This week, we sit down with writer and comedian Grace Guy to unpack the complicated, often unspoken dynamics of assistant culture in the entertainment industry. Drawing from her own experience as a former assistant, Grace shares the inspiration behind her deeply personal play Deckhand—a sharp, emotionally charged story about a boss and assistant trapped together on a boat. We dive into the love/hate tension that defines so many of these relationships, and the uncomfortable truth that while assistants are often told their proximity to power will lead to opportunity, that promise rarely materializes.

Grace also opens up about recognizing when it’s time to leave a job, the importance of self-care and building a real support system, and the danger of tying your dreams to someone else’s success. The conversation then shifts to her creative process—how she approaches writing “forced proximity” stories, and the journey of developing Deckhand, including testing it in front of audiences ahead of its Edinburgh run. 

TIX FOR 50/50 COMEDY FESTIVAL MAY 3RD!!

Grace's Insta (see upcoming show dates & more!)

DECKHAND SHOW

Books Mentioned: Artist's Way, Rick Rubin's Book, Anne Lamont (Bird by Bird, Good Writing)

This week, Chloë Kerwin reflects on church basements, circuses, ghost-hunting, and oh yeah... acting! Chloë grew up dreaming of Broadway, later finding herself drawn to films like True Grit and Moonrise Kingdom. After high school, she brought that curiosity to Emerson, where she collaborated with filmmakers like her cousin (previous podcast guest) Wylie Anderson, and began building the kind of reel that would eventually open doors.

We get into the realities of auditioning (including Little Women with Greta Gerwig), navigating relationships with reps, and her intentional pivot toward comedy—a space she’s found both more challenging and more creatively rewarding. Chloë shares how she’s shaped her artistic voice through on-set experience on shows like MARVELOUS MRS. MAISEL, creative outlets that sustain her passion, and why patience and stability remain central to building a fulfilling career in the industry.

50/50 COMEDY TICKETS MAY 3RD!

CHLOË IMDB

CHLOË WEBSITE

This week, we sit down with director/producer Talia Light Rake to talk about what it really means to self-empower as an artist. Talia dives into redefining her creative identity, how aligning who you are with what you make can unlock new momentum, and the unexpected ways social media gave her work legitimacy and reach.

We also get into her algorithm-driven networking events—bringing creatives together across cities—and the recent success of her indie pilot Too Romantic. 

TICKETS for 50/50 FILM FESTIVAL (MAY 3rd)

TOO ROMANTIC Pilot (FESTIVAL DATES ETC)

HEAVY SHOVEL PRODUCTIONS

TALIA'S INSTA

This week, we’re joined by Allie Kahan, producer at Headgum, who carved out her own lane into entertainment by doing something deceptively simple—paying close attention. After immersing herself in podcasts about the industry, Allie found an authentic entry point that led her to Artists First, where she began building both her career and her creative voice in tandem.

We talk through her transition to Headgum, including the nuanced balance of being a genuine fan of the company while stepping into a professional role. From there, the conversation expands into her work today—navigating high-profile talent, what actually goes into podcast acquisitions, and the evolving process of developing shows in-house. It’s a candid look at a modern producing career, and how staying curious can quietly open doors.

HEADGUM Podcasts!

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'Making It' with Ricky Lindhome (Podcast Archive)

This week, we sit down with Jared Corwin, Co-Executive Director of Silverlake Shorts. After feeling stuck following his first feature, Jared found renewed purpose by helping launch a monthly, sold-out, non-profit film festival alongside collaborator Benjamin Sharpe. What started as a grassroots community event has grown into a meaningful creative engine—one that’s not only spotlighting emerging filmmakers, but actively shaping Jared’s own career as a writer and animator.

We dive into the evolution of the festival, from screening films to funding them through their fellowship program, and what kinds of projects they’re looking to support. Jared also shares insights on expanding beyond Los Angeles, including a recent festival in Atlanta, and how the organization is thinking about local audiences as well as potential collaboration with the broader studio system. The conversation widens into the state of the LA film scene, the cultural value of short films, and Jared’s mission to elevate shorts to the same artistic stature as features—all while helping bring filmmaking energy back to Los Angeles in a major way.

