The Room Podcast

In this episode of The Room Podcast, we speak with Sergi Bastardas, co-founder and CEO of Orbio AI, a platform using autonomous agents to coordinate the employee journey for frontline workforces. Sergi traces his path from a small town near Barcelona to joining Amazon Spain in its earliest days, and building a global supply-chain business. He shares how a family history of entrepreneurship, a curiosity about the wider world, and Amazon’s culture of operational excellence shaped the way he builds companies. He explains why HR is fundamentally a system of conversations and unstructured data and why Orbio was designed as an agent-native product rather than an AI add-on. From screening and scheduling to onboarding, retention, and exit interviews, Orbio’s agents work across voice, WhatsApp, text, and Teams while keeping people in control of employment decisions. In this conversation, Sergi breaks down the company’s expansion across languages and markets, what incumbent HR platforms would need to rebuild to become…

In this episode of The Room Podcast, we speak with Caitlin Leksana, co-founder and CEO of Fazeshift, a company building AI agents for accounts receivable. Caitlin traces her path from growing up outside Washington, D.C., and studying mechanical engineering at Georgia Tech to water-desalination research, BCG, Harvard Business School, and entrepreneurship. She shares how a classmate became her co-founder, why their first crypto startup failed to find product-market fit, and how they found the conviction to pivot instead of walking away. Caitlin explains how her own messy invoicing spreadsheet led the team to hundreds of customer-discovery conversations and eventually to Fazeshift. She breaks down what changed when the founders started with a customer problem instead of a product idea, how Y Combinator helped them find momentum, and what she learned about fundraising, hiring, and building with a co-founder. The conversation also explores vertical AI in finance: why reliable automation starts with connecting…

In this episode of The Room Podcast, we speak with Doug Tallmadge, co-founder and CEO of Gradial, a company building AI agents to help enterprise marketing teams execute work across their tools and campaigns. Doug traces his path from growing up in Cincinnati and studying physics at Dartmouth to joining SpaceX and helping build Starlink. He shares what working through seemingly impossible engineering challenges taught him and why finding a market for a startup can be a very different problem from building a product people already want. After ChatGPT launched, Doug and his longtime friends left their jobs to start a company. He explains how their broad ambition to bring AI into enterprise work became a focused business in marketing, where campaign briefs, creative assets, tickets, and manual handoffs create a significant operational burden. In this conversation, Doug breaks down how Gradial’s agents have evolved alongside the models, what it takes to earn enterprise trust, and why marketers should be able to…

In this episode of The Room Podcast, we sit down with Ann Crady Weiss, co-founder and CEO of Hatch, to trace the path from her Silicon Valley upbringing and early career in law and technology to building one of the most recognizable names in sleep. Ann shares how her family’s connection to Intel shaped her entrepreneurial ambition, what she learned at Wilson Sonsini and Yahoo, and how the acquisition of her first startup prepared her to build again. Hatch began with a personal problem and evolved from a baby-focused hardware company into a broader sleep platform for children and adults. Ann explains how customer behavior led the team into the adult market, why emotional design and organic love became central to the brand, and how Hatch balances slower hardware cycles with a software-led organization and a growing library of bedtime content. The conversation also covers Hatch’s appearance on Shark Tank, the long relationship with True Ventures, an early move into Costco, and the discipline of building with…

In this season 15 opener of The Room Podcast, we speak with Gavriel Cohen, co-founder and CEO of NanoCo and creator of NanoClaw, an open-source framework designed to make powerful AI agents safer and more practical for real-world use. NanoClaw emerged from Gavriel’s own experience using AI agents to run an AI-native marketing agency. After connecting an agent he called “Andy” to his company’s sales pipeline, Gavriel saw the potential for agents to operate less like chatbots and more like persistent digital coworkers—but also recognized the security challenges that come with giving autonomous agents access to sensitive tools, data, email, and business systems. In this conversation, Gavriel shares the core idea behind NanoClaw: rather than weakening an AI agent, give it powerful capabilities while putting clear boundaries around what it can access—what he describes as putting the agent “in a box.” He also explains why he believes the future of work will involve humans becoming managers of increasingly capable…

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 traces his path from growing up around computers in Canada and Silicon Valley to founding a startup, working at 23andMe and Twitter, and building LiveKit. He shares the unexpected relationships and product decisions that shaped the company, including why he calls it the “accidental AI company.” In this conversation, Russ explains why speaking with an AI requires a different kind of infrastructure from typing to one. He also looks ahead to physical AI and reflects on how becoming a father has changed the way he thinks about…

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's career spanned software engineering at Oracle, founding startups during the dot-com era, corporate venture investing, and leading the transformation of SAP Ventures into the independent firm it is today. In this conversation, Jai reflects on the lessons learned across multiple technology cycles, from the early internet to today's AI revolution, sharing how his experiences as an engineer, founder, and investor shaped Sapphire's long-term strategy and investment philosophy.

