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Business, Career, and Life advice from the world’s most successful entrepreneurs – Part 1



Welcome to the first of a four part series:

Business, career, and life advice from the world’s most successful entrepreneurs.

In this article:

  • Bill Gates – Microsoft
  • Ben Silberman – Pinterest
  • Brian Chesky – Airbnb
  • Carlos Slim – America Movil & Telmex
  • David Karp – Tumblr
  • Donald Trump – Trump International
  • Drew Houston – Dropbox
  • Elon Musk – SpaceX & Telsa Motors

I’ve spent the past few weeks reading, watching, and listening to everything I could from the world’s most successful entrepreneurs, curious as to what lessons you and I could learn from them, about success in business, in our careers, and in our lives.

I’ve done my best to capture their best advice and to edit out all of the crap, so each of these quotations is straight to the point and easy to understand without any waffle.

What lessons can we learn from the world’s most successful entrepreneurs?

What can they teach us about success in business, career, and life?

Let’s find out…

Bill Gates – founder of Microsoft (Net worth: $90 Billion) 

Bill Gates, co-founder of Microsoft, Millionaire at age 23, Billionaire by age 31

Be your own biggest critic

“One thing I’ve always loved about the culture at Microsoft is there is nobody who is tougher on us, in terms of what we need to learn and do better, than the people in the company itself.”

Don’t have meetings for the sake of it

“You have a meeting to make a decision, not to decide on the question.”

Don’t make the same decision twice 

“Don’t make the same decision twice. Spend time and thought to make a solid decision the first time so that you don’t revisit the issue unnecessarily. If you’re too willing to reopen issues, it interferes not only with your execution but also with your motivation to make a decision in the first place.”

Embrace bad news

“Once you embrace unpleasant news, not as a negative but as evidence of a need for change, you aren’t defeated by it. You’re learning from it.”

Find people who will tell you the truth 

“We get comfort from those who agree with us, but we get growth from only those who don’t agree with us.”

Learn from customer complaints

“Your most unhappy customers are your greatest source of learning.”

Learning from failure > celebrating success

“It’s fine to celebrate success, but it is more important to heed the lessons of failure. Success is a miserable teacher. It tempts intelligent people to believe they cannot lose. And it is an unreliable guide to the future.”

Measure everything, know your numbers

“The quality that has helped me in lots of things, is a kind of measurement, scientific framework, where I go in and say “did anybody handle this well?” “What are the very best practices?” “Do we have numbers on that?” I like to get everybody measuring what they’re doing, so we can strive to match what the best achievement is, and use that to drive the very best practices.”

“Knowing your numbers is a fundamental precept of business.”

On hard work

“I never took a day off in my twenties. Not one.”

Brian Chesky – founder of Airbnb (Net worth: $3.8 Billion) 

Brian Chesky, co-founder of Airbnb, who started the company in 2007, when as a college student struggling to pay rent, thought of the idea of renting out his living room floor to guests and allowing them to sleep on airbeds, whenever there was a large conference or convention in town (San Francisco) in order to make some extra money.

Forget the “real world”

“Forget the “real world”. The real world to me really just represents whatever you think is the safe path in life. Never take the safe path. You see the safe path, rarely leads to the magical world you want to live in, and the problem with the safe path, is that it’s not actually safe, because you end up pursuing something that you’re not passionate about – and therefore, you’re not as good at it.”

Hire someone better than you

“Every single person is meant to hire a person better than the previous people. You’re constantly raising the bar.”

“You gotta build a team that is so talented that they almost make you slightly uncomfortable.”

“If you could hire anybody in the world, would you hire the person sitting across from you?”

How to create a great product

“If you want to create a great product, just focus on one person. Make that one person have the most amazing experience ever.”

“The best methodology is to start with the perfect experience of just one person, get that right, and then figure out how to scale something great. Instead of scaling something not so great and then trying to improve it. That’s really hard.”

“Build something 100 people love, not something 1 million people kind of like.”

“It’s better to have 100 people love you than to have 1,000,000 people like you.”

How to get the media talking about you

“Whatever the press is talking about, they want to keep talking about it. So instead of asking yourself, ‘How can I get them to start talking about me?’, figure out a way to get yourself involved in what they’re already talking about.”

