Today’s newsletter is coming to you on island time. 🍻 I’m not sorry at all for the delay, as I’ve been taking our travel day home as chill as possible. (definitely pronounce “possible” with a Spanish accent for no reason in your head as you read this, it’s just a way better vibe).

As I write this sitting at the bar at Leatherback, the location of two of our shows this week, I can’t help but feel like my skin is crawling with gratitude (or is that sunburn)?

We had one HELL of a week on island. It has been the coolest adventure to build these shows each return to the point of expanding to bring our pals and absolute stand-out comedians with us.

You can read more about how these shows started in my newsletter from a few weeks ago, but I’ll just recap a bit here. In 2014 one of my best pals moved on a whim to St. Croix, and she mentioned a complete lack of comedic entertainment - literally, none. I came out with a friend from LA in 2015 and we put on a week of rag-tag shows between St. Croix and St. Thomas. It was rough, but we were onto something.

In 2016 I came back out just for a visit, and I was bombarded with so many requests to perform we did a pop-up show last minute at Common Cents, and the rest is history. I came out every year thereafter, even doing a last minute run of my first special in 2019 weeks before filming on my canceled wedding day, a concept only expats and islanders can suspend enough belief to jump on board with. Jake came with me in 2020 in the pandemic when comedy in the states was completely shut down, and we were able to sell out two shows and help a staple of the St. Croix bar scene during a challenging time for business.

Since then we grew to incorporate other island staple businesses and expand it to where we can not only have awesome, sold-out shows, but also share the journey with some of our favorite people in comedy. This adventure has grown to a point that it looks like we will be doing these STX Comedy Fest tours bi-annually with full support of this badass island. This is only the beginning…

The Hustle

Building a comedy festival on an island and expanding who performs with us is definitely a hustle.

First thought with booking - who can hack it on an island? Sounds like a no-brainer, but this island is not for the faint of heart. Audiences have had to be trained by both myself and Jake over the years of how to behave (without comedy clubs and the usual training of audience etiquette, let’s just say we’ve had some rowdy moments).

Also, it’s an island. Parts are beautiful, and parts are rugged. Everything’s a little dirty all the time, there are bugs, rainforest, shit in the ocean that won’t kill you but could fuck your day up - not everyone fits the bill of handling the crowds plus the ebb + flow of daily island life. We adventure and explore day time, quick shower and refresh pre-shows in the evenings, and there may only be enough hot water for the first half of your shower, if any at all. Sometimes power knocks out, wifi is spotty, and by the time you realize you’re burning in the sun it is WAY too late.

I gotta say, my girls Kellye Howard and Amy Shanker CRUSHED it on all fronts. We had THE BEST TIME hanging together, all the shows were packed and just the most fun, and we dealt with bugs and dirt and sweat and sunburn without complaints.

Hell fuckin’ yea. We did it. First ever STX Comedy Fest in the books, babayyy!

The Chill

As I write this section, I’m on a call with Kellye Howard and Kristen Toomey, my fucking GIRLS from Chicago and two of the best comedians in the country. We are doing weekly calls to focus on gratitude and positivity, building our dream careers through conversations surrounding exactly what we want to happen.

I find myself really thankful for where I’m at in my career, not just personally and professionally, but the growth alongside my peers. We have been pals now for 15-20+ years, all hustling on this grand journey through a life in comedy, but we’ve also learned how to be real and supportive, and keep our heads right. In comedy, or in any career, the mentals are the biggest hurdle.

I’m proud of all of us for growing as a collective, being ultimate supporters and fans of each other, and truly acting as a unit to make sure we all land exactly where we should in this journey at the right time.

The island humbles you, makes you feel grateful, and teaches you to chill the fuck out because this is island time!

We had a few bumps on this trip, but it’s funny how little that shit matters when you can reflect on the big picture. Literally a perfect trip - and the “oopsies” can just become jokes we all get to have our versions of.

