Dialectic

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

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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.

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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.

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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

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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.

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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.

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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.

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Timestamps

“Art is For Seeing Evil” was published by Agnes Callard for The Point Magazine on July 15, 2022. My thanks to Agnes and The Point for permission to share this audio version of her essay on Dialectic’s feed.

https://thepointmag.com/examined-life/art-is-for-seeing-evil/

Agnes Callard (UChicago, Substack, X, Wikipedia) is a professor of philosophy at The University of Chicago, focused primarily on ancient philosophy and ethics. She also writes for The Point, The New York Times, and more. I particularly enjoyed her recent conversation with Derek Thompson on her theory of the “uni-context.”

This essay was shared with me by Nan Ransohoff, (Ep. 51). I hope you enjoy it!

Dan Lilienthal (X, LinkedIn) and José Chayet (X, LinkedIn) are childhood friends and cofounders of [untitled] (X, Instagram), a platform for musicians that they describe as a sacred place for work-in-progress music. It is where a song lives between recording and streaming. [untitled] is closer to the Photos app than to a social network: a private place to store, listen to, and slowly share demos, with no feed.

Dan and José are not trained musicians, engineers, or designers, but they have built a product artists love by “method acting” their way into deep empathy. The platform has grown to 50K paying users and now allows artists to share unreleased music directly with fans. Lorde recently released XRAYS on [untitled]: 49 demos and works in progress from her album Virgin, creating a kind of museum behind the record.

We discuss music as a form of communication and a connection to the divine; why they have resisted adding a feed; product inspirations like the iPod and Snapchat; how empathy and QA underpin their product philosophy; designing for 16-year-olds and superstars; AI as an instrument; which parts of the creative process are worth sharing; what it means for software to be sacred; and building a company with your best friend.

I hope you’re inspired to consider what is sacred, share and live with the things you make, seek out music that inspires you, and stay untitled a little longer than is comfortable.

Full transcript and all links: dialectic.fm/untitled

This episode on [untitled].

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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic.

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Full transcript and all links and references: ⁠dialectic.fm/ian-rogers⁠.

Ian and I made a playlist with albums/songs mentioned here (Apple, Spotify).

Ian Rogers (X, LinkedIn) is Chief Human Agency Officer of Ledger, the Paris-based security company whose hardware wallets secure much of the world's crypto. He now focuses on how Ledger can enable us to work with AI agents while maintaining our secrets and value.

His career has spanned music, culture, brand, and "the technolog(ies) people are going to hate next." He built and ran the Beastie Boys web presence in the 90s before working on music on the internet for over a decade: file sharing Nullsoft (Gnutella and WinAmp), early streaming at Yahoo!, direct-to-fan commerce at Topspin, Beats Music, and finally Apple, as an abbreviated list. He then joined LVMH as its first Chief Digital Officer, working with Bernard Arnault and its many Maisons to bring them into the internet era. More recently, he joined Ledger to improve its product experience, including collaborating with Tony Fadell to create Ledger's flagship form factor, Ledger Stax.

Ian's roots are skateboarding and music, which formed alongside a punk rock ideology while growing up in Indiana in the 1980s. I am glad to have captured a long conversation that covers the many flavors of Ian, and the threads that have persisted through his many lives. That includes: individuality; being a participant, not a spectator; what makes a scene; building brands; trying to help Kanye; and why new culture is always being made—it's just that you have to find the 1% that's awesome. Also: ushering forward and translating frontier technologies; being pushed by Jimmy Iovine; why security matters in the AI era; why AIs aren't people; what he wants to automate; learning to fail; advice on relationships across work, parenting, and love; and a whole lot of love for music—from his 2026 pick Twisted Teens to his desert island albums to tea with Paul McCartney.

I hope you're inspired to participate in the world and make great things. Thanks to our friends at Ledger for hosting me.

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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic.

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Zhengdong Wang (Website, X, LinkedIn) is an AI researcher based in London.

He writes annual letters (inspired by Dan Wang), mainly about AI progress, and his 2025 letter blew me away and inspired me to meet him. In it, he describes his ‘compute theory of everything,’ and makes the case that it would be stranger if AI progress slowed down than if it continued. Put a different way, reading his letter helped me get closer to truly feeling the wave of AI progress.

