Crafting a Narrative: Tamara Winter on the Power of Excellence and Storytelling

Tamara Winter is the Commissioning Editor at Stripe Press, the publishing imprint of Stripe, and a board member of the Institute for Progress and the Foundation for American Innovation. Previously, she worked as the head of strategy at the Charter Cities Institute, and at the Mercatus Center. She has written for the Chicago Tribune, Works in Progress, and a16z. She also wrote and hosted Beneath the Surface, a limited-run podcast about infrastructure and some of the most complex challenges facing our world. Known for her keen insights and high standards, Tamara is deeply passionate about storytelling, business development, and championing people with big ideas.
This week, Barrett talks with Tamara about her exceptional career journey, from building a presence on Twitter to curating influential works at Stripe Press. Drawing from her upbringing as an African immigrant and the influence of her parents, Tamara reflects on the importance of surrounding oneself with high achievers, the value of curiosity, and the pursuit of excellence. She emphasizes the transformative power of storytelling, her love for tacit knowledge, and her vision for blending tech with story to influence the world. Barrett and Tamara also discuss the nuances of impactful work, the lasting influence of intentional connections, and Tamara's aspiration to inspire others while shaping a meaningful legacy through publishing.
In this episode:

(00:00) - Intro

(03:39) - Tamara’s journey to Stripe Press

(06:47) - Turpentine and provocations

(09:24) - Challenges and innovations in publishing

(13:03) - The role of Stripe Press in Stripe’s ecosystem

(19:02) - The first book that captured Tamara’s imagination

(26:21) - Tamara’s early days at Stripe

(35:22) - Interviewing Jordan Mechner

(37:48) - The duality of Teddy Roosevelt

(40:13) - Remembering Charlie Munger

(48:58) - The influence of mentors and unconventional career paths

(01:04:55) - The value of high-quality authors and books

(01:13:26) - The desire for excellence

(01:16:08) - Family expectations and developing taste

(01:23:54) - Principles for early career success

(01:38:14) - Tamara’s beautiful future

(01:44:11) - Who Tamara is becoming


Get full show notes and links at https://GoodWorkShow.com.
Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.