The Room Podcast

Claudia Laurie and Madison McIlwain
  • 5.0 (53)
  • TECHNOLOGY
  • UPDATED WEEKLY

Welcome to the Room. A series interviewing your favorite tech founders and funders. Our guests were in the room where it happened and they’re sharing their stories.

  1. 16H AGO

    From Stitch Fix to AI Search with Daydream Founder Julie Bornstein | Inside Summit 2025 [LIVE]

    Welcome back to another episode of The Room Podcast! This week, Claudia and Madison sit down with Julie Bornstein, founder and CEO of Daydream, a new AI-powered shopping platform reimagining how people discover fashion online. Julie is a two-time founder with deep roots in digital commerce, having previously helped build Stitch Fix and later founded The Yes, which was acquired by Pinterest. With decades of experience at the intersection of retail, technology, and consumer behavior, Julie has been at the forefront of how people shop as the internet — and now AI — evolves. In this episode, Julie shares why search has always been the hardest and most important problem in e-commerce, and how generative AI finally unlocks a more human way to shop. She walks through the lessons she learned building algorithmic fashion at Stitch Fix, why inventory ownership limits personalization, and how The Yes shaped her thesis around intent-driven discovery. We also dive into founding Daydream after an acquisition unwind, the challenges of hiring the right early team, navigating retailer relationships without becoming an ads business, and what the future of shopping looks like when your stylist lives in your pocket. Tune in for a masterclass on consumer AI, founder resilience, and why being early — twice — doesn’t make it easier the third time around. (00:00) Introduction (05:20) Where did Julie grow up and how did it shape her view of the world? (06:31) Did Julie always think she would become a founder? (07:42) How did Julie’s early career in retail and e-commerce shape what she’s building today? (09:59) How did Julie’s philosophy evolve from Stitch Fix to The Yes to Daydream? (11:54) Why did Julie decide to become a founder again after selling The Yes to Pinterest? (14:54) How does Daydream avoid getting squeezed between retailers and consumers? (17:58) Who is Daydream’s core customer and why did Julie choose them first? (18:45) Who was the first investor to say yes to Daydream? (19:39) What unexpected challenges did Julie face early at Daydream? (21:41) How is AI changing Daydream’s business model decisions? (22:26) Should retailers rethink site architecture in an AI-driven search world? (23:14) How can companies make products more discoverable in an LLM-first future? (23:33) Does better AI indexing by retailers threaten Daydream’s value? (25:48) How does Daydream think about LLM interoperability and model choice? (26:44) How should retailers think about cloud providers in modern e-commerce stacks? (27:57) Does Julie consider Daydream an AI-native company? (29:23) What does the future of online retail look like? (31:39) What advice does Julie have for new founders? (33:44) Who is a woman in Julie's life that has had a profound impact on her and her 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

    36 min

  2. DEC 16

    Ethical AI, Iteration Velocity, and the Future of Software with Grant Lee (Gamma), Noah MacCallum (Open AI), Malte Ubl (Vercel), Chris Messina (Product Leader), Ash Kumrah (The AI Collective) | Inside Summit 2025 [LIVE]

    In this special live panel episode of The Room Podcast from Inside Summit 2025, host Ash Kumra sits down with an all-star group of AI and product leaders: Noah MacCallum of OpenAI, Grant Lee of Gamma, Malte Ubl of Vercel, and Chris Messina, inventor of the hashtag and longtime product strategist. Together, they represent the cutting edge of applied AI, developer platforms, design tooling, and the social technologies that shaped how we communicate today. Throughout the conversation, the panel digs into what ethical AI actually means in practice, how founders should think about scaling from early demos to real-world robustness, and why “iteration velocity” may matter more than perfection. From Noah’s breakdown of vibes-based iteration versus formal evals, to Chris’s framing of AI as a new expressive medium rather than just a technology, this episode is packed with perspective for builders navigating the next era of software. The discussion ultimately challenges founders to focus less on hype and more on clarity of vision, taste, and long-term impact. (00:00) Introduction (04:28) Who are the panelists and what is each of them building or focused on today? (06:39) How does Noah define ethical AI, and where do the real risks show up in practice? (08:02) How should early-stage AI companies think about trust, safety, and responsibility? (11:26) What advice would the panel give founders trying to scale AI products from one to one hundred? (12:21) How do founders balance intuition, taste, and formal evals when improving AI products? (13:32) Why is long-term founder conviction more important than early AI traction? (14:33) How should founders think about AI as a medium rather than just a technology? (17:42) Which industries remain underexplored for AI, despite the current hype cycle? (20:25) Which customer segments surprised Gamma as adoption scaled beyond early users? (23:30) What unexpected user behaviors emerged during the early days of social media and AI? (27:00) What specific product, feature, or workflow is each panelist most excited about building right now? 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

