Happy Tuesday! It’s week four of Hustle + Chill and let me tell you, I’m enjoying the shit out of this medium. Writing is cathartic. Obviously as comedians we write often, but I’ve been making writing as a whole part of my morning practice for a long time now.

The power of journaling in my life has been immense over these past few years. I’m not talking journaling “dear diary” style or complaining to myself in faux-prose, but rather claiming the things I want for my life and putting it in writing - visualizing it.

Ok ok let me back track here… I’ve always been obsessed with writing. In high school, AP Lit was my jam and I loved writing essays (yep, I was that kid.) But when it came time to present said essays, I’d make it performance art, because thou shalt not be boring (says the Lord). One time I had to write an essay about Hamlet, but when I had to present I performed it with a friend to rewritten lyrics of the rap “Guilty Conscious” by Eminem and Dre …I’m glad smart phones didn’t exist when I was a teen but I wish they did for this moment ‘cause man I’d kill to see that again.

I have my “Natasha’s books of thought” to thank for my eventual foray into comedy. I started writing these when I was 13. I would carry the pocket-sized Memo pad notebooks with me everywhere and write weird thoughts, funny moments and quotes between me and friends, crazy stories — these became so renowned by my freshman year of high school that I would be invited to older kids’ parties to drink beer outside, drink beer in a barn, or drink beer in the back of a pickup truck (Wisconsin!) and perform excerpts.

Do you… want to see some excerpts? Ok, don’t judge, I was 13:

I’m very thankful my brain finally eventually developed. Along with my sense of humor. I’m also thankful I started writing young because eventually, it just became second nature.

My humor is nothing like it was back then, but at the core, I am a storyteller. I talk about my real life on stage, I use my real life experiences to build my business portfolio, and I use my daily writing practices to create my reality and choose how to spend my life and my energy…

The Hustle

A few months ago I was offered a board seat on a new startup. An advisor role. I invested a fair amount of free time and network connections over the past two months into helping this young company out. Yesterday, I turned the final offer down. Let’s discuss.

I launched my first production company in Los Angeles in 2013. It was rudimentary, but it was the beginnings of truly understanding how entertainment deals are made. That year my partner and I were beautifully unhinged — we sent a film canister (Slick. It looked like a movie reel tin) to Netflix with pitch materials for one of our series, we co-created multiple features and tv pilots, and I straight cold-called Warner Brothers and got us a back lot tour.

It was on that three hour, Warner Brothers back lot tour that I learned something really valuable. The power of partnerships.

Remi, our lot tour guide (who of course I still talk to today) was an insightful lucky charm for us, and he taught us that many new directors and producers can get funded by securing brand placement partnerships, and if “picked up,” said brand will be placed subliminally throughout the filming in exchange for $1.5…$2…$5m an episode.

WHAT?

My head exploded when I heard this, and I thought back to all the times in F.R.I.E.N.D.S when a Porsche or Pepsi can could be seen. Sneaky…

I never thought the same again about partnerships after that day, and immediately became a dot-connector for where value can be created for a project to get made.

Cut to 2017 when I was reading Inc. Magazine and I found a startup that was like the Uber of open restaurant tables. They were based in New York. I was headed to New York to perform. I invited them to a show and told them I knew a lot of people in hospitality if they needed help growing. We formed a friendship, I helped get them into fifty-something restaurants in four cities, and they paid me a shit ton of money for those connections (which I wasn’t expecting).

…and my head exploded again. My network held VALUE??

Relationships, time, energy - all of it has value. As your relationships grow, as your network builds, you too can charge more for your time and energy, or choose who/what/how you spend it on with more wisdom.

So why turn down a board seat? That’s free money, right?

The offer included potentially years of unpaid time, access to my connections, helping them raise capital, exclusivity clauses, and an offer to purchase shares at the time of sale. A complete time and network risk. No straight equity.