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 of the pandemic and has since grown into a media platform reaching hundreds of thousands of readers, alongside an early-stage venture fund investing in companies across energy, aerospace, infrastructure, AI, and enterprise software. Rather than chasing trends, Packy focuses on founders building category-defining businesses that require deep conviction and long-term thinking. In this conversation, Packy shares how storytelling became his competitive edge as an investor, why the best founders think several moves ahead of…

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 in assets. In this conversation, Sunil reflects on the entrepreneurial influence of his parents, lessons learned investing through multiple technology cycles, and the conviction that led him to build Amplify around technical founders long before the rest of the venture industry caught on. We also discuss why venture firms need a clear reason to exist, how long-term relationships become your greatest fundraising advantage, what separates durable investors from emerging managers, why founder "fit" matters more than…

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 Founding the fund, Ben shares lessons from moving between operating and investing, what he learned working alongside leaders like Vinod Khosla and Marissa Mayer, and why distribution often matters more than product. We also discuss how Ben built Bling Capital around founder experience, why seed investing has structural advantages over multi-stage funds, how venture investors should think about trillion-dollar outcomes instead of billion-dollar outcomes, and the framework he uses to evaluate both founders and aspiring…

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 PhoneTag and Unsubscribe.com, and learning firsthand that a great product does not always equal a great business. His career has spanned consumer hardware, software, home security, AI-enabled safety tools, and one of the most memorable startup journeys from Shark Tank rejection to Amazon acquisition. In this conversation, Jamie shares the core insight behind Ring: the company was never really about doorbells; it was about making neighborhoods safer. What started as a personal frustration in his garage became a…

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 infrastructure, transforming how contracts are created by shifting from slow, manual workflows to intelligent, data-driven systems. This conversation explores how startups are fundamentally a pursuit of truth, how AI is reshaping legal work, and why building enduring companies requires deep conviction in a problem over many years. Scott shares the core insight behind Spellbook: lawyers don’t need entirely new tools. Rather, they need dramatically better versions of what they already use, seamlessly integrated into…

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 workers can access wages as they earn them, improving financial stability and reducing reliance on overdrafts and late fees. Ram’s journey into founding Earnin didn’t begin with the intention to start a company—it began by manually helping employees avoid overdraft fees by advancing their earned wages. That scrappy, human-first solution evolved into a scaled fintech platform now used by millions, reshaping how payroll is experienced across the U.S. In this conversation, Ram shares the core insight behind Earnin:…

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 startups and hypergrowth companies like AdRoll, where he developed a deep understanding of digital marketing, brand building, and emerging consumer trends. In this conversation, Ben shares the core insight behind Recess: that relaxation would define the next major consumer category, driven by rising anxiety, changing alcohol consumption habits, and a cultural shift toward mental wellness. We dive into lessons on identifying non-obvious trends early, building a lifestyle brand in a crowded CPG market, and navigating…

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 better feedback loops on how their products are used. This episode explores how billing and pricing infrastructure are becoming critical levers for modern software companies and why aligning pricing with value will define the next generation of SaaS businesses. Before founding Metronome, Scott founded Foundry (later acquired by Dropbox) and went on to spend six years at Dropbox leading engineering teams, where he helped scale monetization systems from $200M to over $1B in revenue. His experience operating at scale…

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 while embedding AI into the core of legal execution. In this conversation, Ryan shares the core insight behind Crosby: legal work is only partially about legal expertise, and largely about understanding business context, speed, and responsiveness. AI enables a shift where repetitive work is automated, allowing lawyers to focus on high-judgment decisions that actually impact…

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 and later founded SocialGo, eventually becoming the youngest CEO of a publicly traded company in the UK. His career has spanned early internet startups, hypergrowth technology companies, and now the modern AI platform landscape.

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 witnessed the rise of the early consumer internet and the power of network effects. He later co-founded Round Zero, an early startup studio that helped shape his thinking about entrepreneurship and product development.

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…

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…

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 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…

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…

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…

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…

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…

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.

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…

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…

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.

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.

