Conversations with Jesse Zand

Today we’d like to introduce you to Jesse Zand.

Hi Jesse, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I’ve always been drawn to two things: making people laugh and collaboration. My parents were actors turned TV writers, so I grew up watching the highs and lows of showbiz up close. I always wanted to start a podcast. When I was in film school my roommate (now executive producer) and I grabbed our iPhones one night and started recording just for fun. That was the first spark of what would eventually become Night School.

Back then, I wasn’t ready to admit I wanted a creative career. I watched my parents get chewed up and spit out by the industry, so I took the “safe” route — got my degree, worked in marketing at a big ad agency — until I finally started doing standup. I’ve since performed at The Comedy Store, The Improv, and The Ice House. I host regularly at the Save the Robots monthly show at the Comedy Store. But I wanted a place to be more vulnerable and real than I am on stage. The industry has shifted so much that now young comics are expected to post clips of themselves in order to get discovered, build an audience and stay relevant. I wanted a space where I could be funny without the pressure to churn out crowd work clips or burn material before it’s ready. It’s a place where I can experiment, connect, and evolve as a comic while still making content that resonates and showcasing the other insanely talented creatives and comics I have in my orbit.

My goal with Night School is simple: to make people feel less alone. Our tagline is “It’s not that serious” — because we are at our core a comedy podcast but with the vibe of a slumber party. We crack jokes, talk about the latest drama in pop-culture, and also open up about real-life stuff: mental health, family, relationships, body image, whatever’s on your mind. It’s a safe place to be weird, be vulnerable, and find connection through humor.
We’re self-funded, with only one sponsor and I’ve bootstrapped the show from the ground up, booking guests, producing, marketing, and distributing it myself. We’ve had episodes blow up — like our Jason Earles (Hannah Montana) interview that went viral and got picked up by E! News and Entertainment Weekly, we’ve had legendary comics like Eddie Pepitone on as a guest and interviewed world-renowned pop-surrealist artist Kenny Scharf – all within our first year of launching.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
It’s definitely not been a smooth road. When I first launched Night School, I tried to record everything myself. It was a disaster in the moment but ended up being a gift — I learned the ins and outs of podcast tech, which has been invaluable for episodes we’ve done on the road or outside the studio. I met my technical producer, Keida Mascaro, through standup. He books monthly shows at The Comedy Store and The Improv, and when he told me about the podcast studio he was building, The Cave, I knew he was the right person to partner with. Starting a podcast is like starting a business — you assemble a team, you learn from missteps, course-correct, and stay open to creative possibility and evolution.
The personal challenges are constant. Honestly, there’s a moment every week where I think, “how the f*ck am I gonna keeping doing this?” The thing that keeps me going is the collaboration — sharing a new clip that made us laugh, or a message from a listener across the world who connected with our silly little show. That’s what makes it all worth it.
In standup, you’re trained to think about jokes per minute. In podcasting, the rhythm is completely different. Accepting that I wasn’t always going to be the funniest person on the show — even though I’m a comic — was a big shift. My role is the emotional anchor and the captain of the ship. My job is to make it a safe space for cohosts and guests to be themselves, have deep discussions and have fun. That’s part of what sets us apart from the “three comics on a couch talking about comedy” format. We bring in writers, actors, and a rotating cast of guests that make up the Night School multiverse.
One of my biggest turning points was right before our Jason Earles (Hannah Montana) episode — our editor dropped out, and I had to do the entire edit myself. I usually do a pass to punch up visuals and jokes, but this time, it was all me. I was terrified it wouldn’t be as polished, but it ended up being one of our highest-performing episodes ever. That’s when I realized — no matter what happens, I can pull this off. And honestly, one of the most freeing lessons has been knowing I can carry this ship on my own if I have to. We have an open-door policy for cohosts — if someone wants to leave and pursue other projects, they know I’ll always support them and they can always come back. That mindset has made me stop worrying about what could fall apart, and start focusing on the blessings. I’m surrounded by insanely talented women, and I feel like part of my purpose is to champion them and create a space where we can all thrive and have fun.

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
By day, I work in branding and marketing, developing campaigns that tell a story, connect with an audience, and make an impact. It’s a skillset that’s directly translated into the podcast – because at its core, a podcast is a brand. From how we book guests, to the show’s visual identity, the set dec, to the way we cut clips for social, I approach it like a business, not just a passion project. Working with influencers for my day job — including some who run their own shows — has taught me how every part of our online presence serves a purpose. The same way standup sharpens my comedic timing, the podcast lets me play with that same energy in a completely different way. Both feed each other — the confidence and presence I get from standup make me a better host, and the long-form conversations from the podcast make me a sharper comic. On the business side, I understand how to position a product — in this case, the podcast — so it stands out in a crowded market. I’m most proud of building this from the ground up, completely self-funded – with just a vision, the right collaborators, and a lot of persistence.

Before we go, is there anything else you can share with us?
Subscribe to Night School on Apple Podcast, Spotify, YouTube or wherever you listen to podcasts.
Spotify: https://open.spotify.com/show/3wkYfJqQy50A1ED8gGA89b
YouTube: https://www.youtube.com/@nightschoolpod
Follow on Instagram @nightschoolpod
Follow on TikTok @nightschoolpod

Contact Info:

• Instagram: https://www.instagram.com/nightschoolpod/
• Twitter: https://www.tiktok.com/@nightschoolpod
• Youtube: https://www.youtube.com/@nightschoolpod
• Other: https://open.spotify.com/show/3wkYfJqQy50A1ED8gGA89b

Image Credits
Stella Saldo
Night School Logo by Makenna Snipes
Keida Mascaro