Why Ultra-Successful Entrepreneurs Eventually Fail

Many entrepreneurs believe they’re in the long game and are essentially unstoppable. They have a few wins and become captains of industry, steering their ships to shore.

Unfortunately, though, most of these super successful entrepreneurs eventually fail. Just look at what happened to Steve Jobs in the 1980s or Richard Branson more recently with Virgin Galactic.

The best people in the world can sometimes let themselves down.

But why does this happen?

Well, it turns out that the world is a complicated place. Many ultra-successful entrepreneurs have to go through extreme learning processes to come out on the other side of the people they want to be. Even the likes of Elon Musk can struggle.

That’s what we explore in this post. It looks at why these entrepreneurs fail and what you can potentially do to prevent yourself from experiencing the same issues.

So here goes:

They Forget Failure’s Lessons

One thing that successful entrepreneurs often forget is failure’s lessons. They often look back and reflect but forget about all the times things didn’t work out for them. Instead, they believe that the good times will just keep on rolling.

Forgetting failure’s lessons is a massive mistake. It often leads to hubris and further failures as entrepreneurs bite off more than they can chew.

Eventually, entrepreneurs can outrun their mistakes. However, big ones eventually catch up with them and then overtake them.

Just look at what happened to Theranos Elizabeth Holmes. She kept on going until reality finally caught up with her, and investors demanded their money back, discovering her fraud in the process.

Therefore, always keep your failures in the front of your mind. Remind yourself that things can and will go wrong.

External Forces Strike Them

Forces outside of their control can also be their undoing. Startup and entrepreneurship financial issues are more common than you might think, and they can occur in well-run businesses with visionary and charismatic leaders.

External forces usually start in the economy. There’s a downturn, and suddenly, the company can’t fund its growth anymore, leading to massive financial strain and a desperate influx of new cash. Unfortunately, seeing the recession, investors are unwilling to commit their money, leading to a spate of failures and sell-offs.

Other external forces are political. Politicians can change the game’s rules, putting countless companies out of business overnight.

Then there are the acts of God, like hurricanes or earthquakes. These can also cause issues.

You can’t prevent external forces from taking their toll on your business, but you can mitigate their impact if they strike. Therefore, taking out comprehensive insurance policies is essential.

They Get Burned Out Or Bored

Another common problem that causes successful business leaders to fail is burnout. Eventually, it creeps up on them, and they no longer feel committed to their work or lives.

Boredom is a similar vice. Doing the same thing over and over again is dull for many leading entrepreneurs who want a real challenge. Then, they try to step out and do something new, only to fail.

This occurred when Bill Gates took a step back from Microsoft. He had built the company, but when he left, the firm stagnated. It was only decades later that it recovered and really became an innovative force again. 

Therefore, it’s a good idea to operate according to an exit plan. You want to ensure that you have a strategy for leaving before you get burned out or bored, allowing you to move on to something new. Ideally, you want to get out of the business for the reasons you ultimately got into it.

They Take On Too Much Risk

You also see some very successful entrepreneurs taking on too much risk. They keep chasing bigger dreams, believing that they will pay off or that the world owes them something, but reality ultimately pushes back.

For example, Jeff Bezos wanted to expand Amazon into a phone empire. However, he later discovered that the market was slapping him on the wrist, telling him it wasn’t going to work.

Sometimes, it’s sheer ego that drives this risk-taking. Ultra-successful entrepreneurs see other wealthy people doing the things they want to do, and they feel the need to do the same, often at the expense of their enterprises.

The key here is to remain sanguine but measured. Entrepreneurs should be optimistic about the future, but they shouldn’t take wanton or reckless risks just because they feel the urge to do so (or they “believe in themselves”). Instead, they should still approach cautiously and fearfully, even if they are titans of industry.

They Get Empire Fatigue

Another problem is so-called “empire fatigue.” Eventually, even the most energetic businesses and startups get worn out.

Just look at what’s happening to Google. For the company’s first ten years, it revolutionized digital products from emails to map functionality. It did things better than anyone else, allowing it to rise to the top and dominate the industry.

But now, the company’s achievements are less thrilling. It even sat on its internal AI systems until ChatGPT arrived in 2022, denying the public the opportunity to use language models.

Empire fatigue is a real problem and hard to deal with. The best approach appears to be to set up separate units for innovations that work outside of the existing corporate structure. These units are freer to do the things they want and they don’t suffer from the same disease as the primary business.

They Get Overconfident

Finally, many successful entrepreneurs ultimately wind up feeling overconfident. They get to the point where they think they can do anything and that the universe is somehow on their side.

This excessive confidence is often the pride that comes before the fall. Business leaders think they have unique skills, whereas in reality, many are just in the right place at the right time.

Bold bets can pay off. But taking them all the time is risky. There needs to be a real rationale behind them.

Therefore, temper your confidence. Make sure you are still thinking straight before making any big decisions.