Happy Tuesday, and welcome to the third edition of the Hustle + Chill with NPH.

If you live in Chicago and you haven’t grabbed ‘em yet, I’ll be featuring at Zanies Old Town for Jake’s headlining debut TONIGHT March 11th! Code “Snell5” for discount tix - last grab!

It’s been a busy week, but one that embodies that beautiful blend of Hustle and Chill… maybe a little too heavy on the hustle, but all things I’m excited about - tons of fun shows, a full social calendar of dinners with badass women, and prep for a return to the ISLAND of St. Croix.

Friday I had dinner with Madison Jade, one of the co-founders of Renowned Chicago. Renowned has been hosting events throughout the city for creators and entrepreneurs, and I’ve been meeting incredible people at these events - one that I just finished lunch with (Hi Bob), and one I’m having dinner with Friday!

I had to shout the Renowned crew out. They are a team of young, brilliant, creative, ambitious hustlers. Madison is 20, and I’m 40, and sitting across from her at dinner I was blown away at her accomplishments and grace. I was a hustler at 20, but I was a much sloppier one. 😂 So Madison, Andrew and Toni, you’re an impressive group and I’m just thankful to be included in what you’re building.

I was also able to get Madison and Andrew to their first comedy show at Laugh Factory this weekend… Gotta love when community and comedy come full circle. More on this…

Now, to the island!

The Hustle

I am HUSTLING right now to create an event series I am beyond excited about. I’m bringing comedy back to the island of St. Croix next month, and this time I’m bringing some of my favorite comedians with me!

A little back story here on how these island shows came to be…

Back when I was 24 years old, living in Chicago, me and some friends grabbed a cheap ass vacation package on Expedia for 4 nights on the Island of St. Thomas. I was with my model-esque gay bff and our gal pal Danielle, and it was such a wild trip that our first night got us a wellness check from the gardener the next morning. I ate wild aloe vera in the jungle on the walk home and woke up with an uprooted plant in the sink next to an empty cocktail fishbowl with a shark toy in it. I’ve done an entire Blackout Diaries storytelling performance on this should you ever care for the link. 🙈

We had one hell of a time on that island, so much so that the trip ended in what I call the $500 margarita - we were supposed to leave for the airport on that Friday but the margaritas by the pool were so good that we skipped our flight to stay an extra day. Who knew you can’t just go to the airport the next day and expect a new flight? …we had to buy new flights home. $500 a piece. Most expensive margarita of all time.

I met someone on that island and they ended up moving to Chicago for me. It was my first real adult relationship, and it was… horrible. I won’t get into details, but it was so traumatic that I wanted to get out of the house every night as much as possible, and that was when I started going to standup open mics. Thus was the birth of my standup career.

Traumatic event = Comedy event-ually 🫠

A few years after that relationship ended (Thank God) I was living in Los Angeles and one of my best friends from Chicago had moved to another Virgin Island - St. Croix. The U.S. Virgin Islands is made up of 3 islands: St. Thomas, St. Croix and St. John. Each have their own vibe, their own culture, their own hook bracelet.

It was 2015 when my friend told me I should come out and start doing comedy on “STX” because they had mostly cover bands for entertainment. I put my first tour together that year with a girlfriend from LA, and the rest is history.

Each year, I’ve gone out to St. Croix to do shows, a little bigger each time. In 2017 I did a pop up show that sold out, and on an off day while we were on Buck Island (a day trip, uninhabited island nature preserve with beautiful corral reefs to snorkel), a boat captain pulled up to ask if I could do a show in their friend’s home for a big group that evening since they couldn’t get tickets.

Let’s just say it was one of the funnest, poolside comedy and roast sessions I’ve ever done with a karaoke mic and pool deck as my stage.

These shows have gotten bigger and better with each return. I even went to St. Croix three weeks before filming my first comedy special in 2019 to do an exclusive run-through preview for my island comedy fam and work out much of the poignant material for the taping.

In late 2020 when Jake and I started dating, we were able to go to STX and do two sold out shows, outdoors, during lockdown. One of the first shows we’d been able to do in months. The venue was thrilled to have had two COVID-friendly, big revenue nights, and we were just thrilled to be back on stage.

Last year, we expanded these shows to an even bigger venue, and sellouts happened FAST. I’ve built an entire community of friends on this island, and better yet, a band of comedy lovers excited for each year’s return. Now, Jake and I are taking some friends with us and we get to share what I (and we) have now built!

The Chill

It’s a lot of work putting these island shows together on the front end, but the reward is incredible. Who wouldn’t want to spend a week on an island that’s twice the size of Manhattan with only fifty thousand inhabitants? I’m talking the most beautiful beaches you’ve ever seen, crystal clear waters, basically all to yourself.

There’s something about that Caribbean water. Healing. Rejuvenating. Worth every minute of the hustle it takes to get to this kind of chill.

I love living in big cities, but there’s another piece of me that’s an avid explorer and adventurer. I think that’s why I’ve built creating experiences into curating many of my own tours - I just like to do things different. I love to live.

What better than doing WHAT you love in a place that you LOVE?

Here are some of the things I love most about the island of St. Croix.

First, everyone’s friendly and on island time, so you have to work really hard to have a bad time meeting literally anyone. Two, you never know who you’ll run into. Lots of random celebs have homes on the islands, and it’s where they go to just blend in. I’ll have a home on that island one day. 😉 Three, the island is half beaches and half dense tropical rain forrest. I’ve done everything there from snorkeling with mana rays, to fly boarding through the Caribbean sea, to off-roading through the jungle on a ragtag go-cart built in someone’s garage. No trip has ever been the same. Four, people honk to say “hello” or let you go first - it’s a complete adjustment from city honks. (maybe never repeat “city honks”?) Everything’s chill; no need for stress, hair products or fancy clothes. And last, THE FOOD. Imported foods like beef and dairy are pricey, while fresh fish is stupid cheap. You can get a lobster bigger than your head for forty bucks.

Building this comedy paradise has been the perfect blend of the hustle and the chill, and I cannot wait to be back! I’ll be on island April 8th-15th, with shows on April 9th, 10th and 12th with my pals Amy Shanker and Kellye Howard joining Jake and I!

If you’re on STX, grab tickets before they’re gone. Last year we oversold and had to open up “bring your own chair tickets” for people to sit outside and catch what they could… www.nphcomedy.com/stx2025

Speaking of full circle…

Having been through a chaotic relationship that started on these islands, which led to me starting comedy, and coming BACK to the islands DOING comedy with my badass comedian partner has been such a full-circle, thrilling experience.

I’m not sure how much the people of STX realize this, but as much as they look forward to these shows every year, I do too. This island means more to me than you know.

We are planning to build this out each year and bring more friends with us!

If anyone is interested in helping us expand by being a sponsor on this tour, feel free to reply to this email and I’ll send you various partnership and content package options! We plan to build this into a full-on, annual comedy festival. 💃🏽 I’m personally covering the expenses to put this together, and any partnerships would help take care of the travel/accommodations costs and paying the talent. We offer really badass content + deliverables! Let’s chat…

I mentioned Kellye Howard coming with us this year. She’s been a long time friend, is a BRILLIANT comedian, and she’ll be filming her standup special right after we return from the island. Kellye was diagnosed with multiple sclerosis years ago, and she openly talks about this in her comedy and one-woman show. She’s passionate about bringing awareness to MS, and will be hosting a comedy show and fundraiser in Chicagoland “MS-ing Around” on March 23rd! I would love if you went and supported! There is also a wellness day and retreat to follow, all linked on that same page.

Upcoming Shows

This week, catch me at:

Of course tonight, March 11th, I’ll be at Zanies Old Town with Jake Snell! Tickets are linked at the top of the newsletter 😎

Wed March 12th, Comedy Royalty at Lincoln Lodge 9pm

Friday March 14th, the late show 11pm at Laugh Factory Chicago

A few drop-ins announcing, and tour coming soooooon…

Love you all and cheers to the hustle + chill. Island style.

xx NPH