Dialectic

Joe Gebbia (Website, X, LinkedIn, Wikipedia) is the first U.S. Chief Design Officer, leading the National Design Studio. He is also the co-founder of Airbnb and Samara. The NDS and this role were created by executive order of President Trump in August 2025. I met Joe Washington, D.C, to reflect on the past year and talk about bringing the care and ambition of great product design to the digital services that every American uses. Joe & NDS just launched America.gov, their flagship project of the last year: the central entry point for how Americans get what they need from the government. Joe believes that design is how you respect and value the people who use a product or service. At Airbnb, that meant helping strangers feel comfortable in each other’s homes. In government, it means refusing to accept a low bar for the websites and processes that Americans use to interact with the government. We begin with CritBuns, Joe’s RISD project that taught him that design is as much about storytelling as it is about product. Then, we discuss what he learned about designing for trust at Airbnb and his initial work at DOGE, streamlining and digitizing the federal retirement process. Joe walks me through America.gov, a single, AI-powered front door to government services. We discuss the challenges of scale and designing for people who are skeptical of both government and AI, including what it means to pass the “grandma test.” We wrap up with why ambitious technologists should aspire to work in government and his collaboration with Airbnb co-founders Brian Chesky and Nathan Blecharczyk. I hope this conversation raises your expectations for the things we’ve learned to tolerate, and inspires you to think about how you might serve your community or your country. Full transcript & links at dialectic.fm/joe-gebbia --- Dialectic is presented by Notion. As new models and agents arrive constantly, Notion acts as a context and consolidation layer for all the ways you and your team work with AI: a command center or simply a resilience layer, so your context comes with you even if you switch models or agents. You can also work with agents right inside Notion and share skills with your team through the Skills API. Learn more at notion.com/dialectic. --- Timestamps: 0:00 Opening Highlights 1:26 Intro: Joe Gebbia 4:12 CritBuns & Why Design is Half Story 15:24 Airbnb, The Feeling of Belonging, & Designing for Trust 28:29 Public Service & Fixing Federal Retirement 42:16 Speed, Craft, and Respect 48:43 ND Studio Projects: TrumpRx, Trump Accounts, and Realfood.gov 56:18 America.gov: A New Front Door to Government 1:05:35 Trust, Privacy, and Government AI 1:15:30 America.gov’s Roadmap 1:19:54 Recruiting for ND Studio and Public Service 1:23:41 Reflecting on Year One & Passing the Grandma Test 1:31:05 A Ticking Clock Toward 2028 & Building Beyond One Administration 1:35:44 AI & Product Development 1:38:36 Closing Questions: Charles & Ray Eames, AirBnB Co-Founders, & Trust in People

Adam Mastroianni (Website, X) is an experimental psychologist and the writer of Experimental History. He earned his PhD in psychology at Harvard before leaving academia to pursue research and writing independently. I first came across Adam through “Good conversations have lots of doorknobs,” which remains one of my favorite essays on Substack. We talk about why psychology is stuck, why science needs people willing to look stupid, and how prestige can lead you toward a life you don’t want. From there, unpack Adam’s coffee bean test for figuring out what to do, getting “de-bogged,” and what improv teaches us about better conversations (or: create doorknobs). We also discuss writing that surprises its author, his upcoming book, The Strangest Idea in the World, and the prayer he says before publishing: “Let me be useful.” I hope you leave a little more willing to question what seems obvious, risk looking stupid, and spend your time in ways you actually enjoy. Transcript & links: https://dialectic.fm/adam-mastroianni --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion AI works across your documents and context, while custom workers can automate recurring tasks and connect with your other tools. You can also explore Notion’s Knowledge Board, which evaluates how AI models perform on real knowledge-work tasks. Learn more at notion.com/dialectic. --- This episode is supported by Google. Google Antigravity is Google’s agentic development platform. Describe what you want to build, and its agents can plan the work, write and run code, and test the result, with plans and changes you can review along the way. Gemini 3.5 Transcribe turns audio into text with a choice of verbatim and Smart modes. Verbatim mode keeps fillers and false starts, and supports speaker labels and word-level timestamps to help you check the transcript against the recording. Smart mode removes filler words and repetitions and formats speech into readable text. I used Antigravity and Gemini 3.5 Transcribe to build a Mac app for producing and reviewing Dialectic transcripts. --- Timestamps: 04:33 Start: Why Psychology is Stuck & The Focus of Adam's Blog 14:43 The Scientific Virtues of Stupidity and Rebellion & Escaping the Prestige Trap 25:08 Patronage for Weirdos 33:53 Progress in Psychology 52:15 Figuring Out What to Do, The Coffee Bean Test, and Unpacking Adam's Day-to-Day 01:03:22 Getting De-bogged and Making Ideas Land 01:14:11 Conversational Doorknobs: Giving and Taking 01:22:23 Blogging, Community, and Rules we Invent 01:28:35 Writing Advice, Thick Art, Giving The Reader an Egg to Crack 01:44:03 Adam's First Book: The Strangest Idea in the World 01:53:23 Closing Questions