It took Zhengdong a long time to become “AGI-pilled,” despite years of feeling like he was late to AI and working as a research engineer for the last five. I talked to him about what it will take for the rest of us to see what he sees, and feel what he feels. We also discuss why AGI may be a hazier target than simply seeing AI progress as “the model does the eval,” and why recursive self-improvement may be both happening and less fantastical than it may seem. ZD makes the case that based on the rate of progress and scaling, skeptics will simply be proven right or wrong soon. We talk a bit through what narrative and political challenges the AI industry faces ahead of this transition.

Then there are the implications of all of this—namely how AI progress accelerates the question of what we each value, how we will spend our time, and where we will find or create meaning. ZD takes a stab at some of those impossible questions and shares some other favorite miscellanea that is reflective of the range of his letters.

I hope this conversation helps you feel the wave a bit yourself, and that you remember that, regardless of how much change lies ahead, we still get to make our meaning. We get to choose.

Full transcript and all links: dialectic.fm/zhengdong

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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. You can learn more at notion.com/dialectic.

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Full transcript and all links: ⁠dialectic.fm/jack-conte⁠

Jack Conte (Patreon, YouTube, YouTube Pt2, X, LinkedIn) is the co-founder and CEO of Patreon. He is also a lifelong artist and musician, who at his peak released 100 music videos per year between his bands Pomplamoose (a duo with wife Nataly Dawn) and Scary Pockets (a funk collective), and was a longtime YouTuber.

Jack is not a tech CEO who happens to like music. He is an obsessive, prolific artist whose first conventional job is running Patreon. This has shaped him as a founder and executive, and his mission at Patreon is to build an enduring and truly creator-first company that empowers creators to earn a living from their work.

We began with how he manages to do it all, where his energy comes from, and what it’s like to be “post-chaos.” Then, we talked about art, content, and commerce, Patreon’s model (that isn’t actually pure patronage), and why Silicon Valley undervalues art, brand, and narrative — and Patreon. Jack shared the benefits of a business model that is fully aligned with creators, why he hates the word influencer, and why he’s still the right man for the job after 13 years of leading Patreon. We also covered what great leadership looks like, building fans and community, filmmaking, authenticity (from Charlie Kaufman to Prince), and remembering to take risks until the very end.

I hope you’re inspired to make things you are proud of and to draw the next page even when you have no business doing so.

While I have you: I’d strongly recommend Jack’s recent SXSW talk on AI, creativity, and change.

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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion's new developer platform and workers here. You can learn more at notion.com/dialectic.

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Nan Ransohoff (X, Substack, Website) is Head of Public Goods and former Head of Climate at Stripe. This includes Frontier (which she co-founded): an advance market commitment that accelerates carbon removal by guaranteeing demand for it before it exists. They also recently launched Intercept Fund, a new effort to end respiratory infections, led by Nan and Charlie Petty.

Nan has written extensively about Stripe’s efforts and philanthropy broadly, including her call for general managers for the world’s pressing problems, and on what she calls the third wave of American philanthropy.

We talk about what a "Nan" is and why we need GM’s: ambitious founder-like people who obsess over an outcome and work backwards from it, wearing whatever hat the problem requires. We discuss taste in big problems, slicing them up and making them tractable, and why vision is in short supply. We also discuss the coming wave of new philanthropic dollars (est. ~$40B/year), primarily driven by The OpenAI Foundation, Anthropic Founders, and Anthropic employee matching, and how the ecosystem will need to mature to effectively deploy this much capital. Nan also reflects on her unlikely turn toward philanthropy and what it felt like to get off the ladder of a specific kind of ambition. We wrap up with a range of miscellanea and some fun debates. I hope you are inspired to notice problems you can’t ignore, be optimistic and specific about the world you hope for, and choose an (unlikely) path that you are proud of.

Transcript and all links: https://dialectic.fm/nan

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Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Watch here for more on Notion's new developer platform and workers. You can learn more at notion.com/dialectic.

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