Claire Stapleton spent 12 years at Google from 2007 - 2019. She joined as a fresh grad at a time of peak optimism and idealism in Silicon Valley, and soon became somewhat of a 'Bard' - responsible for shaping the story and sharing the folklore around Google with employees and later the outside world.

In 2018, feeling increasingly disillusioned with what Google had become, Claire was one of the organizers of a 20k employee walkout in protest against the company's handling of sexual harassment allegations against certain senior executives - one of whom, Andy Rubin, had allegations against him deemed credible by an internal investigation - yet walked away with a warm handshake and $90m exit package.

Claire and the other women who organised faced a backlash from Google with their roles and responsibilities being diminished in the aftermath.

Claire eventually left in 2019, and her memoir, 'Don't Be Evil' has recently been released and is available at any good bookshop near you: https://www.nytimes.com/2026/08/04/books/review/dont-be-evil-claire-stapleton.html

Claire's own journey maps to a time in which internal and public sentiment towards big tech in general has shifted so we sat down to talk not just about her own experience at Google, but also the wider vibe shift in the industry as a whole.

Key topics

• The early idealistic days of Google
• Claire's role as 'The Bard' - telling the internal folklore of Google to its employees and the outside world
• Google's Me Too moment - her role as organizer of 20k employee walkout
• The backlash that she and other women at Google faced as a consequence
• The vibe shift from idealism to corporate ruthlessness
• When she stopped believing the story she was telling
• Her experiences of parenting and grief and how that shaped how she felt about her work

Where you can watch/listen

Youtube⁠⁠⁠⁠⁠ - ⁠https://www.youtube.com/@HumansintheLoopPod

Apple podcasts⁠⁠⁠⁠⁠ - ⁠https://podcasts.apple.com/us/podcast/humans-in-the-loop/id1831285114⁠

Spotify⁠⁠⁠ - ⁠https://open.spotify.com/show/4BbslJR0KA5bfqrcYRhJER?si=b5a46211098b4f3e⁠Or wherever you get your podcasts!

Get in touch

Instagram⁠⁠⁠ - ⁠https://www.instagram.com/humansinthelooppod/⁠

Email: ⁠seb@theuncommonfounder.com⁠

Website: ⁠https://www.theuncommonfounder.com

Where to find Claire

LinkedIn: https://www.linkedin.com/in/claire-stapleton-868a935/

Substack: ⁠https://techsupport.substack.com/

X: https://x.com/clairewaves?s=20

Instagram: https://www.instagram.com/clairewaves

Benedict Evans is a tech analyst and former partner at A16z.

His newsletter with rational takes on tech goes out to over 175k people.

In amongst the noise around AI and the tech industry more broadly, Benedict has built a reputation for high quality, level headed analysis.

I sat down with Benedict to discuss topics such as:

• The current state of technology and ongoing platform shifts
• Whether this time is truly different or not
• Historical comparisons of technological revolutions
• Challenges in predicting AI's future trajectory
• Silicon Valley’s naivety about the world
• The cultural and philosophical aspects of AI and art
• The importance of understanding complex systems and markets

Where else you can listen

Youtube⁠⁠⁠⁠ - https://www.youtube.com/@HumansintheLoopPod

⁠⁠Apple podcasts⁠⁠⁠⁠ - https://podcasts.apple.com/us/podcast/humans-in-the-loop/id1831285114

Spotify⁠⁠ - https://open.spotify.com/show/4BbslJR0KA5bfqrcYRhJER?si=b5a46211098b4f3e

Or wherever you get your podcasts!

Chapters

00:00 Introduction and Benedict Evans' perspective on tech noise

03:33 E-commerce growth and retail media expansion

07:05 Historical scale of technological change and exponential growth

10:33 The unpredictability of technological evolution

14:08 The difference between automating tasks and jobs

17:24 The limitations of AI in creating authentic art

18:13 The organizational and deployment challenges of AI

20:39 The emergence of new pathways and the unpredictability of AI evolution

22:20 Historical perspectives on internet and mobile adoption

23:37 The importance of questions and uncertainty in analysis

25:01 The impact of the internet on industries and productivity

26:29 The exponential nature of technological progress

28:23 Organizational inertia and the difficulty of change

30:04 The complexity of automating jobs versus tasks

32:38 The role of models in understanding human work and creativity

36:26 The potential of AI as a pattern matcher and logic system

39:23 The philosophical limits of AI and human judgment

41:24 Cultural perceptions of art, authenticity, and AI

44:52 The enduring human element and cultural value in art

45:46 The future of AI and human creativity

48:47 The broader implications of AI as a platform for a new economy

50:15 Historical context of technological revolutions and their long timelines

52:24 Philosophical debates on existence, value, and AI

54:07 Benedict Evans' perspective on Silicon Valley and tech optimism

55:35 The influence of politics and regulation on AI development

56:49 The mindset needed for startup innovation and large-scale change

57:20 Benedict Evans' optimism about the future and long-term progress

58:47 Reflections on historical hardships and the progress of humanity

01:00:51 The long arc of human history and technological progress

Get in touch

Instagram⁠⁠⁠ - https://www.instagram.com/humansinthelooppod/

Email: ⁠seb@theuncommonfounder.com⁠

Website: ⁠https://www.theuncommonfounder.com

Where to find Benedict

LinkedIn: https://www.linkedin.com/in/benedictevans/

Newsletter: https://www.ben-evans.com/newsletter

Website: https://www.ben-evans.com

Few people understand language quite like today's guest. Emily M. Bender is a Professor of Computational Linguistics at the University of Washington.

She's also the person who coined the term 'Stochastic Parrots' in the now infamous paper that saw Google fire its Ethical AI lead; and the co-author of The AI Con, a book which is unflinching in its criticism of both AI boosterism and doomerism (in fact she objects to the term AI).

I sat down with Emily to discuss topics such as:

• How language really works
• What LLMs are actually doing
• What Stochastic Parrots really means
• Why doomers and boosters are two sides of the same, misleading coin

Where else you can listen

⁠⁠⁠Youtube⁠⁠⁠ - https://www.youtube.com/@HumansintheLoopPod

⁠Apple podcasts⁠⁠⁠ - https://podcasts.apple.com/us/podcast/humans-in-the-loop/id1831285114

⁠Spotify⁠ - https://open.spotify.com/show/4BbslJR0KA5bfqrcYRhJER?si=b5a46211098b4f3e

Or wherever you get your podcasts!

Chapters

00:00 Introduction to AI and Linguistics

02:54 Understanding Computational Linguistics

05:47 The Stochastic Parrots Paper

08:32 The Implications of AI Terminology

10:57 Skepticism Towards AI Claims

12:58 The Illusion of Intelligence in AI

15:55 The Dangers of AI in Professional Settings

18:33 Democratization and Distrust in AI Development

28:02 Doomers vs. Boosters: The AI Narrative

32:57 Skepticism in AI: A Personal Journey

36:30 The Rapid Evolution of AI: Are We Outdated?

40:13 The Role of Software Engineering in AI

48:14 Automation vs. Human Expertise: A Balancing Act

53:02 Geopolitical Narratives: The AI Arms Race

56:33 The Future of AI: Regulation and Ethical Use

57:44 Pride in Expertise: Understanding Our Value

Get in touch

⁠⁠Instagram⁠⁠ - https://www.instagram.com/humansinthelooppod/

Email: ⁠seb@theuncommonfounder.com⁠

Website: ⁠https://www.theuncommonfounder.com