The Room Podcast

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 messy data across ERPs, banks, inboxes, and industry-specific systems; how Fazeshift combines AI agents, browser workflows, and hands-on deployments; and why enterprise buyers want solutions to concrete problems rather than abstract AI capabilities. Learn more about Caitlin Leksana on LinkedIn and explore Fazeshift . (04:12) Where did Caitlin grow up, and how did it shape her worldview? (05:14) Did Caitlin always think she would become a founder? (07:01) Meeting her co-founder at Harvard Business School (09:00) Starting their first company and realizing it was time to pivot (11:17) How founders know when to stop pushing and change direction (12:40) Customer discovery and finding the accounts receivable problem (16:19) Building the MVP and joining Y Combinator (18:52) Finding Fazeshift’s first investors and navigating fundraising (21:50) Hiring mistakes and lessons from building after the pivot (24:10) How the Y Combinator community supported Fazeshift (29:43) Is Fazeshift a vertical AI company? (30:36) Selling the solution versus selling the AI (31:52) Why accounts receivable needed AI instead of traditional software (34:39) Who buys Fazeshift, and who uses it day to day? (36:54) Fazeshift’s product modules, pricing, and customer experience (39:16) Connecting data across ERPs, banks, inboxes, and customer systems (41:27) How Fazeshift deploys agents into messy enterprise workflows (43:50) Letting customer problems shape the product roadmap (45:07) Rebuilding browser agents as the technology improves (46:08) Partnerships with accounting firms, private equity, and industry software (48:38) How Caitlin’s role is changing as Fazeshift grows (49:47) A woman who has had a profound impact on Caitlin’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 Podcasts! Brought to you by: Rippling , Gradial , and Perkins Coie WX Productions

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 plan their budgets without worrying about tokens. He also reflects on fundraising setbacks, managing the emotional swings of building a company, and the professor who backed an unconventional student project that helped launch his career. Learn more about Doug Tallmadge on LinkedIn and explore Gradial . (04:13) Where did Doug grow up, and how did it shape his worldview? (04:50) Did Doug always think he would become a founder? (05:40) Studying physics at Dartmouth and choosing SpaceX over finance (08:31) Building Starlink through existential engineering and business challenges (11:39) Discovering product-market fit versus engineering a product people already want (13:18) The moment Doug decided to start Gradial (14:39) Why enterprise work runs on tickets—and why Gradial focused on marketing (16:49) What goes into a marketing campaign, from brief to distribution (20:22) Starting a company with longtime friends and roommates (22:53) Narrowing the product after the first weeks of disillusionment (24:18) Gradial’s first investor and lessons from early fundraising (29:41) Managing the emotional swings of the founder journey (31:53) When the original plan failed and it was time to focus on marketing (34:19) How Gradial’s agent architecture evolved alongside the models (38:02) Better models and the future of long-duration marketing work (41:23) Enterprise security, procurement, and integration with existing systems (42:37) Helping marketers spend more time on creative work (43:36) Pricing AI agents and making marketing budgets predictable (48:15) What’s next for Gradial (49:36) What’s next for Doug outside the company (49:58) A woman who has had a profound impact on Doug’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: Rippling , Gradial , Ashurst Perkins Coie WX Productions