See what your users are doing

“The office is the laboratory and meeting your users is like going into the field. You can’t just stay in the lab. It’s not just asking users what they want, it’s about seeing what they’re doing.”

Solve your own problems

“I think great ideas are sometimes right in front of your face, maybe an itch that you have, sometimes don’t you ever wonder – wouldn’t it be great if (fill in the blank) – and it’s something that seems totally obvious, and you say “well there’s probably a reason they never did that.”

“I think you should solve a problem that you have yourself. What is something ordinary, day to day in your life, that if it was fixed would make your life better? I think that’s a really good way to start a business. Sometimes people decide to start businesses where they’re not the customer. That’s also OK. But you’ll have an advantage if you try to solve a problem that you are familiar with. That you have a unique insight into.”

“Instead of solving high-profile problems, try to solve something that’s deeply personal to you. If you’re an ordinary person and you’ve just solved your own problem, you might have solved the problem for millions of people.”

Ben Silbermann – founder of Pinterest (Net worth: $1.57 Billion)

Don’t take too much advice, just try things

“Don’t take too much advice. Most people who have a lot of advice to give, with a few exceptions, generalize whatever they did. Don’t over-analyze everything. I myself have been guilty of over-thinking problems. Just build things and find out if they work.”

Surround yourself with people that will give you honest feedback

“I think it’s (entrepreneurship) a horrific process of trial and error, where you just fuck up and someone with the courage to come up to you is like “hey that product review is terrible, you were awkward, it made me feel awkward, it made my team feel unappreciated, you weren’t clear, you said something different than you said two weeks ago” etc.

You need some people that you trust enough that are willing to give you that feedback.”

Carlos Slim – founder of América Móvil and Telmex (Net worth: $65 Billion) 

Carlos Slim, the world’s richest man from 2010-2013. His conglomerate Grupo Carso, owns companies in education, health care, industrial manufacturing, transportation, real estate, media, energy, hospitality, entertainment, technology, retail, sports, and financial services.

Competition is good

“Competition makes you better, always, always makes you better, even if the competitor wins.”

Don’t seek the approval of others

“When you live for others opinions, you are dead.”

Face your problems, learn from failure 

“When we face our problems, they disappear. So learn from failure and let success be the silent incentive.”

Have a sense of urgency 

“Lead with a sense of urgency, when you are building, creating, innovating, and solving problems.”

Invest during a crisis/recession

“In business, you invest when things are not in good shape. When you invest at these times, you take a better position than your competitors. When there is a recession and your competition does not invest, they are giving you the advantage.”

“When there is a crisis, that’s when some are interested in getting out and that’s when we are interested in getting in.”

On luck

“I don’t believe too much in luck. I believe in circumstances. I believe in work.”

Say no to pessimists

“You cannot have people in your organization who are pessimists. They take you to mediocrity.”

David Karp – founder of Tumblr (Net worth $200 Million)

David Karp, who started the micro-blogging website Tumblr in 2007 at the age of 21, as an alternative to Facebook and Twitter, where users could create something “much more free-form, much less verbose” than traditional blog posts. David sold Tumblr to Yahoo! in 2013 for 1.1 Billion

Seek out mentors

“The one piece of advice I’d give to anyone else who is going down this path (entrepreneurship), particularly to young people who are looking for some direction, is just seek out great mentors who’ve been through this stuff before.

Ask them as many questions as you can and really listen to them. Even if you feel stubborn, even if what they’re telling you doesn’t quite gel, even if you want to try doing it differently. Give it a chance to sink in, and don’t forget what they told you. Write it down. Think about it at least every few weeks, because, eventually you kinda figure out what they were trying to tell you.

That has saved me from so many mistakes, and helped steer me back on the right path so many times, just having those types of people in my life.”

Donald Trump – 45th US President (Net worth: $3.1 Billion)

Anticipate the worst

“I happen to be very conservative in business. I always go into the deal anticipating the worst. If you plan for the worst, if you can live with the worst, the good will always take care of itself.”

“I believe in positive thinking, but I also believe in protecting against the downside. You need to think about the challenges, so that when they do come along, you’re ready.”

Controversy = media coverage

“One thing I’ve learned about the press is that they’re always hungry for a good story, and the more sensational the better. If you are a little different, a little outrageous, or if you do things that are bold or controversial, the press is going to write about you.”

