From Stateside to Island Vibes: One Company’s Journey to Puerto Rico (With a Few Laughs Along the Way)

So, you’ve decided to take your business from the continental U.S. to Puerto Rico. Good for you! Get ready for beautiful beaches, delicious food, and, well, some unexpected surprises. Here’s a little story about what happened when a mainland company tried to make that jump.

It all started with a pitch that sounded too good to be true. "Puerto Rico has these amazing tax breaks," said Gary, the CFO, with all the excitement of someone who had just discovered free money. “We move there, save a ton, and sip piña coladas during conference calls. It's a no-brainer!” Gary clearly hadn't been to Puerto Rico before.

Flash forward three months later: the CEO and team were on the island, sunburned, confused, and realizing that their “piña coladas by the pool” vision was, let's just say, a little optimistic. It started with their first government meeting, where they realized that the entire presentation, including the PowerPoint slides, was in Spanish. Gary, confidently clutching his barely-passed-high-school-Spanish skills, tried to break the ice by introducing himself with, “Hola, soy Gary, y tengo un gato en mis pantalones.” He meant to say something like "I'm excited to be here," but apparently, Gary had just informed the room he had a cat in his pants.

Things snowballed from there.

Turns out, setting up a business in Puerto Rico is a bit like going to the DMV on a Monday after a holiday. There’s paperwork, signatures, more paperwork, and, of course, the delightful game of “find the correct government office.” And spoiler alert: none of them are in the same building. One day, the team spent five hours trying to get one permit stamped. After waiting forever in line, they were told they needed three different stamps from three different offices in three different neighborhoods, none of which could be located with GPS.

But the real kicker? The Jones Act. No one had warned them about this little beauty, which essentially means that if you're shipping something to Puerto Rico, it has to be on a U.S.-flagged ship. So, that fancy new office furniture they ordered? It arrived weeks late, cost about twice as much as expected, and somehow came with a bill for shipping that looked suspiciously like the GDP of a small country.

On the bright side, the island’s beauty never failed to impress. While waiting for their internet to be hooked up—which took a month (island time is real!)—they held their team meetings on the beach. Everyone started showing up in flip-flops and tank tops, which wasn’t exactly “business casual,” but, hey, morale was at an all-time high. The company’s CFO, Gary, after the cat-pants incident, became a local legend at the café they frequented, known as “El Gato Hombre.” Not quite the corporate identity they had envisioned, but close enough.

And let's not forget the time their first electricity outage hit—mid-conference call with a key investor. Nothing says “we’ve got this under control” like suddenly going dark for two hours and reconnecting from a hotspot powered by a solar charger purchased on a whim.

In the end, they made it work. The tax breaks were real, the talent pool was incredible, and they got the hang of the bureaucracy (or at least figured out which office had the best coffee while they waited). And while Gary’s Spanish never improved, his island tan did.

So, if you're thinking of making the leap from the mainland to Puerto Rico, just remember: bring a translator, expect the unexpected, and embrace the island vibes. And maybe, just maybe, leave the cats out of your pants.

They learned that doing business in Puerto Rico is like a good mojito—it takes a bit of time and effort to get it right, but once you do, it’s worth every second.