I'm famously humble.

Making '1600 Penn' was really fun, and I learned a lot.

'Pod Save America' will be a kingmaker.

One thing that is for certain is that there are tens of millions of people who are deeply unsatisfied with the way they get their political news.

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.

Humor is a way of saying we're all seeing the same ridiculous, absurd, infuriating things together.

I'm motivated by a bottomless well of anger. It's a joke, but I don't think I don't mean it.

I had never really planned on being a speechwriter.

It's certainly true that presidents have confidantes who rise above what you would call just staff.

There's only so much mistrust we can take before things get much worse.

It's always been a dream of mine to write comedy and be creative.

I would like to be able to write in my own voice.

I personally believe that Donald Trump being elected president is a national emergency and a crisis that stems from a great cascade of failures.

There is an incredible appetite out there for in-depth, high-level conversations about what's going on.

We try to talk when the microphones are on the same way we would when the microphones are off.

I spent three years working at the White House and wanted to do something that wasn't about passing bills and resolutions.

I will never apologize for selective editing to make myself look better.

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.

I could have continued being a speechwriter for as long as I wanted.

'1600 Penn' was a hit. It's 2018. Anything you want can be true.

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.

As we continue to grow, the question is, how do you keep the company as innovative as it was 15 employees ago?

We sell to businesses who sell other stuff, so we're just going to concentrate on doing that.

Just as we are enhancing the customer side of our marketplace, we are also looking for ways to increase our contributor expense.

The growing demand for content across our platform delivers bigger payouts to our contributor base and encourages them to upload fresh content to Shutterstock, further facilitating the network effect of our business.

Any business that is trying to sell something should be willing to spend a couple dollars for a stock photo to not have ads in it and not distract the user from using the product they're trying to sell.

We realized we had high-volume marketplace as a platform. Anyone can come in and buy with a subscription.

Shutterstock has evolved from an image-based marketplace for small businesses to a much broader platform, with a large and expanding addressable market opportunity.

We recognized early on that media consumption was evolving and customers were looking for moving images to include as part of their advertising campaigns, website designs and corporate presentations.

I like San Francisco, but I don't think I'd want to work in Palo Alto. It seems like a pretty rough commute. In many ways, I think New York has a lot of things the West Coast doesn't have.

Was I going to start companies outside of Shutterstock or inside? Going public kind of meant I was going to start them inside, and I kind of thought this through and decided that if I was going to do that, I was going to continue to operate Shutterstock like it was an incubator of startups.

Problems are good. Impossible problems are even better.

I believe anything has to be possible. You have to be able to face any problem that comes along and unravel it into a solution.

Equally important to having the right content is providing the proper tools for the users so they can quickly find the images and videos they need.

There aren't enough people out there that are becoming experts in technology as technology moves.

Rex has photographers around the world - it's a higher touch business: there are a lot of relationships involved. If you throw an event, there are certain photographers you've worked with before and you want there.

I started Shutterstock out of my own need. I'd previously created a few software companies, and each time, I struggled to find affordable images to use on my websites.

In high school, I used to teach guitar and fix computers by the hour. I was looking for some way to make some cash, so I actually learned how to play guitar in order to try to teach it.

While the scale of our library is certainly attractive to our users, equally important is the quality of the content we provide and our state-of-the-art processing operation that vets every single piece of content that's submitted to ensure only the most suitable content is included.

We look for the scrappy entrepreneur: the kind of person who will get things done without looking to spend money right away.

If people want to code, and they want to be entrepreneurs, there's opportunities for them to do that.

As I saw more and more people buying the images that were happy buyers, and people selling the images that were happy with how the market was pricing them, I started to get the sense this could be the go-to place for businesses to get the images they need.

Rex is 60 years old with 13 million images and 10 million in archive. It's the first time we've had a historic archive to work with, which is super interesting.

The best thing is to go public only when you're absolutely sure that's the right move for the company. And in order to make sure that is the case, you need to have as much control over the company as possible, which means not giving up control early on.

Some people are serial entrepreneurs and want to just move on to the next thing. They just want to clean the slate and start from scratch. I feel that sometimes, too, and the way that we do that here is we build things inside Shutterstock: we launch new products all the time.

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