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15 Life-Changing Decisions Self-Made Billionaires Had to Make to Be Successful


12m read
·Oct 29, 2024

There are 2,640 billionaires in the world that we know of. About 65 to 70% built their fortune through their own efforts, and at each pivotal point in their lives, these people had to make a decision that would change their lives. The road is far from easy; the forks are wide and varied, and what they decided could make their success but break their public perception. But their choices got them to where they are now. So let's have a look at them. Here are 15 life-changing decisions self-made billionaires had to make to build their fortune.

Number one: see the ability to work as freedom, not imprisonment. When you look at the life stories of billionaires who built their fortunes themselves, you see that many of them started working the moment they were legally allowed to, and some even before then. Jeff Bezos worked the breakfast shift at McDonald's when he was 16. He spent his childhood doing manual labor at his grandparents' ranch for spare change. Mark Cuban was barely a teenager when he started buying and reselling baseball cards and stamps. You have to make the decision to see your ability to work as a blessing, as something that gives you freedom and choice, not something that's designed to keep you imprisoned and following a system. Well, some of that may be true. If that's the only way you view work, then that's the only way you'll ever see yourself as a prisoner, confined to your desk, never able to quit, never able to run out and start your own story from scratch.

Number two: they become obsessed with a dream others thought was delusional. Imagine if, in the 1980s, you heard a teenager say that his biggest dream was to make intergalactic space travel accessible to everyone. You'd scoff, right? You'd laugh at them. Imagine if in the 1930s, when animated cartoons were less than 5 minutes long, you heard some guy say he wanted to make a feature film that was completely animated. Again, you would scoff; you would laugh at them. And yet Richard Branson and Walt Disney have shown us that the most audacious dreams create incredibly ambitious people who have the ability to make those dreams a reality. They had these audacious dreams, and they had to decide to hold on to those dreams, no matter how much they laughed, doubted, or questioned them.

Number three: allow their past to propel them, not hold them back. Some of the most well-known billionaires didn't come from families who had a lot of money; they came from abandoned, abusive households. Tyler Perry, the owner of one of the largest film production studios in the world, he ran away from his home where his father terrorized him for years. Steve Jobs' biological parents gave him up for adoption. Mark's parents were immigrants from Russia, and while they were as supportive as they could be, they started off in a very new country with next to nothing. Your childhood and your past have a major effect on what you're going to do with your life and your future. If you keep focusing on the past and what you missed out on, if you keep ruminating about the unfairness of life, you're never going to have the mental, emotional, or physical energy you need to focus on building your career or fortune. At some point in your life, you have to decide to let your past push you forward, not hold you back, no matter how difficult it was.

Number four: they set their moves and goals like ladder rungs. Now, despite these billionaires having one big daring dream, they set their goals and moves like rungs on a ladder. They started at the bottom, and they had no problem with how low they had to start. They took deliberate, sequential steps toward their goals, and every rung became a solid foundation for them to make the next step. They might have had big dreams of traveling in space, but they started off with writing a magazine, started as a teacher, or as a salesman. No position is too low or too far from your ultimate goal because no matter where you start, it'll always be the first rung on your ladder. If you keep that fearless dream in mind and build each step on the next step, you'll keep moving up—not to be a billionaire at first, but to be the best at what they do. Oprah started as a broadcaster; she knew she had to start at the bottom and work her way up, no matter how low that rung was. Any opportunity is an opportunity. Jack Ma was a teacher; Rihanna's first job was selling clothes with her father in a stall on the streets of Barbados. It doesn't matter where you start; just start.

