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Episodes from The Room Podcast
S14E3: Ryan Daniels, Founder & CEO of Crosby, on Legal Services in the Age of AI
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 professional services, where AI is not just augmenting workflows but fundamentally reshaping how services are delivered. Instead of selling tools to lawyers, Crosby operates as a full-stack legal provider, meeting customers where trust already exists...
S14E2: Alex Halliday, Founder of AirOps, on Content Engineering and the AI Marketing Stack
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 of a new category emerging in the AI ecosystem: the AI marketing stack, where companies move beyond simple prompt-based tools and instead build repeatable systems for producing high-quality content. Before founding AirOps, Alex built viral fan websites as a teenager...
S14E1: Nirav Tolia, Nextdoor CEO, on Building Community Platforms, Product-Market Fit, and the Future of AI in Local Networks
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 real-world communities. Before founding Nextdoor, Nirav was one of the first 100 employees at Yahoo, where he witnessed the rise of the early consumer internet and the power of network effects. He later co-founded Ro...
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...
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...
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, t...
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...
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...
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...
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...
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 tool...
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 foun...