Win-Win with Liv Boeree

Free speech is often treated as a political issue. But what if it’s the foundational technology that makes peaceful civilization possible in the first place?I sat down with Greg Lukianoff — free speech advocate, first amendment attorney, and longtime leader of FIRE.org — to explore why freedom of expression is humanity’s ultimate win-win innovation.Greg strongly believes free speech is at risk across the globe. It's under threat from government censorship, and from the attitudes of citizens themselves, who have become increasingly intolerant of opposing views. These pressures seem to only be increasing as we enter the AI era, which allows censorship, surveillance and other oppression tools at scale. At the same time, it also offers the democratization of potentially hazardous information to violent actors, only increasing the pressures on governing authorities to clamp down even harder on speech. So how do we navigate this tension? That's what this conversation seeks to answer.Huge thanks to  @TheFIREorg  for collaborating with me on this episode (they were the ones who organised this live event)! Go support their important work at the link the below.Chapters:00:00 — Intro01:42 — Why is Free Speech a Win-Win?05:10 — Is Free Speech At Risk in the USA?08:41 — Charlie Kirk & The Case of Larry Bushart 11:40 — How Is Technology Changing Free Speech?18:49 — ACLU & Institutional Capture21:57 — AI & The First Amendment29:40 — How To Calm The Arms Race?33:50 — The Hidden Cost of LLM Slop38:22 — How To Design Better Social Media Algorithms?41:07 — UK & European Hate Speech Laws & Censorship 47:18 — J.K Rowling & Free Speech Influencers 52:20 — Can Free Speech Survive Gen Z?59:04 — How To Talk To SkepticsLinks:♾️ Greg Lukianoff: https://www.thefire.org/people/greg-lukianoff♾️ FIRE (Foundation for Individual Rights and Expression): https://www.thefire.org♾️ Greg’s TED Talk on Free Speech: https://www.youtube.com/watch?v=noWh8SSeRCo♾️ The Larry Bushart Case: https://www.fire.org/cases/larry-bushart-v-perry-county♾️ The Coddling of the American Mind: https://www.thecoddling.com♾️ Karl Popper — Conjectures and Refutations: https://archive.org/details/karl-popper-conjectures-and-refutations-the-growth-of-scientific-knowledgeCredits:♾️ Hosted by Liv Boeree♾️ Produced by Luca de Vico♾️ Event Production: the team at Fire.orgThe Win-Win Podcast:Poker champion Liv Boeree takes to the interview chair to tease apart one of the most fundamental forces shaping human behavior: competition.Liv speaks with philosophers, technologists, scientists, founders, and public thinkers to understand how seemingly win-lose systems can be redesigned into win-wins.Podcast links:♾️ Website: https://www.winwinpodcast.com/♾️ YouTube: https://www.youtube.com/@WinWinPodcast♾️ Spotify: https://open.spotify.com/show/03bGVUa…♾️ Apple Podcasts: https://podcasts.apple.com/us/podcast…#winwinpodcast #freespeech #AI

Which LLM is best at POKER? What about the social deception game Werewolf? This week I'm collaborating with ⁠ @googledeepmind ⁠ and ⁠ @kaggle ⁠ to explain their new “AI Game Arena” project, designed to test all the top LLMs at various games.
The Game Arena is a massive research project to create new AI benchmarks, and understand what really makes these general-purpose AIs tick. It also helps us evaluate how far along the path to true AGI we are, NBD.So who better to speak to than Deepmind research engineer John Schultz, one of the main brains behind the project.
We discuss why some LLMs are so much better than others, their internal understanding of the games (or lack of it!) and why games are a useful way to evaluate both capabilities and safety of frontier models.And friends - do please note that for the first time ever on this channel, this post is part of a paid partnership (woohoo I made it!).
So while everything I said in this interview, is absolutely my own views, there are also direct financial incentives behind this particular interview.

Chapters
00:00 - Intro
00:55 - What Is Game Arena?
01:25 - John’s Favorite Games
03:18 - Narrow AI Vs LLMs: What’s The Difference?
05:58 - Will LLM Poker Skills Transfer To Other Games?
09:00 - Benchmarks And Evals
10:50 - Prompt Design For Game-Playing LLMs
13:32 - Do LLMs Understand Concepts Like Expected Value?
14:24 - Context Window Length17:27 - Why Do LLMs Have Different Playing Styles?
18:41 - Where Does Their Skill Come From?
21:09 - Surprising Results
23:50 - Why Werewolf?
25:48 - Where Does LLM Reasoning Come From?
27:49 - Could LLMs Learning Social Games Be Dangerous?30:58 - Can Games Teach LLMs Cooperation?
32:48 - Which Games Will Be Hardest To Learn?

