5 Leadership Lessons I Learned from A Billionaire Investor: Ray Dalio

StrategyDriven Management and Leadership Article | 5 Leadership Lessons I Learned from A Billionaire Investor: Ray DalioThe name of hedge fund billionaire Raymond Dalio triggers emotions of adoration, admiration, and even dislike. That’s the effect success has on people. You do not climb your way up without meeting people who have mixed feelings about you. This should not deter you, and if anything, it should motivate you to be a better version of yourself.

The success, and sometimes, failures of Dalio has made him an inspiration to many. He is on record for saying we make millions of decisions during the course of our lifetime. These decisions, or the logic behind them, determine the quality of lives we lead. While many of us are afraid of failure, Dalio fears mediocrity and boredom.

These are the hallmarks of a true leader, be it in business or politics.

Born in 1949, the American investor, philanthropist, and hedge fund manager is the founder, Co-Chief Investment Officer, and Co-Chairman of Bridgewater Associates, one of the world’s leading hedge funds with a more than $130 billion in assets under management.

With a net worth of $18.7 billion, Dalio started investing at the age of 12 and his life has revolved around finance. There is no doubt that he has lot to teach people and you can learn to be a better leader by imitating how he has managed the investment firm he launched from his apartment in 1975, around the same time that Bill Gates and Steve Jobs founded their tech companies.

Here are five leadership lessons that you can learn from Dalio.

1. Hire people who are better than you

The self-made billionaire is a firm believer in the importance of the people you hire for your business. After many decades of hiring, grooming, and firing people, Dalio says one of the best decisions you can ever make as a business leader is hiring someone who is better than you.

The key to this is the ability to recognize talented employees who bring a particular skill set on the table. This means that if you have people on your team that can perform a certain task better than you, it takes away the need to micromanage them.

This has two advantages. It gives you much time and room to focus on the bigger picture of managing your business. You can spend more time growing the business instead of fulfilling tasks that can otherwise be done by your employees. Secondly, employees are more productive when they are left to their jobs with little to no micro-management.

Real leaders know how to choose the members of their team.

2. No harm in making mistakes

Mistakes are a part of life and there should be no shame in making them once in a while. However, Dalio points out that not correcting them is a big mistake. You have probably heard making the same twice is a choice because you have an opportunity to correct it.

A mistake needs to be identified, analyzed, and lessons learned to prevent the same thing from happening again in the future. A common issue that many organizations face is the lack of courage to personalize mistakes, but more often, generalize them.

At one time in the early 1990s, Ross Waller, the head of trading at the time forgot to place a trade and cost the company some money. Dalio did not fire Waller but instead created a management tool to deal with mistakes and errors.

Dalio learned from the experience that people deserve second chances. He also capitalized on the mistake to develop new methods that can be used to achieve desired goals.

3. Be open-minded

Open-mindedness is one of Dalio’s important lesson yet the hardest. Being open-minded goes hand-in-hand with the ability to evolve fast and learn new things quickly. Some of the techniques that go a long way in helping you to be open-minded are:

  • Feedback – try to get as much feedback as you can especially from other successful people that are not in your immediate circle of mentors.
  • Spend around 90 percent of your time on what you don’t know and the remainder putting what you know to good use.
  • Be an avid reader and on the lookout for new ideas.
  • Listen to people who don’t disagree with you.

4. Taking risks with humility

Dalio became popular in the early 1980s when he pointed out that American banks were overloading Latin American countries with debt. He was proved right when Mexico’s president announced that his country was not able to repay its debt amounting to $80 billion.

He became the go-to person on financial issues. Analysts and the U.S. Congress sought his advice on what would happen next. He predicted that the American economy was headed towards a downturn.

It didn’t happen. In fact, the opposite happened. Stocks went up and the U.S. economy was in a bull market. Dalio was wrong and lost money for his clients. He had to borrow money from his father to pay the bills.

After recovering, he realized that he was not going to stop taking risks, but was going to do so with humility and a changed mindset. He became more open-minded and diversified his portfolio. He has tried to maintain a perfect balance between what he knows and doesn’t.

