REWORK

Snapshot · REWORK

We'll do it live

Explore episode Aug 5, 2026
Technology
DHH's first Rails demo 20 years ago

We'll do it live · Aug 5, 2026

David's landmark Rails presentation 20 years ago was built around showing everything Rails removed — the 'negative space' of unnecessary toil — rather than what it added.

Where this was said

Why showing beats telling when it comes to your own product

At 12:21 · chapter starts 7:47

David unpacks why the live format is irreplaceable: most expertise is tacit, embedded so deeply in practice that you can't articulate it even if you try. Written guides and polished videos can't capture it — it has to emerge in the spontaneous moment of showing someone something in real time. He draws an analogy to pair programming: sitting next to a colleague as they work, you pick up tools, techniques, and mental models you'd never learn from documentation. David applies the same logic to university teaching — the best educators don't fully pre-script their lessons because the magic happens in live interaction with the audience. Jason then explains the deliberate choice not to share session recordings: showing up live is the point, and that exclusivity preserves the format's value. He also notes the unexpected benefit of using 37signals' real account — it forces him into corners of the product he rarely visits personally, keeping him sharp and revealing UX rough edges that daily use glazes over.

Business
Demos Make You a Harsher Judge of Your Own Product

We'll do it live · Aug 5, 2026 Business

There's a different part of your brain at work when you're showing something to a real audience. You stop being forgiving. Jason regularly spots UX issues during live sessions that he'd gloss over in daily use — because showing someone else forces you to see through fresh eyes.

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