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 Google's Best App of 2024, Apple's Editor Choice, and recognition as one of Fast Company's Most Innovative Companies for 2025. With its SMS-based approach and frictionless event creation, Partiful has become the go-to platform for gathering people together—so much so that "to partiful" has become a verb! In this episode, Shreya takes us through her unconventional journey from studying political theory at Princeton to building enterprise software, before ultimately founding Partiful to combat social isolation. We dive deep into fascinating topics like launching a party platform during a global pandemic, the strategic…

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 AI model specifically designed for psychology and mental health therapy. In this episode, Neil takes us through his unconventional journey from medical school dropout to D2C pioneer, sharing the serendipitous moments that led to Casper's creation and the harsh realities of going public during a pandemic. We delve into the mental health crisis facing society, the limitations of current AI therapy approaches, and how Slingshot is training models on real-world human therapy data to create more effective interventions. Neil also opens up about his therapy journey, the power of taking nudges when they appear, and why he…

Welcome back to another episode of The Room Podcast! This week, Madison and Claudia sit down with Alex Konrad, former Senior Editor at Forbes and now Founder of Upstarts Media. After a decade covering technology and venture capital at Forbes, where he pioneered coverage from the Midas List to the Cloud 100, Alex has launched his own media company focused on telling the stories of early-stage founders and companies challenging the status quo. Throughout this conversation, Alex shares insights from his front-row seat to some of tech's most defining moments, including interviews with industry leaders like Sam Altman and Mark Benioff. He discusses the evolution of media in the age of AI, his decision to bootstrap rather than raise venture funding, and his vision for building a community-first media company. Alex also reveals how his upbringing in New York City shaped his no-nonsense approach to tech reporting and why he believes the future of media lies in creating direct, authentic connections with audiences.…

Welcome back to another episode of The Room Podcast! This week, we're excited to chat with Anna Kazlauskas, Co-Founder of Vana, a pioneering company creating an alternative to centralized AI monopolies. Vana uses crypto principles like ownership, incentives, and decentralization to build AI models that users collectively own and benefit from, empowering individuals to control their data while earning from its use. In this enlightening conversation, Anna takes us through her journey from growing up in cold places around the world to her time at MIT's AI lab, and how that led to her vision for data ownership. We explore fascinating concepts like Data DAOs (which Anna compares to labor unions for your data), the emergent "DataFi" category, and how Vana enables users to pool their data to create more powerful AI models than any company could build. Anna shares invaluable insights on fundraising across both crypto and AI spaces, emphasizing the importance of aligning with investors on long-term vision. Tune in…

In this episode, we are joined by Elia Wallen, Founder and CEO of Engine (formerly Hotel Engine), the B2B travel booking platform that's streamlining how businesses manage their travel needs. From its origins as an internal tool for Elia's previous company, Travelers Haven, to becoming a $2.1 billion company, Engine has carved out a significant niche by focusing on serving SMBs with a frictionless approach to corporate travel management. In this conversation, Elia shares his unconventional path from dropping out of college to founding multiple businesses, including the fascinating story of how Engine began as a side project that he almost shut down several times. We explore his philosophy of maintaining "strong conviction loosely held," his approach to fundraising (including a nail-biting near-miss with payroll), and why staying focused on doing one thing extremely well before expanding was crucial to Engine's success. Elia also offers valuable insights on bootstrapping versus raising capital, building in a…

Welcome back to The Room Podcast! In this episode, we sit down with Matan Grinberg and Eno Reyes, co-founders of Factory, a company building the command center for software development. With backgrounds in physics and computer science, this dynamic duo is unifying all engineering contexts from GitHub to Notion, empowering product and engineering teams to collaborate with autonomous AI systems. Their impressive journey has already attracted $20 million in funding from Sequoia, Lux Capital, and Mantis Ventures, positioning them at the forefront of the AI-native movement. During our conversation, Matan and Eno share their unexpected journey from Princeton classmates who barely interacted to co-founders who launched their company just eight days after reconnecting at an AI hackathon. They dive deep into how AI is shifting the center of gravity in software development from coding to understanding and planning, the challenges of enterprise adoption, and why they believe we're currently at "the lowest number of…

