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The chance of failure is almost always better than the guarantee of never knowing.

Aaron Levie

Startups often win because it’s easier to see what comes next when you don’t have to worry about maintaining what came last.
AARON LEVIE

Come Easier Last Startup Winning Worry
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
Every single industry is going through a major business model and technology oriented disruption.
AARON LEVIE

Building Business Disruption Model Oriented Technology
Start with something simple and small, then expand over time. If people call it a ‘toy’ you’re definitely onto something.
AARON LEVIE

Definite Expand People Simple Toy
If every customer is using your product “correctly”, you’ll never learn anything interesting about what to do next.
AARON LEVIE

Correct Customer Interest Interesting Next
The IT model of the enterprise has become a lot more user lead.
AARON LEVIE

Building Enterprise IT Lead Model
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
A lot of being productive personally is determined by how you organize your entire business. You can’t separate those two things.
AARON LEVIE

Business Determined Organize Productive Two
The only way to avoid disruption is to constantly do what you would if you were just starting out.
AARON LEVIE

Constant Disruption Out Starting Way
Better to be right about the trend and wrong about the implementation, than the other way around.
AARON LEVIE

Around Better Implementation Right Trend Way Wrong
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
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
In the enterprise you want to start intentionally small.
AARON LEVIE

Building Enterprise Intention Small Want
We’re going from a world of customized software to standardized platforms.
AARON LEVIE

Building Custom Platform Standard World
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
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

The chance of failure is almost always better than the guarantee of never knowing.

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The chance of failure is almost always better than the guarantee of never knowing.

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