We are back with another live rendition of The Room Podcast! This week, Madison sits down with Jack Barrett, Co-Founder and CEO of Almost Friday Media, the creative force behind the viral comedy brand Friday Beers. After starting and leaving his career in investment banking, Jack followed his storytelling instincts into media, co-founding a creator-first company that now spans comedy, live events, digital media, and even its own beer brand. Almost Friday Media has quickly become a cultural touchpoint for millennial and Gen Z audiences craving authenticity, humor, and community online.

In this episode, Jack shares how moments of failure shaped his path, how comedy can connect people across generations, and what it takes to build a modern media business in the era of TikTok, YouTube, and Instagram Reels. Listeners will hear insights on evolving with algorithms, scaling creator ecosystems, and staying true to a mission that celebrates friendship, optimism, and laughter. Listen in as we take a look at how Almost Friday Media became a blueprint for the future of entertainment—where community meets creativity.

(00:00) Introduction
(02:00) Jack’s upbringing in Greenwich and how family and sports shaped his creative drive.
(04:20) Madison on her childhood and early curiosity about tech and creativity online.
(06:10) The role of siblings, humor, and community in shaping perspective.
(06:50) Jack’s Dartmouth years, finding identity, rejection from Yale, and lessons on belonging.
(08:45) Discovering campus culture & humor, how fraternity life and writing led toward comedy.
(09:50) What Jack learned (and hated) about his first career path.
(10:45) Meeting Radical Media’s John Kamen and discovering the power of storytelling.
(11:10) Launching a podcast during COVID and finding purpose in connection.
(13:40) Why storytelling became essential for investors and founders alike.
(15:00) Birth of Friday Beers, from Instagram memes to a viral cultural brand.
(16:45) Defining “Friday Beers” ethos, friendship, humor, and inclusion as the new comedy tone.
(17:40) Building Almost Friday Media, from side hustle to full-scale creative network.
(18:40) How The Room connects founders, investors, and community.
(20:00) Digital disruption and audience ownership.
(21:40) Shifts from TV to streaming to creator-led entertainment.
(22:50) Adapting to algorithm changes and engagement analytics.
(23:40) Indie creators vs. traditional media networks.
(24:10) Expanding Almost Friday Media across content, live events, and culture.
(25:30) Closing reflections, celebrating creativity, collaboration, and the next era of storytelling.

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Brought to you by Perkins Coie and Mercury.*
*Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust; Members FDIC.

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