Immad Akhund (⁠X⁠, ⁠LinkedIn⁠) is the co-founder and CEO of ⁠Mercury⁠. He is also a prolific angel investor and co-hosts the ⁠Founders in Arms⁠ podcast. Mercury is a fintech banking platform used by one in three startups. It is Immad's fourth company in 20 years of entrepreneurship. Mercury is in the process of becoming an FDIC-insured bank and recently launched ⁠Mercury Books⁠, AI-powered accounting software. Immad grew up in Pakistan, moved to London at nine, and left for San Francisco at 23 to become an entrepreneur "for real." Mercury is built on something rare in finance: a willingness to spend a disproportionate amount of energy on details, the kind of care Immad admits "seems irrational.” We start with a simple question (what is a bank?) and discuss why banking stayed bad for so long, what stays hard as AI makes software easy to build, and why Mercury's motto is "be extremely helpful." Entrepreneurship has shaped Immad's life, and he hopes Mercury can empower a generation of entrepreneurs. I hope you come away a little more annoyed by the mediocre things we've all learned to tolerate and inspired to put an irrational amount of care into making them better. ⁠https://dialectic.fm/immad-akhund⁠ --- Dialectic is presented by ⁠Notion⁠. Notion is an AI-powered connected workspace where teams ⁠think together⁠ and create their best work. It works with all of your agents and keeps context across them and your team. ⁠Check out the new Notion Skills API⁠. You can learn more at ⁠notion.com/dialectic⁠. --- Timestamps: (0:00) Opening Highlights (1:50) Intro: Immad Akhund (4:16) Start: Banks and Why Immad Was Suited to Build One (20:30) What Traditional Banks Do Well & What Mercury Got Right (29:33) Why Mercury Wants a Bank Charter (35:57) What's Scarce When Software Is Easy (49:00) Becoming the Default for New Entrepreneurs (53:34) Product: 100 Little Things Better (1:06:51) The Right to Win (1:09:19) Brand as Care (1:15:19) Culture and Being Extremely Helpful (1:22:51) Command, Agents, and AI (1:34:26) Ambition, Investing, and Leading (1:46:54) Family, Pakistan, and America (1:52:56) Money, Freedom, and Energy (1:59:14) Outro

Independent Study is a series of bonus episodes to accompany the interviews on Dialectic. I read essays and other writing that has influenced me. "Personal Renewal" was given as a speech by John W. Gardner to a group at McKinsey & Company in Phoenix, AZ on November 10, 1990. The transcript is available at PBS here. John W. Gardner was a public servant, educator, and public reformer. Learn more at PBS. This is one of my favorite things I've ever read. I hope you are similarly inspired. Transcript and audio for the also mentioned David Foster Wallace's "This is Water" available here, from Farnam Street. https://www.pbs.org/johngardner/sections/writings_speech_1.html⁠

Miles Grimshaw (X, LinkedIn) is an investor at Thrive Capital. He’s spent most of his career there, there, partnering with founders at the early stages of company building, including Cursor, Turbopuffer, Chai Discovery, Mesh Optical, Revel, XDOF, Socket, Benchling, GitHub, and many more. Miles was also briefly an investor at Benchmark before returning to Thrive in 2024. The conversation focuses on Miles’ appetite for change and continuing to begin anew, again and again. That starts with “adventure racing” as a teenager, and continues through his career as an investor in search of world-changing companies. We talk about how Miles proactively puts himself in position to work with great founders in a style that resembles courtship, his disposition of impatient patience, and why he loves change. The latter includes the dramatic shift in his primary domain: software. As the underlying assumptions for software businesses change due to AI, what traits will great companies have? And what moats if any will persist? Is software investing over? Miles also talks through how great companies and founders go where they are looking, prioritizing customers that help you live in the future, the learned intuition of greatness, and joining the expedition squad alongside the founders Thrive partners with. Finally, we talk a bit about Thrive, his departure to and return from Benchmark, and endurance. I hope you are inspired to find an infinite game where you are excited to see the stone roll back down the hill and begin to push again. Transcript & links available at https://dialectic.fm/miles-grimshaw Disclaimer: This podcast is for informational purposes only. The views expressed are the speaker's own as of the recording date and are subject to change. Thrive funds and their affiliates have investments in certain companies discussed in this episode. References to those companies are illustrative, do not represent all investments made by Thrive, and should not be viewed as recommendations or indications of future investment performance. Past performance is not indicative of future results. --- Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Notion's custom agents are AI teammates that handle recurring work across your tools. Learn more about their new developer platform and workers here. Notion is hiring across product, storytelling, design, engineering, and more. You can learn more at notion.com/dialectic. --- Timestamps (0:00) Opening Highlights (1:37) Intro: Miles Grimshaw (4:30) Infinite Games, Adventure Racing, and Starting Anew, Over and Over (11:01) Staying Hungry: Proactive Hunting and the Turbopuffer Story (17:35) Impatiently Patient: Courtship, Cursor, Recruiting, and Joining the Team (25:33) Loving Change: London to America, the Himalayas, and Learning New Sports (31:36) The Genetics of Companies: "What Is It?" and "Who Cares?" (38:08) House Cats & Tigers: Where Is the Founder Looking? (47:00) Confidence in Uncertainty and Customers That Pull You Into the Future (54:25) What Remains for Software: Moats, Cities, Wall-Clock Time, and the Barbell of Scale & Luxury (1:04:54) Craft, Trust, and Why Software Isn't Over (1:11:13) Intuition: Gradient Descent and Seeing Greatness Up Close (1:18:07) "I Don't Know" and "I'll Figure It Out" (1:22:12) Commitments, Not Bets: Closing People and Board Work (1:29:06) Joining Thrive, Being a Punk, and Music Studios over Jury Trials (1:36:18) Leaving for Benchmark and Returning to Thrive (1:43:18) Dream Bigger: Lessons from Josh, Teaching Agency to Kids, and Going the Distance (1:51:36) Outro