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 real unit economics. Ann shares what she has learned as both a founder and venture partner, why timing and luck matter more than entrepreneurs often admit, and why Hatch emphasizes better sleep habits, phone-free routines, and contactless tracking rather than scores or constant monitoring—even as AI changes how products are built. Learn more about Ann Crady Weiss on LinkedIn and check out Hatch on their website. (04:13) Ann’s Silicon Valley childhood and family connection to Intel (05:05) How Ann’s uncle joined the early Intel team (05:35) Did Ann always think she would become a founder? (06:54) How law, Wilson Sonsini, and Yahoo shaped Ann’s early career (08:59) The acquisition of Ann’s first startup and the path to Hatch (10:45) The personal need and original product behind Hatch (12:47) Why Hatch expanded from baby products into the adult sleep market (14:53) How founders can pursue a large opportunity without losing focus (16:22) Building emotional connection through product and brand design (18:14) What founders should understand about hardware iteration (19:30) The Hatch Sleep Clock and a different approach to sleep tracking (22:47) Pitching on Shark Tank and partnering with Chris Sacca (26:03) True Ventures and the first investors to believe in Hatch (29:27) Setbacks, Costco, and lessons from expanding too early (32:09) Building a sustainable business with real unit economics (34:05) Hatch+ content and the case for phone-free sleep (37:37) Building customer trust and protecting bedroom privacy (39:29) How Hatch differs from wearables and other sleep trackers (41:05) What Ann has learned as a founder and venture partner (44:24) The future of sleep technology in the age of AI (46:47) Building products that make people feel calmer, not monitored (48:17) What’s next for Hatch (49:33) A woman who profoundly shaped Ann’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: Rippling , Gradial , Ashurst Perkins Coie WX Productions

In this episode of season 15 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 teams of agents, rather than simply replacing people with AI. Learn more about Gavriel Cohen on LinkedIn and explore NanoCo . (04:08) Gavriel’s childhood and how it shaped his worldview (05:33) Did Gavriel always think he would become a founder? (06:40) Moving from New York to Israel and studying at Tel Aviv University (08:08) The aha moment behind NanoClaw and Gavriel’s entry into AI agents (12:52) Why the AI agent market was getting security wrong (15:32) What is a “Claw” and how do AI agents fit into everyday work? (20:03) The most surprising ways people are using NanoClaw (23:50) Raising $12 million and finding NanoCo’s first investors (37:34) Why Gavriel turned down acquisition interest and kept building independently (40:18) NanoClaw’s architecture decisions and what still isn’t ready for primetime (45:13) A woman who has had a profound impact on Gavriel’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: Rippling , Gradial , Ashurst Perkins Coie WX Productions

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 success and his values. Learn more about Russ on LinkedIn and explore LiveKit . (03:54) Where did Russ grow up, and how did it shape him? (06:42) Did Russ always expect to become a founder? (07:30) What screen did Russ watch the documentary on? (09:09) Has Russ read *Tomorrow, and Tomorrow, and Tomorrow*? (09:17) What was Russ’s first Y Combinator company? (09:24) Was Russ's company a gaming company? (11:13) What year did Russ start that company? (11:40) Did Russ join Twitter after his first startup? (11:51) How did Russ make the transition to 23andMe? (13:22) How did 23andMe eventually lead Russ to Twitter? (16:51) Was Russ's Twitter role in software or content? (22:45) What was the original idea behind LiveKit? (30:17) Did LiveKit finally arrive at the right time? (30:37) Who was LiveKit’s first investor? (35:35) What has gone differently than planned while scaling LiveKit? (37:34) Where does LiveKit fit between AI models and the software built around them? (43:07) What makes building voice agents different from building text agents? (47:51) What still prevents AI voice conversations from feeling fully natural? (52:08) What is Russ excited about on LiveKit’s roadmap, and what can he share? (55:43) Which woman has had a profound impact on Russ'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: Rippling , Gradial , Ashurst Perkins Coie WX Productions

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. Learn more about Jai on LinkedIn - https://www.linkedin.com/in/jaidas Explore Sapphire Ventures on their website - https://sapphireventures.com/ (05:38) Jai's upbringing in India and journey to Silicon Valley (08:20) Did Jai always think he would become a founder (09:37) What was it like being an engineer at Oracle in the 1990s? (11:51) Did Oracle miss its opportunity in cloud computing? (13:10) Jai’s startup journey after Oracle and the path to SAP Ventures (17:53) How did Jai’s first venture investing experience shape your career? (18:50) What was early corporate venture capital like at Intel and SAP? (20:57) How should founders think about taking money from corporate VCs? (23:33) How did SAP Ventures become Sapphire Ventures? (25:06) How did Sapphire differentiate itself in a crowded VC market? (28:19) When did Sapphire experience its biggest growing pains? (32:40) Who was Sapphire Ventures' first LP? (34:18) Why did Sapphire build a fund-of-funds strategy? (35:59) What was the first portfolio company that believed in Sapphire? (37:37) Why has the developer become such an important buyer? (39:58) How has AI changed who the modern "developer" really is? (41:50) How does the rise of AI agents influence your investment thesis? (44:42) How does venture capital stay relevant in the age of AI? (48:11) What is Jai most excited about right now? (49:37) Who is a woman that has had a profound impact on Jai’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! WX Productions

