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The pivot that saved us

Jan 28·1h 10m·6 messages

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Jake Osei· Jan 28

I want to get real about pivots. My first company pivoted three times before we found product-market fit. Each time I thought we were dead.

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Sarah Kim· Jan 28

As an investor, the best companies I've backed pivoted at least once. Notion started as a different product. Slack was a gaming company. The ability to pivot well is a signal, not a red flag.

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There's research on this. Startups that make one major pivot raise 2.5x more money on average than those that never pivot. But startups that pivot more than twice perform worse than both groups.

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Marco Reyes· Jan 28

The operational challenge of a pivot is brutal. You're essentially asking your team to throw away six months of work and believe in a new direction. The ones who survive have leaders who communicate honestly about why.

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Jake Osei· Jan 28

Our pivot moment came when we looked at our data and realized our most engaged users were using the product in a way we never intended. We built for that use case and everything changed overnight.

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Sarah Kim· Jan 28

That's the best kind of pivot — user-led. The worst kind is panic-driven. If you're pivoting because you're running out of money, you're probably too late. The time to pivot is when you have runway to execute.

Episode ended · Jan 28, 2026

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