Links:
♾️ Kaggle Game Arena (Main Hub): https://www.kaggle.com/game-arena
♾️ Introducing the Kaggle Game Arena (Official Post): https://www.kaggle.com/blog/introducing-game-arena
♾️ Poker Benchmark – 900,000 Hands: https://www.kaggle.com/blog/game-arena-poker
♾️ Werewolf Benchmark (Social Deception Game): https://www.kaggle.com/benchmarks/kaggle/werewolf
♾️ Google DeepMind (Research Organization): https://deepmind.google
♾️ Polaris Library (DeepMind, Open Source): https://github.com/google-deepmind/polaris

Credits:
♾️ Hosted by Liv Boeree
♾️ Produced by Luca de Vico

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:
♾️ Website: https://www.winwinpodcast.com/
♾️ 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 #AI #poker #kaggle

Superintelligence is predicted to arrive within a decade. If that's true, then what comes AFTER? And how can we prepare for it?Which is why I sat down with one of the few people actively thinking about this: philosopher Will MacAskill. Will heads up Forethought, a research nonprofit focused on how to navigate the transition to a world with superintelligent AI systems. He’s also a former Oxford University professor, and a co-founder of the effective altruism movement. In this special Win-Win Live conversation, we discuss why “utopias” often fail, the growing risks of authoritarian lock-in, whether moral progress survives in a post-labor world,, and how the transition to a post-superintelligence world may be more crucial than the development AGI itself. Also, lots of chat about the sun, space and the high seas.

Chapters: 00:01:10 — Intro00:04:11 — Frameworks For Thinking about The Future00:06:40 — Why We Need to Think About These Questions Now00:10:50 — Post AGI Worlds00:14:16 — Blockers of Positive Futures00:20:11 — Hedonium00:23:45 — Universal Basic Resources00:29:23 — Suffering Risks00:33:52 — Viatopia00:37:50 — Can We Understand — and Steer — Moral Fashions?00:43:06 — Can AI Repair Our Shared Reality?00:49:45 — Pluralistic Futures: Choosing How We Want to Live00:54:57 — The Dangers of Elites Controlling AI01:03:14 — Can We Measure How Well We See the Future?01:06:50 — Purpose in a World of Abundance01:09:20 — Sci-Fi Ideas Worth Writing Now01:16:29 — Meaning in a Post-labor Economy 01:21:24 — How Does Moral Progress Actually Happen?01:27:45 — Will’s Call to ActionLinks: ♾️ Will MacAskill’s website: https://william-macaskill.com ♾️ Forethought: https://www.forethought.org/♾️ Essay on Viatopia https://www.forethought.org/research/viatopia♾️ What We Owe the Future (Will MacAskill): https://www.amazon.com/dp/1541618629 ♾️ Deep Utopia (Nick Bostrom): https://www.amazon.com/dp/1914741128 ♾️ Utopia (Thomas More): https://www.gutenberg.org/ebooks/2130 ♾️ The Republic (Plato): https://www.gutenberg.org/ebooks/1497 ♾️ Island (Aldous Huxley): https://www.amazon.com/dp/0061561791 ♾️ Anarchy, State, and Utopia (Robert Nozick): https://www.amazon.com/dp/0465051006 ♾️ The Archipelago (Scott Alexander): https://slatestarcodex.com/2014/04/09/the-archipelago/ ♾️ Grabby Aliens Model (Robin Hanson): https://grabbyaliens.com ♾️ The Fermi Paradox: https://en.wikipedia.org/wiki/Fermi_paradox ♾️ WEIRD Psychology (Joseph Henrich): https://www.hup.harvard.edu/books/9780374173227 ♾️ Protopia (Kevin Kelly): https://kk.org/thetechnium/protopia/ ♾️ Universe 25 (John B. Calhoun): https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2636191/ ♾️ Dyson Swarm (Concept): https://en.wikipedia.org/wiki/Dyson_sphere ♾️ Effective Altruism: https://www.effectivealtruism.org ♾️ Giving What We Can: https://www.givingwhatwecan.org ♾️ 80,000 Hours: https://80000hours.org Credits:♾️ Hosted by Liv Boeree♾️ Produced by Luca de VicoThe 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:♾️ Website: https://www.winwinpodcast.com/♾️ 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 #AI #superintelligence

What if the biggest risk from AI isn’t superintelligence gone rogue, but the inflexibility of our human institutions?

