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The great thing about writing jokes for President Obama is that he is not afraid to tell jokes that are actually funny - and not just funny for a politician.
There is that definition of leadership that says, 'Leadership is convincing people to do things that they otherwise wouldn't have done because you've made them believe it's the right thing to do.' And a great speech can do that.
A great speech can make you remember something about what you believe, about who you are, about who you want to be. It's rare when that kind of thing happens. But it is important, and it is real.
Because the speech is an argument, and a great speech makes an argument well, the act of making that argument is a really important part of how the policy process coalesces and solidifies both for the candidate and also the people serving that candidate.
Republicans paint everything that Democrats have been for as socialism, too far to the left, as extreme, and it didn't matter how moderated it was; it didn't matter that Obamacare started out as a compromise. You might as well say what you're actually for and show what you really are.
People say that making money in the content-media game is hard, and that is just, like, not my experience. It's super-confusing, 'cause everyone's like, 'Oh, how are you going to monetize?' It's easy: just start talking, and then money rolls in.
You look at what animates Democratic voters; you look at what animates Democratic politicians: it's health care. It's increasingly climate. It is wages and economic issues. It's issues around reproductive freedom and criminal justice reform and inequality.
Every technology company should have a red button somewhere in the headquarters where, if they realize they've caused more societal harm than they expected and done more harm than good, they press the button, and the company dissolves instantly.
Little things had to go wrong for Donald Trump to become president: Comey, emails, all that stuff. Big things did make Trump possible. Big, cultural, political, economic forces opened the door to someone like Trump.
Nationalism is not that hard. It's not that hard to incite people against another, and it's also - and this is the harder thing: Democrats have, and the challenge we have all the time, is we believe in governing and governance and trying to find middle ground.
If you can make someone laugh about something that your opponent or your opposition thinks, that means you've done a really good job of highlighting what's wrong with their argument or their position.
Most of my time at the White House, I wrote very unfunny speeches, but every year, I would work on the correspondents' dinner, which was a reminder of this other kind of writing that I loved to do.
The problem with taking venture capital is if you take $5m from someone, it may feel great; you may feel like they're validating your business model. But they're giving $5m out to 20 different people, hoping one of them will be a hit. They don't really care if it's you.
When I started Shutterstock, I tried to get people access to big events. It's very hard to keep up, to publish them quick, and to get the right photographers.
Business is a string of seemingly impossible problems looking for solutions. Each problem you solve creates a new barrier to entry for your next competitor.