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Tom Verrilli is the chief product officer at Whatnot, a live shopping platform that’s become the fastest-growing U.S. marketplace business in history, with over $8 billion in GMV. Before joining Whatnot, Tom was CPO at Twitch and director of product growth at Twitter (during one of the most turbulent periods in the company’s history). In our in-depth conversation, we discuss: 1. Why Whatnot’s product team was founded on the premise “we regret that product management exists” 2. How AI is reshaping the PM role 3. What Tom looks for when hiring PMs 4. The shift toward senior ICs doing the work 5. How AI has transformed data science at Whatnot 6. Tom’s “play the accordion” mental model 7. Why “hire great people and get out of their way” fails 8. His biggest lessons from his time at Twitter — Brought to you by: WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more Mercury—Radically different banking, now with Command — Episode transcript: https://www.lennysnewsletter.com/p/this-cpo-regrets-that-product-management — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Tom Verrilli: • X: https://x.com/tdrobbo • LinkedIn: https://www.linkedin.com/in/tom-robertson-042 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction (02:40) “We regret that product management exists”: what it means and why (08:30) When specialization makes sense, and when it doesn’t (15:20) How Whatnot structures its PM org (17:28) What 31,832 PM applications revealed about the function (19:40) How to develop systems thinking (22:10) The shift to senior ICs doing IC work (32:26) Advice for PMs struggling in today’s market (35:22) How AI has transformed work at Whatnot (41:14) The data scientist problem (42:48) Which roles are trending up and down (44:48) What the product team of the future looks like (46:29) Why core PM skills are the most durable in an AI world (49:23) How to get the most out of the people you hire (53:32) Navigating the CPO-founder relationship (57:34) Advice for aspiring CPO’s (59:16) How to know when to stand firm and when to step back (01:01:38) Play the accordion: balancing strategic vision with fast iteration (01:06:35) Agentic commerce vs. live commerce (01:09:46) Lessons from Twitter (01:13:07) Failure corner (01:15:45) Lightning round and final thoughts — Referenced: • Whatnot: https://www.whatnot.com • Building, and Whatnot: https://www.linkedin.com/pulse/building-whatnot-tom-verrilli-bwkdc • Twitch: https://www.twitch.tv • Why Netflix is betting on systems thinkers—not specialists—in the AI era | Elizabeth Stone (CPTO): https://www.lennysnewsletter.com/p/netflix-cpto-on-ai-and-the-future • Peter Bailis on LinkedIn: https://www.linkedin.com/in/pbailis • Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Ben Kus on LinkedIn: https://www.linkedin.com/in/benkus • Henry Shi on LinkedIn: https://www.linkedin.com/in/henrythe9th • Hex Threads: https://hex.tech/product/threads • Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty • Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine • Logan Head on LinkedIn: https://www.linkedin.com/in/logan-head • Emmett Shear on LinkedIn: https://www.linkedin.com/in/emmettshear • Kara Swisher on X: https://x.com/karaswisher • Jeff Bezos: Amazon and Blue Origin—Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY • Star City on AppleTV+: https://tv.apple.com/us/show/star-city/umc.cmc.2l8p785osmtmiyk64bh6tfde1 • For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7 • Service NSW Mobile App: https://www.service.nsw.gov.au/services/service-nsw-mobile-app • Rudyard Kipling: https://en.wikipedia.org/wiki/Rudyard_Kipling • E-fish.com: https://www.e-fish.com — Recommended books: • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/dp/0062273205 • The Purpose Driven Church: Every Church Is Big in God’s Eyes: https://www.amazon.com/dp/0310201063 • Babel: Or the Necessity of Violence: An Arcane History of the Oxford Translators’ Revolution―An Historic Fantasy of Dark Academia: https://www.amazon.com/Babel-Necessity-Violence-Translators-Revolution/dp/0063021439 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Tom Verrilli

