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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.

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21 episodes
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Avg 45 min
English

Episodes 21

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#1
Tuesday · 1 hr
S15E1: Building the Infrastructure for Voice AI with Russ d'Sa, Co-Founder and CEO of LiveKit
In this season 15 opener of The Room Podcast, we speak with Russ d'Sa, co-founder and CEO of LiveKit, a platform for building real-time voice, video, and AI agents. LiveKit began as an open-source project for live audio and video. As developers adopted it, the team built cloud infrastructure to help them scale. A second turning point came when OpenAI used LiveKit to build a voice interface for ChatGPT, revealing how technology built to connect people could also connect people with AI. Russ trac
#4
August 4 · 53 min
Building an Enterprise VC Firm with Jai Das, President and Co-Founder of Sapphire Ventures | Founding the Fund 4
In this bonus episode of The Room Podcast, we speak with Jai Das, President, Partner and Co-Founder of Sapphire Ventures, one of the world's leading enterprise venture capital firms backing category-defining B2B software and AI companies. Sapphire Ventures has invested in companies including monday.com, Box, Square, MuleSoft, Fitbit, ExactTarget, and many others, while building one of the industry's most recognized enterprise-focused venture platforms. Before co-founding Sapphire Ventures, Jai'
#3
July 9 · 44 min
Turning Content into Competitive Advantage with Packy McCormick | Founding the Fund 3
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 businesses to customers, talent, and investors. Not Boring began as a newsletter during the early months
#2
June 25 · 1 hr 9 min
Backing Technical Founders with Amplify Partners Founder Sunil Dhaliwal | Founding the Fund 2
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 dot-com boom and bust before launching Amplify in 2012, which today manages more than $2.7 billion i
#1
June 16 · 52 min
Investing in Trillion-Dollar Outcomes with Ben Ling of Bling Capital | Founding the Fund 1
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 seat to some of the most important technology platforms of the last two decades. In this rendition of
#8
May 5 · 45 min
S14E8: From a Shark Tank No to Billion-Dollar Exit with Ring Inventor, Jamie Siminoff
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 brands in the world, Jamie was an inventor building things in his basement, launching companies like Ph
#7
April 28 · 39 min
S14E7: Building the AI Layer for Legal Work with Scott Stevenson, Co-Founder and CEO of Spellbook
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, editing, and comparison against market data. The company sits at the intersection of legal tech and AI
#6
April 21 · 29 min
S14E6: The End of Waiting for Payday with EarnIn Founder, Ram Palaniappan
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. Instead of the outdated two-week batch system, Earnin is pioneering a streaming model for income, where
#5
April 14 · 40 min
S14E5: Building the Red Bull for Relaxation with Ben Witte, Founder and CEO of Recess
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 themselves as the “Red Bull for relaxation.” Before launching Recess, Ben built his career in early-stage
#4
April 7 · 49 min
S14E4: Why Usage-Based Billing Is Inevitable with Metronome Co-Founder Scott Woody
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 directly with value delivered, rather than seats or static tiers, giving companies more flexibility and
#3
March 31 · 44 min
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
#2
March 24 · 50 min
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 s
#1
March 17 · 1 hr 9 min
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 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 wi
#4
Dec 23, 2025 · 36 min
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 bee
#3
Dec 16, 2025 · 36 min
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 di
#2
Dec 9, 2025 · 35 min
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. Together, they unpack the increasingly complex M&A landscape that founders are navigating in 2025. With perspectives spanning legal, investor, financial, and operator experience, the panel breaks down how deals get sourced, what drives acquirer
#1
Dec 2, 2025 · 26 min
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 hund
#8
Nov 18, 2025 · 47 min
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 pers
#7
Nov 11, 2025 · 40 min
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 t
#6
Nov 4, 2025 · 31 min
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 touch

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