“Good publicity is preferable to bad, but from a bottom line perspective, bad publicity is sometimes better than no publicity at all. Controversy, in short, sells.”

Hire the best people from your competitors

“I have a very simple rule when it comes to management: hire the best people from your competitors, pay them more than they were earning, and give them bonuses and incentives based on their performance. That’s how you build a first-class operation.”

3 Lessons

“Experience taught me a few things:

  1. One is to listen to your gut, no matter how good something sounds on paper
  2. The second is that you’re generally better off sticking with what you know
  3. And the third is that sometimes your best investments are the ones you don’t make.”

Never lose momentum

“Momentum: A word you never hear when you’re talking about success…

Momentum works like this: When you start anything new, you have no momentum. You have no contacts and no track record. Nobody is calling you and nothing is happening. Nobody knows you and they do not believe you because you have never done anything before. They can’t tell if you’re the real deal or just another fly-by-night operation that will fold up and move on when things get too tough.

That is when things are hard. You go out and beat your head against a wall looking for deals, with no luck. You do not seem to be getting anywhere.

But if you keep at it and keep working towards your goals one day at a time, with each passing day and each contact you make, pretty soon you get into the flow of people and events, and slowly you are building momentum.

You are showing people that you are not going away and then one day, something breaks for you. You land an account or sign a deal.

All of a sudden your credibility rises. People start to believe in you. After a while you have so much momentum built up that things start to come to you in multiples: two or three jobs or clients or deals come your way all at once. Everybody sees you have momentum, and they want to be a part of it. You get contacts, you gain credibility, you build a track record of success, and then things get much easier. Each success will create another success.

When you have momentum going, play the momentum, and do not take momentum for granted. If you lose your momentum, all your success ends, and things get much more difficult. It is dangerous to do anything when you have lost your momentum. Your timing is off, and people and events are no longer in your favor. So watch out never to lose your momentum.

There is a funny thing about momentum: when you stop, it stops.”

How to establish momentum

“Momentum is all about energy and timing. To get momentum you must focus on a specific goal with passion and intensity. You have to find out what makes you excited. What makes you want to get up each morning and go to work. If you love what you do, and dedicate yourself to your work, then you will gain momentum, and each success will create another success.

Pick something you are very good at or have the ability to become good at and become very knowledgeable in your field. Getting a good mentor helps create momentum too. Find someone knowledgeable about your field and make them your friend. Ask their advice. If you have a question about something, ask your mentor. Do something you love, work hard, and never, ever, give up.”

On deal making

“My style of deal-making is simple. I aim very high, and then I just keep pushing and pushing and pushing to get what I’m after.”

“The worst thing you can possibly do in a deal is seem desperate to make it. That makes the other guy smell blood, and then you’re dead. The best thing you can do is deal from strength.”

“I never get too attached to one deal or one approach…I keep a lot of balls in the air, because most deals fall out, no matter how promising they seem at first.”

On luck

“I do believe that some people are luckier than others, but I also believe that you can develop luck through hard work. The harder I work, the luckier I get.”

Tackle big challenges to make the big money

“Be the one to solve tough problems and you will be the one people pay big money for. Anyone can do things that are easy. It is rare to find people who can tackle big challenges. If you do, you will stand out from the crowd. I have found that if something is too easy, it is not usually even worth doing. Lots of other people are already doing it, and there usually is not much profit in the easy jobs.”

Take risks

“Many people are afraid to fail, so they don’t try. They may dream, talk, and even plan, but they don’t take that critical step of putting their money and their effort on the line. To succeed in business, you must take risks. Even if you fail, that’s how you learn. There has never been, and will never be, an Olympic skater who didn’t fall on the ice.”

Drew Houston – founder of Dropbox (Net worth: $1 Billion) (In blue)

Drew Houston, founder of Dropbox, an idea he thought up during a bus ride at University, when he really wanted to access some files he’d accidentally left on a USB drive somewhere else.

Find what pulls you

“The happiest and most successful people I know don’t just love what they do, they’re obsessed with solving an important problem, something that matters to them.

They remind me of a dog chasing a tennis ball: their eyes go a little crazy, the leash snaps and they go bounding off, plowing through whatever gets in the way.