SILVER LAKE SHORTS Website

SILVER LAKE SHORTS Instagram

SUBMIT TO 50/50 COMEDY FESTIVAL

This week, we’re joined by John Li (Development at Amazon TV) where we dive deep into how careers in entertainment really take shape. From being the guy who’s always grabbing drinks to mastering the art of authentic networking, John shares how genuine relationships—not transactional ones—have driven his path. He reflects on landing at USC just as the industry was being flipped upside down, and why adaptability, curiosity, and getting specific about what you actually want are key to finding your footing.

We also dive into why being an assistant might be one of the most fun—and valuable—jobs in Hollywood, offering unmatched exposure early on, and how to reach the point where people rely on you so much your mistakes are actually felt. John opens up about what working at an agency taught him (including the reality that everyone’s “faking it” to some extent), how his taste has evolved over time, and why he’s focused on making impactful, high-quality content that reaches the largest possible audience.

JOHN LI LINKEDIN

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This week, we sit down with actor/comedian Natalie Ortega to talk about carving out your own lane in an industry that rarely hands you one. Natalie shares how she found her niche in musical comedy (and why it’s not just because the bar is low), her complicated relationship with stand-up, and why she believes actors shouldn’t sit around waiting for the next audition.

We get into her time performing in Wicked on Broadway — including the unspoken rules of the Broadway social scene — and what she learned on set alongside Brett Goldstein and J.Lo, where stand-up unexpectedly became her greatest asset. Natalie also opens up about her evolving relationship with agents and managers, and how taking initiative in your own career changes everything: do more for yourself, and your reps will too.

Plus, we dive into her creative partnership with Cam Gavinski on PARTNERS, what’s next for the project, and some exciting TV development news on the horizon.

NATALIE'S INSTA (Watch PARTNERS HERE TOO!)

Submit Your Comedy Short

This week, 50/50 Festival WINNER Ali Rosenthal traces her path towards comedic purpose; after cutting her teeth in New York City, she forged her voice as a comedy filmmaker at Stanford, where she made ICE QUEENS a self-described “fiercely feminist fantasy.” We then dive into her breakout short TEEN MARY - making the film at AFI while managing the creative risk of approaching religion from a fresh, comedic perspective—and why that very risk pushed her to make the film in the first place.

From there, we move to bigger questions: why pitching yourself can sometimes be harder than pitching a project, what truly separates a comedic short film from a sketch, and why a strong director’s statement can be essential to articulating your artistic purpose, especially in comedy. We wrap by discussing the project Ali is currently taking out to town and the process of refining drafts with her manager—plus the perennial question: how do you know when a script is actually ready to pitch?

TEEN MARY - Instagram

ICE QUEENS (Stanford Short)

Submit Your Comedy Short

This week, filmmaker Elijah Davis breaks down how he swung big on his debut feature, Three Colors: Pan African — and what it actually took to get it made. We talk about the influence of French cinema on the film’s visual language, and Elijah’s larger mission: creating real authorship opportunities for Black creatives across every department. He shares how funding the first portion of the project as a proof of concept unlocked momentum — and why fundraising proved to be one of the most difficult stretches of the process.

We also discuss representation theory and Elijah’s perspective on the relationship between Blackness and media — who gets to tell stories and who controls the frame. Finally, he opens up about balancing all of this while working full-time as an assistant at WME — and what it means to build a filmmaking career from inside the industry machine.

THREE COLORS INSTAGRAM/TRAILER

THREE COLORS IMDB

THREE COLORS LETTERBOXD

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This week, we sit down with Chris Rutledge, whose knowledge of animation extends far beyond his own work and into the underground, deeply influential network of visual artists shaping the medium from the edges. What stands out immediately is Chris’s ability to recognize artistic movements before they even have names, mapping out how ideas circulate through communities long before they surface in the mainstream. His perspective reframes animation not as isolated projects, but as a living conversation between artists pushing each other forward.

We also break down the fundamentals of various animation software tools and why teaching them has helped Chris re-familiarize himself with the art form, keeping his creative instincts sharp and reinvigorated. The episode traces how he’s organically emerged as a producer, leaning into his natural role as a connector—bringing trusted collaborators into his own projects and opening doors that have led to work on Adult Swim Shorts and even an A$AP Rocky music video. It’s a conversation about community, curiosity, and how collaboration often becomes the most powerful creative tool of all.

HELICOPTER (A$AP ROCKY)

BABY BRECK (w/ Tim Robinson)

STREET RACE (Adult Swim's 'Off The Air')

Chris's Other Work / Insta

Submit Your Comedy Short