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 everyone else, and how developing a unique perspective can create opportunities that traditional venture firms often overlook. Learn more about Packy on LinkedIn: https://www.linkedin.com/in/packymccormick/ Explore Not Boring at https://www.notboring.co/ (04:11) Packy's upbringing and entrepreneurial family (05:01) Did Packy always think he would become a founder? (05:50) Early career in finance and startups (09:16) Starting Not Boring during the pandemic (12:48) The first article that proved Not Boring was working (14:04) Growing the newsletter and launching Not Boring Capital (15:57) The thesis behind Not Boring Capital (17:23) The first investor to back Not Boring Capital (17:48) What Packy looks for in exceptional founders (21:57) Building a venture firm around a personal platform (23:56) The future of venture capital (26:36) How storytelling creates an investing advantage (28:45) Investing in complex businesses (31:08) An investment that didn't go as planned (33:19) How AI is changing writing and investing (35:23) Advice for building an audience today (37:05) What's next for Not Boring (38:20) A woman who had a profound impact on Packy'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! WX Productions

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 pattern matching, how technological shifts create entirely new categories of entrepreneurs, and the importance of staying early to transformational markets even when the timing isn't immediately obvious. Learn more about Sunil on LinkedIn: https://www.linkedin.com/in/sunilnagaraj/ Explore Amplify Partners at https://www.amplifypartners.com/ . (05:52) Sunil's childhood and growing up in Rochester, New York (08:09) Did Sunil always think he would become a founder? (09:22) Transferring from Rochester to Georgetown (11:39) The story behind Sunil's transfer from Rochester to Georgetown (11:55) Discovering venture capital after college (15:10) Lessons from investing through the dot-com boom and bust (16:58) The insight behind founding Amplify Partners (20:27) The first investor who backed Amplify (23:13) Starting a venture fund then versus today (27:09) Bringing Mike Dauber on as a partner (29:43) How Amplify evaluates technical founders (32:47) The characteristics of exceptional founders (36:00) Why founder-market fit matters more than pattern matching (38:46) A portfolio company that changed Sunil's perspective (41:25) Why infrastructure investing requires patience (44:38) How AI is changing venture investing (48:58) Areas of AI Sunil is most excited about (52:17) Advice for aspiring venture capitalists (55:04) Advice for founders raising their first round (57:56) A moment when Sunil's conviction was tested (01:00:47) What keeps Sunil motivated after nearly three decades in venture (01:03:07) Someone who had a profound impact on Sunil'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! WX Productions

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 fund managers. Learn more about Ben on LinkedIn - https://www.linkedin.com/in/benjaminling And Bling Capital on their website - https://blingcap.com (06:12) Ben Ling's upbringing between Taiwan and the United States (07:03) Did Ben always know he wanted to become a founder? (07:51) Lessons from Google, Facebook, and YouTube on scaling products (10:45) Why Ben started angel investing (12:30) What is the modern equivalent of being the "platform insider"? (13:35) Why Ben joined Khosla Ventures (16:24) Angel investing versus institutional venture capital (18:25) Developing conviction as an investor writing larger checks (22:42) Lessons learned from working with Vinod Khosla (25:21) Why Ben started Bling Capital (28:10) Building a founder-first venture firm (30:51) The first founder and LP who backed Bling Capital (33:24) Maintaining investment conviction through market cycles (34:32) Building the team at Bling Capital (36:00) What Ben looks for when hiring investors (38:07) How Bling Capital has evolved over time (40:25) What makes investor-founder relationships durable (45:37) Advice for aspiring fund managers (47:00) What Ben is excited about next (47:24) A woman who had a profound impact on Ben'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! WX Productions

