Vaughn Tan is an innovation expert who had never built software. He now builds his own tools, and he argues the software worth building is the boring kind: very small, does one dull job, made for you and maybe three other people. He is the author of The Uncertainty Mindset and executive director of Tangent, a zero to one incubator in Singapore.

in this conversation we cover:

- why the most useful software is the boring, tiny kind, and why almost nobody builds it
- two live demos, a task tracker that reads his own message channels and a receipts bot he built in four and a half hours
- how he decides which work goes to a machine and which work he refuses to hand over
- why he uses the best models to build a tool and then the cheapest, dumbest ones to run it
- the case against chasing venture capital in a region that is not venture capital scale
- the four kinds of meaning making he says machines cannot do

our guest: Vaughn Tan, author of The Uncertainty Mindset and executive director of Tangent.

chapters

0:00 cold open
5:22 what restaurant kitchens teach about innovation teams
7:04 a sociologist who had never built software
11:06 framework for clarity of thought in building
14:49 why do boring tiny tools matter?
18:24 live demo: the tracker that reads your messages
24:26 situated software, built for a handful of people
29:50 live demo: receipts to expense reports on telegram
36:36 he built this expense tool in four and a half hours
39:52 boring tiny tools as a model for southeast asia
43:58 four ways ai changes a business model
48:04 why SMEs cannot get digital transformation to work
52:01 get to free cash flow positive, fast
58:46 why a nonprofit?
1:03:49 four kinds of meaning making
1:09:59 quickfire round

what Vaughn asked for, if you want to be useful

- if you know someone who wants to start something small and unglamorous, and every programme they meet keeps pushing them to be more ambitious, send them to Tangent
- if you work in an SME, or with SMEs, and want to help them go from zero to one, get in touch
- his writing: https://vaughntan.org
- Tangent: https://tangent.org.sg

the research behind this conversation

vaughn restates five of his own essays and his book on tape:

- The Uncertainty Mindset (2020), Columbia University Press: https://cup.columbia.edu/book/the-uncertainty-mindset/9780231196895/
- Boring Tiny Tools (2025): https://vaughntan.org/boringtinytools
- A Boring Tiny Tooling paradigm (2026): https://vaughntan.org/bttparadigm
- Singapore needs a technology Mittelstand (2026): https://vaughntan.org/techmittelstand
- The Tangent thesis (2026): https://vaughntan.org/tangentlogic
- AI's meaning-making problem (2024): https://uncertaintymindset.substack.com/p/ai-meaningmaking

not covered in the episode, if you want to go deeper: What makes us human (for now)? https://vaughntan.org/what-makes-us-human-for-now and his full meaning making series, fifteen essays in order: https://vaughntan.org/meaningmakingai

books mentioned

- Seeing Is Forgetting the Name of the Thing One Sees, Lawrence Weschler, on the artist Robert Irwin
- For the Time Being, Annie Dillard
- The Uncertainty Mindset, Vaughn Tan

connect with us

- Eric: https://www.linkedin.com/in/erictisme/
- Yaohong: https://www.linkedin.com/in/yaohongchng/
- Substack: https://substack.com/@coderiff
- email: code.riffs.ai@gmail.com

Code Riff, interviews with leading minds and practitioners in AI so you can flourish and have fun with ai.