Why comedians have to be entrepreneurs
I always had a unique mentality when it came to building my career, and a big catalyst to that was a comment from one of my earliest improv directors at Second City Chicago. ‘Natasha, you’re smart and talented. You’re going to make it, just remember it’s likely to take 15 years. So use your smarts as much as your talent.’
You wouldn’t think that would be motivating or encouraging in any way, but honestly, it was the best little reality jolt I could get as an early improviser, determined to one day be on Saturday Night Live. With every win along the way, I would think, ‘OK, Natasha, this may or may not be your big break. Take it with a grain of salt and keep hustling. Nobody’s going to hand this to you.’
After moving to Los Angeles, that comment echoed in my head even more. I co-founded my first production company in 2013 having no clue what I was doing, but all the guts in the world. My co-founder and I would straight up cold call and cold email major studios with our projects. We even mailed dolls to Netflix to get their attention for a script. We got nothing, except an invite to tour the backlot of Warner Brothers one day. I’m sure they simply felt sorry for us wildly naive, self-proclaimed executive producers.
Over the last decade I continued to discover ways to monetise my slow-growing career. Doing things ‘by myself’ didn’t mean I had to do them alone. First, I started curating small brand patnerships and sponsorships for projects. If I had an idea, I would create a deck for it and just put it out there. It’s amazing what a pitch deck can do. If nothing else, it establishes an air of professionalism. [A pitch deck is a visual presentation of an idea to engage potential backers].
I created decks for so many projects for TV and film that I landed a few network shopping deals for scripts, holding deals as talent, and came oh-so-close to selling my first series to a major network. Notice I said, close. Spending months or even years at a time on projects that never see the light of day or end up in the trash can is wildly disheartening.
I had to find another way to make it work. I couldn’t bet on a studio or network to give me the opportunity I so desperately wanted.
I started partnering with boutique hotels while touring, generating content packages for them during my road gigs. I launched a podcast, wrote for top magazines, continued hustling in stand-up; anything I could do to get my name out there while learning more and more ways to fill my calendar with the type of work I wanted to be doing. I always viewed myself as a brand in the making, and would consider any interests of mine as a piece of a giant spider web that would eventually create an entire ecosystem of Natasha Pearl Hansen. Oftentimes this felt like throwing spaghetti at the wall to see what would stick, and sometimes a noodle would stick for awhile, giving me hope, only to eventually crust up and fall to the floor.
In 2019, I was engaged to be married, had been doing stand-up for nine years, I was starting to tour as a headliner more regularly, my podcast was in its third year with top sponsors starting to come on board, and I had launched a weekly show in Las Vegas off a cold call with a hotel, branded with the same name as my podcast, that I traveled to and produced from LA.
I did it this way because I had to. Little did I know, doing things this way was becoming the cornerstone of my career. My Vegas show was where I was able to bring in many of my podcast sponsors, giving them access to the Las Vegas nightlife scene and brokering deals to generate revenue on top of what the hotel was providing for a budget. I even worked with some emerging tech brands and startups during that time. The web was starting to come together. The web was still making me far less money than my efforts equated to, but it was something.
Summer of 2019, my wedding was canceled and I decided to shoot my first comedy special, I Was Supposed To Get Married Today, instead. I wanted to still celebrate my day, my family, my friends, and throw a party in the venue that I’d found in my home city in Wisconsin. It ended up being one hell of a memorable night, despite the circumstances. After my relationship officially ended early 2020, and the pandemic hit and live performance was shut down, I felt I needed to do more with my career and branch out to help people beyond my comedy.
That’s when mybreakupregistry.com was born, a platform for people to rebuild their lives after a breakup with the help of their support system. It felt right to be vulnerable about my experience with my art, but also invest to build something to take what I’d been through and create a space to help others through the same thing. It was the first time I felt like I could turn a hard time in my life into multiple monetisable channels, while also helping people deal with their own life’s bullshit. A win win.
I spoke about this recently to a few younger comedians, that you have to be so willing to invest in yourself and build a financial base to be able to do so, even if that means taking jobs you don’t love for awhile or slinging drinks behind a bar. I’ve done it all.
Now I’m performing my debut at Edinburgh Fringe, another big investment in my career, but one I’m better equipped to handle after years of trial and error. Something I can bring my past years of experience and personal story to with humour, and do so in a way that connects with a global audience.
To be able to support my Fringe efforts, I worked brand partnership deals, secured sponsorships, and also heavily invested my own money from touring to make it possible. In a way, that’s what the show is about. My show The Right Amount Of Wrong is a testament to trial and error, in both life and career, that will allow people to see firsthand the need for the ‘right' way and the ‘wrong’ way to coalesce. You can’t do it right if you’ve never done it wrong.
There are so many ways to build a comedy career into a business as a whole. I love sharing my business knowledge with people, and will soon be launching a newsletter called The Hustle And Chill that goes behind the scenes of both my comedy and entrepreneurship journeys, and ways I’m learning to chill out and be mindful during the endless hustle. I also wear a lot of jumpsuits on stage, and plan to launch a line of them eventually.
Anything you talk about on stage; any rare perspective or interest or talent you have other than comedy can become the very thing that propels you forward, and a unique angle on who you are that sets you apart offstage. If anyone relates to something specific about you, that something is brandable. You’d be surprised what people will pay to work with you if you’re branded right. The key is being you, and expanding on who you can be.
I’m currently at year 14 of my standup career, and those words from my director at Second City continue to stick in my mind. One more year till my big break, right? At this point, I’ve built a base of a personal brand that’s ready to carry me to the next level, whatever that is.
Regardless of what opportunities present themselves to me for my career, I know I’ll be good because I’ll continue to create those opportunities for myself as well. I think that’s what it comes down to as an artist and entrepreneur; giving yourself no other option but to succeed, however that looks for you.
• Natasha Pearl Hansen’s debut stand-up show The Right Amount of Wrong is at Just The Tonic Cabaret Voltaire at 2pm.
Published: 10 Aug 2024