#45 - Dominic Cummings on why the West is eating itself

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#45 - Dominic Cummings on why the West is eating itself

...like an Ouroboros, but an incompetent bureaucratic self-defeating one

Liv Boeree

and

Dominic Cummings

Jul 31, 2025

Dominic Cummings

is one of the most polarizing figures in Britain. He's also one of its greatest strategists: he was one of the main masterminds behind Brexit. He served as Chief Advisor to Prime Minister Boris Johnson for a stint. He even had Benedict Cumberbatch play him in a movie!

What I find most interesting about him is his mind for systems. He’s had a deeper view into the inner machinations of the British & European governments than most could hope for in a lifetime. This gives him a unique perspective on this blog’s main theme: how to build more omni-win institutions that adapt and grow with the times?

As you’ll hear in this conversation, what he saw in there was not pretty. To paraphrase: “it’s a rotting carapace that cares only for itself”. Given the many soul-crushing scandals that have plagued Britain & America (and frankly much of the world) like cover-ups around grooming gangs and countless other horrors, we should take heed of his warnings.

So if you’re craving real talk about deep states, governance structures, personal competitiveness and what it might take to rebuild the West and its systems, this is one for you! Chapters etc below.

Much love,

Liv

Thanks for watching Win-Win! This post is public so feel free to share it and subscribe, it’s all free!

Chapters:

1:51 Is Dominic competitive?

7:30 First Interest in Politics

12:18 Beginning of his Euroskepticism

16:50 The current state of the British regime

23:04 His Time in No.10 Downing Street

33:00 Who is actually in charge?

36:38 More COVID screwups

40:05 Is the System conscious?

45:15 Avoiding future pandemics

1:01:27 Importance of stability

1:07:17 Bureaucratic Nightmares

1:11:57 Machiavelli And Escaping the Wheel

1:15:53 Singapore

1:19:34 Digitize the Government?

1:22:00 Moloch, Incentives & Political sacrifice

1:25:28 The Media Is A Simulation of Reality

1:29:12 How to design better social media platforms

1:31:05 Sensemaking in the AI age

1:37:24 UK Grooming Gangs Coverup

1:48:21 Political Gaslighting, Freedom of Speech & 2nd Amendment

1:50:38 Blasphemy and Islamophobia Laws in UK

1:56:10 The Sacred Cow of Multiculturalism

2:02:22 Core Principles To Live By

2:07:48 Smart vs Dumb Approaches to Regulation

2:17:05 Rapidfire Predictions

The Win-Win Podcast:

Poker champion Liv Boeree takes to the interview chair to tease apart the complexities of one of the most fundamental parts of human nature: competition. Liv is joined by top philosophers, gamers, artists, technologists, CEOs, scientists, politicians and more to understand how competition manifests in their world, and how to change seemingly win-lose systems into Win-Wins.

Links:

♾️ Dominic’s X: https://x.com/Dominic2306

♾️ Dominic’s Substack: