23: Tamara Winter - Tacit Trust & Caring Curiosity
Dialectic28 Jul 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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