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June 29 - July 23, 2020
“Strong Views, Loosely Held”
“He says the key to success is, ‘Be so good they can’t ignore you.’”
“Get inside the heads of the people who made things in the past and what they were actually like, and then realize that they’re not that different from you. At the time they got started, they were kind of just like you . . . so there’s nothing stopping any of the rest of us from doing the same thing.”
“Life can be much broader, once you discover one simple fact, and that is that everything around you that you call
‘life’ was made up by people that were no smarter than you. And you can change it, you can influence it, you can build your own things that other people can use. Once you learn that, you’ll never be the same again.”
“My goal is not to fail fast. My goal is to succeed over the long run. They are not the same thing.”
“To do original work: It’s not necessary to know something nobody else knows. It is necessary to believe something few other people believe.”
“Show me an incumbent bigco failing to adapt to change, I’ll show you top execs paid huge cash compensation for quarterly and annual goals.”
“Every billionaire suffers from the same problem. Nobody around them ever says, ‘Hey, that stupid idea you just had is really stupid.’”
“My confidence came from my vision. . . . I am a big believer that if you have a very clear vision of where you want to go, then the rest of it is much easier. Because you always know why you are training 5 hours a day, you always know why you are pushing and going through the pain barrier, and why you have to eat more, and why you have to struggle more, and why you have to be more disciplined. . . . I felt that I could win it, and that was what I was there for. I wasn’t there to compete. I was there to win.”
“In negotiation, he who cares the least wins.”
When deal-making, ask yourself: Can I trade a short-term, incremental gain for a potential longer-term, game-changing upside? Is there an element here that might be far more valuable in 5 to 10 years (e.g., ebook rights 10 years ago)? Might there be rights or options I can explicitly “carve out” and keep? If you can cap the downside (time, capital, etc.) and have the confidence, take uncrowded bets on yourself. You only need one winning lottery ticket.
“Even today, I still benefit from that because I don’t merge and bring things together and see everything as one big problem. I take them one challenge at a time.
“Cincinnatus. He was an emperor in the Roman Empire. Cincinnati, the city, by the way, is named after him because he was a big idol of George Washington’s. He is a great example of success because he was asked to reluctantly step into power and become the emperor and to help, because Rome was about to get annihilated by all the wars and battles. He was a farmer. Powerful guy. He went and took on the challenge, took over
Rome, took over the army, and won the war. After they won the war, he felt he’d done his mission and was asked to go and be the emperor, and he gave the ring back and went back to farming. He didn’t only do this once. He did it twice. When they tried to overthrow the empire from within, they asked him back and he came back. He cleaned up the mess through great, great leadership. He had tremendous leadership quality in bringing people together. And again, he gave the ring back and went back to farming.”
It’s not what you know, it’s what you do consistently.
“How to thrive in an unknowable future? Choose the plan with the most options. The best plan is the one that lets you change your plans.”
“Be expensive”
“Expect disaster”
“Own as little as ...
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Ricardo Semler, CEO and majority owner of the Brazil-based Semco Partners, practices asking “Why?” three times. This is true when questioning his own motives, or when tackling big projects.
The standard pace is for chumps.
“Well, I meet a lot of 30-year-olds who are trying to pursue many different directions at once, but not making progress in any, right? They get frustrated that the world wants them to pick one thing, because they want to do them all: ‘Why do I have to choose? I don’t know what to choose!’ But the problem is, if you’re thinking short-term, then [you act as though] if you don’t do them all this week, they won’t happen. The solution is to think long-term. To realize that you can do one of these things for a few years, and then do another one for a few years, and then another. You’ve probably
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So $35 setup fee, $4 per CD sold, and then, Tim, for the next 10 years, that was it. That was my entire business model, generated in 5 minutes by walking down to the local record store and asking what they do.”
