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
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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
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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
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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
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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.
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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