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

Key Takeaways

Crafting compelling narratives is essential for influencing the world; people’s beliefs about themselves and the world shape everything in life.
Forgiveness, reconciliation, and high standards for conduct are foundational elements of a successful career.
Understanding that your heroes are just as flawed as everyone else leads to deeper insights and inspiration.
Surrounding yourself with high achievers is crucial for honing your skills and achieving professional excellence.

Quotes

“There are so many people who've just never been told that you can actually think bigger. You can have higher standards.” ~ Tamara Winter

“I don't think anything is as important as who is on the other line when you're going through the worst night of your life, and who feels like they can call you when that's happening.” ~ Tamara Winter

“Have you made peace with where you come from? I feel like there's so much unlearning, especially in our therapy culture. You can't unlearn anything. What happened, happened. And so you sort of get to choose how you relate to your past.” ~ Tamara Winter

“You hope that everybody hits a point in their early career where they have enough people who care about them and who want to hold them to high standards that they can say, confidently, ‘I know what I'm doing now. We haven't won yet. There's plenty to learn. It's an ever-evolving journey, but I know what I'm doing now.’” ~Tamara Winter

“I think almost everything is downstream of what people believe about themselves, their capabilities, their own ambitions for their lives, and what they generally believe about the world. It's the reason why you're starting to see more technologists get interested in storytelling in some capacity because they appreciate that being able to craft a narrative is maybe one of the most valuable things that you can spend your time on.” ~ Tamara Winter

Links