This week, we're excited to speak with Tiancheng Lou, Co-Founder and CTO of Pony AI, a leading autonomous vehicle technology company that went public in November 2024. As a two-time Google Code Jam champion and former engineer at both Google X and Baidu's Autonomous Driving Division, Tiancheng brings exceptional technical expertise to his pioneering work in developing driverless technology with over 40 million kilometers of autonomous driving testing. In this episode, Tiancheng shares fascinating insights into the evolution of autonomous vehicle technology, explaining the difference between level two and level four autonomy and why highway driving is more challenging than city driving for AI. We explore Pony AI's virtual driver technology, their approach to commercialization, and how they're training AI through imitation learning and reinforcement learning in virtual environments. Tiancheng also offers valuable advice for founders on balancing technical ambition with market realities, the importance of…

In this episode, we're joined by Alexa Grabell, Co-Founder and CEO of Pocus, a company revolutionizing how sales teams work by creating AI agents that supercharge sales representatives. Pocus has developed a suite of tools that combine internal and external data to help sales teams identify opportunities, prepare for calls, and close deals more effectively, generating over half a billion dollars in pipeline for their customers in a single quarter. During our conversation, Alexa shares her journey from consulting at KPMG to Stanford Business School and eventually founding Pocus with her co-founder, Isaac, through the Lean Launchpad program. She offers valuable insights on building a sales team, navigating design partnerships, fundraising strategies for B2B startups, and the evolving landscape of AI-powered sales tools. Alexa also candidly discusses the challenges of being a female founder, the importance of finding community among peer founders, and how her mother's entrepreneurial spirit influenced her own…

Welcome back to another season of The Room Podcast! To kick off season 12, we are joined by Ryan Petersen, Founder and CEO of Flexport, the revolutionary digital freight forwarder transforming how goods move around the world. Launched in 2013, Flexport combines technology and logistics expertise to bring transparency and efficiency to the complex world of global trade, having grown to become the third-largest American company in the ocean freight industry. In this episode, Ryan takes us through his entrepreneurial journey, from his early days running an e-commerce business importing Chinese motorcycles to identifying the massive inefficiencies in international shipping that led to Flexport's creation. We dive into fascinating topics like building a company that combines tech talent with logistics veterans, navigating highly regulated international markets, and leveraging AI to transform an industry that still largely runs on email attachments. Ryan also shares valuable insights on fundraising strategies,…

In this special holiday episode of The Room Podcast, we sit down with Agatha Kluk and Sonia Farber, the co-founders of Kluk Farber Law (now part of Perkins Coie), a specialized law firm dedicated to supporting innovative founders and startups. Their firm provides strategic legal guidance to entrepreneurs navigating the complex landscape of building and scaling companies. This candid conversation explores the evolution of their practice, from its founding in 2017 to its strategic partnership with Perkins Coie. Throughout our discussion, we explore the intersection of law and entrepreneurship, highlighting how the right legal partnership can empower founders to achieve their vision. At its core, Kluk Farber Law provides comprehensive legal services tailored specifically for startups and emerging companies. Key topics in this episode include strategic guidance for company sales and earn-out negotiations, balancing tech automation with historically successful advisory services, and AI regulation and compliance…

Welcome back to another episode of The Room Podcast! This week, we’re thrilled to chat with Wade Foster, CEO and Co-Founder of Zapier, the tool that’s revolutionized workflows by making automation accessible to anyone. Zapier helps businesses and individuals connect the apps they rely on, creating seamless integrations that save time and boost productivity. In this episode, Wade takes us through Zapier’s origins, its flagship no-code-needed automation platform, and how the company has carved out a niche as the go-to solution for streamlining business processes. We also dive into fascinating topics like growing a fully remote team before it was trendy, navigating the unique challenges of bootstrapping in a venture-driven world, and the surprising lessons Wade learned while literally counting telephone poles during a college internship. Tune in for insights on building impactful products, a behind-the-scenes look at Zapier's innovative culture, and a glimpse into what it takes to lead one of today’s most…

In this LIVE version of The Room Podcast, we’re thrilled to chat with Immad Akhund, Co-Founder and CEO of Mercury, a fintech company built specifically for startups and tech companies. Immad walks us through his journey from founder to industry leader, and how Mercury is reimagining banking with streamlined financial tools for growing businesses. Mercury’s core product offers an intuitive digital banking experience, designed to handle startups' unique cash flow and management needs. Join us as we explore Immad’s early entrepreneurial journey, his strategic shift from gaming with Hayzap to founding Mercury, and the insights he gained along the way. This episode highlights Mercury’s goal to simplify banking for tech founders, Immad’s take on the importance of resilience and adaptability, and how Mercury’s modern approach is transforming financial services for the startup ecosystem.

