After a bit of a hiatus (happy summer!), Dialectic is back, and with momentum. Episodes will return weekly, starting with a conversation with my friend and Commissioning Editor of Stripe Press, Tamara—or Tammy—Winter.
Tammy oozes charisma, is the life of every room she is in, has exquisite taste (in ideas for Stripe Press and more broadly), and is deeply thoughtful about the hidden infrastructure that supports so much of what makes healthy society. Spoiler: it all comes down to caring deeply about other people.
I hope you enjoy the conversation as much as I did. More conversations coming your way soon.
Dialectic Ep. 23: Tamara Winter - Tacit Trust & Caring Curiosity
Dialectic Episode 23: Tamara Winter - Tacit Trust & Caring Curiosity - is available on Spotify, Apple Podcasts, and YouTube, and all podcast platforms.
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.
Timestamps
2:09: Taste, absorption, 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 & delightfulness 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
Links & References
Sort By Controversial - Scott Alexander (Scissor Statements)
Walt Disney: The Triumph of the American Imagination - Neal Gabler