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 mission-driven company after his wife said the prototype made her feel safer at home. We also discuss: • Why timing matters when building hardware • The brutal reality of venture dilution and capital-heavy businesses • Going from $70 million in debt to a billion-dollar Amazon acquisition • Why AI needs hardware “appendages” to impact the real world • How Ring thinks about privacy, surveillance concerns, and community safety • Why founders should look for the “infinite truth” behind what they are building (05:30) Jamie’s childhood and early inventor mindset (06:18) Whether Jamie always saw himself becoming a founder (06:57) Building PhoneTag and learning from voicemail-to-text (07:52) The idea behind Unsubscribe.com (08:56) Realizing Ring was more than a personal annoyance (11:30) The product unlock that made Ring innovative (13:34) Surprising customer use cases that shaped Ring’s roadmap (14:41) When Ring launched and how social video was emerging (16:12) The first investor who believed in Ring (17:19) Turning down Kevin O’Leary on Shark Tank (18:35) Going from $70M in debt to the Amazon deal (21:16) Advice for founders raising venture capital (24:27) How AI is changing the future of hardware (25:45) Expanding Ring beyond the original doorbell product (28:56) Ring’s role in the broader neighborhood safety ecosystem (31:28) Why Jamie decided to write Ding Dong (33:26) Why Amazon was the right next chapter for Ring (35:21) Leaving Amazon, building Door.com, and returning to Ring (37:20) Balancing AI innovation with privacy concerns (42:14) A woman who had a profound impact on Jamie’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 Rippling and Perkins Coie . WX Productions

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 their workflow. We also discuss: • Growing up in Newfoundland and developing an outsider’s perspective on innovation • The philosophical lens of “competitive truth-seeking” in startups and investing • Why early product iterations failed despite traction and how the team stayed disciplined on product-market fit • The generative AI breakthrough moment inspired by GitHub Copilot • Why most vertical AI companies overcomplicate their tech stack and how leveraging foundation models creates leverage Learn more about Scott on LinkedIn and explore Spellbook at https://www.spellbook.legal/ (03:13) Scott’s background growing up in Newfoundland (05:13) Did Scott always see himself becoming a founder? (05:58) Scott’s philosophy background and metaphysical idealism (12:13) How music and creativity led to Scott’s first company (14:33) Why Scott chose to build in legal tech (16:13) How Scott navigated early product-market fit struggles (18:23) The pivot moment into generative AI (22:33) Who was Scott’s first investor? (24:43) What drove the early growth and waitlist explosion (27:43) How Spellbook thinks about its tech stack and AI strategy (30:43) What’s next for Spellbook (34:03) A woman who had a profound impact on Scott’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 Rippling and Perkins Coie . WX Productions

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: payroll is fundamentally a broken digital product, and like all digital systems, it should evolve from batch processing to real-time streaming. We also discuss: • Why payroll has remained one of the last “batch-based” systems in a real-time world • The infrastructure behind streaming wages second-by-second • Lessons from navigating COVID when usage dropped 60% almost overnight • How Earnin used capital to forgive millions in consumer debt • Why giving employees control over pay improves income, attendance, and financial outcomes Learn more about Ram on LinkedIn and explore Earnin at https://www.earnin.com/ (04:55) Ram’s childhood and early experiences growing up in India (06:40) Whether Ram always saw himself becoming a founder (08:12) The fintech landscape when Earnin was first being built (09:58) Why payroll has remained a batch-based system (11:12) The transition from RushCard to launching Earnin (12:42) The infrastructure behind real-time and streaming payroll (15:57) The first investor who backed Earnin (16:43) A defining moment when things did not go as planned (17:49) The decision to buy and forgive user debt (19:04) How Earnin thinks about equity vs. debt financing (20:01) How AI is changing how Earnin builds and ships products (21:05) How consumer fintech is evolving alongside AI (22:17) How Earnin helps employers better support employees (24:19) How government and regulation are catching up to earned wage access (25:51) A woman who had a profound impact on Ram’s 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 Rippling and Perkins Coie . WX Productions