Once You Have Some Success—If It’s Not a “Hell, Yes!” It’s a “No”
“Every time people contact me, they say, ‘Look, I know you must be incredibly busy . . .’ and I always think, ‘No, I’m not.’ Because I’m in control of my time. I’m on top of it. ‘Busy,’ to me, seems to imply ‘out of control.’ Like, ‘Oh my God, I’m so busy. I don’t have any time for this shit!’ To me, that sounds like a person who’s got no control over their life.”
Lack of time is lack of priorities.
I think I would make a billboard that says, ‘It Won’t Make You Happy,’
I believe you shouldn’t start a business unless people are asking you to.
I believe that music and people don’t mix; that music should be appreciated alone without seeing or knowing who the musicians are and without other people around. Just listening to music for its own sake, not listening to the people around you and not filtered through what you know about the musician’s personal life.”
Treat Life as a Series of Experiments “My recommendation is to do little tests. Try a few months of living the life you think you want, but leave yourself an exit plan, being open to the big chance that you might not like it after actually trying it. . . .
“Even when everything is going terribly, and I have no reason to be confident, I just decide to be.”
‘We are whatever we pretend to be.’”
When you make a business, you’re making a little world where you control the laws. It doesn’t matter how things are done everywhere else. In your little world, you can make it like it should be.
When you’re thinking of how to make your business bigger, it’s tempting to try to think all the big thoughts, the world-changing, massive-action plans. But please know that it’s often the tiny details that really thrill someone enough to make them tell all their friends about you.
“Take the pain and wear it like a shirt”
You Have to Give a Lot of Damns
“Founders have to realize the bar is set so low because most companies stopped giving a fuck so long ago. . . . It’s something that I really expect other founders to do, and it ends up being pretty easy. Compared to building out the actual site or architecting the back end, this doesn’t require a few years of programming expertise. It just requires you to gives lots of damns, which not enough people do.”
“Invest that little bit of time to make it a little bit more human or—depending on your brand—a little funnier, a little more different, or a little more whatever. It’ll be worth it, and that’s my challenge.”
“What are you doing that the world doesn’t realize is a really big fucking deal?”
“letting the silence do the work”: “I really think a lot can be conveyed with a raised eyebrow.”
“The moment that you feel that, just possibly, you’re walking down the street naked, exposing too much of your heart and your mind and what exists on the inside, showing too much of yourself. That’s the moment you may be starting to get it right.” —Neil Gaiman, University of the Arts commencement speech
Wake up at least 1 hour before you have to be at a computer screen. Email is the mind-killer. Make a cup of tea (I like pu-erh) and sit down with a pen/pencil and paper. Write down the 3 to 5 things—and no more—that are making you the most anxious or uncomfortable. They’re often things that have been punted from one day’s to-do list to the next, to the next, to the next, and so on. Most important usually equals most uncomfortable, with some chance of rejection or conflict. For each item, ask yourself: “If this were the only thing I accomplished today, would I be satisfied with my day?” “Will
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Block out at 2 to 3 hours to focus on ONE of them for today. Let the rest of the urgent but less important stuff slide. It will still be there tomorrow. TO BE CLEAR: Block out at 2 to 3 HOURS to focus on ONE of them for today. This is ONE BLOCK OF TIME. Cobbling together 10 minutes here and there to add up to 120 minutes does not work. No phone calls or social media allowed. If you get distracted or start procrastinating, don’t freak out and downward-spiral; just gently come back to your ONE to-do.
What you do is more important than how you do everything else, and doing something well does not make it important.
Being busy is a form of laziness—lazy thinking and indiscriminate action.
Being busy is most often used as a guise for avoiding the few critically important but uncomfortable actions.
When I’m in the pit of despair, I recall what iconic writer Kurt Vonnegut said about his process: “When I write, I feel like an armless, legless man with a crayon in his mouth.”
Don’t overestimate the world and underestimate yourself. You are better than you think. And you are not alone.
“When you can write well, you can think well.”