Number five: they decided when a door opens, they should immediately walk in. You have to decide to see every opportunity that comes up as an opportunity that was meant for you. When that door opens, you have to walk in—no questions asked and no doubts in your mind. For these billionaires, they knew they couldn't hesitate and ask, "Are you sure? Should I even be here?" Because even if people made them feel unwelcome, they had to act like they belonged there. In fact, even when they were kicked out—like when Steve Jobs was kicked out of Apple or co-founder of Tinder Whitney Wolfe Herd was kicked out of her position—they came barging right back in. Whitney Wolfe Herd went on to found Bumble; Steve Jobs went on to found NeXT, which would eventually become Mac. There will always be rooms that people want to keep you out of, opportunities that they want to keep for an elite group of people. We still see it now. We see people who believe that certain types of opportunities or investments—like venture capital, offshore banking, or commercial real estate, even fine art sales—are reserved for the rich, but they're not. Okay? You have access to these areas, and you can be a part of them. Before you get rich, companies like Masterworks make buying and owning artwork accessible to everyone by giving everyday investors the opportunities to buy shares in masterpieces by artists like Picasso and Basquiat. They're opening doors that were previously closed to all but a select few. They empower modern investors to enter into a world of exclusive opportunities. Their art investing platform has distributed back a total of over $60 million in investor proceeds across their 23 exits. If you watched our past videos, you already know about Masterworks. As an Alexer, you're eligible for an offer where you can skip the waitlist and start investing today by scanning that QR code on screen or heading to masterworks.io. The door that's opened for you, my friend. And now, it's up to you to decide to take that opportunity and walk in, or wait on the sidelines, questioning yourself, while others walk in ahead of you and find their own success.

And speaking of success, number six: they tie their identity to success. When you look at the lives of billionaires now, you'll see that everything they do revolves around their work, money, and success. The friends they have, the dinners they go to, their vacations, and their communication—it's always about their next move. No matter how old or young they are, their identity is success, and it's always been this way. At some point, they decided to make that their lives. They never had the thought of work-life balance; it was about work. That is their balance. Most people compartmentalize their lives; it's broken up into work, family, friends, vacations, where you shut off from work, and nights out with people that have nothing to do with their work. You can't do that if you want to be a billionaire, though. Everything you do is tied to your drive for success. You don't have a minute to waste. All roads lead to work, and you know what? They love it.

Number seven: they chose a moment to sacrifice their relationships. Now, the commitment and time it takes to build a fortune doesn't leave very much room for anything else—not even family. You will have to sacrifice your relationships and hope that the people who love you love you enough to stick by you, even when you're not physically there. These billionaires realize they won't be around for birthdays, concerts, and sports days because they'll be traveling, working, and meeting up with people to make million-dollar deals. They had to make the decision to miss out on something, and then they had to decide to get over feeling bad about it. There was a moment they realized that the main plot was success, and friends and families were a part of a side story. But this often changes as they get older and more successful. We often hear them say that it's important to value family, friends, and their time, but the reality is there's not much space for that when you're still building your billion-dollar fortune.

Number eight: they also decide to be proud, not ashamed, of wanting more—more recognition, more victories, more money, more people, more power. Our world looks down on people who are vocal about wanting more. You might even try to hide it, not wanting everyone else to know how hungry you are for more of everything. But you can't be ashamed or embarrassed about it. Billionaires are not afraid to talk about wanting more, even when the world criticizes them for it. They're not afraid of failing in front of everyone and then trying again. If that's what you want, then you have to make a decision today to let go of any shame or embarrassment around it. Because people will question you and ask you if you're happy. They'll ask you if there's any point in wanting more. Is that what life is all about for you? Is it about feeling that where you are now and what you have isn't enough? If you're shooting for billionaire status, you should be able to say yes and say it proudly.

Number nine: first, they are obsessed with winning, then money, then power. For many billionaires, despite having big dreams, their initial goals weren't to be billionaires. They wanted to be the best at what they did, no matter what that was. They started the ladder on the lowest rung, but they knew they wouldn't be there forever. They wanted to be great at their first jobs; at first, all they wanted to do was win, to be better than everyone else. But once they got a taste of victory, they wanted more, and that brought in some money. When you start making money, you realize how much easier it becomes to make more money, to keep winning, and to get what you want. And as they amassed the money, they began to enjoy the power that came with it. There are stages to this kind of success. It doesn't start with wanting power or with wanting to be a billionaire; it starts with wanting to beat everybody else, and from there, you build.

Number ten: billionaires decide to drive with tunnel vision and ignore the noise. Now, we're getting into the kind of decisions that separate multi-millionaires from billionaires. As they reach meteoric levels of success, there's going to be a lot of noise. There will be people who don't like them simply because they have so much more than everyone else and they're not willing to give it all away. They would have to make hard decisions—who to let go, how much to pay the people who work for them, to lobby for certain laws that will help them on what they've built. If they always feel bad about what they did or question their decisions, they wouldn't be able to keep moving. They have to decide that if they want to reach the next level of success, then they have to shut out the noise of the people who don't support them.

