Creative lives, talked through in real time.
Wear Many Hats moves through casual interviews with artists, creators, food people, DJs, writers, and fashion-adjacent guests. The conversations feel loose and fast, turning everyday banter into sharp observations about work, taste, ambition, and online life.
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Wear Many Hats is a conversational portrait show about people who build lives around creative work. Its center is not a single industry so much as a shared condition: having taste, making things, posting about them, and trying to keep a real personality intact. The format is loose. The host and guest often begin with whatever is directly in front of them, from Fort Greene and Brooklyn to Oslo, London, a regular Coke, a camera setup, or a video-call mix-up. Then the talk opens up. Recent episodes move through Claire Parker’s comedy world, creative partnership, podcast culture, and online recognition. Justin Bazdarich brings the conversation into restaurants, hospitality, Speedy Romeo, Oshimoko, simple food, Michelin attention, and the long emotional life of a neighborhood place. Claire Murashima talks about London, UCL, journalism, Substack, editing, bad ideas, and the temptation of posting anyway. Ramell Frederick’s episode points toward fashion, long-haul experience, Tattoo'd Cloth, buttons, threads, and the stories that come from seeing an industry up close. Sydney Frost brings TikTok, fashion school, closets, Depop, and the language of content into the room. Macy Gilliam’s conversation turns playfulness into a professional style, touching Morning Brew, sketch instincts, UCB, Google Street View in Bosnia, and the difference between stiff news delivery and human interaction. Jewelssea brings club culture, DJ learning, tech house, studying what came before, and the saturation of nightlife scenes. Carli Gordon’s episode considers the pull between freelance freedom and the nine-to-five structure. Across all of it, Wear Many Hats stays brisk, friendly, and slightly unruly. It is not a clean lecture series. It is closer to overhearing a smart table conversation where every guest has a different scene, but everyone understands the pressure to make culture while also making rent, content, community, and a self.
Made for: For listeners who like informal interviews with comedians, writers, DJs, fashion people, creators, and hospitality figures. It especially suits people interested in culture work, internet visibility, and the strange job of turning taste into a life.
What sets it apart: Wear Many Hats stands out by keeping the rough edges of conversation intact. Instead of flattening guests into career arcs, it lets small details, jokes, digressions, and scene-specific language reveal how creative work actually feels.
Wear Many Hats is from Rashad Rastam and takes on what you create with culture. Do you wear many hats?
Based on 6 episodes we listened to · September 2026
Rashad turns relaxed guest conversations into revealing accounts of how creative work meets money, identity, social media, and everyday life.
Wear Many Hats lets creative work emerge through conversation rather than formal career summaries. Rashad begins with immediate details such as where a guest is calling from, then follows the exchange toward painting, restaurants, journalism, comedy, podcasting, and video…
A regular Coke leads you into the work of making news videos funny.
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Short reviews from the PlayNext desk, based on the episodes we processed.
A casual, thoughtful conversation about online recognition, creative risk, and the stories that make failure easier to carry.
Claire Parker's conversation with Jassar and Rashad frames making work online as a question of recognition, friendship, and the private stories that keep people moving.
A warm restaurant conversation about moving countries, making food people return to, and becoming part of family histories.
Justin Bazdarich's conversation starts with a cloudy look toward the Oslo Fjord and settles into the harder question of how a restaurant keeps mattering after the first rush of attention.
A loose, thoughtful conversation about moving abroad, posting online, and why public ideas still need an editor.
Claire Murashima's move from California to London for a master's at UCL gives this Wear Many Hats conversation its useful pull: the long-held wish to live abroad landing at a moment when the wider noise is hard to shut out.
Macy Gilliam makes a warm, convincing case for leaving "robot mode" out of creative work.
Macy Gilliam describes a video style at Morning Brew built around staying loose and treating people like people. She has little interest in sounding like a news anchor or slipping into "robot mode," and she argues that genuine interaction makes the work more engaging and more…
Jewelssea makes the case for an open DJ culture that still values study, craft, and musical history.
Jewelssea takes on a club culture crowded with new DJs and moneyed promoters. Her position is welcoming without being soft: anyone drawn to DJing should pursue it, since every listener hears music differently, but enthusiasm does not replace study.
A borough debate becomes a thoughtful look at how much of a city can stay unseen.
Wear Many Hats turns a loose scheduling snag into a bigger conversation about how New York is lived, imagined, and kept at a distance by familiarity.
Marleigh Culver's shifting paintings and cities reveal a practice built around following the next visual idea.
Marleigh Culver's conversation with Wearing Many Hats follows an artist mapping the practical and emotional terrain around her work: a move from Los Angeles to Phoenix, a painting studio that remains in LA, and a New York trip planned around seeing ballets.
Pop culture trivia, argued fast and with affection.
Pop culture, personal stakes, and room for a tangent.
A Brazilian journalist spends years reinvestigating unsolved child disappearances in Paraná.
Cris Bartz and Juva Lauer alternate debate and interview episodes on Brazilian social issues.
Robert Wright interviews specialists on Iran, Gaza, Ukraine, Taiwan, and open-source AI.
The guest joins from Phoenix.
Kyle gets there first.
Carli Gordon discusses her transition from traditional nine-to-five jobs to freelance work and back, exploring the challenges and benefits of each lifestyle.
Rashad and Stacey discuss their preferences for cold versus hot weather, their childhoods, and the costs associated with different vacation styles.
The cafe bit sets the tone.
Justin calls from Oslo.
It starts with location-check banter: Claire Murashima is in London for a master's at UCL, turning a move from California into a shot at living abroad.
Two old friends catch up and discuss their long history in the fashion industry in New York City.
Sydney Frost discusses her start in TikTok content creation, focusing on fashion and selling items on Depop.
Regular Coke gets the first laugh, and the episode stays loose from there.
A missed Google link kicks off the riff.
Carli Gordon discusses her transition from traditional nine-to-five jobs to freelance work and back, exploring the challenges and benefits of each lifestyle.
Dave Ortiz discusses leaving New York City during the pandemic, buying a house in the woods, and renting out his St.
Skyler Stanley discusses his 100-day vlogging challenge and the 21/90 rule for building habits.