Claudia Laurie and Madison McIlwain

The Room Podcast

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.

Author

Claudia Laurie and Madison McIlwain

Category

Technology

Podcast website

the-room.castos.com

Latest episode

Jul 9, 2026

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Episodes

Turning Content into Competitive Advantage with Packy McCormick | Founding the Fund 3 09.07.2026

In this bonus episode of The Room Podcast, we speak with Packy McCormick , founder of Not Boring and Not Boring Capital, an investment firm focused on backing ambitious technology companies tackling large, complex industries. Through his writing, investing, and storytelling, Packy has built one of the most influential platforms in venture capital, helping founders explain difficult technical busin...

Backing Technical Founders with Amplify Partners Founder Sunil Dhaliwal | Founding the Fund 2 25.06.2026

In this episode of The Room Podcast, we speak with Sunil Dhaliwal, founder and managing partner of Amplify Partners, an early-stage venture capital firm focused on backing technical founders building infrastructure software, developer tools, cybersecurity, AI, and other foundational technologies. Before founding Amplify, Sunil spent 14 years at Battery Ventures, where he invested through both the...

Investing in Trillion-Dollar Outcomes with Ben Ling of Bling Capital | Founding the Fund 1 16.06.2026

In this bonus episode of The Room Podcast, we speak with Ben Ling , Founder and General Partner of Bling Capital , an early-stage venture firm that has backed companies including Airtable, Lyft, Square, Palantir, and many others. Before becoming a full-time investor, Ben held leadership roles at Google, Facebook, and YouTube, where he helped build products at massive scale and gained a front-row s...

S14E8: From a Shark Tank No to Billion-Dollar Exit with Ring Inventor, Jamie Siminoff 05.05.2026

In our season finale episode of The Room Podcast, we speak with Jamie Siminoff , inventor of Ring , the smart home security company best known for turning the front door into a connected safety platform. Ring builds video doorbells, cameras, alarms, and neighborhood safety tools that help people monitor and protect what matters most. Before Ring became one of the most recognizable home security br...

S14E7: Building the AI Layer for Legal Work with Scott Stevenson, Co-Founder and CEO of Spellbook 28.04.2026

In this episode of The Room Podcast, we speak with Scott Stevenson , CEO and Co-Founder of Spellbook . Spellbook is an AI-powered platform helping lawyers draft and review contracts faster using generative AI directly within their existing workflows. Spellbook enables legal teams to accelerate contract creation and negotiation by embedding AI into workflow tools allowing for real-time drafting, ed...

S14E6: The End of Waiting for Payday with EarnIn Founder, Ram Palaniappan 21.04.2026

In this episode of The Room Podcast, we speak with Ram Palaniappan , founder and CEO of Earnin , a fintech company reimagining how people get paid by giving employees access to their earnings in real time rather than waiting for traditional payroll cycles. Earnin is building a new kind of payroll system—one that shifts power from employers to employees by enabling on-demand and continuous pay. Ins...

S14E5: Building the Red Bull for Relaxation with Ben Witte, Founder and CEO of Recess 14.04.2026

In this episode of The Room Podcast, we sit down with Ben Witte , Founder and CEO of Recess , a consumer wellness brand pioneering a new category of functional beverages designed to help people relax, unwind, and feel better in an increasingly high-stress world. Recess blends ingredients like magnesium, adaptogens, and other functional compounds into beautifully branded drinks that position themse...

S14E4: Why Usage-Based Billing Is Inevitable with Metronome Co-Founder Scott Woody 07.04.2026

In this episode of The Room Podcast, we speak with Scott Woody , Co-Founder of Metronome , a platform helping companies implement usage-based billing and modernize how they monetize software. Metronome enables businesses to move beyond rigid subscription pricing and instead charge customers based on actual product usage. The platform sits at the core of a new shift in SaaS: pricing that aligns dir...