The problem is a lot of people don’t find their tennis ball right away.

It took me a while to get it, but the hardest-working people don’t work hard because they’re disciplined. They work hard because working on an exciting problem is fun. So it’s not about pushing yourself, it’s about finding your tennis ball, the thing that pulls you.”

How many days do you have left?

“There are 30,000 days in your life. When I was 24, I realized I’m almost 9,000 days down. There are no warm-ups, no practice rounds, no reset buttons. Your biggest risk isn’t failing, it’s getting too comfortable.”

How to learn

“The fastest way to learn is by doing. If you have a dream, you can spend a lifetime studying, planning, and getting ready for it. What you should be doing is getting started.”

Start now

“You’re not going to become a great manager overnight. You’re not going to become a great public speaker or figure out how to raise money. These are the things you want to start the clock on as early as possible.”

“It really helps to start the clock early. I’ve always found it valuable to ask myself, “One year from now, two years from now, five years from now, what will I wish I had been learning today?”

The most dangerous thought

“The most dangerous thought you can have as a creative person is that you know what you’re doing.”

The 2 qualities entrepreneurs need

“One misconception is that entrepreneurs love risk. Actually, we all want things to go as we expect. What you need is a blind optimism and a tolerance for uncertainty.”

What will you want 5 years from now?

“People make basic assumptions based on what they have now. But you have to ask yourself, ‘Is this really what people are going to be doing in five years?’ Very few people ask themselves what they would actually want instead if they could wave a magic wand.”

Where you live matters

“Where you live matters: there’s only one MIT, there’s only one Hollywood, and only one Silicon Valley. This isn’t a coincidence: for whatever you’re doing, there’s usually only one place where the top people go. You should go there. Don’t settle for anywhere else. Meeting my heroes and learning from them gave me a huge advantage. Your heroes are part of your circle too – follow them. If the real action is happening somewhere else – move.”

Why ignorance sometimes pays off

“A lot of times it’s an asset to not know everything about everything… A lot of really great, innovative things have happened when people just didn’t know it wasn’t supposed to be possible.”

What to work on

“Sometimes you just get this feeling – it’s a compulsion or an obsession. You can’t stop thinking about it. You just have to work on this thing.”

Work where you will learn the most

“If you join a company, work with world-class people because that’s the fastest way to learn how to do things. If you start your own thing, you can learn a lot really fast from doing things wrong. Ask yourself, ‘Where can I find an environment where I can work really hard and learn the most?”

Elon Musk – founder of Paypal, SpaceX, and Tesla Motors (Net worth: $20 Billion) 

Constantly seek out criticism 

“Constantly seek out criticism and negative feedback. A well thought out critique of whatever you’re doing, is as valuable as gold. And you should seek that from everyone you can, but particularly from your friends. Because generally they will be thinking it, but they don’t want to tell you because they don’t want to hurt you.

It doesn’t mean your friends are right. But very often they are right. And you at least want to listen very carefully to what they have to say.”

Constantly think about what you’re doing

“I think it’s very important to have a feedback loop, where you’re constantly thinking about what you’ve done and how you could be doing it better. I think that’s the single best piece of advice: Constantly thinking about how you could be doing things better and questioning yourself.”

Critical thinking vs following the process

“I don’t believe in process. In fact, when I interview a potential employee and he or she says that ‘it’s all about the process,’ I see that as a bad sign. The problem is that at a lot of big companies, process becomes a substitute for thinking. You’re encouraged to behave like a little gear in a complex machine. Frankly, it allows you to keep people who aren’t that smart, who aren’t that creative.”

How to evolve your ideas

“As an entrepreneur, you should take the approach that you’re wrong. Your goal is to be less wrong.”

“In terms of creating a company, what Thomas Edison said about it being 1% inspiration and 99% perspiration is true. You start off with an idea, and that idea is mostly wrong, and then you adapt that idea, and keep refining it, and you listen to criticism, you try to discard the wrong criticism, try to listen to the correct criticism, and then you engage in recursive self improvement, and constantly refine your idea and make it better.”

How to learn

“It is important to view knowledge as sort of a semantic tree – make sure you understand the fundamental principles, I.e. the trunk and big branches, before you get into the leaves/details or there is nothing for them to hang on to.”

