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.

WX Productions

We are back with another live installment of The Room Podcast! This week, we sit down with Barry McCardel and Caitlin Colgrove, Co-Founders of Hex, the collaborative data workspace trusted by teams around the world. Hex empowers data scientists, analysts, and business operators to explore, visualize, and share insights in one connected platform—bringing together code, no-code tools, and now AI-powered features that make data storytelling seamless and accessible to everyone.

In this episode, Barry and Caitlin unpack Hex’s origin story, from their early days at Palantir to building one of the most beloved modern data tools. They share how deep empathy for early users shaped their product decisions, why great co-founding relationships require shared values and “stress testing,” and what it means to truly be “AI-first” in 2025. You’ll also hear lessons on problem-driven entrepreneurship, managing investor relationships, and how Hex is redefining what it means for everyone to be a data person.

(00:00) Introduction
(06:47) Where did Barry and Caitlin grow up and how has that shaped their view of the world?
(09:12) Did Barry and Caitlin always think they would become founders?
(10:02) How did time at Palantir shape Barry and Caitlin’s conviction to start Hex?
(12:45) What was the “aha” moment that made Barry and Caitlin decide to actually start Hex full-time?
(15:02) What advice would Barry and Caitlin give to founders looking to find or choose the right co-founders?
(16:48) What is Hex’s core product and who is it built for?
(18:18) Is Hex an AI-native company, and how does AI integrate into the product and strategy?
(22:16) What is “Hex Magic,” and what has building AI features taught you about product development?
(25:13) Who was the first person to believe in Hex and invest?
(27:29) How do Barry and Caitlin work with their board, and what’s that dynamic like as founders?
(30:07) How do Barry and Caitlin think about scaling culture as the company grows?
(32:21) What are some of the biggest leadership lessons Barry and Caitlin have learned since founding Hex?
(34:54) How do Barry and Caitlin maintain product focus while expanding features and teams?
(37:12) What’s the vision for the future of data collaboration and AI in analytics?
(39:15) How is the role of the data team evolving with AI?
(40:15) So… humans — we’re here to stay?
(42:05) What’s next for Hex and for Barry and Caitlin personally?
(43:49) Who is a woman in Barry and Caitlin’s lives who has had an impact on them and their career?

For The Room Podcast in your inbox every week, subscribe to our newsletter.
Follow us on Instagram
Follow us on TikTok
Check out our guide to podcasting here!
Don't forget to subscribe to our channel on YouTube, Spotify, and Apple Music!

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.

WX Productions

Welcome back to The Room Podcast! This week, Claudia and Madison sit down with Eric Simons, Co-Founder and CEO of StackBlitz and creator of Bolt.new, the AI-powered development platform redefining how people build web and mobile apps. From humble beginnings coding in Naperville, Illinois, to literally living inside AOL’s Palo Alto offices at age 19, Eric’s journey is a Silicon Valley legend. StackBlitz emerged from a desire to eliminate setup friction for developers, enabling instant browser-based coding environments that reimagined how software gets built.

In this episode, Eric shares the highs and lows of the founder journey — from near-shutdown to a $20M ARR turnaround powered by Bolt’s viral AI tools. He offers candid advice on knowing when to pivot, how to approach investors during uncertain times, and why obsession and experimentation are critical to surviving the startup grind. Tune in for insights on product-market fit, storytelling as a leadership superpower, and what the “vibe coder” movement means for the next generation of builders.

(00:00) Introduction
(04:40) Where did Eric grow up and how has that shaped his view of the world?
(06:08) Did Eric always think he would become a founder?
(08:06) How did Eric’s early interests, like acting, shape his storytelling and leadership today?
(08:08) How did Eric gain attention as the “AOL Squatter” and what did that experience teach him?
(12:04) What was the original idea behind StackBlitz and the aha moment that started it?
(14:52) How did Eric convince early investors and engineers that StackBlitz was even possible?
(16:48) How did StackBlitz navigate finding product-market fit and monetization challenges?
(19:55) What advice does Eric have for founders at a crossroads between pivoting or shutting down?
(21:51) In Eric’s words, what is Bolt and who is it built for?
(22:59) How did Eric shift his storytelling as Bolt expanded beyond developers?
(24:37) Who was the first person to believe in Eric and say yes to his vision?
(25:43) What advice would Eric give to founders raising early-stage capital in 2025?
(27:01) How did Eric approach his investors and board during the pivot from StackBlitz to Bolt?
(27:05) Can Eric peel back the curtain on how he approached investors about the pivot?
(31:25) How did Bolt turn a viral spark into durable long-term traction?
(38:16) What is Eric most excited about for Bolt this year—and personally?
(39:51) Who is a woman who profoundly shaped Eric and his career?

For The Room Podcast in your inbox every week, subscribe to our newsletter.
Follow us on Instagram
Follow us on TikTok
Check out our guide to podcasting here!
Don't forget to subscribe to our channel on YouTube, Spotify, and Apple Music!

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.

WX Productions