Question I get fairly frequently: is it still possible to make money in startups or as a creator on the Internet, or has the opportunity passed or been sewed up by AppAmaGooBookSoft or similar? The answer to this: unambiguously, yes, opportunities are changing but *better.*
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You should prefer being a founder in 2019 to being in the same position in 2009 or 1999. The larger market, much better ecosystem, existence of mobile, better OSS, etc swamp the impact of year to year availability of capital or increased competition or what have you.
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Now given that you may not have a time machine available and aren’t choosing between those periods but are actually choosing “start now” or “start later” I think it’s a nuanced conversation but in general I’d be in the “bias towards earlier” camp.
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The nuance is mostly about your relative rate of skill/network/etc growth and leverage available at whatever the thing you’re doing right now versus the likely higher-but-different skill growth and very variable leverage available from running something.
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(When Stripe does employee surveys there is a question “So you ever think about leaving?” And my answer is always “I know that this answer will be coded as negative but dispute the basis for that because if I didn’t think of it daily I’d be rubbish at this job.”)
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Replying to @patio11
Do you think about leaving? Or do you think about being somewhere else? Very different things IMHO -- I often think about working at Stripe but I very rarely think about leaving Tarsnap.
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Replying to @cperciva
Mostly I think about starting software companies, which is sort of an occupational hazard of a) having done that and b) being professionally involved in reducing all the barriers to starting software companies while c) talking to lots of people doing lots of interesting software.
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Also knowing about upcoming products like the thing that would do the thing that I previously wept tears of blood over and thinking "Darn it I now want to do a software company specifically so that I never have to do that thing ever again because of the new feature."
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