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