How self-made billionaires overcome their biggest obstacles–and how you can, too | Inquirer Business

How self-made billionaires overcome their biggest obstacles–and how you can, too

/ 04:10 AM May 02, 2022


Fortune magazine has called me “the mentor of the giants.” In this article, I want to share with you how the famous business leaders, Fortune 500 CEOs, and self-made billionaires I have interacted with, advised, or coached, develop enormous levels of tenacity and resilience to reach their most ambitious goals.

What is the secret of the mental toughness these famous business leaders have? Is it genetics? Inborn character? Far from it. Do they have some special magical powers or super talents? Most of them do not. You do not need to be a genius to become a billionaire entrepreneur. In fact, it is enough to have only above-average intelligence. And some of them would argue even that is not needed!


They have simply cultivated the right habits that allow them to reach their goals and overcome obstacles even when they face the hardest of challenges. What are the secret ingredients that allow them to overcome hardship and adversity? It is the principles they apply, and how they deal with obstacles that are important.

They know that big goals come with big obstacles

The higher your goals, the more you should be prepared for challenges. This is a natural equation in any profession. In whatever field, to reach the top, you will have to master new skills, gain new insights, grow and become a better version of yourself. This should be obvious but it is surprising how many people in business complain about obstacles and challenges after they have set ambitious goals.


Embrace them! They mean that you are on the right track to grow and reach the next level. The contrary is also true: the less you want to achieve, the fewer challenges you will encounter. I know some brilliant people with great potential but very little success who hold themselves back by clinging to this one belief: it always has to be easy. And if it is not easy, they believe they are not on the right path. If you believe that even to some extent, you hold yourself back from reaching your full potential.

Most outstanding business leaders and certainly many of the richest people in the world have studied biographies of important world leaders, business leaders or political leaders. Why? To be inspired by their courage, strength, perseverance and belief in their abilities to accomplish the impossible!

They are masters at delaying gratification

Life is about growth. And growth brings pain, natural growing pains. The same is true for going to the gym and getting in shape as for getting into business and building a billion-dollar company. You should welcome and embrace growing pains, not run away from them.

Ray Dalio, an American self-made billionaire investor and hedge fund manager, calls these “first-order” and “third-order consequences.” What does that mean? First-order consequences mean: you give in to whatever urges or desires you have right now. Third-order consequences mean: you do whatever is best for your long-term goals, even if that means enormous sacrifices.

But how do you do that? And why do most people who never achieve extraordinary success fail so miserably at it? The secret is to keep your mind firmly on your goal. To make it so big and shiny that it is always there, cheering you on. To make the ultimate goal you are striving for larger than life, to blow up the images in your mind and make them life-size or bigger, and to constantly affirm to yourself that it is going to happen no matter what.

The vision of their goals fulfilled in all of their glory serves as a magnet pulling them through even the toughest of times.

They cultivate a champion’s mindset

Winston Churchill said: “Never give in. Never, never, never, never—in nothing, great or small, large or petty—never give in, except to convictions of honor and good sense. Never yield to force. Never yield to the apparently overwhelming might of the enemy.”


The greatest battles are fought in the mind first before they are ever fought on the battlefield. That is especially true in business. It is almost as if life wanted to test our resolve by throwing stones in our way. Most people give up a few meters before the finish line.

There is one essential mindset I have written about before but it bears repeating. This mindset is the one major difference between founders of startups that reach a billion dollars in value (so-called unicorns) and the ones that do not. It is also the fundamental difference between world-record champion athletes, whom I have coached as well, and athletes who just compete but never stand out. And it is the number one difference between the business leaders who defy all odds and the ones no one will remember.

Contrary to conventional belief, it is not talent or naturally superior physical abilities, except for a few exceptions. It is their constant inner affirmation that they will be successful, that they will accomplish their ambitious goals, even if no one believes in them.

The same is true for the business leaders and entrepreneurs who go on to defy the impossible: they constantly work on that inner conviction, their champion’s mindset.

They master pain and sacrifice

Viktor Frankl, an Austrian psychiatrist, philosopher, writer and Holocaust survivor, summed it up perfectly by saying: despair equals sacrifice without meaning. What does that mean for you? It means that your purpose and the vision of your ideal future need to be as clear as possible for you to endure high levels of stress and sacrifice. The more the meaning of what you do is clear and compelling enough, the higher the levels of pain and sacrifice you can endure on the way to your goal, and the higher obstacles you can overcome.

Consequently, the clearer the meaning, the clearer your vision of what it is that you want to accomplish for yourself or for your business, the faster you will reach your objectives. It is a simple equation. As Friedrich Nietzsche said: “He who has a why to live for can bear almost any how.” If you want to reach your most ambitious goals, work on the “why” first.

They double down when things get hard

It becomes very lonely at the top, and in the moment of their most difficult decisions and biggest personal challenges, most famous business leaders have to rely on their natural instinct and intuition. And they all do. From the president of eBay to Richard Branson, all business leaders I have had the pleasure to interact with draw on their inner strength and guidance system at the moments of their greatest trials to accomplish the impossible

Yes, they ask others for advice and get the best experts they can. But then they have to call the ultimate shots. They know how to quieten their mind and regularly engage in activities that get them into a free flow where they can produce their best ideas. Billionaires like Branson and the Google founders both love kitesurfing, and so do I. I always advise my clients to have one or more foolproof activities that allow their minds to go into that free drive, whatever these activities are. INQ

Tom Oliver, a “global management guru” (Bloomberg), is the chair of The Tom Oliver Group, the trusted advisor and counselor to many of the world’s most influential family businesses, medium-sized enterprises, market leaders and global conglomerates. For more information and inquiries: or email

[email protected]

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