Welcome back to The Room Podcast! Today, we’re thrilled to explore the fast-evolving world of B2B tech innovation with Shensi Ding, co-founder of Merge. Merge has become a leader in unified APIs, creating a category that addresses the challenges many companies face with complex integrations. Shensi’s journey is a unique one—from her coding days in Boston to Columbia, then a career at Silver Lake, all of which prepared her to tackle the 'SAAS sprawl' problem head-on. Together with her co-founder, Gil Feig, Shensi has built a powerhouse team and a product that’s essential for clients like Ramp and BambooHR. Their customer-first approach has secured $75 million in funding and a growing presence across SF and NYC. In this episode, we delve into topics like using customer insights to drive category creation, balancing skills in co-founder dynamics, and navigating fundraising from seed stage through metrics-driven growth.

In this episode of The Room Podcast, we sit down with Jason Lee, the founder of Salt Labs and DailyPay, to explore his journey from finance to fintech entrepreneurship. Salt Labs, Jason’s latest venture, focuses on empowering workers to maximize their earnings potential, while DailyPay revolutionized the way employees access their wages. We cover a range of topics such as the need for improvement in front-line workers' payment structures, how Jason’s years in investment banking shaped his approach to entrepreneurship, his pivotal "aha" moment that led him to create DailyPay and Salt Labs, and advice to founders looking to start fundraising.

In this episode of The Room Podcast, we sit down with Kevin McCarthy, the CEO of Unreal, a company dedicated to creating healthier alternatives to classic candy. Unreal is known for creating delicious, better-for-you snacks that ditch artificial ingredients, offering cleaner, more natural options in the world of sweets. We discuss the intersection of entrepreneurship and health-conscious innovation, bringing a refreshing approach to an industry ripe for disruption. Kevin shares his journey to becoming CEO at just 24 years old, the pivotal changes Unreal made to become a leader in the health-conscious snack market, and how leadership lessons from his political campaign days shaped his approach to business.

In this episode of The Room Podcast, we’re joined by Sami Inkinen, co-founder of Virta Health, a company transforming the treatment of type 2 diabetes. Virta Health’s mission is to not just manage, but reverse diabetes using personalized nutrition plans backed by clinical research. Sami also shares his journey from humble beginnings on a Finnish farm to co-founding the real estate platform Trulia, and ultimately, Virta Health. Key highlights include the current state and effect of GLP1 drugs in America alongside the growing prevalence of diabetes, overcoming skepticism and resistance to adopting non-traditional treatments for chronic diseases, and the intersection of technology and healthcare overall.

In this episode of The Room Podcast, we sit down with Ariel Kaye, the founder of Parachute, a brand known for elevating the home essentials industry with a focus on comfort and wellness. Ariel shares her journey from a creative upbringing to her path through advertising, where she discovered her passion for building brands, eventually leading to the founding of Parachute. Join us as we dive into how Parachute taps into the wellness movement by focusing on the importance of sleep and home comfort. We explore the company's core product—bedding— and why it resonated with consumers looking for better home essentials. Ariel also shares insights on creating a brand from scratch while disrupting a market, the importance of consumer insights and communication in building a business, and the ups and downs of running a business while raising a family.

Welcome back to a new season of The Room Podcast! To kick off Season 11, we're joined by Johnny Ho, co-founder of Perplexity, an AI-powered platform transforming the way everyday consumers interact with search. Johnny shares his path from competitive programming to entrepreneurship and offers insights into the development of Perplexity’s core product, which aims to deliver precise, reliable answers in a simple, intuitive way. In this episode, we covered topics such as how Perplexity uses AI to deliver accurate and reliable search results using multiple LLMs, building a user-first product in a competitive tech space, and the importance of finding investors who want to work with you in the right ways.

In this episode, we dive into the Future of DTC panel from this summer’s Inside Summit. This panel was moderated by our very own Claudia Laurie, who is also the founder of Prive, a leading eCommerce billing platform. In this discussion, the panelists explore the future of DTC, how to build authentic brand communities, building a celebrity brand, challenges and opportunities around customer acquisition and retention, and advice for brand founders and builders. This conversation includes an incredible mix of perspectives from leading brands, agencies, and tech partners. Our panelists included: Nik Sharma is widely known as “The DTC Guy,” a Forbes 30 Under 30 member, AdWeek’s Young & Influential, and a resource that brands and investors turn to for growth. Nik is the founder and CEO of Sharma Brands, where clients include Feastables, Jolie, Milk Bar, Everlane and more. Outside of Sharma Brands, Nik writes a newsletter to 50,000 investors, founders, and marketers and is also the co-host of Limited Supply, an…