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Retool's CEO circulates an annual 'Crazy Ideas' document for 10x bets

Eeke de Milliano · How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe) · Feb 2, 2023 · at 25:21

Eeke de Milliano, Head of Product at Retool, shares an internal ritual adapted from Stripe to encourage high-upside, non-obvious ideas across the company.

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“Another really neat tradition that we had at Stride, we have a retail now too, is this idea, this thing called crazy ideas. So at the beginning of every year, David will send out a blank Like a blank doc to the org, and it's titled Crazy Ideas, and the prompt is crazy ideas are ideas that we shouldn't obviously do. There's a 90% chance that they make no sense, but in the 10% chance that they do, they will make, you know, a 10 to 100 x difference for the retail business, and then it's just, it's literally just a call, a request for crazy ideas”

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