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 major challenges like regulatory uncertainty and COVID-driven disruption. Ben also unpacks his philosophy on category creation, why great brands market outcomes instead of ingredients, and how founders should think about fundraising, timing, and long-term vision when building enduring companies. We also discuss: • How Recess validated product-market fit through user behavior • Building a brand-first flywheel using digital and DTC channels • Navigating the CBD regulatory crisis and COVID simultaneously • Fundraising strategy in capital-intensive categories like beverages • The long-term evolution of alcohol moderation and non-alcoholic drinks Learn more about Ben on LinkedIn and explore Recess at https://takearecess.com/ (04:59) Ben Witte’s childhood and early influences (05:24) Whether Ben always saw himself becoming a founder (06:15) Early career and entry into startups through AdRoll (08:36) The aha moment behind starting Recess (11:16) Choosing adaptogens and betting on the relaxation trend (13:54) Early signs of product-market fit for Recess (15:57) Building the initial marketing flywheel and go-to-market strategy (18:04) The first investors who backed Recess (18:43) Fundraising strategy in a modern CPG environment (20:30) A major challenge and unexpected twist in building Recess (23:59) Scaling operations and evolving the supply chain (34:15) Ben’s favorite Recess products and flavors (34:28) What’s next for Recess and Ben personally (34:45) Perspective on alcohol moderation and consumer behavior trends (35:51) A woman who had a profound impact on Ben’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 Rippling and Perkins Coie . WX Productions

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 deeply informed how he approached building billing infrastructure from the ground up. In this conversation, Scott shares the core insight behind Metronome: pricing is one of the most important yet underbuilt parts of software, and usage-based billing unlocks a more accurate reflection of customer value. He also reflects on early founder lessons, recognizing product-market fit, and why solving “unsexy” problems can lead to the biggest opportunities. We also discuss: • Lessons from building and shutting down his first startup, Foundry • Scaling monetization systems inside Dropbox during hypergrowth • Why usage-based pricing is more aligned with long-term customer value • Early signals of product-market fit and how to recognize them • Building trust and reliability in core infrastructure products • Navigating the acquisition of Metronome by Stripe Learn more about Scott on LinkedIn and explore Metronome at https://metronome.com/ (04:50) Scott’s childhood and how it shaped his worldview (06:11) Did Scott always think he would become a founder? (07:15) The founding of Foundry and lessons from his first startup (09:29) Lessons from scaling monetization at Dropbox (12:37) The core insight behind Metronome and usage-based billing (15:43) Surprising ways customers used Metronome early on (18:55) The first customer that signaled product-market fit (21:27) The first investor who backed Metronome (23:48) A time during the founder journey when things didn’t go as planned (30:32) Building trust and reliability in billing infrastructure (41:15) Navigating the Stripe acquisition and transition (43:26) What Scott is most excited about for the future of usage-based billing (44:49) A woman who had a profound impact on Scott’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 Rippling and Perkins Coie . WX Productions

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 outcomes. We also discuss: • Why selling tools to lawyers wasn’t enough and the importance of building a full-stack service • The broken incentives behind billable hours and how Crosby rethinks pricing • How trust plays a central role in legal services and in adopting new technology • The concept of “taste” in AI and maintaining high-quality outputs in critical workflows • The future role of lawyers as AI handles more of the repetitive work • Lessons from early customer behavior and product iteration • The mindset required to build in a rapidly evolving AI landscape This episode explores how AI is transforming professional services and why the next generation of legal companies will be built around integrated systems, speed, and aligned incentives rather than legacy workflows. Learn more about Ryan on LinkedIn and Crosby at their company website . (04:14) Crosby’s exciting news! (06:31) Ryan’s childhood and how it shaped his worldview (07:22) Growing up in a legal household (08:47) Whether Ryan always saw himself becoming a founder (10:02) Early career decisions from law into startups (11:51) The moment Ryan decided to build Crosby full time (12:00) The insight that selling tools to lawyers wasn’t enough (14:53) Rethinking legal pricing beyond billable hours (17:35) Early customer behavior and unexpected product usage (22:11) Dividing responsibilities with his co-founder (22:35) How Ryan’s legal background informs product development (26:33) The first investor who backed Crosby (32:43) Maintaining high taste in AI-driven legal work (34:46) Pareto efficiency in AI-powered legal negotiations (41:06) Personal growth as a founder and CEO (42:11) A woman who had a profound impact on Ryan’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 Rippling and Perkins Coie . WX Productions

