Personal Choices of CEOs Under Pressure

The early internet was built on big hopes—access, openness, connection, and the belief that technology could make the world fairer. In this episode of The Radical Candor Podcast, Kim & Jason are in conversation with Steven Levy. His recent article, “I thought I knew Silicon Valley. I was wrong.”, becomes the lens through which they revisit tech’s early promise and its reality today.

They take an honest look at the optimism that shaped Silicon Valley’s early culture and how those ideals unraveled. Kim & Steven candidly share their unique perspective of  how it feels to recognize the gap between what they believed and what actually happened as two people who had a front row seat. 

If you’re looking for a thoughtful, grounded, and honest conversation about how tech’s story was written—and rewritten—in real time, and what today’s leaders can learn from examining both intention and impact, this episode offers clarity and perspective you can apply right now.

Get all of the show notes at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠RadicalCandor.com/podcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.

Episode Links:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠"I Thought I Knew Silicon Valley, I was Wrong"
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠About Steven Levy⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Steven Levy's Newsletter⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Steven Levy's Books⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠"Virtual Love" by Kim Scott
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠"Enshittification" by Cory Doctorow⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠"The Age of Extraction" by Tim Wu⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Connect:

• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Bluesky⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Chapters:

(00:00) Introduction

Kim, Jason, and Steven set the stage for a reflective look at Silicon Valley’s promise and reality.

(01:39) “I Thought I Knew Silicon Valley. I Was Wrong.”

Steven shares what led him to write the article and how his perspective shifted.

(03:38) From Idealism to Influence: When Tech’s Culture Shifted

Exploring the moment Silicon Valley’s playful, rebellious spirit hardened into something more powerful—and less accountable.

(06:30) Recalling the Internet We Hoped For

Revisiting the early optimism that shaped the web and the disillusionment that followed.

(12:27) The Claims of AI

Examining the bold promises tech leaders make about AI—and why skepticism matters.

(15:01) The Long Tail

Early optimism about the internet’s potential to democratize opportunity.

(16:56) Enshittification & The Age of Extraction

Cory Doctorow’s framework, antitrust debates, and how market consolidation reshaped the online ecosystem.

(20:05) Do a CEO’s Values Matter?

A look at how leaders like Mark Zuckerberg and Jeff Bezos have evolved—and what that means for their companies.

(24:37) What to Do When You Don’t Align With Your Company

Reflecting on how to stay true to your values when the culture around you shifts.

(29:36) Looking Back with Clearer Eyes

Kim reckons with past choices, blind spots, and what accountability looks like now.

(32:29) What Corrupted Silicon Valley

When too much money and power are concentrated in too few hands.

(33:56) Conclusion

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