, almost. It doesn’t come easy though.”
While talking to Josh, his unwavering confidence and independence become increasingly apparent. Hearing about how he made the decision to relocate to NYC and how he pushed forward with the East New York project despite the naysayers, I couldn’t help but ask, how does one get to be so self-assured in the face of obstacles? Josh gives me an unexpected answer: his solitary childhood.
“Growing up on the island, I always felt like an only child because my little brother is eight years younger than me and there were no other kids in the neighborhood. So it was just me, alone on this mountain with a strict mom,” he says. “I’m used to doing everything and thinking by myself, to the point where I don’t let myself get influenced by anything or anyone else.”
This ability to trust in his own intuition has enabled Josh to pursue all things with clarity and purpose, unaffected by the noise around him. “I think it really helped me out in real estate because it gave me the chance to do things that other people won’t do, and do them well.”
Case in point: after the East New York project was complete, Josh went to check out a new luxury building that Nooklyn had just started leasing at 321 Wythe in Williamsburg. He was immediately floored by what he saw and felt that he had to be a part of it. “My tropical a-s had never been to a luxury building like that. I was like oh my god, this building is amazing. I didn’t think I had what it takes to rent these kinds of units!” he says. But he reached out to the listing agent anyway to try to get on the building’s leasing team. When he wasn’t selected, he took it upon himself to show clients the building, and in a matter of days, he started getting deals. Soon enough, the listing agent officially let him onto the team. Again, instead of giving up, Josh had proven himself.
Adjusting to the concrete jungle
Though moving to NYC has undoubtedly been a challenge, Josh has decided to embrace it and make the most of his time here rather than fixating on what he left behind. Still, he can’t help but feel uneasy about the change.
“In Puerto Rico, I was straight up in the jungle. I was always going to rivers, beaches, all of these secret natural spots. I loved exploring,” he says, a bit wistfully. “Then I found myself in the city, trying to figure out real estate and how to make money. There’s some nature here, but it’s really no comparison.”
Josh recently moved to his current neighborhood, Middle Village, Queens, where he resides with his wife. They met at a Brazilian restaurant in Jackson Heights not long after he arrived in New York, and now they’re married and expecting a baby. Another game changer for an already surprise-filled year! So far, he’s enjoying the pace and peacefulness of Middle Village, saying, “We live right across from Juniper [Valley] Park. I actually really love the neighborhood. It’s super quiet, very family oriented, residential,” he says of the area. “And I can always find parking. I love that.”
Josh doesn’t know what life will look like in the long run, but he’s more than okay with taking things day by day for now. For the immediate future, he’s decided to trade in a brutal New York winter (notoriously a slow season for NYC real estate) for the Florida sun. As he contemplated this decision, Josh thought back to when he first began working in real estate late last year. “It was winter and I was basically starving. I remember for two months I didn’t make a deal,” he says. “Granted, I was extremely new and learning. But now I have a wife, a kid coming, I can’t have one month where I’m not making a dollar.” If there’s one thing for certain, it’s that Josh can make big decisions with conviction and a level head.
Over the winter, Josh plans to get licensed and work in real estate in Florida, gain his footing, and head back to NYC come spring. Whatever unfolds next, there is no doubt that Hurricane María altered the course of Josh’s life for good. And despite what he lost, relocating to New York not only brought him to a new career path — it enabled him to find love and start a family.
“Real estate has put me in a business mindset. I saw over the summer that hard work does pay off,” he says. “My motive used to be my house in Luquillo. Now, my family is my motive. And it feels like the sky’s the limit.”
All photos by Chris Setter.
