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!

Jaksot(38)

38: Molly Mielke McCarthy - The Art of Peopling

38: Molly Mielke McCarthy - The Art of Peopling

Transcript and all links: dialectic.fm/mmm Molly Mielke McCarthy (Website, X, Substack) is an investor, writer, and founder of Moth Fund, an early-stage fund focused on backing "moths": quirky, quiet...

29 Tammi 2h

37: Trevor McFedries - Creative People Should Be Rich

37: Trevor McFedries - Creative People Should Be Rich

All linked references & transcript available at dialectic.fm/trevor-mcfedries. Trevor McFedries (X, Instagram, Wikipedia) is a musician, technologist, and entrepreneur. Today he is the founder of Runn...

20 Tammi 2h 18min

36: C. Thi Nguyen - Measurement, Meaning, and Play

36: C. Thi Nguyen - Measurement, Meaning, and Play

Full episode transcript and all linked references available at https://dialectic.fm/c-thi-nguyen. C. Thi Nguyen (Website, Philpeople.org, X) is a professor of philosophy at the University of Utah foc...

13 Tammi 2h 21min

35: Brie Wolfson - Loving Attention & Ease in Craft

35: Brie Wolfson - Loving Attention & Ease in Craft

Full transcript and all links: ⁠https://dialectic.fm/brie-wolfson⁠ Brie Wolfson (X) is a marketer, writer, storyteller, and curator. She’s Chief Marketing Officer of Positive Sum & Colossus, where she...

6 Tammi 2h 31min

34: Ryo Lu - It's All the Same Thing

34: Ryo Lu - It's All the Same Thing

All links and transcript at dialectic.fm/ryo-lu Ryo Lu (Website, X) is the head of Design at Cursor. Prior, he was a designer at Notion, Stripe, and Asana, working on some of the most influential soft...

18 Joulu 20251h 59min

33: TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler

33: TBPN (John Coogan & Jordi Hays) - Inside Tech's Water Cooler

John Coogan & Jordi Hays are the hosts of TBPN (X, YouTube, Spotify, Substack), a daily live show covering the technology business. TBPN was launched only about a year ago, but has become a mainstay i...

17 Marras 20252h 22min

32: Chris Sacca - Drifting Back to Real

32: Chris Sacca - Drifting Back to Real

Chris Sacca is an investor and founder of Lowercarbon Capital and Lowercase Capital. Prior to becoming an investor, Chris grew up in Buffalo, NY; studied around the world by way of the Georgetown Sch...

5 Marras 20252h 36min

31: Gabe Whaley - Playing the Crowd & Outlasting the Hype

31: Gabe Whaley - Playing the Crowd & Outlasting the Hype

Gabe Whaley is co-founder and CEO of MSCHF (Instagram, Wikipedia), the art collective, fashion and footwear brand, startup, and fill-in-the-blank, famous for its viral products and cultural interventi...

15 Loka 20252h 3min

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