The Room Podcast

Claudia Laurie and Madison McIlwain
  • 5.0 (58)
  • TECHNOLOGY
  • UPDATED WEEKLY

Welcome to the Room. A series interviewing your favorite tech founders and funders. Our guests were in the room where it happened and they’re sharing their stories.

  1. 5D AGO

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

    In our season finale episode of The Room Podcast, we speak with Jamie Siminoff, inventor of Ring, the smart home security company best known for turning the front door into a connected safety platform. Ring builds video doorbells, cameras, alarms, and neighborhood safety tools that help people monitor and protect what matters most. Before Ring became one of the most recognizable home security brands in the world, Jamie was an inventor building things in his basement, launching companies like 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 InstagramFollow us on TikTokCheck 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

    46 min

  2. APR 28

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

    In this episode of The Room Podcast, we speak with Scott Stevenson, CEO and Co-Founder of Spellbook. Spellbook is an AI-powered platform helping lawyers draft and review contracts faster using generative AI directly within their existing workflows. Spellbook enables legal teams to accelerate contract creation and negotiation by embedding AI into workflow tools allowing for real-time drafting, editing, and comparison against market data. The company sits at the intersection of legal tech and AI 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 InstagramFollow us on TikTokCheck 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

    40 min

  3. APR 21

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

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 Instead of the outdated two-week batch system, Earnin is pioneering a streaming model for income, where 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

    30 min

  4. APR 14

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

    In this episode of The Room Podcast, we sit down with Ben Witte, Founder and CEO of Recess, a consumer wellness brand pioneering a new category of functional beverages designed to help people relax, unwind, and feel better in an increasingly high-stress world. Recess blends ingredients like magnesium, adaptogens, and other functional compounds into beautifully branded drinks that position themselves as the “Red Bull for relaxation.”  Before launching Recess, Ben built his career in early-stage 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 InstagramFollow us on TikTokCheck 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

    41 min

  5. APR 7

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

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

    50 min

  6. MAR 31

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

    In this episode of The Room Podcast, we speak with Ryan Daniels, Founder and CEO of Crosby, an AI-first law firm rethinking how legal work gets delivered. Crosby combines AI systems with human legal expertise to provide faster, more transparent, and more scalable legal services, moving away from traditional billable hours toward outcome-driven work. Crosby is part of a broader shift in professional services, where AI is not just augmenting workflows but fundamentally reshaping how services are delivered. Instead of selling tools to lawyers, Crosby operates as a full-stack legal provider, meeting customers where trust already exists 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

    45 min

  7. MAR 24

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

    In this episode of The Room Podcast, we speak with Alex Halliday, founder and CEO of AirOps, a platform helping companies build AI-powered content workflows and automate complex marketing operations. AirOps enables marketing and growth teams to orchestrate large-scale content generation using structured workflows, AI models, data integrations, and human-in-the-loop systems. The platform is part of a new category emerging in the AI ecosystem: the AI marketing stack, where companies move beyond simple prompt-based tools and instead build repeatable systems for producing high-quality content. Before founding AirOps, Alex built viral fan websites as a teenager 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

    51 min

  8. MAR 17

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

    In this season opener of The Room Podcast, we speak with Nirav Tolia, the co-founder and CEO of Nextdoor, the neighborhood network designed to connect verified neighbors and strengthen local communities. Nirav shares and refelcts the story behind building Nextdoor, one of the world’s largest hyperlocal social platforms, and reflects on the lessons he has learned scaling a product designed around real-world communities. Before founding Nextdoor, Nirav was one of the first 100 employees at Yahoo, where he witnessed the rise of the early consumer internet and the power of network effects. He later co-founded 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

    1h 10m
See All (140)

Trailer

5
out of 5
58 Ratings

About

Welcome to the Room. A series interviewing your favorite tech founders and funders. Our guests were in the room where it happened and they’re sharing their stories.

Information

  • Creator
    Claudia Laurie and Madison McIlwain
  • Years Active
    2020 - 2026
  • Episodes
    140
  • Rating
    Clean
  • Copyright
    © 2020
  • Show Website
    The Room Podcast

You Might Also Like