    36 min

  3. DEC 9

    Navigating the New M&A Landscape with Indy Guha (VMG), Jared Roesch (OctoAI), Dan Kang (Mercury), Michelle Edwards (Perkins Coi) | Inside Summit 2025 [LIVE]

    In this special Inside Summit episode of The Room Podcast, Claudia moderates a powerhouse panel featuring Michelle Edwards, Partner at Perkins Coie, Indy Guha, GP of VMG, Dan Kang, CFO of Mercury, and Jared Roesch, a founder who recently exited to NVIDIA.  When startups challenge incumbents, winning deals requires more than just a great product. This episode shares how to master founder sales by building strong relationships and leveraging insider knowledge. Learn about crafting a compelling sales strategy and how to sell effectively, even when facing executive changes. With perspectives spanning legal, investor, financial, and operator experience, the panel breaks down how deals get sourced, what drives acquirer motivation, and how macro conditions—from AI acceleration to shifting public markets—are reshaping the paths available to startups. In this conversation, the group shares tactical lessons on preparing your company years before an exit, cultivating strategic relationships, and understanding the human and emotional realities of selling a business. They explore why deals fall apart, how founders can signal readiness to buyers, and why the best outcomes often begin long before a term sheet is drafted. Whether you're raising, scaling, or fielding interest from potential acquirers, this episode offers clear, actionable insights for building toward a successful transaction. (00:00) Introduction (06:05) What has each panelist’s experience been with M&A? (08:51) How is M&A shifting in 2025 from the investor side? (10:56) What is driving more companies towards M&A? (12:25) What are some of the most common structural shifts in deals today versus the past? (14:49) When does a founder know acquisition is the right path? (17:41) What is something that most founders don’t think of when it comes to being acquired? (21:28) How does a founding team build relationships with investors? (23:28) What red flags should a buyer or seller be looking for during negotiations? (28:27) How do you manage a team that's working and building that might not know that an acquisition is happening? (29:48) What do buyers wish founders did more of to set themselves up for a successful transaction? (32:36) How should founders approach the conversation of acquisition with their investors? 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

    35 min

  4. DEC 2

    Solving Data Fragmentation at Scale with Michel Tricot, Co-Founder & CEO of Airbyte | Inside Summit 2025 [LIVE]

    Welcome back to another LIVE rendition of The Room Podcast! This week, we are back at our live conference, Inside Summit. Listen in as we sit down with Michel Tricot, Co-Founder and CEO of Airbyte — the open-source platform that’s transforming how companies move data across their modern stacks. Airbyte gives teams the ability to extract and load data from virtually any source, empowering both AI-native companies and legacy enterprises to sync their information seamlessly and securely across hundreds of tools. In this conversation, Michel shares the lessons behind scaling Airbyte from its first connector to 600+, building open source community momentum, and navigating shocks like COVID and a disrupted engineering team during the war in Ukraine. We dive into why ELT architecture matters, what separates AI-native companies from incumbents trying to adopt AI, and why founders should optimize for survival before anything else. Tune in for tactical guidance on fundraising, building at “internet scale”, breaking data silos, and how to stay grounded when the journey becomes nonlinear — because it always does. (00:00) Introduction (04:23) Where did Michel grow up and how did that shape his view of the world? (05:09) Did Michel always think he was going to become a founder? (05:35) What early career milestones led Michel to move to San Francisco? (07:56) What insights brought Michel to want to develop a better data stack? (09:25) How did Michel transition from full-time work to launching an open-source solution and building Airbyte? (11:05) Why did Michel choose to name Airbyte’s architecture as “ELT”? (12:01) How did the “ELT” architecture choice influence decisions around scaling the company? (13:15) What was Airbyte’s first connector? (13:33) What was harder — going from 1 to 50 connectors or from 50 to 600? (14:20) Who was the first person to ever say yes to investing in Michel? (14:47) What metrics convinced investors that Airbyte was a billion-dollar-plus market? (15:23) What advice does Michel have for first-time founders preparing for their first fundraise? (16:00) What is something that went wrong during the founder journey? (16:31) What does “AI data infrastructure” really mean — is it just rebranding? (17:39) Where does Airbyte fit in the evolving AI ecosystem? (18:47) How does Airbyte think about competing with giant platforms building internal integration tools? (20:08) What separates AI-native companies from larger incumbents trying to cross the AI chasm? (21:21) When data infrastructure is fully solved, what does that mean for the world? (22:26) What general career and life advice does Michel have for future founders today? (23:49) Who is a woman in Michel’s life that had a profound impact on him 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