Chief Product Officer

Whatnot

Quinn Nelson returns to the show to discuss OpenAI’s ChatGPT/Codex “native” app migration fiasco, Siri AI in Apple’s OS 27 betas, MacOS 27 Golden Gate, and the hottest new cell phone of the year, the Trump T1. Sponsored by: Notion: Try the powerful, all-in-one Notion AI today. Factor: Healthy eating, made easy. Get 50% off your first box, plus free daily greens, with code talkshow50off. Squarespace: Save 10% off your first purchase of a website or domain using code TALKSHOW. Transcripts: Unofficial but surprisingly good. Links: Quinn’s hilarious but utterly fair review of the Trump T1. Quinn: “Apple Just Fixed Mac Gaming and Said Nothing”. John Siracusa on ATP endorsing Quinn’s idea for an Apple gaming console. Valve founder/CEO Gabe Newell on working with Apple. “Stupid-Americans are the New Irish-Americans, Trump is Their JFK”, by “tarltontarlton” on Reddit (and posted here on Daring Fireball). This episode of The Talk Show was edited by Caleb Sexton.

Quinn Nelson

Founder & Creator

Snazzy LabsSnazzyLabs

Nathan Benaich is the founder of Air Street Capital and author of the State of AI report. On its eighth year, the report is a year-long effort on the biggest things happening in AI, across research, industry, politics, and safety. This episode covers the biggest takeaways from the latest report, like the rise in reasoning, the surge in China’s open source models, where AI is working in practice, the rise of sovereign AI, where he thinks value will actually accrue over the long-term, if we’re in an AI bubble, and how he’s investing in AI today at Air Street. Thanks to Nico at Adjacent and Dan at Michigan for helping brainstorm topics for Nathan. Try Numeral, the end-to-end platform for sales tax and compliance: ⁠https://www.numeral.com⁠ Sign-up for Flex Elite with code TURNER, get $1,000: https://form.typeform.com/to/Rx9rTjFz Timestamps: (3:39) State of AI 2025 (6:22) Takeaway #1: Reasoning & tool calling (13:01) Takeaway #2: Rise of Chinese open source (15:25) Open vs closed source models (26:46) Takeaway #3: AI revenue is real (27:51) Takeaway #4: Sovereign AI (36:44) Are we in an AI bubble? (59:23) Starting Air Street Capital (1:05:18) Raising Fund 1 (1:16:20) Air Street portfolio strategy (1:25:15) When and who Nathan decides to invest (1:35:04) How important are AI benchmarks? (1:39:31) When to train your own models (1:45:56) Rise of European defense tech (2:01:43) Nathan’s personal AI stack (2:07:32) Is niching down too risky? (2:16:12) Nadal vs Federer Referenced State of AI Report: https://www.stateof.ai The Thinking Game Documentary: https://www.youtube.com/watch?v=d95J8yzvjbQ V7: https://www.v7labs.com Follow NathanTwitter: https://x.com/nathanbenaichLinkedIn: https://www.linkedin.com/in/nathanbenaich Follow TurnerTwitter: https://twitter.com/TurnerNovakLinkedIn: https://www.linkedin.com/in/turnernovak Subscribe to my newsletter to get every episode + the transcript in your inbox every week: https://www.thespl.it/

Nathan Benaich

Founder

Air Street Capital

SPONSORED BY MONGODB Pete Johnson, Field CTO, Artificial Intelligence at MongoDB, joins the podcast to talk about a recent OpenAI paper on the impact that AI will have on jobs and overall GDP. Pete, who reads the papers (and datasets) so you don’t have to, says that looking at AI’s impact as a job killer is a flawed metric. Instead, he and Ryan talk about how AI will be a collaborator for actual human workers, how embeddings and vectorization will move the productivity needle, and the five decisions you need to make to realize ROI on AI. Episode notes: If you’re curious, read the OpenAI blog post and paper yourself. For those of you looking for inspiration, check out Werner Vogel’s keynote from re:Invent 2025. MongoDB provides a flexible and dynamic database that excels with AI data. Connect with Pete on LinkedIn. Congrats to Populist badge winner Scheff's Cat for dropping a banger of an answer on error: non-const static data member must be initialized out of line. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Pete Johnson

