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From the article it seems like Jack floundered around a fair amount in his early life. This makes me think his success was a fluke, in the sense that there are

From the article it seems like Jack floundered around a fair amount in his early life. This makes me think his success was a fluke, in the sense that there are many people who are just as determined and talented who don't end up succeeding. Of course, it's quite possible that every successful person's success is a fluke. And for what it's worth, I'm just trying to figure out how much to copy successful people in order to be successful myself--Jack sounds like a great guy and I don't mean to dis him.

axiom 16y ago
If you try once and succeed, you're lucky. If you try 10 times and succeed, that's called hard work.
erikpukinskis 16y ago
My instinct is the opposite. I suspect his floundering is precisely what has made him successful. Particularly in entrepreneurship, a key skill is being able to see opportunities where others don't. The article highlights the fact that before Square, the banks said regular folks aren't allowed to accept credit card payments. Jack looked at that and asked "why not?" In the same way that with Twitter, conventional wisdom was "No one cares that you are at Dolores Park" and Jack asked "why not?" If you only participate in one community, and you only hone one skill, you will only be able to toe the party line. It's only when you are able to wear your different hats in the places where they don't belong that you can really push boundaries as an entrepreneur. Larry and Sergei were wearing their Academic hats while doing engineering. Steve Jobs was wearing his typography hat while designing an operating system, at a time when all computers had fixed-width fonts. Where else do these kinds of breakthroughs come besides "floundering"?
- skrish 16y ago
  Great point. As Steve Jobs mentioned in one of the convocation speeches he delivered: "connecting the dots forward is impossible...but is is very clear looking backwards" - I don't remember the exact text but pretty much what he expressed. Most often it is the ability to see the opportunities while messing with different things that seem interesting at that point of time and THEN running with that one idea seems to be one common theme of several successful entrepreneurs.

axiom 16y ago

If you try once and succeed, you're lucky. If you try 10 times and succeed, that's called hard work.

erikpukinskis 16y ago

My instinct is the opposite. I suspect his floundering is precisely what has made him successful. Particularly in entrepreneurship, a key skill is being able to see opportunities where others don't. The article highlights the fact that before Square, the banks said regular folks aren't allowed to accept credit card payments. Jack looked at that and asked "why not?" In the same way that with Twitter, conventional wisdom was "No one cares that you are at Dolores Park" and Jack asked "why not?" If you only participate in one community, and you only hone one skill, you will only be able to toe the party line. It's only when you are able to wear your different hats in the places where they don't belong that you can really push boundaries as an entrepreneur. Larry and Sergei were wearing their Academic hats while doing engineering. Steve Jobs was wearing his typography hat while designing an operating system, at a time when all computers had fixed-width fonts. Where else do these kinds of breakthroughs come besides "floundering"?

skrish 16y ago
Great point. As Steve Jobs mentioned in one of the convocation speeches he delivered: "connecting the dots forward is impossible...but is is very clear looking backwards" - I don't remember the exact text but pretty much what he expressed. Most often it is the ability to see the opportunities while messing with different things that seem interesting at that point of time and THEN running with that one idea seems to be one common theme of several successful entrepreneurs.