The Jim Rutt Show

Jim talked with Cory Doctorow—prolific sci-fi and nonfiction author, journalist, activist, EFF special adviser, and author of Enshittification: Why Everything Suddenly Got Worse and What to Do About It—about how structural forces degraded the internet, and what citizens (not consumers) can actually do about it.

They discussed:

The origin of "enshittification"—Cory's January 2023 blog post, its viral spread, and its naming as Word of the Year by the American Dialect Society
Two-sided markets & the persistence of intermediaries
Crad Kilodney as a self-publishing illustration, and why platform middlemen survive even when they shouldn't
Monopsony vs. monopoly
The real statistics of Amazon's dominance of book sales
The three-stage enshittification life cycle, using Facebook as the case study
The brittle equilibrium of late-stage enshittification—the thin line between "I hate this but can't leave" and mass exodus
The metaverse as Facebook's terminal pivot—Zuckerberg's "legless, sexless, low-polygon" avatar world stolen from a 25-year-old cyberpunk novel, and why it still served him by forestalling investor sell-offs
Zuckerberg as Rich Uncle Pennybags, not Willy Wonka
Amazon's early history & Bezos's "your margin is my opportunity" mantra
Amazon's junk fees (now 50–60% and rising) and the $80 billion/year advertising payola business
The consumer welfare doctrine—Robert Bork's antitrust theory that monopoly is efficient, and why allowing monopsonies inevitably produces monopolies
Jim's personal experience with the Thomson-West legal publishing merger
Tech workers as a structural check on enshittification
The convergence enabling enshittification: merger to monopoly → regulatory capture → loss of worker leverage → DMCA blocking entrants → abuse
The moral decay of business culture—from "we won't do profitable things we think are wrong," to "do whatever's arguably legal," to "do whatever's illegal if the fine is less than the benefit"
Google's $20 billion/year payment to Apple to stay off the search market
Why predatory pricing cases went unenforced
What citizens (not consumers) can do
The death of federal antitrust enforcement and international ripple effects
State-level antitrust action as a remaining avenue
The right to repair as an easy entry point
Trump's "Liberation Day" tariffs as a paradoxical opportunity
Tech as geopolitical weapon—Microsoft accounts bricked for a Brazilian judge who sentenced Bolsonaro; the ICC chief prosecutor's accounts shut down after the Netanyahu arrest warrant
The vision for open, auditable, sovereign digital public goods to replace the enshittified American Internet—run internationally, controlled locally

… and much more.

Links

Episode Transcript
Enshittification: Why Everything Suddenly Got Worse and What to Do About It, by Cory Doctorow
The Reverse Centaur's Guide to Life After AI: How to Think About Artificial Intelligence Before It's Too Late, by Cory Doctorow
JRS EP 198 - Cory Doctorow on Seizing the Means of Computation
JRS EP4 - Cory Doctorow – “Radicalized,” Race and Resilience
Radicalized, by Cory Doctorow
The Internet Con, by Cory Doctorow
The Bezzle, by Cory Doctorow
"TikTok's enshittification," by Cory Doctorow
Pluralistic.net
Electronic Frontier Foundation

Bio

Cory Doctorow is a science fiction author, activist, and journalist. He is the author of many books, including the forthcoming The Reverse Centaur's Guide to Life After AI: How to Think About Artificial Intelligence Before It's Too Late. Previous works include Enshittification: Why Everything Suddenly Got Worse and What to Do About It, the subject of this interview; The Internet Con: How to Seize the Means of Computation, a Big Tech disassembly manual; Red Team Blues, a science fiction crime thriller; Chokepoint Capitalism, nonfiction about monopoly and creative labor markets; the Little Brother series for young adults; In Real Life, a graphic novel; and the picture book Poesy the Monster Slayer. In 2020, he was inducted into the Canadian Science Fiction and Fantasy Hall of Fame.

Jim talks with Tyson Yunkaporta—indigenous Australian scholar and author of Sand Talk, one of Jim's top ten favorite books—about his metaphysics and worldview, the ecology of sex and creation, and how to wear rationalist and traditional knowledge frameworks simultaneously.

They discuss:

Jim's editorial endorsement of Sand Talk—"one of the top 10 best books I have ever read"
Tyson's trilogy of books
Humans as a custodial species—sacred carers embedded in nature
Who Tyson is when he wakes from deep sleep
Tyson's experience under general anesthesia—ten thousand years of deep dark oblivion
How Jim shifted Tyson toward rationality and evidence-based thinking
Tyson's reassessment of peer review and collective scientific inquiry as similar to Indigenous processes of collective knowledge-building
Tyson's late initiation into the Apalech clan
The distinction between "knowledge systems" and "knowledge of systems"
Color blindness as a biological advantage in traditional systems knowledge
What's missing in people who haven't gone through full initiation
Men's "belly spirit" (nenwi) and "spirit womb" in the Apalech tradition
Images and ghosts—the shadow spirit as ego, and how infinite self-replication on social media drains the spirit
Tyson's cousin Eric becoming a viral meme and TikTok phenomenon
Forager social operating systems and mechanisms to prevent dominant individuals
Aboriginal law's three core rights
Sex as the center of everything
Tyson's response to Plato's Cave
Dreamtime and songlines as mistranslations
Dreamtime as not an altered state but a continuous orientation
The irony of mutual influence—Tyson becoming a rationalist skeptic partly through Jim; Jim becoming more open to spirit partly through Tyson
The 3D glasses metaphor for wearing Indigenous and rationalist-materialist lenses simultaneously

… and much more.