Field CTO, Artificial Intelligence

MongoDB

Mati Staniszewski, co-founder and CEO of ElevenLabs, explains how staying laser-focused on audio innovation has allowed his company to thrive despite the push into multimodality from foundation models. From a high school friendship in Poland to building one of the fastest-growing AI companies, Mati shares how ElevenLabs transformed text-to-speech with contextual understanding and emotional delivery. He discusses the company's viral moments (from Harry Potter by Balenciaga to powering Darth Vader in Fortnite), and explains how ElevenLabs is creating the infrastructure for voice agents and real-time translation that could eliminate language barriers worldwide. Hosted by: Pat Grady, Sequoia Capital Mentioned in this episode: Attention Is All You Need: The original Transformers paper Tortoise-tts: Open source text to speech model that was a starting point for ElevenLabs (which now maintains a v2) Harry Potter by Balenciaga: ElevenLabs’ first big viral moment from 2023 The first AI that can laugh: 2022 blog post backing up ElevenLab’s claim of laughter (it got better in v3) Darth Vader's voice in Fortnite: ElevenLabs used actual voice clips provided by James Earl Jones before he died Lex Fridman interviews Prime Minister Modi: ElevenLabs enabled Fridman to speak in Hindi and Modi to speak in English. Time Person of the Year 2024: ElevenLabs-powered experiment with “conversational journalism” Iconic Voices: Richard Feynman, Deepak Chopra, Maya Angelou and more available in ElevenLabs reader app SIP trunking: a method of delivering voice, video, and other unified communications over the internet using the Session Initiation Protocol (SIP) Genesys: Leading enterprise CX platform for agentic AI Hitchhiker’s Guide to the Galaxy: Comedy/science-fiction series by Douglas Adams that contains the concept of the Babel Fish instantaneous translator, cited by Mati FYI: communication and productivity app for creatives that Mati uses, founded by will.i.am Lovable: prototyping app that Mati loves

Mati Staniszewski

Co-Founder and CEO

ElevenLabs

The epic show with Adam Jacob has been remastered! Now with full-length video on YouTube. Adam goes solo with Adam Jacob for an epic pod into his journey to get to System Initiative. From SysAdmin at 8 years old, to discovering Linux and working for Mom-and-pop ISPs, to open source changing his life and starting Opscode and building Chef. Buckle up and enjoy. Join the discussion Changelog++ members save 7 minutes on this episode because they made the ads disappear. Join today! Sponsors: Depot – 10x faster builds? Yes please. Build faster. Waste less time. Accelerate Docker image builds, and GitHub Actions workflows. Easily integrate with your existing CI provider and dev workflows to save hours of build time. Auth0 – The identity infrastructure for the age of AI. Built by developers, for developers—Auth0 helps you secure users, agents, and third-party access across modern AI workflows. Token vaulting, fine-grained authorization, and standards-based auth, all in one platform. Start building at Auth0.com/ai CodeRabbit – AI-native code reviews, built for the modern dev stack. — CodeRabbit is your always-on code reviewer—flagging hallucinations, surfacing smells, and enforcing standards, all without leaving your IDE or GitHub PRs. Trusted by top teams to ship better code, faster. Start free at CodeRabbit.ai Fly.io – The home of Changelog.com — Deploy your apps close to your users — global Anycast load-balancing, zero-configuration private networking, hardware isolation, and instant WireGuard VPN connections. Push-button deployments that scale to thousands of instances. Check out the speedrun to get started in minutes. Featuring: Adam Jacob – Website, GitHub, X Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X Show Notes: System Initiative Ximian Any Given Sunday speech I’ll Devour You! (I shall look forward to the fight) RIP Ezra Zygmuntowicz Something missing or broken? PRs welcome!

Adam Jacob

Founder

System InitiativeChef