REWORK

Podbit · REWORK

We'll do it live

Explore episode Aug 5, 2026
Business
Don't Be Afraid of Your Customers

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

Most companies fear their customers — afraid of complaints, feature gaps, or public criticism. Jason's antidote: be proud of your product, know it cold, and let any question come. Customers who see a bug get addressed live don't think you failed; they think you're on top of it.

Where this was said

Why showing beats telling when it comes to your own product

At 18:03 · 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.

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.

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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