Eating glass and staring into the abyss

“A lot of times people think creating a company is going to be fun. I would say it’s really not that fun. There are periods of fun. And there are periods where it’s just awful. And particularly, if you’re the CEO of the company, you actually have a distillation of all the worst problems in the company, you’re only spending your time on things that are going wrong, things that other people can’t take care of. You have a filter for the crappest problems in the company. The most pernicious and painful problems.

I think you have to feel quite compelled to do it, and have a fairly high pain threshold.

There’s a friend of mine who says starting a company is like eating glass and staring into the abyss. And there’s some truth to that.

When you first start a company there’s lots of optimism, and things are great.

What tends to happen is that it’s quite exciting for the first several months of starting a company, and then reality sets in, things don’t go as well as planned, customers aren’t signing up, the technology on the product isn’t working as well as you thought, and that can sometimes be compounded by a recession, and it can be very painful for several years. Frankly, starting a company, I would advise people to have a high pain tolerance. Expect a long period of high difficulty.

The staring into the abyss part is that you’re going to be constantly facing the extermination of the company. Because most start-ups fail. It’s like 90%. Maybe 99% of start-ups fail. That’s the staring into the abyss part, you’re constantly saying “If I don’t get this right – the company will die” – which can be quite stressful.

The eating glass part is, you’ve got to work on the problems that the company needs you to work on. Not the problems you want to work on. So you end up working on problems that you really wish you weren’t working on. So that’s the eating glass part. And that goes on for a long time.”

“To be successful at almost anything, you have to do your chores, the tough stuff, as well as the enjoyable stuff. You have to do the boring stuff as well as the non boring stuff. If you don’t do your chores, then bad things will happen. If you don’t do the things you don’t like to do, than the company will be in trouble. It’s more fun to cook the meal than to clean the dishes, but you need to clean the dishes.”

Elon Musk’s mindset

“Optimism? Pessimism? Fuck that. We’re going to make it happen. As God as my bloody witness, I’m hell-bent on making it work.”

Elon’s biggest mistake when hiring someone

“The biggest mistake in general that I’ve made is to put to much of a weighting on someone’s talent, and not enough on their personality, and I’ve made that mistake several times. It actually matters whether somebody has a good heart. It really does. And I’ve made the mistake of thinking sometimes, that it’s just about the brain.”

PS: No assholes

“It’s very important to like the people you work with. Otherwise life, your job, is going to be quite miserable. We have a strict no assholes policy at Space-X. And we fire people if they’re assholes, I mean we give them a little bit of a warning, but if they continue to be an asshole then they’re fired.”

Failure is necessary 

“Failure is an option here. If things are not failing, you are not innovating enough. It’s not like I like failing, I mean who likes failure? It’s terrible. But if you only do things that are certain to succeed, than you’re only going to be doing very obvious things.”

It has to be really great

“You gotta make sure that whatever you’re doing is a great product or service. It has to be really great. If you’re a new company, unless it’s like some new industry, or new market, but if you’re entering anything where there is an existing marketplace, against large entrenched competitors, then your product or service needs to be much better than theirs, it can’t be a little bit better, because then you put yourself in the shoes of the consumer, and why would you buy as a consumer?

As a consumer you’re always going to buy the trusted brand unless there’s a big difference. A lot of times an entrepreneur will come up with something which is only slightly better. It can’t just be slightly better. It has to be a lot better.”

“You want to be extra rigorous about making the best possible thing you can. Find everything that’s wrong with it (your idea or product) and fix it.”

Successful vs unsuccessful start-ups

“When you’re building something new there’s going to be mistakes, and it’s important to recognize those mistakes, acknowledge them, and take corrective action. The success of a company is about how quick are you to fix the mistakes, not will you make mistakes.

The difference between a startup that is successful and one that is not, is they both made mistakes, but the successful one recognizes the mistakes and fixes them very quickly, and the unsuccessful one tries to deny that the mistakes exist.”

Work super hard (80 – 100 hours a week)

“What you want to do when you’re starting a new company, you need to work super hard.

What does super hard mean?

