Readings on digital product
The Shape That Repeats: Networks, Fractals, and the Geometry of Decentralisation
Why the same acentred, self-similar, scale-free structure keeps appearing across mathematics, philosophy, biology, computer science and political theory.
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On the Dangers of Stochastic Parrots: Can Language Models Be Too Big? 🦜
This is the paper that gave the era its metaphor. A large language model, the authors argue, is a "stochastic parrot": a system that recombines linguistic form from its training data according to probabilistic patterns,…
Climbing towards NLU: On Meaning, Form, and Understanding in the Age of Data
This is Searle's Chinese Room rebuilt for the technology in your stack. Bender and Koller distinguish form (the observable signal of language) from meaning (the relation between that signal and communicative intent, grou…
Interviewing Users: How to Uncover Compelling Insights
If the rest of this collection is the argument, Portigal's handbook is the answer. It teaches the actual craft of talking to real people: building rapport, asking open and non-leading questions, sitting in silence, follo…
Alone Together: Why We Expect More from Technology and Less from Each Other
This is Turkle's turn from optimism to alarm. Having spent earlier books celebrating the computer as an evocative object for exploring the self, she spends this one documenting, through years of fieldwork with sociable r…
The Media Equation: How People Treat Computers, Television, and New Media Like Real People and Places
Reeves and Nass proved, in about three dozen tidy experiments, something we would rather not believe about ourselves: people treat computers and media as if they were real people — being polite to them, reciprocating the…
Foucault's Pendulum
Three bored editors feed fragments of occult lore into a computer they call Abulafia and let it generate connections. It obliges — plausible, coherent, endless links between templars and kabbalah and secret history — and…
The Reflective Practitioner: How Professionals Think in Action
Schön demolished the comfortable idea that professional work is applied science — pick the right general technique, apply it to the case. Watching architects, therapists, and engineers actually work, he found something e…
Computer Power and Human Reason: From Judgment to Calculation
The man who built the first convincing chatbot spent the rest of his life warning us not to be fooled by it. Weizenbaum's ELIZA (1966) faked a therapist with a few pattern-matching rules, and he was horrified to watch pe…
Plato's Pharmacy
Derrida's long essay is a forensic reading of a single word. Plato calls writing a pharmakon, and the word means, at once, remedy and poison — an ambivalence Plato's own translators keep quietly resolving, choosing "cure…
His Master's Voice
If Solaris is the mirror rendered as emotion, His Master's Voice is the mirror rendered as epistemology. A vast, brilliant, well-funded team sets out to decode a signal from space, and never manages to confirm they have…
Technological Revolutions and Financial Capital: The Dynamics of Bubbles and Golden Ages
Technological revolutions follow a four-phase pattern: irruption, frenzy, turning point, deployment. Each phase comes with its specific financial dynamic — bubbles in the frenzy, institutional consolidation in the deploy…
The Art of UNIX Programming
Raymond gathers and articulates the design principles that made Unix what it is — modularity, clarity, composition, transparency — and argues they are not Unix trivia but a general ethics of engineering. Read it alongsid…
Coding Freedom: The Ethics and Aesthetics of Hacking
The product of years of anthropological fieldwork inside the Debian community, tracing how free software developers construct an ethics of labour, meritocracy, and legal activism that challenges conventional intellectual…
The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
Horowitz wrote the book for CEOs going through the specific kinds of pain that are not covered in business school — firing executives, laying off staff, competing while nearly insolvent, managing your own psychology unde…
Technologies of distinction for indiscriminate killing: What can the Israeli war on Gaza teach us about the social meaning of AI
Schwarz's central paradox — that a technology of distinction was deployed to produce indiscriminate killing — is more analytically productive than most AI critique because it refuses to locate the problem in error or bia…
The Black Box Society
Pasquale is a legal scholar, and he brings a normative framework that most algorithmic criticism lacks. The book examines three domains where opaque algorithms exercise decisive power: search engines that determine reput…
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The Oracle That Only Repeats: Simulacra of Inquiry from Plato to the LLM
Why interrogating a language model has the form of dialogue and the substance of a shuffled secondary source — and why fieldwork exists to reach what no corpus contains.
The Compass and the Terrain: Readings on the Direction of Digital Products
Essential product management reading list: 30+ annotated books on product leadership, strategy, discovery, and team design — from Drucker, Ohno, and Grove to Cagan, Ries, and Team Topologies.
The Place That Was Named Before It Was Built: Literature, Philosophy, and the Invention of Digital Space
How cyberspace was imagined in fiction, designed by engineers, inhabited by communities, and questioned by philosophers — from Borges to Carr.
The Theory in the Code: A History of the Practice of Building Software
What does it mean to build software well — and who gets to decide? An itinerary through six decades of the craft, from the theoretical foundations that defined programming as an intellectual activity to the ongoing negotiation between the organisation's need for legibility and the builder's need for discretion.
From Coase to AI: Technology, Organizations, and the Frontier Between Compacting and Decentralizing
Why firms exist, why they grew, and how each technological wave redraws their boundaries — from Coase to AI.