Vaughn Tan

tl;dr: I’ve generated or collected ~75k images over the last 20 years and I want to search over the text in them.

tl;dr: Now that AI tools can generate many outputs that look like they were made by humans, we begin to fear that there’s nothing exclusively human left for humans to do.

Meaningmaking is a simple concept but one that is counterintuitively powerful, concrete, and applicable to understanding how we think about work and technology in a world where AI exists.

tl;dr: Organisations say they want innovation but keep killing it.

tl;dr: AI has quietly changed the economics of software.

tl;dr: Tangent is a new incubator in Singapore I’ve just started.

tl;dr: Most people use “AI business” to mean one of two things — building the AI itself, or building products that call AI at runtime.

tl;dr: Content and representation are different things, and re-presentation is different again: selecting from and translating a body of content to produce new artifacts for different audiences and purposes.

tl;dr: The agentic AI field treats the agent as the unit you build and improve.

tl;dr: When you’re matching capabilities to applications — AI tools to roles, research teams to industry sectors, platforms to use cases — the relationship has two properties: how tightly each capability connects to each application, and how many relevant…

tl;dr: Innovation requires uncomfortable unfamiliar work, but people instinctively resist discomfort.

tl;dr: The most important knowledge in any organisation—what makes your work distinctively yours—can’t be written down or taught through training programmes.

tl;dr: Small-medium businesses are missing a huge opportunity because of three imagination failures: they believe digital transformation must be big and disruptive, they haven’t recalibrated software buying for the collapse in software development costs,…

tl;dr: Critical thinking is foundational for making decisions that require subjective judgment.

I’m now incubating and funding AI-informed businesses at Tangent.

For 3 years during Covid, I lived in crumbling houses in depopulated hamlets on two different mountains in the Haute-Loire, one of the departements of France located on the volcanic plateau of the Auvergne.

tl;dr: Online workshops rarely work well, and we keep on doing them because they would be too expensive/infeasible to do in-person.

tl;dr: Why borrowing private sector strategic thinking and values undermines public strategy — and a practical tool for using tradeoffs to develop robust public strategy that serves diverse stakeholders over long time horizons.

tl;dr: Every important decision requires subjective reasoning about objective facts—deciding what matters and why.

tl;dr: I’ve been prototyping an AI tool that uses Socratic mirroring to build a reasoning scaffold that helps users develop stronger arguments.

tl;dr: Students now have access to LLMs that can write essays, but seem to be losing the capacity to think critically.

tl;dr: After over a decade teaching strategy in private and public sector settings, I’ve developed a new public sector strategy course that flips the conventional wisdom.

What if you could experience what it’s like to make decisions when the actions and outcomes available to you are truly uncertain?

Current AI interfaces lull us into thinking we’re talking to something that can make meaningful judgments about what’s valuable.

In June, I ran a workshop with 15 researchers from diverse fields to develop practical, implementable mechanisms for experiencing different types of not-knowing firsthand.

tl;dr: Categories aren’t academic conceits—they’re tools that enable more effective practical action.

tl;dr: Hidden behind an unmarked doorway in Barcelona, two coffee businesses share the same small space — one roasting and selling, the other teaching and tasting — but not at the same time.

This is an overview essay for a series about not-knowing.

tl;dr: I’m looking for — or would like to build — games that operationalise true uncertainty, not just simple risk, to help players become better at making decisions when facing different types of not-knowing.

tl;dr: Current LLMs can’t truly or create new knowledge on their own; but they can help humans do that innovation work more quickly.

tl;dr: A futurist friend recently made an expensive, early exit from the Middle East during a flare-up in the Israel-Iran conflict … then felt embarrassed when the situation de-escalated theatrically.