Number eleven: billionaires decide to risk it all because mediocrity is worse than failure. At some point, these billionaires had to make a decision to risk it all and leave their old life behind. They decided to drop out of college, quit a good job, sell their business and build another one, or pour every ounce of their savings into a dream. Sometimes they failed, and they had to start over again. Sometimes the progress was slow, and they were broke and stressed for years. And sometimes, they soared. They had no idea which way it was really going to go, but they still knew they had to take a risk because if they didn't, they would be average and mediocre, and that is unacceptable to them. They would rather fail and fall a thousand times than stay where they are forever.

Number twelve: they decide to lean into madness, but they do it behind closed doors with close people. We get whispers of the craziness that happens behind closed doors. Rising to the level of billionaire requires you to embrace ideas, strategies, and dreams that seem mad or outlandish to others. These are the moments when the line between genius and madness starts to blur. If they behave the way everyone else did, they would be working for somebody else. The bold moves work best when they're shared with their closest allies. They keep the madness behind closed doors, show everyone else a clever, kind, enthusiastic entrepreneur, but that's just the PR spin. We only get glimpses of the personality it truly takes to be a billionaire, thanks to a few louder, more prominent folks who like a little bit of extra attention.

Number thirteen: billionaires always decide to deliver more than what everyone else expected. No matter what they do, whether they're working as a janitor or a bartender, they always delivered more than what everyone else expected. Jan Koum founded WhatsApp, but before that, he worked as a janitor in a grocery store. He said that the work humbled him and gave him a strong work ethic and resilience. He put in the hours, no matter how boring and laborious the work seemed. Howard Schultz didn't found Starbucks, but he played a crucial role in its success. He worked as a bartender in college, and he said that it was this job that gave him people skills, the ability to multitask, and a sense of determination to hit all the marks in record time. So, whatever you're doing for work right now, ask yourself: am I delivering more than what everyone else expects? If you're not and you're happy with coasting by on an easy life, that's totally okay, all right? But if you want more for yourself, then you have to start with delivering more for others. Deliver beyond what they expect from you.

Number fourteen: find the right allies and hold on to them for dear life. Billionaires don't get to be billionaires all on their own. They have one ally, one person who sticks with them through it all. That person will become a billionaire too. They'll hold them accountable and pull them back in when they need to. They'll push them to places where they're uncomfortable if they have to. They're just as smart, maybe smarter, but slightly more sane. They're just as charismatic, ambitious, and focused. If you want to be successful, you have to look for the right ally, someone who's just as good or even better than you, someone who's just as driven and just as loyal. You may betray or be betrayed by everyone else in your life, but you can never betray each other. For Warren Buffett, it's Charlie Munger; Steve Jobs and Steve Wozniak; Mark Zuckerberg and Sheryl Sandberg; Oprah Winfrey and Gayle King. You can't do it alone; you need a partner in crime.

And number fifteen: billionaires decide that no matter what they do, they don't ever stay still—ever. At a young age, these billionaires have learned that their greatest failure would be to stay still and get complacent because there is no one ultimate decision to success. The excitement lies in constantly moving and enjoying that movement. Everything can be improved; everything can be better. Your money can always grow; you can always have a better time; you can make a better deal than your best deal ever. Age doesn't warrant stillness either; you could be 93-year-old Warren Buffett, who still handles and trades billions of dollars of other people's money. George Joseph, the 103-year-old founder of Mercury General, is still chairman emeritus, which allows him to give guidance and oversight. You don't stop once you reach your goal; you just create another one.

Since you stuck with us through these 15 life-changing decisions, we had to save a bonus for you. Our last life-changing decision that self-made billionaires have had to make: they decide that complaining is for those without control because they see complaining as a sign of powerlessness. It's a way of giving up control rather than taking decisive action. To be successful, you have to believe that you have control in everything, especially yourself. It doesn't matter if the market is plummeting, if a product launch failed, or if you lost millions in a bad venture. Complaining is not going to change the situation, and if you complain, then you're letting other people know that you don't have control. And you can never have people believing that; they need to believe in your abilities fully. So whatever complaints you have, keep them to yourself until that habit disappears from your mind completely and the only thought popping into your head is: how can I make this better?

All right, Alexa, that's all for today, my friend. You can see that these decisions aren't just about financial moves. No financial achievements happen as a result of these life decisions. They're not easy decisions; they're certainly not all roses and rainbows. They're tough to make and even tougher to follow through on. So the question remains: what will you decide?

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