The Room Podcast

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1. S15E7: Building Legal AI Agents with GC AI Co-Founder and CEO Cecilia Ziniti

   3 november 2026 · 58 min

   Afspelen
   In this episode of The Room Podcast, Madison and Claudia sit down in the studio with Cecilia Ziniti, co-founder and CEO of GC AI. Cecilia shares how growing up as an immigrant, working inside Yahoo’s early trust and safety team, and serving as counsel at technology companies shaped her path from law to entrepreneurship. Cecilia explains the moment a pre-ChatGPT language model convinced her that legal work could change, and how she and co-founder Bardia set out to build a tool for in-house legal teams. She talks about finding early customers, following unexpected signals from the market, fundraising, and why legal buyers quickly saw value in a product built around their actual work. Lees meer

   The conversation turns to agents: how a legal team can delegate multistep work, why lawyers need a clear record of what an agent checked, and what AI may free them to do creatively and strategically. Cecilia also looks ahead to how legal teams could work in 2029, the questions of trust and responsibility that come with more capable agents, and the teachers in her family who shaped her approach to helping people adopt new technology.

   Learn more about Cecilia Ziniti and explore GC AI.

   (04:15) Where did Cecilia grow up, and how did it shape her worldview?
   (05:14) Did Cecilia always think she would become a founder?
   (06:34) Working at Yahoo before law school
   (07:50) What trust and safety meant in the early days of consumer technology
   (10:14) Helping the law keep pace with new technology at Cruise
   (11:46) What Amazon Alexa and autonomous vehicles taught Cecilia about AI
   (13:58) The pre-ChatGPT moment that led to GC AI
   (15:57) Meeting co-founder Bardia and deciding to build together
   (19:37) Finding early customers and following signals from the market
   (20:46) GC AI’s first investors and fundraising lessons
   (23:34) Building a legal AI product around what in-house teams need
   (26:50) What an investor called violent product-market fit
   (27:10) Staying focused when a new model launch shakes the m…

2. S15E6: Building an AI-Native HR System with Sergi Bastardas, Co-Founder and CEO of Orbio AI

   27 oktober 2026 · 49 min

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   In this episode of The Room Podcast, we speak with Sergi Bastardas, co-founder and CEO of Orbio AI, a platform using autonomous agents to coordinate the employee journey for frontline workforces. Sergi traces his path from a small town near Barcelona to joining Amazon Spain in its earliest days, and building a global supply-chain business. He shares how a family history of entrepreneurship, a curiosity about the wider world, and Amazon’s culture of operational excellence shaped the way he builds companies. Lees meer

   He explains why HR is fundamentally a system of conversations and unstructured data and why Orbio was designed as an agent-native product rather than an AI add-on. From screening and scheduling to onboarding, retention, and exit interviews, Orbio’s agents work across voice, WhatsApp, text, and Teams while keeping people in control of employment decisions.

   In this conversation, Sergi breaks down the company’s expansion across languages and markets, what incumbent HR platforms would need to rebuild to become truly agent-native, and why he believes AI will empower frontline workers rather than simply replace them. He also reflects on fundraising, building a global company from Europe, balancing marriage with constant travel, and the coach who changed how he experiences the founder journey.

   Learn more about Sergi Bastardas on LinkedIn and explore Orbio AI.

   (03:52) Where Sergi grew up and how it shaped his worldview
   (06:48) Did Sergi always think he would become a founder?
   (08:13) Joining Amazon Spain in its earliest days
   (11:18) From Amazon and supply chains to the frontline workforce problem
   (13:04) Choosing experienced co-founders for Orbio
   (15:52) What AI-native HR means—and why agents are not a bolt-on
   (19:03) A day in the life of an Orbio agent
   (26:53) Launching first in Spanish and adapting voice agents across markets
   (28:07) Orbio’s Series A and the first investors who said yes
   (30:07) Building a global company from Europe
   (33:02) AI adoption across differ…

3. S15E5: Finding Product Market Fit with Fazeshift Co-Founder & CEO Caitlin Leksana

   20 oktober 2026 · 53 min

   Afspelen
   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. Lees meer

   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…

4. S15E4: From Starlink to AI Marketing Agents with Doug Tallmadge, Co-Founder and CEO of Gradial

   13 oktober 2026 · 54 min

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   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. Lees meer

   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 th…

5. S15E3: Building the Future of Sleep with Hatch Co-Founder & CEO Ann Crady Weiss

   6 oktober 2026 · 53 min

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   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. Lees meer

   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 connect…

6. S15E2: Secure AI Agents for the Future of Work with NanoCo Co-Founder & CEO, Gavriel Cohen

   29 september 2026 · 50 min

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   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. Lees meer

   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.
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7. S15E1: Building the Infrastructure for Voice AI with Russ d'Sa, Co-Founder and CEO of LiveKit

   22 september 2026 · 1 uur 1 min

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   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. Lees meer

   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?…

8. Building an Enterprise VC Firm with Jai Das, President and Co-Founder of Sapphire Ventures | Founding the Fund 4

   4 augustus 2026 · 53 min

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   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. Lees meer

   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 p…

9. Turning Content into Competitive Advantage with Packy McCormick | Founding the Fund 3

   9 juli 2026 · 44 min

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   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. Lees meer

   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 …

10. Backing Technical Founders with Amplify Partners Founder Sunil Dhaliwal | Founding the Fund 2

    25 juni 2026 · 1 uur 9 min

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    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. Lees meer

    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 character…

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