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 conversation, Alex shares the core insight behind AirOps: great AI-generated content requires content engineering, meaning multi-step workflows that combine models, structured data, and human review rather than relying on a single prompt. We also discuss: • Alex’s early experience building viral websites and the origin of SocialGo • Lessons from becoming one of the youngest public-company CEOs in the UK • The importance of learning velocity as a competitive advantage for startups • Why the gap between AI-generated text and publishable content is larger than most teams realize • The concept of content engineering and why structured AI workflows matter • How AirOps discovered its initial product-market fit with marketing teams • Advice for founders raising venture capital in the AI startup environment • Why early-stage startups should focus obsessively on a narrow user segment • The emotional discipline required to navigate the founder journey This episode explores how AI is reshaping marketing infrastructure and why the next generation of software companies will be built around AI workflows, automation, and operational systems, not just models. Learn more about Alex Halliday on Linkedin and AirOps at https://www.airops.com/ (05:03) Introduction and overview of AirOps (05:13) Alex Halliday’s childhood and early internet projects (05:54) Did Alex always think he would become a founder? (06:54) The viral fan website projects that led to SocialGo (08:09) Becoming the youngest CEO of a publicly traded company in the UK (10:15) Transitioning from SocialGo to product leadership and founding AirOps (13:36) Lessons learned operating inside hypergrowth companies (14:52) The original insight behind AirOps and the pivot to AI content workflows (18:36) What “content engineering” means and why AI content requires multi-step workflows (21:13) Interesting and unexpected use cases customers are building with AirOps (23:00) The first investor who backed AirOps (25:05) Fundraising advice for founders raising capital in the AI era (28:51) A founder moment where things did not go as planned (31:57) How to compete with other SEO platforms (40:14) How AirOps thinks about integrations and building an AI agent ecosystem (44:28) What’s next for AirOps (46:00) Personal growth as a founder and CEO, of their fourth company (47:20) A woman who had a profound impact on Alex’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 Rippling and Perkins Coie. WX Productions

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 Round Zero, an early startup studio that helped shape his thinking about entrepreneurship and product development. In this conversation, Nirav discusses: • Growing up in Odessa, Texas, as the child of Indian immigrant physicians, and how those experiences shaped his understanding of belonging and community • Why he never planned to become a founder and how failure at Stanford University helped him find his strengths • The early days of Yahoo and how the dot-com era influenced his entrepreneurial path • The founding story behind Nextdoor and the challenge of building a platform designed for neighborhoods rather than global networks • How founders can identify product-market fit, including his framework of building a “painkiller vs. vitamin” product • The responsibility technology companies have when platforms surface bias, trust, and safety challenges • Why Nextdoor prioritizes quality of interactions over pure scale and engagement metrics • How Nirav thinks about the role of artificial intelligence in local communities, and why he believes AI should act as an advisor rather than a driver Learn more about Nirav Tolia on LinkedIn and explore Nextdoor at nextdoor.com . (03:51) Growing up in Odessa, Texas, and how early experiences shaped Nirav’s worldview (07:31) Why Nirav never planned to become a startup founder (09:51) Transitioning from pre-med to an English major at Stanford (12:41) Lessons from failure and discovering personal strengths (15:51) Joining Yahoo as one of its earliest employees during the dot-com era (18:01) How the early internet shaped Nirav’s view of network effects (20:51) Why Nirav left Yahoo at its peak to pursue entrepreneurship (22:21) The story behind Round Zero and how it prepared him to build companies (22:51) The founding story of Nextdoor and the opportunity in hyperlocal networks (25:21) How founders know when to pivot versus persevere (29:51) Identifying product-market fit and early signals of traction (34:25) The “painkiller vs. vitamin” framework for product strategy (36:25) Trust, safety, and moderation challenges in community platforms (37:55) Lessons from addressing racial profiling and bias on Nextdoor (40:25) How technology can help people become better neighbors (48:55) Why Nextdoor prioritizes quality interactions over traditional network effects (49:55) Nirav’s perspective on artificial intelligence and community platforms (1:00:25) A woman who had a profound impact on Nirav’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 Rippling and Perkins Coie . WX Productions

