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“Among many things that Ray has taught me are five rules for happiness. So the first one is living in the moment. The second is that it’s better to be loving than to be right, and if you’re in a relationship, you know how challenging that can be. The third one is to be a spectator to your own thoughts, especially when you become emotional, which is almost impossible to do. The fourth is to be grateful for at least one thing every day, and the last is to help others every chance you get. So I’m incredibly fortunate to have people in my life like that.”

“When you don’t have any money, you get really good at making money. When you have a lot of money, you get really good at spending money.”

“The real purpose of a loyalty program in today’s environment is to get actionable data via a permissioned relationship.”

“After we launch a new feature, I keep a close eye on how many people are using it. If it’s unpopular, we’ll discontinue it and try something else. Every feature has some maintenance cost, and having fewer features lets us focus on the ones we care about and make sure they work very well. For every new feature we add, we take an old one out.”

“You probably only have to interrupt someone a couple times a day before they’re unable to work on hard problems at all.”

“Usage is like oxygen for ideas. You can never fully anticipate how an audience is going to react to something you’ve created until it’s out there. That means every moment you’re working on something without it being in the public it’s actually dying, deprived of the oxygen of the real world.”

We are what we repeatedly do.

“You can’t improve a design when you’re emotionally attached to past decisions. Improvements come from flexibility and openness.”

“Entrepreneurship is about living a few years of your life like most won’t, so that you can live the rest of your life like most can’t.”

“Progress has little to do with speed, but much to do with direction.”

“Innovation is almost insane by definition: most people view any truly innovative idea as stupid, because if it was a good idea, somebody would have already done it. So, the innovator is guaranteed to have more natural initial detractors than followers.”

“You never change things by fighting the existing reality. To change something, build a new model that makes the existing model obsolete.”

“When a distinguished but elderly scientist states that something is possible, he is almost certainly right. When he states that something is impossible, he is probably wrong.”

“If you can’t draw as well as someone, or use the software as well, or if you do not have as much money to buy supplies, or if you do not have access to the tools they have, beat them by being more thoughtful. Thoughtfulness is free and burns on time and empathy.”

“You can probably take it as a rule of thumb from now on that if people don’t think you’re weird, you’re living badly.”

“A goal is a dream with a deadline.”

“The Master of the art of living makes little distinction between his work and his play, his labor and his leisure, his mind and his body, his education and his recreation, his love and his religion. He hardly knows which is which. He simply pursues his vision of excellence in whatever he does, leaving others to decide whether he is working or playing. To him he is always doing both.”

“I will hazard a prediction. When you are 80 years old, and in a quiet moment of reflection narrating for only yourself the most personal version of your life story, the telling that will be most compact and meaningful will be the series of choices you have made. In the end, we are our choices. Build yourself a great story.”

The abuse of words like innovation, disruption, game changing and breakthrough is killing us. We’re tripping over our own egos, lost in the ignorance of romance for the vagaries of pseudo-thinking associated with these words. The more often people in a company use this word, the less likely anything worthy of that label is actually happening, as it’s often the confused and the desperate who believe simply saying a word again and again like a magic spell causes anything at all to happen.

Windows knocked him off the main stage for 10 years; then the Internet seemed to sideline him; not to mention that serious business people (along with many others) thought he was nutty; then he had problems with the SEC (and not insignificant ones); then he nearly died.

“Sometimes a design isn’t working because you think you can’t change the one element that needs to be changed.”

“I try to buy stock in businesses that are so wonderful that an idiot can run them. Because sooner or later, one will.”

“Design almost invariably involves compromise…. Rarely can the designer simply optimise one requirement without suffering losses elsewhere…. There are no established methods for deciding just how good or bad solutions are, and still the best test of most design is to wait and see how well it works in practice. Design solutions can never be perfect and are often more easily criticised than created, and designers must accept that they will almost invariably appear wrong in some ways to some people.”