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Better to be too early and have to try again, than be too late and have to catch up.

Aaron Levie

Companies have never won. You’re always either fighting for survival, or fighting for relevance.
AARON LEVIE

Entrepreneur Fighting Relevance Survival
You’ll learn more in a day talking to customers than a week of brainstorming, a month of watching competitors, or a year of market research.
AARON LEVIE

Competition Customer Research Talking Watch Year
That’s already been tried before only means the first attempt got it wrong.
AARON LEVIE

Attempt First Mean Tried Wrong
Startups live at the intersection of existential crisis and everything going perfectly great.
AARON LEVIE

Crisis Existential Great Perfectly Startup
Innovation in tech favors the naive and the stubborn. If you are too rational you won’t tackle problems that others once failed at.
AARON LEVIE

Favor Innovation Problem Stubborn Tech
If you don’t go to every level of your company, you distance yourself from the marketplace and from your people.
AARON LEVIE

Company Distance Level Marketplace People
I’m obsessed with speed. I’m always asking myself, ‘Why can’t we do things faster? Why can’t it happen more efficiently? Why is this requiring three meetings instead of one?’
AARON LEVIE

Asking Brilliant Fast Obsessed Three
All we’re really doing is repeating technologies that were tried 10, 20, 30 years ago… it’s just that it was too expensive, too unusable, and we didn’t have the enabling technologies to make it possible.
AARON LEVIE

Ago Done Enabling Repeat Technology Year
The product that wins is the one that bridges customers to the future, not the one that requires a giant leap.
AARON LEVIE

Bridge Future Giant Leap Require Winning
When you’re doing something you’re passionate about, stress becomes a featurenot a bug.
AARON LEVIE

Bug Feature Passionate Something Stress
Start with the assumption that the best way to do something is not the way it’s being done right now.
AARON LEVIE

Assumption Best Done Start Way
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
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
We’re enamored with the concept that there’s always a price. But sometimes, your goal is to build a great company, not sell it.
AARON LEVIE

Build Company Concept Enamore Goal Great Sometimes
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
If there could’ve ever been a magical time to build an enterprise software company, now is absolutely that time.
AARON LEVIE

Building Company Enterprise Magical Software Time

Better to be too early and have to try again, than be too late and have to catch up.

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Better to be too early and have to try again, than be too late and have to catch up.

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