Work hard every waking hour. Work like hell. I mean you just have to put in 80 to 100 hour weeks every week. This improves the odds of success. If other people are putting in 40 hour workweeks and you’re putting in 100 hour workweeks, then even if you’re doing the same thing, you know that you will achieve in four months what it takes them a year to achieve.”

Summary of lessons

  • Anticipate and plan for the worst. The good will take care of itself.
  • Be your own biggest critic
  • Build products and tools for yourself
  • Build something 100 people love, not something 1 million people kind of like
  • Competition is good. It always makes you better. Even if the competitor wins.
  • Constantly seek out criticism and negative feedback from everyone you can. Especially from your friends.
  • Create your own luck. The harder you work the luckier you get
  • Critical thinking is better than following the process
  • Don’t ever seem desperate to make a deal. If you do, you’re dead.
  • Don’t have meetings for the sake of it. Have a meeting to make a decision. Not to decide on the question.
  • Don’t just ask your users what they want, see what they’re doing
  • Don’t take too much advice. Just try things.
  • Face your problems, learn from failure
  • Find what pulls you. What can’t you stop talking and thinking about? What gets you excited? What is your obsession?
  • Focus on problems not competitors
  • Get rid of pessimists from your organisation
  • Hire people who are better and smarter than you, super passionate, and good at the things you’re not
  • Hire the best people from your competitors
  • If you are entering an established market, your product or service can’t just be a little bit better than the competitors, it must be much better. Otherwise why would a consumer buy from you instead of from an established brand?
  • If you want to create a great product, just focus on one person. Make that one person have the most amazing experience ever.
  • Learn from customer complaints, failure, doing, and mentors
  • Learn to let go, and let other people do it better
  • Listen to your gut
  • Measure everything. Know your numbers.
  • Maintain a feedback loop. Constantly think about how you could be doing things better.
  • Never, ever, ever, give up
  • Never lose momentum, and if you start to lose momentum, work your ass off to get it back immediately
  • Say no to pessimists because they will take you to mediocrity
  • Seek out mentors. People that have achieved what you want to achieve and listen to them.
  • Solve your own problems. Solve problems that you have yourself, things that annoy you, that are deeply personal to you. Something you know should be better. Scratch your own itch.
  • Solve hard problems and tackle big challenges if you want to make big money
  • Start now. What will you had wish you had started today 1, 3, 5 years from now?
  • Surround yourself with people who will give you honest feedback and tell you the truth
  • Take risks. To succeed in business you must
  • Where you live matters. If the action is happening somewhere else – move.
  • Work in companies and with people where you will learn the most
  • Work super hard. Bill Gates never took one day off in his twenties. Elon Musk recommends working 80-100 hour weeks.

This is part 1 of a 4 part series: Business, Career, and Life Advice from the world’s most successful entrepreneurs:

Business, Career, and Life Advice from the world’s most successful entrepreneurs – part 2

Business, Career, and Life Advice from the world’s most successful entrepreneurs – part 3

Business, Career, and Life Advice from the world’s most successful entrepreneurs – part 4

If you’re looking for more career advice, I highly recommend you check out the following articles:

150+ Career tips from the CEO’s of Apple, Google, LinkedIn, Microsoft, JP Morgan and more!

35 Interview Mistakes to Avoid

How to get your Dream Job

25 CV Mistakes to Avoid

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Ben Silbermann image credit: By Mike Deeroski ( [CC BY 2.0 (], via Wikimedia Commons
Bill Gates image credit: By Joi Ito from Inbamura, Japan (Steve Jobs and Bill Gates on Flickr) [CC BY 2.0 (], via Wikimedia Commons
Brian Chesky image credit: By U.S. Department of State from United States [Public domain], via Wikimedia Commons
Carlos Slim image credit: José Cruz/ABr (Agência Brasil [1]) [CC BY 3.0 br (], via Wikimedia Commons
David Karp image credit: By Yahoo Inc [CC BY 2.0 (], via Wikimedia Commons
Donald Trump image credit: Frederic Legrand - COMEO /
Drew Houston image credit: By Nancy Pelosi from San Francisco, CA [CC BY 2.0 (], via Wikimedia Commons
Elon Musk image credit: Steve Jurvetson from Menlo Park, USA (Elon Musk and Chris Anderson at TED 2017) [CC BY 2.0 (], via Wikimedia Commons


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