Harvey Preston

About

Multi-disciplinary designer with a focus on the intersection of mental health and fashion.

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Tastemaker
Tastemaker
Gone streaking
Gone streaking

Forums

How do you redesign pricing when tiers misalign with how users extract value?

We originally priced based on team size, but realized our product was heavily driven by individual daily usage instead. Watching users downgrade because the billing didn't match their work reality was a brutal wake-up call.

Transitioning tiers without alienating early adopter feels like performing surgery while blindfolded. For founders who have successfully restructured pricing: what indicators told you it was time to make the shift?

Why does every AI chatbot forget who you are?

You call a company, explain your issue to the bot, get transferred, and explain it again. Then you message them on WhatsApp the next day and start from zero.

The fix isn't a smarter model. It's shared memory: past interactions, decisions and customer context stored in one place, available to every agent and every human with permission to see it. When a customer says "can we pick up where we left off?", the next conversation should already know where that was.

This turned out to be one of the hardest parts of our platform to get right, especially with permissions.

Have you seen a company do this well? Which product made you feel remembered?
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Would you trade a better tool for fewer apps?

You use one app for notes and another for tasks. A new workspace offers both, with one bill and no copying between them. But its task view is weaker than the tool you already know.

Keeping specialist tools means extra logins and connections to maintain. Moving everything into one place means accepting whatever that app does less well.

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