The Room Podcast

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:

(05:30) Jamie’s childhood and early inventor mindset

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!

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:

Learn more about Scott on LinkedIn and explore Spellbook at https://www.spellbook.legal/

(03:13) Scott’s background growing up in Newfoundland

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!

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:

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

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!

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:

Learn more about Ben on LinkedIn and explore Recess at https://takearecess.com/

(04:59) Ben Witte’s childhood and early influences

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!

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:

Learn more about Scott on LinkedIn and explore Metronome at https://metronome.com/

(04:50) Scott’s childhood and how it shaped his worldview

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! 

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

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!

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! 

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

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

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! 

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

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

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! 

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