23: Tamara Winter - Tacit Trust & Caring Curiosity
Dialectic28 Heinä 2025

23: Tamara Winter - Tacit Trust & Caring Curiosity

Tamara Winter (X) is the Commissioning Editor of Stripe Press, where she exercises her taste to identify the knowledge and "ideas for progress" that matter most in alignment with Stripe's mission: to increase the GDP of the internet. "Tammy" worked at the Charter Cities Institute and the Mercatus Center at George Mason University, which is chaired by Tyler Cowen. Tammy is obsessed with tacit knowledge and the illegible parts of the world that actually support so much of our lives, work, and societies. This includes taste, charisma, relationships, and a wide-range of load-bearing infrastructure that supports healthy and trustful societies, from small-talk and manners to hidden forces that prevent anti-social behavior and maintain safe places to live and work. We discuss this and more, including how she selects the ideas worthy of Stripe's audience, her unique career path, her refreshing take on agency, her standards for herself, reading and writing, and how she chooses how to spend her time. Above all, Tammy's incredible love of other people shines throughout the conversation. Full episode transcript with all linked references: https://dialectic.fm/tamara-winter Timestamps 2:09: Taste, absorbtion, and influences 10:54: Deploying your taste 15:49: Ideas that matter and taking yourself seriously 22:13: Aesthetics 24:16: Choosing Teachers and Authors 28:15: Charisma & delightfullness privilege 34:59: Living a relational life 44:07: Trust, social scaffolding, and small talk 51:01: Erosion of social norms, low-trust environments, and load-bearing infrastructure 1:02:17: Cultural arson and the dark sides of "you can just do things" 1:15:44: The healthy kind of agency 1:20:45: Tammy's N-of-1 path and who she aspires to rhyme with 1:28:38: Red herrings of success and focusing on outcomes 1:32:22: Assortive everything 1:37:52: Personal and professional standards 1:43:06: Journaling, great writing, and audience 1:57:29: Reading & Biographies Key Links: The Art of Doing Science and Engineering - Richard Hamming On Self-Respect - Joan Didion Scaling People - Claire Hughes Johnson High Growth Handbook - Elad Gil Virginia Woolf on Montaigne Ava on Tammy Old Enough!

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22: Nadia Asparouhova - Ideas that Infect

22: Nadia Asparouhova - Ideas that Infect

Nadia Asparouhova (Website, X, Substack) is a writer and researcher who has spent much of her career in service of the question: 'what's happening here?' across various parts of the internet. Nadia re...

3 Heinä 20252h 4min

21: Geoffrey Litt: Software You Can Shape

21: Geoffrey Litt: Software You Can Shape

Geoffrey Litt (Website, X) is a designer, engineer, writer, and researcher at Ink & Switch, where he champions malleable software: the idea that ordinary people should be able to mold the digital tool...

19 Kesä 20252h 29min

20: Yancey Strickler - Constellations of Creativity

20: Yancey Strickler - Constellations of Creativity

Yancey Strickler (Website, X, Metalabel) is a writer, entrepreneur, creative, and founder of Metalabel, a network and platform that allows creative people to release work together. He is also a board ...

12 Kesä 20251h 54min

19: Henrik Karlsson - Cultivating a Life that Fits

19: Henrik Karlsson - Cultivating a Life that Fits

Full transcript and all links: dialectic.fm/henrik-karlsson Henrik Karlsson (Substack, X) is an independent writer focused on "writing a few good essays." Two of them are among my most consistently re...

3 Kesä 20252h 44min

18: Tom Morgan - Wisdom in the Woo

18: Tom Morgan - Wisdom in the Woo

Tom Morgan (X, Substack) is a "curiosity sherpa," writer, and podcaster who runs The Leading Edge, a community for leaders focused on personal transformation and authenticity. I first encountered Tom ...

28 Touko 20251h 42min

17: Alex Danco - Innovation Begins with Gifts

17: Alex Danco - Innovation Begins with Gifts

Alex Danco (Website, X, Substack) is a writer and Product Director at Shopify. Alex rose to prominence while writing his Snippets newsletter while at VC firm Social Capital in 2015. He wrote prolifica...

21 Touko 20253h 9min

16: Anjan Katta - A Sunrise Over Computing

16: Anjan Katta - A Sunrise Over Computing

Anjan Katta (X) is Founder and CEO of Daylight, a new type of computer company. Having a conversation with Anjan is a bit like trying reign in a wild animal: his horsepower, wide-ranging philosophical...

5 Touko 20252h 37min

15: D.A. Wallach - Serendipity & Systems

15: D.A. Wallach - Serendipity & Systems

D.A. Wallach (Website, X, Substack, Spotify) is an investor, musician, writer, and polymath. Today he co-runs Time BioVentures, backing frontier life-science and healthcare startups. Before that, he w...

28 Huhti 20252h 32min

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