ENTREPRENEURSHIP

I built thinkorswim because I was angry. The tools that professional options traders had were not available to retail investors. That was wrong. So I fixed it.

I started a YouTube channel in college about credit cards. I made more from that channel than I would have made from any internship.

Every time I see a new regulation, I think to myself: there goes another business opportunity.

I got fired from Facebook after two weeks for telling them their user metrics were misleading. They went on to become one of the most valuable companies in the world. I went on to bet on Bitcoin.

When something is important enough, you do it even if the odds are not in your favor.

The first step is to establish that something is possible. Then probability will occur.

Failure is an option here. If things are not failing, you are not innovating enough.

I could either watch it happen or be part of it.

I knew that if I failed I wouldn't regret that, but I knew the one thing I might regret is not trying.

Move fast and break things. Unless you are breaking stuff, you are not moving fast enough.

The biggest risk is not taking any risk. In a world that is changing quickly, the only strategy that is guaranteed to fail is not taking risks.

I started the site when I was 19. I did not know what I was doing. Most great things are started by people who do not know what they are doing.

Speed is incredibly important. Whatever you want to do, you have to do it now. Not tomorrow. Now.

Massive action is the cure to all problems.

The difference between a good entrepreneur and a great one is that great ones know their next five moves.

The best time to start a business was yesterday. The second best time is today. Stop planning. Start doing.

The secret to AppSumo's success is not genius. It is that we kept showing up and kept shipping.

If you don't believe in what you're selling, nobody else will either.

I bet on the jockey, not the horse. I can always fix the business. I cannot fix the person.

I don't care about your feelings. I care about your numbers.

Know what you're good at and stop doing everything else.

It doesn't matter how many times you fail. You only have to be right once.

Sweat equity is the most valuable equity there is.

What I've learned is that if you really want to be successful at something, you'll find that you put the time in. You won't just ask somebody if it's a good idea — you'll go figure it out.

The easiest way to make money is to create something of such value that everybody wants it and go out and give it to them.

You don't need permission to start a business. You need a plan, a customer, and the guts to begin.

The best founders are the ones who see the world differently and refuse to accept no for an answer.

Hustle isn't a dirty word. Outworking the competition is a legitimate edge.

Don't optimize for money. Optimize for learning. The money follows.

I failed at my first business at 16 and lost $5,000. Best money I ever spent.

Most people overestimate what they can do in one year and underestimate what they can do in ten.

The fastest way to become wealthy is to build a business. The best way to stay wealthy is to invest.

If we tried to think of a good idea, we wouldn't have been able to think of a good idea. You just have to find the solution for a problem in your own life.

I'm a developer who accidentally became a CEO. Snowboards were the gateway drug.

Arm the rebels. That's what Shopify does. We give superpowers to the little guys.

Life is too short to work at a company that makes something nobody cares about.

I told Cisco we needed to rebuild WebEx from scratch. They said no. So I went and built it myself.

I dropped out of college because I couldn't sit still long enough to finish a degree. Turns out that energy is pretty useful for building a startup.

I dropped out of college at 20 with a Thiel Fellowship and no idea what to build. It took pivoting from drones to flight search to design tools before we found it.

I was rejected by over 100 investors. One literally fell asleep during my pitch. You just keep going. The hundred-and-first meeting is the one that changes everything.

There are 150 million people who wake up every morning and don't want to go to the office. We are going to save those people.

Traffic is driving me nuts. Am going to build a tunnel boring machine and just start digging.

I got kicked out of Facebook and decided to build autonomous weapons for the Pentagon. I'm not sure which job my parents were more confused about.

Our first delivery was pad thai. I drove it myself. The customer tipped $5 and I thought we were rich.

I failed at 20 startups before Instacart. The secret is that each failure taught me what not to build. Instacart was the first thing I actually needed myself.

We didn't win our Harvard business plan competition. The judges said the idea wouldn't work. We built it anyway and Uber surrendered the entire region.

My first app was a total failure. Nobody downloaded it. But I noticed users were saving products obsessively. The collecting behavior was the product.

I retired at 23 and was miserable. Turns out, having nothing to do is the worst thing that can happen to someone who loves building things.

We started because buying Funko Pops on eBay was boring and full of fakes. Live selling fixes both problems — you see the item, you see the seller, and the energy is addictive.

Our professor gave us a B on the business plan for Cloudflare. Most expensive B in Harvard Business School history.

I bootstrapped UiPath from a Bucharest apartment for ten years. Then in three years we went from unknown to a $35 billion company. Patience has a way of compounding.

We sold our last company to Microsoft for $320 million. This time we said let's aim higher. Thirty-two billion higher, as it turned out.

I spent six months taking screenshots to prove our security controls worked. Then I spent another six months doing it again the next year. There had to be a better way.

I got fired from my own company. Most people would have given up. I started a better company six months later. Failure is information, not identity.

I built Expedia to make travel prices transparent. Then Zillow for home prices. Glassdoor does the same for salaries. My whole career is ruining information asymmetry.

I was a CPA sitting in a cubicle thinking, this can't be it. I quit to teach yoga, started designing shorts in my apartment, and ten years later SoftBank valued the company at $4 billion. Life is weird.

At 19, I was the youngest Indian to receive the Thiel Fellowship. Peter Thiel paid me $100,000 to drop out of college. Best education I never got.