Dominic Cummings is one of the most polarizing figures in Britain. He's a political strategist who masterminded the main campaign for Brexit. He was also Chief Advisor to Prime Minister Boris Johnson for some of his term, including through COVID. He even had Benedict Cumberbatch play him in a movie! He's also a student of systems, having worked in or around government and civil institutions all his life, which is why I wanted to talk to him, because he's someone who has seen the depth of systemic rot pervading not just the UK, but the whole West.

In this wide-ranging, no-holds-barred conversation, Igor and I hear why our governments are collapsing under their own weight, the rise of algorithm-driven politics and civil service monopolies, and the general systemic dysfunctions hollowing out the West's institutions. We also explore whether scientific and technological leadership and a whole lot of radical transparency can save us — or if we’re already past the tipping point.

So if you’re craving real talk about power, governance, and what it might take to rebuild from the rubble, you'll enjoy this conversation!

Chapters:

01:51 - Is Dominic competitive?

07:30 - 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 - The Consciousness of the System

45:15: Avoiding Future pandemics

1:01:27 - Isn't the role of the government to provide stability?

1:07:17 - The Issue of Bureaucracy

1:11:57 - Machiavelli And Escaping the Wheel

1:15:53 - Singapore

1:19:34 - Digitizing 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 - Rapid fire Predictions

Links:

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

♾️ Dominic’s Substack: https://dominiccummings.substack.com

♾️ Simulacra and Simulation: https://www.goodreads.com/book/show/22613.Simulacra_and_Simulation?ref=nav_sb_ss_1_6

♾️ Moloch explainer: https://www.youtube.com/watch?v=PRz54V7rU4U

♾️ Brexit The Movie: https://www.imdb.com/title/tt8425058/

♾️ Mary Wakefield (Dominic’s wife) response to the movie: https://www.spectator.co.uk/article/benedict-cumberbatch-on-playing-my-husband-dominic-cummings/

Credits:

♾️ Hosted by Liv Boeree

♾️ Produced by Luca de Vico

♾️ Intro by Perry Sinclair

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.Podcast links:

♾️ Youtube: https://www.youtube.com/playlist?list=PLWgq0OZMtwtOIyMsVM_vksqdfWcM-b68S

♾️ Spotify: https://open.spotify.com/show/03bGVUaFZmJUmEvSHNDPdI?si=64379cc23696454f

♾️ Apple Podcasts: https://podcasts.apple.com/us/podcast/win-win-with-liv-boeree/id1724791350

♾️ Pocketcast: https://play.pocketcasts.com/podcasts/7f708340-d17c-013b-f46e-0acc26574db2

#winwinpodcast #systemchange #politics