Just like some relationships, some deals you have to walk away from. This is the sunken cost theory, and it’s OK to have wasted some time in order to realize you don’t have to waste anymore…

The Chill

I’m taking this week off of shows to see my family!

I love my family. I love my friends. I love breaks. Breaks from the stage actually make me excited to get back up there. Breaks from performing let me live and actually write from a place of lived experience.

If you’ve been following me on social media, you probably know I took the whole month of January off of performing…

On December 23rd just two days before Christmas, my best pal of the last eighteen years passed away unexpectedly. Top three worst phone calls of my life, and the other two were the passings of my grandfathers.

The loss of Matt was completely unexpected, and it wrecked me.

Matt and I met when I was twenty-one years old. He was a regular at the bar I worked at across from Second City in Old Town Chicago while attending classes and finishing conservatory there. At first, he was just a familiar face I’d see at work. But eventually, we started hanging outside of work, and he took on the role of the big brother I never had - former military, smart business guy, connected to literally everyone in Chicago - he was just a good fucking friend.

When I moved to LA in 2011, he was one of the first people I would call when heading back to the Chicago, one of the must-sees while in town. We talked all the time. Saw each other every three months and would meet up in whatever cities we could on our travels. In January of 2020 when my last relationship fell apart, he was the first I called - I met him and some friends in Palm Spring, chatted about this crazy idea I had to launch a break-up registry with my first special, and he was allll for it.

When I moved back to Chicago, Matt and I would meet up multiple times a week, sometimes to just chat life, sometimes to talk business. He believed in me; believed in everything I was doing - from comedy to business - he just had my fucking back. I believed in him too - I helped him talk through hard decisions as he would with me. Big bro.

In early 2024 Matt became the only person besides myself to invest money into my company. We were so excited to be biz partners for what was to come in 2025. He even flew half way around the world to see my Edinburgh Fringe debut - met my mom and my aunt in Scottland. What a time to be alive…

Grief is weird. They say there are stages of grief, but I disagree. All the stages and feelings come at you all at once, almost to the point of breaking through your skin. The weeks following the news I would cry in a guttural way. If you’ve experienced deep sorrow, you know - it’s like your insides are being pulled out and exposed and it takes every muscle in your body to push them back inside only to have them spill out again.

Losing people we love sucks. There’s no more eloquent way to say this. It just does. It’s unfortunately a reality we all have to face. Sometimes reality just, sucks.

We always think there is going to be more time.

Not trying to be morbid here, just honest. Time with people you love is everything. Time creating memories and experiences with these people is everything. Time “off” is not a loss, but a gain. Time is the one thing we can’t get back.

It’s time to know your value. Never waste your time.

Creating Experiences

I’m so excited for St. Croix next month. And I’m absolutely fine spending money to create great experiences with my friends. I will always, always, ALWAYS invest in something if it means new memories. These are the types of things we remember forever. Success, credits, acknowledgements, awards; these are great things to strive for, but what is any of it without the people that matter to us?

I journal for this today - experiencing the outcome of time and hustle well spent to truly enjoy life. While I’m still here.

Matt would be proud. Cheers to my friend - I’ll eventually write about him on stage, but I’m not there yet.

Nobody likes a sad clown.❤️ Hard things take time to become funny. We know the equation.

Zanies was a success this week! Jake’s headlining debut went off great, and we had a packed house on a Tuesday. Thank you to those who shared and bought tickets!

Upcoming Shows

Thursday March 27th, Laugh Factory Chicago 7pm

Saturday March 29th, Mikey O’s show (+ a likely drop in or two at the Den Theater on Michael Yo’s shows) - didn’t even realize the rhyme scheme there

April 2-4, San Francisco (details coming soon)

April 8-15 - FIRST EVER St. Croix Comedy Fest: TICKETS + INFO

Thursday March 24th, headlining Big Break Chicago

Tuesday March 29th, Best Night Ever at Lincoln Lodge 8pm

Lot’s more dates in the next newsletter drop.

Love you all and cheers to the hustle + chill. We know our value.

xx NPH