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My workday begins around 11 A.M., with a cup of black coffee in each hand. If I had more hands, there would be more coffee.

Aaron Levie

Tip: Take the stodgiest, oldest, slowest moving industry you can find. And build amazing software for it.
AARON LEVIE

Amazing Industry Moving Slow Software Stodgiest
Better to be too early and have to try again, than be too late and have to catch up.
AARON LEVIE

Catch Early Late Too Try Trying
Companies have never won. You’re always either fighting for survival, or fighting for relevance.
AARON LEVIE

Entrepreneur Fighting Relevance Survival
Go after the customers that are working in the future, but haven’t totally lost their minds.
AARON LEVIE

Building Customer Future Lost Mind Working
That’s already been tried before only means the first attempt got it wrong.
AARON LEVIE

Attempt First Mean Tried Wrong
I think I’m the kind of person who would be very difficult to employ – I’m pretty annoying, but driven.
AARON LEVIE

Annoy Driven Kind Thinking Would
Any time where the delta b/w what is possible and how things work today is at its widest, that’s an opportunity to go build new technology.
AARON LEVIE

Delta Opportunity Possible Technology Today Wide
I think bad politics are incredibly dangerous, so it’s important to make sure that people are communicating well. Culture and morale are super important. It’s best to not force it, but let it happen organically and genuinely.
AARON LEVIE

Dangerous Important Incredible People Politics Thinking
In an IT lead world, incumbents generally win because they have the existing relationship with the IT organization.
AARON LEVIE

Incumbent IT Organisation Organization Relationship Winning World
Entrepreneurship: 10% coach, 20% player, 30% cheerleader, 40% waterboy.
AARON LEVIE

Cheerleader Coach Entrepreneur Player Waterboy
I think people are always able to achieve more than they think they can. While that’s cliche, I don’t know if managers think about that enough. You have to set your sights extremely high.
AARON LEVIE

Achieve Cliche People Sight Thinking
Uber is a $3.5 billion lesson in building for how the world *should* work instead of optimizing for how the world *does* work
AARON LEVIE

Billion Doe Instead Optimize Uber World
In a user lead model, users are bringing in their own technology… and you can build software then, around the user.
AARON LEVIE

Bringing Building Lead Model Software Technology
Everything about the enterprise, and then by definition the software the enterprise uses has changed – just in the last 5 years.
AARON LEVIE

Change Definition Enterprise Software Use Year
What happens to the Microsofts, Oracles and IBMs of the world is that when they get big enough, they don’t think they need to bring that same level of focus and energy to the end-user experience.
AARON LEVIE

Energy Focus IBM Microsoft Oracle Thinking World
Sometimes things are the way they are and can’t be changed, other times it’s because no one ever tried. Your job is to find the latter.
AARON LEVIE

Change Jobs Latter Sometime Tried Way

My workday begins around 11 A.M., with a cup of black coffee in each hand. If I had more hands, there would be more coffee.

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My workday begins around 11 A.M., with a cup of black coffee in each hand. If I had more hands, there would be more coffee.

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