Lessons from Billionaires: Key Takeaways and Regrets for Self-Starting Entrepreneurs

6 Jun 2024

Life can be full of regrets, and not even the world’s richest billionaires and most successful founders are immune to encountering some regrets in their lives. While standing at the pinnacle of their careers, we often assume that successful leaders, self-starters, and self-made millionaires don’t have any regrets while amassing immense wealth.

While successful startup founders and chief executives tend to hide their regrets and mistakes in the shadows, shining a light in these corners reveals that they are just as human as everyone else.

By taking billionaires' regrets and mistakes, and turning them into an avenue through which entrepreneurs can learn, they can equip them with the knowledge and tools to develop new ideas, survive in a competitive marketplace, build their team, and make a name for themselves.

Though the problems some of the world’s richest people face may look a lot different compared to the everyday person, as an entrepreneur on the road toward building a successful business or startup, it’s possible to learn from billionaires’ mistakes and use it as an opportunity to navigate the many obstacles one may face in the world of business.

A First-Class Ticket To Regret

There are billions of people in the world, and in the countries with the most billionaires, even self-starting entrepreneurs would most likely jump at the chance to strike up a conversation with the most successful business leaders.

Perhaps it’s safe to say that the likelihood of this happening is somewhat slim, taking a front-row seat to their life’s biggest regrets and mistakes can help to paint a different picture of their success.

Losing Sight of Your Mission

Cultivating success is more than making the right business decisions. For successful entrepreneurs, it’s important to keep sight of their mission, standing by its purpose, even when others are denying its credibility.

A prime example of someone who has continued to stand by their mission, despite the social and political backlash is Elon Musk, who in his pursuit of technological innovation, has maintained an attitude towards success, even when that comes at the expense of his business.

Musk has remained a steadfast believer in the development of sustainable technology, pushing the boundaries of technological ingenuity, and using his failure as a roadmap towards improving past mistakes.

Losing sight of the bigger picture is common among self-starters. When things become difficult, cash flow problems restrict growth, or even when others are denying the long-term success of something, many might feel compelled to rest their tools, instead looking toward starting over or doing something new altogether.

Missing Out On Golden Opportunities

There are countless stories of entrepreneurs missing out on great opportunities that would’ve pushed them into a completely different stratosphere of success.

Taking on every opportunity that comes your way might seem perplexing, however, leaving something on the table for someone else, when you know it might turn out to be something worthwhile can leave a feeling of regret throughout your career.

This, however, doesn’t mean that you shouldn’t have a goal, but instead means that as an entrepreneur, you need to decide on something you believe in and take that on with full force, even if you begin to doubt yourself.

Jeff Bezos, founder of Amazon and Blue Origin, has previously said in an interview with Business Insider that anyone will most likely regret the things they never did when they turn 80 years old. He continued by saying that it’s unlikely for someone to regret something they did and failed or never worked out.

While it may never be clear at the moment whether something will turn out to be a success or a failure, it’s better to try and know what the outcomes may be than leave great opportunities up for someone else to take.

Ignoring the World’s Problems

There are a lot of things we still don’t know about the world. Everything around us is constantly changing, and as an entrepreneur, seeking to learn about the world’s problems can provide a different perspective on a person’s current state of problem-solving.

Back in 2017, the founder of Microsoft and philanthropist, Bill Gates shared on a series of Tweets on X (formerly Twitter) about the one thing he regrets the most of his career. For Gates, it was being oblivious to the world’s problems around him, and never really learning more about the issues of inequality the people around him were facing.

In the posts he made at the time, Gates shared that by the time he left school, he knew very little about the world's issues, something which took him decades to learn after attending college and before founding one of the largest and most successful technology companies in modern history.

Ignoring serious matters won’t make any of your problems less important. However, as Gates, and perhaps many others have said before, knowing the current state of the world’s inequities will provide any person with a great value of knowledge that they can carry with them for the rest of their life.