    26 min

  5. NOV 18

    S13E8: Designing Payroll for Small Businesses with Gusto’s Co-Founder, Tomer London

    Welcome back to The Room Podcast! This week, Claudia and Madison sit down with Tomer London, Co-Founder and Chief Product Officer of Gusto, the all-in-one people platform that simplifies payroll, benefits, and HR for over 400,000 small businesses across the U.S. From humble beginnings as ZenPayroll, Gusto has become one of the most beloved products in the SMB ecosystem—known for turning one of the most stressful business tasks into a delightful experience. In this episode, Tomer shares the personal roots behind Gusto’s mission—growing up around his family’s small clothing store in Israel—and how those early lessons shaped his empathy for small business owners. He walks us through finding the right customer base, building emotional resonance into product design, and why “customer love” is the most powerful growth channel. Listeners will gain valuable insights into startup decision-making, measuring true product–market fit, and the mindset needed to scale from a scrappy YC-backed idea into a category-defining company. (00:00) Introduction (05:25) Where did Tomer grow up and how did that shape his view of the world? (05:50) Did Tomer always think he would become a founder? (10:13) What early challenges inspired Tomer to build something of his own? (11:23) What were Tomer’s first experiences like coming to the U.S. as an immigrant? (13:33) What was the “aha” moment that led to starting Gusto? (16:38) What were some early moments when things didn’t go as planned? (20:11) How did Gusto find product–market fit with small businesses? (23:51) What advice does Tomer have for founders navigating their beachhead market? (26:26) How did Gusto create emotional connection and delight through product design? (29:11) What has leading Gusto taught Tomer about building teams and company culture? (33:11) How does Gusto approach innovation while staying true to its mission? (36:04) How does Gusto assist businesses and customers during crisis moments? (38:04) How is Gusto adapting to the AI era? (44:08) Who is a woman in your life that had a profound impact on you? 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

    48 min

  6. NOV 11

    S13E7: Reimagining Content, Provenance, and AI with Cloudflare’s VP of Product, William Allen

    Welcome back to another episode of The Room Podcast! This week, Claudia and Madison sit down with William Allen, Head of Emerging Tech and AI at Cloudflare, and previously a key leader at Adobe and Behance. Will has spent his career at the intersection of creativity, technology, and infrastructure—from helping launch TED Talks and building Behance into a global hub for creatives, to leading initiatives like the Content Authenticity Initiative that aim to make the internet more trustworthy. In this episode, Will shares insights on the evolution of digital content, the challenges of building authenticity in an AI-driven world, and what it takes to create infrastructure that both empowers creators and protects their work. He discusses lessons learned from scaling startups, navigating acquisitions, and fostering innovation within large companies. Listeners will walk away with actionable takeaways on balancing speed with integrity, building products for real users, and creating a “better internet” rooted in trust and transparency. (00:00) Where did Will grow up and how did that shape his view of the world? (01:09) Did Will always think he would become a founder like he did with Chamber? (03:17) Was that first startup what led him to Adobe? (04:38) What was it like launching TED Talks for the first time? (06:35) What did Will learn from his decade at Adobe and leading Behance? (09:06) How did those experiences shape what Will wanted to do next in his career? (10:25) How did Will transition from Chamber to joining Cloudflare? (11:12) What was it like selling his startup and choosing not to join the acquiring company? (12:21) What was the idea that finally convinced him to join Cloudflare? (14:00) How is Cloudflare balancing protection and innovation in the AI era? (16:05) What advice does Will have for founders building resilient infrastructure in the age of AI? (18:18) What’s something that didn’t go as planned while building or launching a product? (21:04) How does Cloudflare communicate with creators and non-technical users? (23:00) How does Will think about policy and communicating with broader stakeholders? (24:40) What does the end-to-end C2PA workflow look like from capture to display? (27:30) In five years, what will creators’ relationship be with AI model providers? (32:45) What’s next for Will personally, and what is he excited about? (34:10) Who is a woman that has had a profound impact on Will’s life and 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

    41 min

  7. NOV 4

    S13E6: How Almost Friday Media is Shaping the Next Era of Entertainment with Jack Barrett

    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. 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

    32 min

  8. OCT 28

    S13E5: From Palantir to Hex — How Barry McCardel and Caitlin Colgrove Built the Modern Data Workspace

    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

    47 min
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About

Welcome to the Room. A series interviewing your favorite tech founders and funders. Our guests were in the room where it happened and they’re sharing their stories.

Information

  • Creator
    Claudia Laurie and Madison McIlwain
  • Years Active
    2020 - 2025
  • Episodes
    132
  • Rating
    Explicit
  • Copyright
    © 2020
  • Show Website
    The Room Podcast

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