Links

Episode Transcript
Snake Talk: How the World’s Ancient Serpent Stories Can Guide Us, by Tyson Yunkaporta and Megan Kelleher
Sand Talk: How Indigenous Thinking Can Save the World, by Tyson Yunkaporta
Right Story, Wrong Story, by Tyson Yunkaporta
JRS EP 282 - Tyson Yunkaporta on Indigenous Law, Lore, and Learning
JRS Currents 032 - Tyson Yunkaporta on Spirits, GameB & Protopias
JRS EP 65 - Tyson Yunkaporta on Indigenous Complexity
JRS EP 66 - Tyson Yunkaporta on Indigenous Knowledge
JRS Currents 010 - Tyson Yunkaporta on Humans As Custodial Species
"A Minimum Viable Metaphysics," by Jim Rutt

Bio

Dr. Tyson Yunkaporta is an Aboriginal scholar, founder of the Indigenous Knowledge Systems Lab at Deakin University in Melbourne, and author of Sand Talk; Right Story, Wrong Story; and Snake Talk. His work focuses on applying Indigenous methods of inquiry to resolve complex issues and explore global crises.

Jim talks with Lisa Buckingham—a veteran HR leader at Vialto Partners, US Soccer, Lincoln Financial, and Thomson—about how the LLM era is reshaping hiring and job architecture, and how companies and workers can roll with the changes.

They discuss:

Jim and Lisa's shared history in natural language processing labs thirty years ago—and the contrast with today, where "everybody can be an AI expert"
The kind of people to hire in the age of LLMs: intellectual curiosity, learning agility, and willingness to work differently
"Trust the machine, but always validate"—the principle of embracing AI while maintaining human oversight
COVID as an accelerant of technology adoption
Workforce adoption realities at Vialto—evangelists, pessimists, and the change management challenge
Shark Tank-style internal AI contests as a model for engaging employees with new tools
Why the "future of work" is dead
Programmers and product managers merging roles; job architectures flattening into skills-based, fluid inventories
AI's historical weight—"as pivotal as electricity"—and the limits of anyone's ability to predict machine learning's trajectory
Jim's "what, when" framework and the twin failure modes of AI projects
"Test and learn" as the right posture toward AI transformation, and whose responsibility "what, when" actually is—CEO, CTO, and sales as a coalition
The productivity multiplier for programmers—7–10x gains—and Jim's argument that demand for software could actually increase total programmer headcount
Why sales jobs are probably not highly "AI-able" anytime soon, and what salespeople need to communicate to retain relevance
Lisa's personal use of Claude and Copilot 365
The leveling effect of AI for non-STEM people
Jim's argument (since November 2022) that top liberal arts graduates are the most natural prompt engineers
Lisa's 1999 Georgetown thesis—"Are liberal arts majors the answer to the .com era worker shortage?"—and its uncanny parallel to the 2026 humanities debate
The education paradox: how Lisa's son was banned from using AI in class but required to be an AI expert for his summer internship
The calculator analogy, and whether AI in education follows the same arc
Resistance to the AI voice in writing
Jim's technique for capturing stylistic tendencies with AI
The rising costs of frictional bureaucracy and the unreasonable effectiveness of small teams
What Lisa saw on a recent safari about what AI can't replace, and the choice between evolving and being overtaken
Learning agility as the core HR question—how to handle employees who cannot or will not embrace AI
The shifting meaning of "owning your work"

… and much more.

Links: 

Episode Transcript
Co-Intelligence: Living and Working with AI, by Ethan Mollick
The Elements of Style, by William Strunk Jr. and E.B. White

Bio: 

Lisa M. Buckingham is a globally recognized human resources executive with over twenty-five years of experience leading people, culture, and transformation strategies across complex, mission-driven organizations. As Chief People & Culture Officer for Vialto, she oversees the company’s global people strategy, driving organizational performance and advancing a culture of inclusion and agility that supports Vialto’s purpose of helping people thrive in a global, mobile world.

Jim talks with Peter Wang—chief AI officer, cofounder and CEO of Anaconda, board member of the Center for Humane Technology, and founder of the Austin STEM Center—about Robert Pirsig's metaphysics of quality, how modernity encourages defection, and a secular conception of the sacred.