5. Don’t build walls in your company

One of the biggest mistakes that companies make is personalizing their departments so much that the employees are isolated from each other.

Dalio suggests that employees should be allowed to mingle as much as they can in order to share knowledge and motivate each other to perform their jobs better. Having no walls allows team members to bond and increase productivity when they work together on projects.

This does not literally mean that companies have to break down walls and have an open office space. It’s all about encouraging communication amongst employees and possibly having an open-door policy where employees can feel comfortable approaching each other with their problems.


One of the traits of intelligent people is learning from the experiences of others. Whether it’s value investing in Singapore or learning a new language, it makes sense to learn from those that have traveled the journey before you.

The investment world is filled with successful figures such as Dalio, Warren Buffett, George Soros, and more. They have made a few mistakes along the way. We should learn from them. These great leaders also teach us what it takes to be a great leader. There is no shame in copying what is right and noble.

Three Ways to Become a Better Leader

StrategyDriven Management and Leadership Article |Leadership|Three Ways to Become a Better LeaderLeaders are made and not born. That’s a saying that has stood the test of time and is true whether on the sports field or in the boardroom.

If you don’t consider yourself a natural leader but need to find ways to inspire your team on towards success, you’ve come to the right place. In this blog, we take a look at three great attributes of a leader, attributes you can learn as you go.

Step out of your comfort zone and start making a real difference to your business.

1 Get Organised

With your time, with your paperwork, with your approach and with the details, such as appointing your business immigration attorney. Seeing someone in control and on top of the details shows your team that you take them and their roles seriously.

Not being up to speed on their annual leave requests and so on, sends out a signal that you’re not interested or don’t care about the small details that mean a lot to them.

Instead, show them that you’re the kind of person who leads by example. Who is able to prioritise and who pays attention.

2 Lead, not Boss

This is where so many managers fall down. Quite simply you will get the best from your staff if you lead them, if you’re in the thick of it with them. Gone are the days of the boss sitting several floors up in a glass office away from the hub-bub. Now, you need to be available and to be involved.

Demonstrate your tenaciousness by driving forward sales and working to the best of your ability but also back your team. It’s true to say that sometimes things go wrong and people get things wrong but that doesn’t mean you then have to start throwing your weight around along with blame.

Instead work together to look for solutions and to move the situation forward. This is the kind of behaviour that will inspire loyalty and hard work.

3 Respect Boundaries

When work is over for the day, it’s over. Your team members should see you leading the way by leaving work at a consistent time and making it a priority to spend time with your family. Respect the home lives of your team members too and try to avoid having them spend too much time working late but instead encourage a healthy work/life balance.

You might even give them the option to work from home when childcare is an issue or the trains are not working as they should.

Being in charge is a tough role and a lot of responsibility lies on your shoulders, so give yourself time to grow and relish the role of becoming a leader. Treat your staff as your best asset and find ways to motivate and inspire them as they give their all and help you to achieve your business goals.

As you grow into your leadership role, your team will respond with even greater good will, so work together and become the leader you know you’re capable of becoming.

4 Guiding Principles That Serve as a Foundation for Leadership Success

StrategyDriven Management and Leadership Article |Leadership Success|4 Guiding Principles That Serve as a Foundation for Leadership SuccessEarly in my business career, I worked as a team leader on a high-level project. I had what I thought were great ideas, and I was excited to jump in and get started. I immediately doled out assignments, telling everyone exactly what to do and how to do it. Unfortunately, one of my team members disagreed with the vision that I tried to share.

I didn’t spend the time I should have explaining my reasoning and collaborating with my team to ensure that we all felt we were moving in the right direction. As a result, this lone team member did all they could to sabotage the project, and it was ultimately a failure.

Since then, I’ve come a long way, leading many successful and profitable companies, and I’ve learned a few things about the best way to do it. In fact, I have come up with a set of 4 guiding principles that have been successful for me many, many times over.

1. Trust

Trust is perhaps the most important principle in leadership. If you build trust within your organization, then it will run smoothly. I’ve learned through experience that micromanaging doesn’t work. If someone can do the job, and build that trust with me, they deserve to play an integral part in the company. If they don’t build that trust, they probably don’t belong in our organization. While everyone needs self-discipline, it can’t come from the top down. It has to come from personal ownership and pride in what they’re accomplishing.

