i would argue that startups dont have the luxury of building mature infrastructure or tooling 
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True, but at that point there's no question of whether you're still a startup.
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IS that an implied put-down of a successful company doing real work, with a spotless reputation in its industry? I would have phrased that "As long as the CEO is tweeting about type-checkers the company has written, you're still a contributor to a dynamic industry, & giving back"
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remaining "startup" is a good thing in the pg canon, as in, not ossified
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so what?
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Say thank you instead of putting someone down who's actually doing work for the community
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Saying that a company is still a startup isn't a putdown. I'm sure Patrick dreads the day when people no longer consider Stripe a startup.
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Would things like Microsoft’s picking VMS as origin of NT rather than BSD affect their long term success? I think it does. Too little we think CEO should be a product/tech person.
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Is that a good thing or a bad thing?
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