They discuss:



Peter's self-description as "the music in a violin that can kind of hear itself"
The "Peter Wang-shaped hole in the universe" thought experiment
Subject-object Cartesian dualism as a false alienation
Minimum viable metaphysics & atheistic agnosticism
Religion as an evolutionary emergent coherence mechanism for human collectives
Figure and ground as a metaphysical lens—the anonymous soil that allows religion to sprout
The Unix fortune "Man was invented by water to carry itself uphill" & Peter's teleology origin story
Process metaphysics & presentism—"we're not going anywhere, we're becoming someone"
Pirsig's metaphysics of quality & the four strata of static patterns of value
The intellectual plane vs. the social plane & Ken Wilber's pre-trans fallacy
Defection within collaborative groups as the dynamic all human social systems try to constrain
"Death from a Distance"—throwing, beta coalitions & the emergence of a middle class of power
Modernity's shrinking locus of care & the collapse of embedded social context
The agglomeration of defectors & how fluid capital enables sociopathic hoarding
Money-on-money return as today's dominant pruning rule
Joint attention as a scarce collective resource & social media's perforation of shared intersubjective infrastructure
Human agency & "micro-abdications" as the aggregate source of Moloch / Game A
The augmented currency thought experiment—metering human thriving alongside financial returns
Broken collective sense-making & the search for dynamic, adaptable values
Peter's secular conception of the sacred—the "eternal golden braid of humanity"
"Ofness"—holding both distinctness and belonging to the world



... and much more.

Links:


Episode Transcript
JRS EP 278 Peter Wang on AI, Copyright, and the Future of Intelligence
JRS Currents 092: Peter Wang on The Meaning Crisis and Consequentiality
JRS EP 16 Anaconda CTO Peter Wang on The Distributed Internet
"The Silent Sky and the Test Ahead," by Jim Rutt
"A Minimum Viable Metaphysics," by Jim Rutt
Zen and the Art of Motorcycle Maintenance, by Robert M. Pirsig
Lila: An Inquiry into Morals, by Robert M. Pirsig
Chaos: Making a New Science, by James Gleick
Death from a Distance and the Birth of a Humane Universe, by Paul M. Bingham and Joanne Souza
The Selfish Gene, by Richard Dawkins
Center for Humane Technology

Peter Wang is the Chief AI and Innovation Officer and Co-founder of Anaconda. Peter leads Anaconda’s AI Incubator, which focuses on advancing core Python technologies and developing new frontiers in open-source AI and machine learning, especially in the areas of edge computing, data privacy, and decentralized computing.

Jim talks with recurring guest and deep systems thinker Jordan Hall about the scaffolding of his worldview. They discuss the waking-up scenario as a window into consciousness and personal identity, Jordan's phenomenology of waking and the "latent potential of all possible memory," the soul as the binding of finite and infinite, Jim's counter-framing of consciousness as a fusion of perception, interoception, and unconscious memory, the infinite as genuinely real, the Platonic triangle as a concrete example of transcendentals that have no particular location in the causal field, Forrest Landry's distinction between being and existence, knowing with confidence vs. knowing with certainty, Jordan's basic ontological commitment to realism, the incoherence of simulation theory, Jim's "Minimum Viable Metaphysics," the incoherence of unmediated access as the meaning of the word reality, Father Stephen DeYoung's critique of Western substantive essentialism, Bonitta Roy's idea that reality is shareable and participatory, Michael Levin's pragmatic epistemology, how purpose collapses reality to a tractable slice, "begottenness" in Christian metaphysics and the generativity of relationships, Jordan's onto-epistemology as the register before ontology and epistemology are distinguishable, Jordan's recent adoption of "smorthodox" Christianity, the phenomenology of waking as evidence that space-time is secondary, prioritizing meaningfulness over causation as a metaphysical commitment, Updike as "still alive" in the realization of his work, the Greek preoccupation with legacy and honor after death, Eric Weinstein's desire for Einsteinian legacy as a category error, love as the real currency of legacy, the Mark Twain reading as an example of a soul genuinely present in a room, Jim's father as an ongoing example of realization twenty-six years after his death, noticing a parent's turn of phrase in oneself, the sweetness of impermanence, the good vs. abusive father and different relationships to a parent's memory, values and virtues as real, the distinction between courage and bravery, culture as the progressive discovery and embodiment of virtue space, the crab-in-the-bucket problem, fallenness as local optimization, and much more.

Episode Transcript
deepcode (Jordan's Substack)
JRS EP 284 Jordan Hall on AI, the Commons, and the Church
JRS EP 255 Is God Real? (with Jordan Hall)
JRS EP 223 Jordan Hall on Cities, Civiums, and Becoming Christian
JRS EP 170 John Vervaeke and Jordan Hall on The Religion That Is Not a Religion
JRS EP26 Jordan Hall on the Game B Emergence
JRS EP8 Jordan "Greenhall" Hall and Game B
"Minimum Viable Metaphysics", by Jim Rutt
JRS EP 341 Worldviews: Bonnitta Roy on Post-Formal Actors, Stage Theory, and the Character Void in Leadership

Jordan Hall is the Co-founder and Executive Chairman of the Neurohacker Collective. He is now in his 18th year of building disruptive technology companies. Jordan’s interests in comics, science fiction, computers, and way too much TV led to a deep dive into contemporary philosophy (particularly the works of Gilles Deleuze and Manuel DeLanda), artificial intelligence and complex systems science, and then, as the Internet was exploding into the world, a few years at Harvard Law School where he spent time with Larry Lessig, Jonathan Zittrain and Cornel West examining the coevolution of human civilization and technology.