The Room Podcast

Claudia Laurie and Madison McIlwain

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. 1 दिन पहले

    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 मिनट

  2. 11 नव॰

    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 मिनट

  3. 4 नव॰

    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 मिनट

  4. 28 अक्टू॰

    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 मिनट

  5. 21 अक्टू॰

    S13E4: From Sleeping at AOL to Building Bolt with Eric Simons, Founder and CEO of Bolt.new

    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

    42 मिनट

  6. 14 अक्टू॰

    S13E3: Creating Longevity Drugs for Dogs with Celine Halioua, Founder of Loyal

    Welcome back to another episode of The Room Podcast! This week, we sit down with Celine Halioua, Founder and CEO of Loyal, a biotech company pioneering FDA-approved longevity drugs for dogs. From a childhood surrounded by rescue animals to an academic journey through neuroscience, health economics, and venture capital, Celine’s path to entrepreneurship is as winding as it is inspiring. Today, Loyal is leading the charge in redefining what’s possible in veterinary medicine—aiming not just to treat disease, but to extend healthy lifespan itself. In this episode, Celine shares how her scientific curiosity about aging and her love for animals converged into a singular mission. She takes us behind the scenes on the founding story of Loyal—from a chance conversation around a campfire, to navigating the capital-intensive world of biotech, to winning over regulators and pet parents alike. Listeners will walk away with hard-earned insights about fundraising in uncertain markets, balancing ambition with operational discipline, and the importance of being both scientifically rigorous and soulfully driven when building something truly generational. (00:00) Introduction (05:00) How did Celine’s early upbringing in Austin shape her worldview? (06:31) Did Celine always think she’d become a founder? (06:49) What early research made Celine believe in longevity as a real field? (08:51) How did Celine’s love for dogs intersect with her scientific passion? (10:48) What was the aha moment behind starting Loyal? (16:14) What was it like convincing early investors and team members to believe in Loyal? (19:41) Who was the first person to invest in Celine and Loyal? (21:29) How did Celine build trust with both regulators and pet owners? (24:24) What’s a moment that didn’t go as planned, and how did Celine turn it around? (30:47) Is it challenging to build a brand while the product isn’t ready to go to market? (34:17) Is getting a drug for animals approved by the FDA different than a drug for humans? (36:41) What did Celine consider when building her team at Loyal? (40:21) Can Loyal’s work in dogs translate to longevity solutions for humans? (42:34) Who is a woman in your life who has had a profound impact on you and your 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

    45 मिनट

  7. 7 अक्टू॰

    S13E2: Scaling Warp and Supercharging Developers with AI with Founder Zach Lloyd

    This week on The Room Podcast, Claudia and Madison sit down with Zach Lloyd, Founder and CEO of Warp. Before founding Warp, Zach spent nearly a decade at Google, where he led engineering on Google Sheets and Docs, and later co-founded the startup Self-Made before launching Warp in 2020. Warp is a modern re-imagining of the command line, transforming one of the most widely used developer tools into an AI-powered, productivity-boosting experience. In this episode, Zach shares lessons from his challenge of finding the right founder–market fit, we explore how Warp integrates AI into developer workflows, why timing mattered during the ChatGPT wave, and the importance of retention before growth. Tune in for insights on building developer-first products, rethinking foundational tools, and how to adapt a startup in a fast-moving AI landscape.   (0:00) Introduction (04:54) Where did Zach grow up and how did that shape his view of the world? (06:04) Did Zach always see himself becoming a founder or CEO? (07:07) How did Zach’s early years shape his career path, and why did he leave law school after one year? (09:37) How did Zach’s time at Google shape some of the insights behind Warp? (11:47) What did Zach’s first startup Self-Made do, and how did that experience influence Warp? (15:08) Why was the developer tools space so exciting and important for Zach to tackle with Warp? (18:41) In Zach’s words, what is Warp and how does AI supercharge the new terminal experience? (21:52) What was Zach’s “oh shit” moment in November 2022 when AI changed Warp’s trajectory? (24:58) How did Zach explain this AI-driven shift in product direction to investors? (26:53) What were Warp’s first growth inflection points and what drove that traction? (29:34) How did Warp differentiate itself from the explosion of AI coding tools after ChatGPT’s launch? (31:27) Who was the first person to invest in Warp? (33:29) What were some of the toughest user-experience or branding challenges Warp faced early on? (35:25) How is Warp growing into a dual approach of PLG and enterprise? (37:17) Do we need new business models to support what is happening in tech? (39:24) Who does Zach see as Warp’s true competitors in the AI developer tools space? (40:49) What’s Zach’s quick take on Model Context Protocol and how it fits into Warp’s future? (42:13) What can new users look forward to next with Warp? (43:11) Who is a woman in Zach’s life that has 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

    46 मिनट

  8. 30 सित॰

    S13E1: Reinventing Work Through AI-Native Communication with Craig Walker, Founder & CEO of Dialpad

    In this episode of The Room Podcast, hosts Claudia Laurie and Madison McIlwain sit down with serial entrepreneur Craig Walker, founder and CEO of Dialpad. Craig’s story begins in Cupertino, back when apricot orchards defined the neighborhood and a young Steve Jobs lived just a few houses down. From those early days in Silicon Valley, Craig went on to earn degrees from Berkeley and Georgetown before starting his career as an M&A lawyer advising Cisco, Kleiner Perkins, and Sequoia. That legal lens shaped his entrepreneurial instincts and prepared him for the rollercoaster ride of building companies through both downturns and booms. Craig shares the pivotal moments behind: Rescuing Dialpad Communications in the wake of the dot-com crash, cutting $3M in monthly burn down to $100K.Founding GrandCentral, which became Google Voice after its acquisition by Google in 2007.Launching UberConference, later rebranded as Dialpad Meetings, and returning to his passion for modern communications.We dive deep into how Dialpad became an AI-native platform, from the bold $50M acquisition of TalkIQ in 2018 to pioneering real-time transcription, sentiment analysis, and call coaching. Craig explains why “work isn’t a place, it’s what you do” has been his guiding philosophy—and how that mindset shaped Dialpad’s remote-friendly, AI-first culture long before the pandemic. The conversation also covers: What it means to build an AI-native company vs. bolting on AI features.Lessons for founders raising capital in today’s market.How to balance automation with maintaining authentic human connection.Craig’s vision for the future of Dialpad and AI-powered work.The woman in Craig’s professional journey who has had a profound impact.This is a masterclass in resilience, reinvention, and leading at the edge of technological change

    53 मिनट
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ट्रेलर

परिचय

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.

जानकारी

  • निर्माता
    Claudia Laurie and Madison McIlwain
  • सक्रिय वर्ष
    2020 - 2025
  • एपिसोड
    128
  • रेटिंग
    अश्लील
  • कॉपीराइट
    © 2020
  • कार्यक्रम की वेबसाइट
    The Room Podcast

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