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In an IT lead world, incumbents generally win because they have the existing relationship with the IT organization.

Aaron Levie

I have a lot of faults. I often interrupt in meetings. I talk too loud. I talk too fast.
AARON LEVIE

Fast Fault Loud Meeting Talk
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

Begin Black Coffee Cup Hand Workday
The IT model of the enterprise has become a lot more user lead.
AARON LEVIE

Building Enterprise IT Lead Model
The chance of failure is almost always better than the guarantee of never knowing.
AARON LEVIE

Always Chance Failure Guarantee Know Knowing
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
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
There’s a lot of pride that business owners have. It’s actually really critical that pride and ownership extends to everyone in the organization. I think of everyone is in the same boat in driving the company forward.
AARON LEVIE

Extend Organization Ownership Pride Thinking
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
Look for new enabling technologies that create a wide gap between how things have been done and how they can be done.
AARON LEVIE

Done Enable Look Technology
The benefit to building a startup is that customers don’t have the same kind of friction when they adopt new technology.
AARON LEVIE

Adopt Benefits Customer Friction Kind Technology
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’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
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
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
Jeff Bezos is opening a retail store and owns a newspaper. Turns out everything we thought about the Internet is wrong.
AARON LEVIE

Internet Newspaper Retail Store Wrong
Companies have never won. You’re always either fighting for survival, or fighting for relevance.
AARON LEVIE

Entrepreneur Fighting Relevance Survival

In an IT lead world, incumbents generally win because they have the existing relationship with the IT organization.

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In an IT lead world, incumbents generally win because they have the existing relationship with the IT organization.

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