Entrepreneurs
The Top 10 Dare Devil Entrepreneurs Who Embrace Risk
To become truly great in business, you have to take risks. Risk is also something most people are afraid of and as a result, they shy away from building a successful business in order to avoid it. However, risk taking is also the reason most billionaires came to become some of the richest people on the planet.
Do you consider yourself to be a risk taker? Do you evade or embrace risk as a part of your life?
Well this article will take a look at 10 of the biggest risk takers in business.
Perhaps one day you can borrow a leaf from these dare-devil entrepreneurs and become a major success.
10 Highly Successful Risk Takers In Business
1. Donald Trump
With his monster TV show The Apprentice, a sprawling business empire and a billion dollar fortune, Donald Trump appears to be on top of the world. What you may not know is that it was not always this way. As a matter of fact, there used to be a time when he was facing personal bankruptcy with personal debts of $900 million. Donald Trump’s business also declared bankruptcy with debts of about $3.5 billion.
However, he had cleared his personal debt within a period of 4 years, greatly reduced his business debt and even merged some of his business interests into a publicly held company, all in a short period of time. Trump is living proof that risk takers can win big in business and lose big as well. As a matter of fact, Trumps success was due to his willingness to take huge risks.
2. Bill Gates
The billionaire Bill Gates took a great amount of risks while founding Microsoft. He had to drop out of college in order to help create Microsoft. He took a huge risk, starting his business based on his vision that the personal computer would be a useful tool in every office and home.
Bill Gates was prepared to travel in the wilderness of the unknown and would do anything to win. He even went up against Steve Jobs and was not threatened to copy or borrow ideas from other great innovators and tech companies. This paid off in the end when his company became a tech giant worth billions of dollars.
3. Henry Ford
The world famous inventor of the automobile was very imaginative and willing to take risks. He slashed prices so steeply that he risked taking losses yet he managed to meet the crushing demand for Model T’s.
In order to satisfy consumer wants, Ford had to take it to the next level with a do or die attitude. Henry Ford even cut down the working hours and increased minimum wages for his workers so that they could work for a longer period of time before quitting. A very risky move that could be considered a mistake to most but was a strong reason why Henry Ford was able to conquer the automobile world.
4. J. Paul Getty
Known for his many failed marriages and his capacity for bearing risk, this billionaire oil baron is one of the most successful business people in our history.
J. Paul Getty founded and controlled Getty Oil Company in addition to 200 other companies. He left some of his wealth to the Getty Foundation which he created while still alive.
5. Larry Ellison
The founder of Oracle and one of the richest people in the world, Larry Ellison’s net worth is somewhere around $50 billion.
Much of his success has been attributed to taking huge risks. Larry Ellison would promise people non-existent features, only to go back to his developers and demand them to build the products. He would also hire staff unqualified for their position only to train them later with manuals and books.
6. Richard Branson
The founder of Virgin airways and the 4th richest man in the United Kingdom, Richard Branson’s success has been attributed to taking huge risks in business. With Virgin Records, Branson grew his label by signing controversial acts of the time. He took this risk in order to raise some eyebrows and establish his label in a crowded industry.
At one point, Richard Branson had 125 law suits against his empire, for weird and oddly pathetic reasons. He knows that there are going to be haters out there when you are doing big things, but that doesn’t stop him, he loves the thrill of a risk.
7. Warren Buffett
As an investor, Warren Buffett has never been afraid of taking risks and making mistakes along the way. It is his readiness to take huge risks that have contributed to his astounding success.
Warren Buffett understands that stocks and shares are a huge game of risks, but he knows the investment of risk taking experience over time minimises his investment risks for the future, and so nowadays he tries his luck investing in various different industries with a huge measure of success.
Right now Warren Buffett is extending out side of investments and branding companies with his Berkshire Hathaway name. Something he has never really done before.
8. Jeff Bezos
Founder and CEO of Amazon.com, Jeff Bezos’ success has been hugely due to the risks he has been taking all throughout his career. Recently, he bought The Washington Post, a struggling new operation and looks to turn it around into a revenue generating business.
Jeff Bezos started his first company from a garage in 1995 and by 1998 he was in charge of a $22.1 Billion market presence.
9. Elon Musk
Elon Musk, co-founded PayPal, he created America’s first viable fully electric car company Tesla Motors, started the nation’s biggest solar energy supplier, and rolled the dice with NASA to launch his space exploration company SpaceX all in the space of 15 short years.
Elon has managed to solidify Tesla Motors in a high risk, high cost industry. He faced the critics and haters when he funded his own SpaceX mission to Mars and was on the verge of company collapse when he played Russian Roulette between funding both failing companies Tesla & SpaceX, not knowing if both companies will fall apart or not. Elon Musk is known as this generations well known biggest risk taker.
Elon Musk’s Net-worth is estimated to be $6.4 Billion and growing.
