“Jack’s biggest insights have nothing to do with technology,” says Greg Kidd. “His insights are always social first. It’s always a democratization machine."
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.
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"?
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.
When I was reading up on Twitter's history, I think Evan Williams had actually told all the staff to take some time (a day?) to come up with ideas for a new direction, and Dorsey suggested Twitter
"Dorsey talks about how Square must be “pixel-perfect,” and staffers tell stories about him agonizing over the exact location and thickness of a line on e-mailed receipts."
And it shows. The first thing I noticed after installing Square was the amazing experience - the design is incredibly polished and it affects the whole feel of the app.
Not 'relaunch' – though sometimes that happens with new features, promotions, or positioning, and is perfectly legitimate.
Launch new products and services to implement the big vision the article discusses. Launch to wide adoption. Launch into the public consciousness.
The first-time-launch of Square's first-version two years ago is obviously not what the writer meant, so why quibble based on an extremely literal interpretation?
If there are multiple equally-good ways to interpret human language, locking onto the one interpretation that's false, to the exclusion of the others that are true, is a distracting digression. Language is not unforgiving, rigorous, deterministic code.
Most people read such articles and come away aspiring to be more like the person described in it. What Jack Dorsey has done is amazing. It shows what's possible when someone is really driven.
I worry about how Jack feels. Is this a happy, content guy? It's certainly possible, but I thought I'd offer a slightly different perspective, based on the work I've done with people like this.
The impression from the outside is that they are on top of the world. The private story is often very different. Usually there is a huge drive at play in order to compensate for something else that is lacking inside.
You can look at it this way: One would get the impression that this person is extremely content because he is starting the biggest companies, driving a BMW, wearing the latest and best Prada clothes and Rolex watches. The implication is that by having, doing, and being the best, that person feels best internally. But if you needed all that in order to feel good, then the other 99.999% of the world would have to feel absolutely miserable. This is where the logic of the implication breaks down, because that is simply not the case.
The other way to see it is that one success is never enough. Neither are two. Or three, or four. The sense of having 'arrived' (finally being satisfied, approved of, secure) never comes. Even if the current endeavor becomes the biggest success, as soon as it's checked off, so to speak, a big sense of disappointment will follow, which will re-create the need to prove it again. So here too, it becomes clear that the external successes have almost nothing to do with how the person feels.
Why I'm in total agreement with you that happiness does not arrive in the shape of a Vanity Fair article and 300 million dollars, I don't nesscessarily agree that their drive is because they're lacking something or have Great Inner Pain(TM).
I have a great driving force that I suspect many people here share. Making things. I NEED to make things. Not want, or would like to, or enjoy, I NEED to. I wake up and start thinking about what I can make today, I do chores and I'm thinking about how quickly I can get them done so I can make things.
There's no motivation to make things for a reason, just that I have to, like a clock has to tell time and a fridge has to keep things cold... It's my raison d'être in life. Just like those things, if I'm not making things I'm broken.
I'm building a few things because I want other people to notice them, to use them, because the more something is used the more made it is, the more worthwhile forming ether into substance was. So gradually I'm coming to need to make things other people want, and this NEED is what drives me, what makes me happy.
This reminds me of what seemed to be the fundamental misunderstanding of The Social Network. Zuckerberg himself commented that he didn't build Facebook to get into the exclusive clubs or achieve fame, power, or money... he just wanted to make Facebook.
Many non-makers seem constitutionally incapable of understanding that someone might want to make something just for the thrill of seeing it come into being.
And as a maker, I have a hard time seeing how that could be a hard concept to grasp.
IMO, if I were in Jake's shoes - I'd be able to look back at what I had BUILT; Twitter, Square, and be content in those accomplishments.
But that doesn't mean "OK, done here - good game." -- Everything I build I see as a stepping stone to the next thing I am working on, that everything prior serves as foundational experience from which to build upon.
Even though I am not a developer, I am a builder. I design systems and networks and datacenters and hospitals -- I am not the ONLY designer/builder that works on these projects, but I can see my contribution clearly. And I am satisfied with my ability, and driven to add more value at every opportunity.
I haven't made 300 million yet, but I keep on moving. Keep on going, no matter what.
Finally, I try to learn from the experiences of others - avoid their mistakes, emulate their wisdom.
I donno, but being "content" is the last thing I expect to find in entrepreneurs. And as far as happiness goes, doesn't it largely depend on what yard stick you're using to measure it?
I am not saying they don't matter. But because of their subjective nature, it is hard to really consider the role of happiness and "contentness" in such situations.