Using this knowledge as a tool could mean new opportunities for entrepreneurs, but more importantly, help level the playing field for others who may not be in the same boat as you. Taking the world’s issues on your shoulders won’t solve anything, however, it’s important to become involved and determine how you can make a difference.

Not Taking More Aggressive Risks

Reward comes with taking risks, and in business, the bigger the risk the bigger the reward. However you might feel about this statement, taking calculated risks can present entrepreneurs with the ability to pursue wealth and other opportunities more actively while working on their missions to achieve their ultimate goal.

Starting any business comes with its set of risks which can lead to financial success and new opportunities. The opposite can also be true; by taking risks, you may put yourself in the direct line of fire of being a failure or missing out on key opportunities elsewhere.

Regardless of how you might approach this, it’s important to consider that taking risks can eventually lead to better opportunities, and perhaps the success you’ve been working to achieve.

Above everything else, taking risks is about finding value in the things you are doing, and being open-minded to approaching a problem differently. By finding balance in the things you do, and learning the importance of overcoming fears and taking action, entrepreneurs and self-starters can build toward their goals and achieve their mission without hesitation.

Seeing Mistakes as Drawbacks, Not As a Learning Opportunity

The Oman of Omaha, Warren Buffet, is well-known for his investment strategies and his ability to keep a long-standing position on his investments. However, back in the early days of Berkshire Hathaway, things were looking a lot more grim for the then-textile company compared to the success it generated over the years.

In an attempt to outbid the then-CEO of Berkshire, Buffet decided to purchase a controlling interest in the company, cashing out more than $200 billion in a business that was struggling to stay afloat. Buffet would later call this one of the biggest miscalculations in his professional career, saying that the strategic blunder cost him billions in his own money, while yielding subpar returns.

Though the decision to hold onto his majority stake in the company would eventually pay off, Buffet took the opportunity as a learning curve, leveraging his decisions to work in his favor, instead of downplaying the meager outcomes.

Making mistakes is part of the process, but more importantly, learning from these mistakes presents entrepreneurs with a unique opportunity to learn and grow from them. Instead of using his miscalculated blunder as a way to misguide him, Buffet turned around and leveraged the mistake as a valuable lesson instead.

Failing to adapt and innovate

Remember the infamous video renting company, Blockbuster that employed more than 84,000 people at its peak? Or the technology and software company, Research In Motion, which owned BlackBerry and had around 80 million users globally?

Other names such as Kodak, Xerox, MySpace, and Sears are only a few examples of companies that failed to remain relevant as the world around them was quickly changing. There are many companies that have gone under due to poor leadership and executives failing to adapt their business model to an ever-changing market.

Adapting to a changing market environment is crucial to the long-term success of any business, and while it’s important to deliver a consistent product or service, keeping track of the changing consumer market or demand helps to make it possible for companies, of any size or scale to remain a competitive and relevant brand.

Similar to the importance of adapting is the ability to innovate. For instance, Blockbuster, which had more than 9,000 stores during its height in the early 2000s, quickly noticed a sharp decline in customer support following the release of services such as Netflix and Redbox.

While there may be other factors that have contributed to the company's demise as well, failing to innovate and adopt new ways of doing business meant that the company experienced a tremendous loss in business almost overnight.

By keeping a finger on the pulse of developments within your respective industry, you and your business can learn to become more tangible, adapt to a changing consumer environment, and present more innovative solutions that are not only relevant but present you with a more competitive edge.

Leveraging Regrets For Success

Starting a business or building a multinational empire doesn’t happen overnight, and nor does it come without any regrets, positive and negative.

As an entrepreneur, still at the beginning of their career, taking the opportunity to learn from other successful leaders’ mistakes and regrets can help you avoid these problems once you encounter them.

Making the decision to learn from your mistakes is a way to approach a problem from a different perspective, but more than this, using it as a learning experience can help shape how you see new opportunities.

There will most likely come a time in your career where you will realize that having regrets, and not taking action in the moment, is not only one of the biggest mistakes of your professional endeavors but were perhaps the things that withheld you from achieving success sooner.