10. John D. Rockefeller
Owning the world’s largest oil supply known as Standard Oil, John D is the wealthiest person that ever lived. A strategic risk taker, John never settled and was always looking for greater things. He would give up good for great and this lead to his huge success. He knew that with the right intentions, anything could be achieved. He was a humble person who left behind a great legacy.
John D. Rockefeller is well known for taking positive calculated risks in every business venture that he got into. So as you can see, taking risks comes with huge success.
The very things that we stand to lose when we take risks are the very same ones that we stand to gain. The dare devil entrepreneurs that are listed above were able to become successful billionaires because they were ready and willing to take risks. If they had stayed in their comfort zones, they probably wouldn’t have made it to the financial heights that they accomplished. In business, great success comes with taking great risks and trusting your instincts that everything will turn out quite right.
You never know what you can accomplish until you do something that you have never attempted.
Taking the risks gives you the opportunity to step into some of the biggest you could ever imagine.
Entrepreneurs
The Leadership Shift Every Company Needs in 2025
Struggling to keep your team engaged? Here’s how leaders can turn frustrated employees into loyal advocates.

In workplaces around the world, there’s a growing gap between employers and employees and between superiors and their teams. It’s a common refrain: “People don’t leave companies, they leave bad bosses.”
While there are, of course, cases where management could do better, this isn’t just a “bad boss” problem. The relationship between leaders and employees is complex. Instead of assigning blame, we should explore practical solutions to build stronger, healthier workplaces where everyone thrives.
Why This Gap Exists
Every workplace needs someone to guide, supervise, and provide feedback. That’s essential for productivity and performance. But because there are usually far more employees than managers, dissatisfaction, fair or not, spreads quickly.
What if, instead of focusing on blame, we focused on building trust, empathy, and communication? This is where modern leadership and human-centered management can make a difference.
Tools and Techniques to Bridge the Gap
Here are proven strategies leaders and employees can use to foster stronger relationships and create a workplace where people actually want to stay.
1. Practice Mutual Empathy
Both managers and employees need to recognize they are ultimately on the same team. Leaders have to balance people and performance, and often face intense pressure to hit targets. Employees who understand this reality are more likely to cooperate and problem-solve collaboratively.
2. Maintain Professional Boundaries
Superiors should separate personal issues from professional decision-making. Consistency, fairness, and integrity build trust, and trust is the foundation of a motivated team.
3. Follow the Golden Rule
Treat people how you would like to be treated. This simple principle encourages compassion and respect, two qualities every effective leader must demonstrate.
4. Avoid Micromanagement
Micromanaging stifles creativity and damages morale. Great leaders see themselves as partners, not just bosses, and treat their teams as collaborators working toward a shared goal.
5. Empower Employees to Grow
Empowerment means giving employees responsibility that matches their capacity, and then trusting them to deliver. Encourage them to take calculated risks, learn from mistakes, and problem-solve independently. If something goes wrong, turn it into a learning opportunity, not a reprimand.
6. Communicate in All Directions
Communication shouldn’t just be top-down. Invite feedback, create open channels for suggestions, and genuinely listen to what your people have to say. Healthy upward communication closes gaps before they become conflicts.
7. Overcome Insecurities
Many leaders secretly fear being outshone by younger, more tech-savvy employees. Instead of resisting, embrace the chance to learn from them. Humility earns respect and helps the team innovate faster.
8. Invest in Coaching and Mentorship
True leaders grow other leaders. Provide mentorship, career guidance, and stretch opportunities so employees can develop new skills. Leadership is learned through experience, but guided experience is even more powerful.
9. Eliminate Favoritism
Avoid cliques and office politics. Decisions should be based on facts and fairness, not gossip. Objective, transparent decision-making builds credibility.
10. Recognize Efforts Promptly
Recognition often matters more than rewards. Publicly appreciate employees’ contributions and do so consistently and fairly. A timely “thank you” can be more motivating than a quarterly bonus.
11. Conduct Thoughtful Exit Interviews
When employees leave, treat it as an opportunity to learn. Keep interviews confidential and use the insights to improve management practices and culture.
12. Provide Leadership Development
Train managers to lead, not just supervise. Leadership development programs help shift mindsets from “command and control” to “coach and empower.” This transformation has a direct impact on morale and retention.
13. Adopt Soft Leadership Principles
Today’s workforce, largely millennials and Gen Z, value collaboration over hierarchy. Soft leadership focuses on partnership, mutual respect, and shared purpose, rather than rigid top-down control.
The Bigger Picture: HR’s Role
Mercer’s global research highlights five key priorities for organizations:
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Build diverse talent pipelines
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Embrace flexible work models
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Design compelling career paths
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Simplify HR processes
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Redefine the value HR brings
The challenge? Employers and employees often view these priorities differently. Bridging that perception gap is just as important as bridging the relational gap between leaders and staff.
Treat Employees Like Associates, Not Just Staff
When you treat employees like partners, they bring their best selves to work. HR leaders must develop strategies to keep talent engaged, empowered, and prepared for the future.
Organizational success starts with people, always. Build the relationship with your team first, and the results will follow.
Entrepreneurs
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