Puerto Rico Changed My Perspective

Hey y’all, Jack here.

This one’s honestly hard to even put into words because my week in Puerto Rico was genuinely one of the most fun, refreshing, and eye opening weeks I’ve had in a very long time.

Last week, one of my sponsors, Ashwavana, flew me out to Puerto Rico to film content, teach clinics, and get involved with the pickleball community over there. First off, huge shoutout to them because they’ve genuinely become one of the biggest reasons I’m able to do what I do on the pro side of things. They’ve supported me heavily this year, and I truly love the team behind the company. Their products have become a huge part of my day to day routine too. I’ve got Guru Focus in my water bottle basically every morning, creatine every day, and Zen Relax at night has genuinely helped me a ton with recovery and sleep.

But honestly, this trip ended up becoming so much bigger than just sponsor content.

Puerto Rico completely blew me away.

Dorado, Golf, and Meeting New People

The trip started in Dorado, which is one of the nicest communities I’ve ever been in. We stayed right by the beach, played one of the PGA golf courses there, and immediately settled into island life.

One thing I’ve realized lately is that pickleball keeps putting me in rooms and situations I never would’ve experienced otherwise. Every single trip introduces me to people with completely different backgrounds, stories, and relationships with the sport, and honestly, that’s probably my favourite part about what I do now.

I played some three and me games while I was there, met a bunch of awesome people, and just spent a lot of time talking with players about how they got into pickleball and what the sport means to them. I genuinely love those conversations because pickleball affects people in such positive ways, and every person seems to have their own story attached to it.

That first night, I also ran a clinic for some kids in the community and had an absolute blast doing it.

And honestly… that was just the beginning.

These matches were a grind. Pool play into a single-elimination bracket, one game to 15- which means no “let’s warm up and settle in” nonsense. You get behind? You’re done. Mentally, it was tough, but it really forced me to stay locked in every single point.

Why Puerto Rico Felt So Different

After Dorado, we headed down to Palmas, and that’s where the trip really took off.

This whole week was what I call “fun work.” I was still waking up every morning to train, drill, workout, and stay locked into my routine from around 8 to 10:30, but instead of sitting behind a computer doing admin work afterward, I’d spend the afternoons exploring Puerto Rico, teaching clinics, filming content, golfing, or just being around really good people.

That’s honestly why I love travelling so much. As long as I have a pickleball court and some drill partners, I can basically work from anywhere in the world.

And the pickleball culture in Puerto Rico was unlike anything I’ve ever experienced in the States.

At one of the clinics, we had around twenty people on court, and a lot of them didn’t even speak English. I had translators helping me the entire time while I taught, which reminded me a lot of some of the clinics I’ve done in Asia.

But what happened afterward was the coolest part.

Once the instruction portion ended, I started running live ball on two courts, which is basically my happy place. We had ten people packed onto each court playing king of the court, music blasting in the background, everybody laughing, chirping, smiling, and having the time of their lives… and half of us barely even spoke the same language.

That honestly hit me pretty hard.

I’m 22 years old, and being able to connect with people through a sport without even needing the same language is such a surreal feeling. It really made me appreciate how powerful pickleball can be as a community builder.

And the atmosphere itself was unbelievable.

Seriously, picture this for a second.

You’re teaching a clinic in Puerto Rico on packed public courts while Bad Bunny is blasting through speakers, one of the moms is cooking street tacos on the sideline, everybody’s wearing basketball and soccer jerseys, people are drinking beers courtside, laughing, talking trash, and fully treating pickleball like a pickup basketball run at the park.

It genuinely reminded me of street basketball culture in Brooklyn.

That’s the closest comparison I can even make.

And I absolutely loved it.

Jersey Culture Was Unreal

One of the coolest parts of Puerto Rico was honestly the jersey culture around pickleball.

There’s a group over there called Cocolias that’s deeply tied into the pickleball scene, and if you wear one of their jerseys, people immediately know you’re legit.

But then there’s another level called El Guayo, which is basically reserved for the top players in Puerto Rico. It’s this limited edition jersey that carries real status within the pickleball community there, and the owner of Cocolias actually gifted me one during the trip.

And I’m not gonna lie… I wore that thing proudly.

It was such a cool feeling getting fully immersed into the culture there and seeing how much identity and pride people attach to pickleball in Puerto Rico. They’ve genuinely built something special around the sport.

And honestly, I want to bring that same energy and culture back to the States so badly.

Pickleball in Puerto Rico feels alive in a completely different way.

Exhibitians, Jet Skis, and One of the Best Weeks Ever

One of the coolest moments of the trip was getting to play an exhibition with JJ Barea, former NBA player for the Dallas Mavericks and honestly one of the biggest celebrities in Puerto Rico outside of Bad Bunny.

We played this huge exhibition match with hundreds of people watching, music blasting, fans chanting, jerseys everywhere, and just nonstop energy the entire time. It didn’t even feel like a normal pickleball event. It felt like a community block party built around the sport.

And once again, that pickup basketball energy kept showing itself everywhere.

After that, we spent a day out on a boat riding jet skis around some of the islands, which if you know me, you know is basically my dream day. I could genuinely ride jet skis for ten hours straight and still not want to stop.

The water was crystal clear, the vibes were amazing, and honestly the whole week just felt refreshing in a way I didn’t even realize I needed.

I was still training hard every morning, but mentally, the trip gave me such a reset.

One Thing Puerto Rico Taught Me

One thing that really stood out to me while I was there was how underrated the level of international pickleball still is.

The DUPR ratings overseas honestly don’t tell the full story.

A 4.0 player in Puerto Rico, Malaysia, or Vietnam honestly feels closer to a 4.5 in the States skill wise, and I think that comes from how competitive and community driven the environments are.

There were multiple players in Puerto Rico who genuinely had the talent to go pro if they fully committed to it.

And one piece of advice I kept giving them is something I think applies to everyone trying to improve:

You can’t be the biggest fish in your pond forever.

At some point, if you really want to grow, you need to go challenge yourself somewhere bigger. Otherwise you start reinforcing bad habits because nobody around you is pushing you hard enough.

That applies to pickleball, business, life… honestly everything.

What’s Next

For everyone in the Cincinnati area, I’ve got something really fun coming up with Jilly B!

We’re hosting a Partner Masterclass on June 9th at Sawyer Point Park, and honestly this is going to be one of the coolest clinics I’ve been part of in a while. We’re diving deep into doubles strategy, communication, positioning, patterns, and all the little things that actually help partnerships win matches consistently. A lot of people focus only on shots, but high level doubles is really about how well you move, think, and problem solve together as a team.

We’re keeping it super limited with only 16 players, so it’s going to be very hands on and personalized. Whether you play mixed or gender doubles, bring your partner and come learn with us. It’s going to be competitive, high energy, and honestly just a really fun environment to get better in.

Really excited for this one!!

That’s a Wrap

Puerto Rico genuinely gave me one of the best weeks of my life.

The people, the culture, the energy, the openness, the love for pickleball… everything about it just felt special. It reminded me why I fell in love with this sport in the first place. Not just because of competing or winning, but because of the people and experiences that come with it.

Huge thank you again to Ashwavana for making this trip happen and to everybody in Puerto Rico who welcomed me in like family. I’ll definitely be back.

And as always, if you guys want to stay more up to date with everything behind the scenes, travel, tournaments, training, and all the chaos in between, make sure to follow along on my socials. I’ve been posting a ton more on Instagram and YouTube lately, and honestly, some of my favourite content yet is coming soon.