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Uber has an information advantage, a computational advantage. There's massive structural advantages to the player who's smartest about how to deploy cars, where to deploy cars, how to adjust pricing dynamics, how to ensure supply of drivers - the party that understands best the behavior of riders.

Ride-sharing is one of the biggest math problems that's ever been approached, that's ever been attempted to be solved.

I have one of the self-driving Teslas; it drives itself periodically. It's a marvel of science, but it's still frightening. I think we've got a while before regulators and the general public wrap their heads around the path that will lead to the ubiquity of driverless cars. There's no doubt Uber will be a leader in that space.

When I first agreed to do 'Shark Tank,' they asked me to wear a suit, and I was just like, 'No. I can't. It'll end my career.'

A great idea can't succeed without a great operator. But rarely can a great operator squeak by with a bad idea. So, as pithy as it sounds to say 'It's all about the people,' I only invest when I think I have found the right team for the right business.

Travis Kalanick was and is the perfect person to lead Uber, a product I knew from day one was going to be big.

Effective storytelling is the key to getting users to understand and adopt your product as well as imperative to recruiting team members and future investors.

'Shark Tank' has been a sincere joy. As our traditional venture-backed companies get bigger, the investing side tends to get more political and complicated. 'Shark Tank' takes me back to my early days working with ambitious founders in their earliest and scrappiest days. The show reminds me of what I deeply love about this business.

I've definitely sold some Twitter shares. I don't own as many as I used to, because I'm not an idiot, but I own more than I should because I'm an idiot.

I literally should go to a Twitter therapist, just the 10 years of stress and trauma with this company.

They are desperate for surrogates to get behind Trump, and they can't find anyone who has actually had genuine success who is willing to stand behind him. That is because he is all smoke and mirrors. We know he doesn't have all the money he claims he has.

I want broadband to grow, more mobile devices available, particularly in underprivileged communities. I want STEM education to go ahead and fund the next generation of engineers.

I wasn't put on the Earth only to be an investor. That wasn't my only thing in life. The problem is that as you get good at something and you keep getting better at something, more and more people just know you as that, and they have you in that box.

When I was 20 years old, I was living in Ireland, going to school in Cork. There was this girl in my film class that I was kind of flirting with. We had this notebook that we passed back and forth. We would write 10 questions and then pass it back while we were supposedly paying attention.

There I was - 20 years old, living in Ireland, and I'd never heard the word 'venture capitalist.' But I'd said that I wanted a job that involved a lot of negotiation, a lot of yelling at people on the phone, and for it to be high-risk, high-reward.

The United States... is the greatest nation on Earth, and I believe there are things that make us special - and one is this grand democratic experiment.

When I posted the 8,500 words on what Twitter should be, I wanted to make clear this wasn't a vision statement for the future. What was so frustrating about it is that's what it should've been already.

There is a greed case for diversity. Diverse perspectives bring us into markets we didn't know existed.

Twitter is 'Black Twitter'. That is a brand that 'Black Twitter' has given itself. That's where the hashtags happen... where the excitement is.

American computer science grads often have very little exposure to the human condition. They've rarely had manual labor or service jobs. They grow up in a bubble of privilege lulled into thinking this country is a true meritocracy.

A deep appreciation for politics comes from empathy for our fellow human beings and their diverse paths through life.

When you're fundraising for a venture fund, you're supposed to not talk.

2009 was one of the busiest, most insane, stressful periods in my entire career. I was raising a bunch of money, buying a bunch of Twitter. I saw my friend fired as CEO of Twitter. Uber was growing like a weed. As these companies get bigger and bigger, there's more and more friction. Being public was the last thing I wanted to do at the time.

I spent a lot of time learning how to define myself internally rather than externally. I learned how to care less about external validation. I think that's given me a renewed confidence in speaking out loud. I kind of don't care what people think about me. I feel a lot more confident in saying what I believe.

Work at a place like Google for awhile: if you do an interview and you say all the right things, no one really cares. But the day you say the wrong sentence, it's attributed to 'Senior Google Executive,' and the stock moves, and everybody hates you.

I think our election proved to us that 'billionaire' is an incredibly magical word in our language in that people just defer to it. Donald Trump is not a billionaire, but he knew it was vital for him to be perceived as one.

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