S14E3: Ryan Daniels, Founder & CEO of Crosby, on Legal Services in the Age of AI 31.03.2026

In this episode of The Room Podcast, we speak with Ryan Daniels , Founder and CEO of Crosby , an AI-first law firm rethinking how legal work gets delivered. Crosby combines AI systems with human legal expertise to provide faster, more transparent, and more scalable legal services, moving away from traditional billable hours toward outcome-driven work. Crosby is part of a broader shift in professio...

S14E2: Alex Halliday, Founder of AirOps, on Content Engineering and the AI Marketing Stack 24.03.2026

In this episode of The Room Podcast, we speak with Alex Halliday , founder and CEO of AirOps , a platform helping companies build AI-powered content workflows and automate complex marketing operations. AirOps enables marketing and growth teams to orchestrate large-scale content generation using structured workflows, AI models, data integrations, and human-in-the-loop systems. The platform is part...

S14E1: Nirav Tolia, Nextdoor CEO, on Building Community Platforms, Product-Market Fit, and the Future of AI in Local Networks 17.03.2026

In this season opener of The Room Podcast, we speak with Nirav Tolia , the co-founder and CEO of Nextdoor , the neighborhood network designed to connect verified neighbors and strengthen local communities. Nirav shares and refelcts the story behind building Nextdoor, one of the world’s largest hyperlocal social platforms, and reflects on the lessons he has learned scaling a product designed around...

From Stitch Fix to AI Search with Daydream Founder Julie Bornstein | Inside Summit 2025 [LIVE] 23.12.2025

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...

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] 16.12.2025

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...

Navigating the New M&A Landscape with Indy Guha (VMG), Jared Roesch (OctoAI), Dan Kang (Mercury), Michelle Edwards (Perkins Coi) | Inside Summit 2025 [LIVE] 09.12.2025

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...

Solving Data Fragmentation at Scale with Michel Tricot, Co-Founder & CEO of Airbyte | Inside Summit 2025 [LIVE] 02.12.2025

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-...

S13E8: Designing Payroll for Small Businesses with Gusto’s Co-Founder, Tomer London 18.11.2025

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 t...

S13E7: Reimagining Content, Provenance, and AI with Cloudflare’s VP of Product, William Allen 11.11.2025

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 init...

S13E6: How Almost Friday Media is Shaping the Next Era of Entertainment with Jack Barrett 04.11.2025

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 event...

S13E5: From Palantir to Hex — How Barry McCardel and Caitlin Colgrove Built the Modern Data Workspace 28.10.2025

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-p...

S13E4: From Sleeping at AOL to Building Bolt with Eric Simons, Founder and CEO of Bolt.new 21.10.2025

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. Sta...

S13E3: Creating Longevity Drugs for Dogs with Celine Halioua, Founder of Loyal 14.10.2025

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, Lo...

S13E2: Scaling Warp and Supercharging Developers with AI with Founder Zach Lloyd 07.10.2025

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 in...

S13E1: Reinventing Work Through AI-Native Communication with Craig Walker, Founder & CEO of Dialpad 30.09.2025

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 be...

New York Tech Week Special: Live Recording with Partiful Co-Founder and CEO, Shreya Murthy 01.07.2025

Welcome to a special bonus episode of The Room Podcast, recorded live at New York Tech Week! This week, we're thrilled to chat with Shreya Murthy , Co-Founder and CEO of Partiful , the modern social events platform that is revolutionizing how we make plans and build real-world relationships. Since launching in 2021, Partiful has scaled to millions of users and earned major accolades, including Goo...

S12E8: Direct-to-Consumer Pioneer to AI Psychology with Neil Parikh, Co-Founder of Casper and Slingshot 27.05.2025

In this season’s finale of The Room Podcast, we're thrilled to chat with Neil Parikh , Co-Founder of Casper and current Co-Founder of Slingshot . Neil first disrupted the mattress industry by building Casper into a household name, pioneering the direct-to-consumer sleep revolution before taking the company public. Now, he's tackling an even bigger challenge with Slingshot, building a foundational...

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