“Startups live at the intersection of existential crisis and everything going perfectly great.”

You want to find the really crazy but still somewhat reasonable outliers within the customer ecosystem.

You intentionally start small, because you will not be able to compete with an incumbent… because the incumbent is always going to go for the full solution.

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

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.

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.

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

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.

The 10% between 90% done to 100% done takes most of the time, causes most of the stress, but is all of the value.

Jeff Bezos is opening a retail store and owns a newspaper. Turns out everything we thought about the Internet is wrong.

Modularize, don’t customize. Build a platform as opposed to building all of the custom technology and custom vertical experiences.

We’re going from a world of customized software to standardized platforms.

Why we do what we do: that moment when you get to see the future on your computer screen before the rest of the world.

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

If you don’t go to every level of your company, you distance yourself from the marketplace and from your people.

In a user lead model, users are bringing in their own technology… and you can build software then, around the user.

You can keep ‘consumer’ DNA at the center of your product. That will always mean that adoption is easier.

The environmental crisis is a signal of this approaching catastrophe.

Most men are reasonably useful in a crisis. The difficulty lies in convincing them that the situation has reached a critical point

to have a crisis, and act upon it, is one thing. To dwell in perpetual crisis is another.

Crisis precedes transformation.

Our world is in crisis because of the absence of consciousness

I love business. I love helping urban communities grow. I love putting people to work of color. I love making sure – like right now the whole mortgage crisis, I want to help people get back into their homes.

Capitalism does live by crises and booms, just as a human being lives by inhaling and exhaling.

In my first few years of being in New York, I had a major identity crisis because I’d never stayed in one place for so long.