On the day leaving for St. Croix, both Jake and I had food poisoning. He got it early in the day, it started hitting me that night, but we had to pull an all-nighter to leave for our flight at 4am… let’s just say food poisoning while packing and flying is probably the worst timing.

We landed in St. Croix 2 hours after Kellye (we were supposed to land 3 hour ahead of her) due to a 5 hour delay in Miami, and THANKFULLY we made it at all. Most other flights in Miami were getting cancelled. As Kellye learned waiting for us, the airport DOES shut down about 6:30 pm. MF-ers just leave the airport. 😂 We got in about 7:30, and Kellye was just hanging getting mopped around. I was wiped-out upon entry and got sick next to our rental car before leaving the airport. I held the illness in somehow.

Kellye and Amy both had flights out Sunday so Jake and I could take a two-day unwind together to wrap out the island. Amy missed her flight, so with Truly’s in hand on the beach with our island pals Sunday, we collectively got her rebooked on a flight with a new airline to San Juan (a bigger hub to get flights to the states) and then a rebooking from San Juan to Atlanta to Austin.

This was one of the rougher in’s and out’s of STX travel for us, but it STILL didn’t matter, because the middle - that Oreo creamy center - was so divine that none of us gave a shit.

This is what the island teaches you; patience, flexibility, and a new-found “who the fuck cares” level of rolling with what comes. It truly chills you out.

The Perfect Island Button

I mentioned a few newsletters ago that we happened to connect with the owners of a new hotel, The Cove Hotel, before we arrived to island. We stayed our last two nights on their property, and WOW was it the most incredible stay we could have asked for.

What originally drew me to this hotel was the story behind the couple that built it. They left their life and careers in Minnesota to pursue a dream of building an aesthetically beautiful and unique boutique hotel experience that the island doesn’t have, and they’ve done exactly that. Also, their hotel’s entire decor is sourced from female entrepreneurs in various countries, brining them business while giving the hotel a distinct charm that simply is nowhere to be found on St. Croix.

What I didn’t know is that Martha and Doug, the owners of The Cove, are living on property and building as they go. Every piece of that property has been gutted and scraped and curated by hand, by them.

There aren’t many pleasantries on island, and food spots close early, leaving weary travelers pretty hungry some evenings. Martha and Doug thought of every possible thing when building their hotel - including the most adorable snack bar and market, affordable curated toiletries and goodies, a charm bracelet and necklace bar (I totally forgot to make one before I left and I’m so bummed! Next time!), and an eventual plant check-out wall for travelers to add live greenery to their rooms.

I could go on and on, but we were able to have dinner Sunday evening with Doug and Martha, and coffee this morning, and I really feel like we’ve made two amazing new friends on the island. I’m excited to see how The Cove grows and thrives on St. Croix - its the cleanest, most stylized hotel we’ve stayed at yet, with FRESH NEW bedding and mattresses - a detail many hotels unfortunately overlook…

We did it! A week on the island and everyone is alive and safe, and most of all, happy.

New friends, new island adventures, and just a new found love of this life I get to continue building.

We may have invested quite a bit of money into making this particular experience happen, but I know we’re building something dope AF here, and this is going to become something I never imagined possible.

Or maybe, I did. 🤓

Our shows were awesome enough that a TSA supervisor at the airport in STX gave us a shout out while going through security. THAT’S someone you want on your side…

Upcoming Shows

Saturday April 19: Laugh Factory Chicago 7 + 9 pm (message me if you’d like guest list!)

Monday April 21: Standup Sitdown at Laugh Factory Chicago 9 pm

Thursday April 24: Headlining Big Break Comedy at the Holiday Club, Northside Chicago

Tuesday April 29: Best Night Ever at Lincoln Lodge 8 pm

May 22nd I have the Group Chat Comedy Show with the KILLERS in my group chat out at Zanies Rosemont. Get ahead of this and spread the word, as we want to sell this b**** out!

… and some drop-ins (catch my stories on IG) with a fat lineup of shows in May.

Love you all and cheers to the hustle + chill. We love da island 🌺 🌊 🏝

xx NPH