My guest today, Tyler Cowen, thinks so. Tyler is a professor at George Mason university and one of the most celebrated economists in the world. And unlike many AI proponents, Tyler strongly challenges the idea that intelligence alone determines outcomes in society, and instead points to us humans as the real bottlenecks shaping our future, for better or worse.

Together with my occasional co-host Igor Kurganov, we debate why he thinks diffusion and human adoption matter more than raw capability, and why markets remain one of the most under-appreciated signals in conversations about AI risk. Tyler also shares his views on economic growth, UBI, automation, persuasion, state capacity, why fears of mass unemployment and civilizational collapse are often overstated.

And of course, we explore what it takes to design win-win systems that scale without collapsing under their own incentives.

Oh and we discuss aliens too! A really fun one, hope you enjoy.

Chapters: 
00:00 - Introduction
01:40 – Market Driven Addiction
14:38 – Wealth Plus
17:28 – State Capacity Libertarianism
25:29 – Why Is Carbon Tax Failing?
27:14 – Climate Engineering
29:45 – Pharmaceutical Pricing
36:45 – Designing Incentives
37:24 – AI’s Impact on the Economy
53:24 – AI’s Impact on Tyler
55:25 – Universal Basic Income
59:25 – AI Timelines
01:10:45 – AI Risk Reflected in Markets
01:18:25 – Convincing Future Risk Scenarios
01:20:57 – AI as a Super Persuader
01:30:51 – Is Tyler Competitive?
01:41:39 – Strangest Beliefs & Aliens
01:46:14 – Rapid-Fire Predictions

Links: 
♾️ Tyler’s X: https://x.com/tylercowen?lang=en 
♾️ Tyler’s website: https://tylercowen.com 
♾️ Tyler’s blog: https://marginalrevolution.com 
♾️ Meditations on Moloch: https://www.slatestarcodexabridged.com/Meditations-On-Moloch

Credits:
♾️ Hosted by Liv Boeree
♾️ Produced by Luca de Vico

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

What if the purpose of life is to find ways of harmonizing the forces of nature, including the nature of ourselves?
My guest this week thinks so. I sat down with systems thinker and "True Human" author Samantha Sweetwater to talk about the metacrisis and the future of civilization in the age of AI. Samantha’s work bridges complexity science, indigenous wisdom, embodiment, and systems theory to explore how humans might transition from domination and extraction toward relationship, reciprocity, and long-term resilience.
We discuss why modern institutions are struggling to adapt, how technology differs fundamentally from biological systems, and why aligning AI without accounting for the biosphere may be a category error. The conversation also explores kinship versus the hero’s journey, power over life versus the power of life, and what a truly win-win civilization might require.
If you’re interested in AI alignment, systems change, ecology, or the deeper roots of the meta-crisis, this conversation offers a radically different lens.
Chapters:
02:18 – Samantha’s Backstory
11:55 – Finite And Infinite Games
17:00 – True Human
21:55 – Exploring Dreams
34:28 – The Great Separation
38:51 – Power Of Life vs Power OVER life
44:36 – The Balance Between Masculine And Feminine
1:05:23 – Observing An Animate World
1:14:45 – Achieving Transmigration
1:24:28 – Practices To Become More True Human
1:42:14 – On AI Alignment
1:59:58 – Begin To Embody Intelligence
2:06:31 – Why Homo Sapiens Exist To Serve Sentience
Links:
♾️ True Human Book: https: //www.samanthasweetwater.com/truehuman
♾️ Samantha’s Linkedin: https://www.linkedin.com/in/samanthasweetwater
♾️ Samantha's Substack: https://enlifenment.substack.com
♾️ Daniel Schmachtenberger x Win-Win: https: //youtu.be/KCSsKV5F4xc?si=lM7urTngFNuJ4oZx
♾️ Silent Spring: https: //en.wikipedia.org/wiki/Silent_Spring
Credits:
♾️ Hosted by Liv Boeree
♾️ Produced by Luca de Vico
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
#AI #indigenouswisdom