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 challenges of hiring the right early team, navigating retailer relationships without becoming an ads business, and what the future of shopping looks like when your stylist lives in your pocket. Tune in for a masterclass on consumer AI, founder resilience, and why being early — twice — doesn’t make it easier the third time around. (00:00) Introduction (05:20) Where did Julie grow up and how did it shape her view of the world? (06:31) Did Julie always think she would become a founder? (07:42) How did Julie’s early career in retail and e-commerce shape what she’s building today? (09:59) How did Julie’s philosophy evolve from Stitch Fix to The Yes to Daydream? (11:54) Why did Julie decide to become a founder again after selling The Yes to Pinterest? (14:54) How does Daydream avoid getting squeezed between retailers and consumers? (17:58) Who is Daydream’s core customer and why did Julie choose them first? (18:45) Who was the first investor to say yes to Daydream? (19:39) What unexpected challenges did Julie face early at Daydream? (21:41) How is AI changing Daydream’s business model decisions? (22:26) Should retailers rethink site architecture in an AI-driven search world? (23:14) How can companies make products more discoverable in an LLM-first future? (23:33) Does better AI indexing by retailers threaten Daydream’s value? (25:48) How does Daydream think about LLM interoperability and model choice? (26:44) How should retailers think about cloud providers in modern e-commerce stacks? (27:57) Does Julie consider Daydream an AI-native company? (29:23) What does the future of online retail look like? (31:39) What advice does Julie have for new founders? (33:44) Who is a woman in Julie's life that has had a profound impact on her and her 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

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 clarity of vision, taste, and long-term impact. (00:00) Introduction (04:28) Who are the panelists and what is each of them building or focused on today? (06:39) How does Noah define ethical AI, and where do the real risks show up in practice? (08:02) How should early-stage AI companies think about trust, safety, and responsibility? (11:26) What advice would the panel give founders trying to scale AI products from one to one hundred? (12:21) How do founders balance intuition, taste, and formal evals when improving AI products? (13:32) Why is long-term founder conviction more important than early AI traction? (14:33) How should founders think about AI as a medium rather than just a technology? (17:42) Which industries remain underexplored for AI, despite the current hype cycle? (20:25) Which customer segments surprised Gamma as adoption scaled beyond early users? (23:30) What unexpected user behaviors emerged during the early days of social media and AI? (27:00) What specific product, feature, or workflow is each panelist most excited about building right now? 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

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, 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 raising, scaling, or fielding interest from potential acquirers, this episode offers clear, actionable insights for building toward a successful transaction. (00:00) Introduction (06:05) What has each panelist’s experience been with M&A? (08:51) How is M&A shifting in 2025 from the investor side? (10:56) What is driving more companies towards M&A? (12:25) What are some of the most common structural shifts in deals today versus the past? (14:49) When does a founder know acquisition is the right path? (17:41) What is something that most founders don’t think of when it comes to being acquired? (21:28) How does a founding team build relationships with investors? (23:28) What red flags should a buyer or seller be looking for during negotiations? (28:27) How do you manage a team that's working and building that might not know that an acquisition is happening? (29:48) What do buyers wish founders did more of to set themselves up for a successful transaction? (32:36) How should founders approach the conversation of acquisition with their investors? 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