2. Vision

Clear business goals are almost always the key to success in both the short and long-term. You need a clear vision of where you want to go, what you want to accomplish and how you will achieve it. Stephen R. Covey, someone I admired greatly, said, “If your ladder is not leaning against the right wall, every step you take gets you to the wrong place faster.” This is true in both personal and organizational goals as a whole.

3. Unity

As my opening example illustrated, if everyone in your organization doesn’t share a unified goal, you will have a much tougher time reaching it. If someone doesn’t believe in the vision, they won’t give their best effort to push for that final destination. That is why it’s critical to spend the time and energy necessary to truly sell your vision inside your organization. Build that trust, and keep the end goal in mind as you go, and everyone is more likely to get behind you.

4. Execute the Vision With Kindness

People respond to the best kind of treatment. As you move forward with your vision, keep kindness at the forefront of all you do. Employees that are treated with respect are employees that will continue to respect both you and your vision.

I truly believe in these principles. Last year in one of my current ventures, we made building trust our internal priority for the entire year. We focused on extending trust to every employee in their role – giving guidance, then empowering them with what they needed to get their job done. From there – we let them find the best way to accomplish the company vision. Without the burden of micro-management, our sales improved by around 30%! It’s difficult to argue with that kind of success.

Building trust takes time and energy, but it is always worth it in the long run. With a foundation of trust, sharing a unified vision becomes easier. Respecting your employees can turn into expecting more from your employees – and because they trust you in return, they will rise to the occasion.

About the Author

Glenn JakinsGlenn Jakins is a serial entrepreneur with a multi-decade track record of taking creative ideas and turning them into successful products that change lives. With a strong background in logistics and operations, he has helped launch multiple 8-figure companies and been instrumental in the increase of tens of millions of dollars in sales for many more. Currently, in addition to other investment ventures, Glenn heads Humless as CEO, pioneering reliable power systems based on clean energy sources.

3 Core Differences Between a Boss and a Leader

StrategyDriven Management and Leadership Article |Leaders|3 Core Differences Between a Boss and a LeaderWhen it comes to management in the workplace, it takes a real person to be a leader for their employees. There is a big difference between the word “boss” and “leader,” as these two words do not mean the same thing. Below is a closer look at three characteristics a leader possesses and why employees look up to them.

What a Boss is

Simply put, some bosses are just a boss. They have attained a position in the management section of the corporate world with a nice office and a designated parking space. They sit back behind their desks and make decisions that affect the direction of the company and often dictate how money is spent. Although these aspects are needed, they are not enough to make the people holding those positions leaders. Fortunately, a boss can become a leader by learning the differences and applying them to the job.

Leading, Rather Than Pushing

Leaders motivate their employees and find practical solutions together to make sure the employees are inspired and follow their leader’s example. Bosses tend to push employees into doing something without really giving them much guidance. This not only forces employees to work without having clear directions, but the results will most likely be less than favored. A good leader will present ideas and work alongside their employees to demonstrate that communication is key and working together to achieve goals as a team is the way to succeed.

Leaders Listen

A good leader spends time listening to their employees instead of talking above them. True leaders see the value of asking employees about their opinions and incorporating those opinions into the decision-making process. On the other hand, a boss will dominate the conversation while expecting employees to listen attentively and carry out commands while giving them little or no direction. Listening will build a team of engaged employees who know they are valued for their skills and knowledge and will want to work harder and more efficiently to complete projects.

Invest Time in Their Employees

Some bosses tend to ignore the majority of their employees, giving those employees the sense of an uncertain future within the company. A leader does not ignore an employee. They invest time and effort in helping each employee develop in their profession, teaching them new skills and allowing them to advance in their careers. Not only that, but a leader will look at their management style and make changes where needed to ensure they are giving employees the attention and guidance needed to perform at their best.

Many people in positions of authority seem to think they only need to stand aside and supervise their employees rather than taking the initiative and working alongside their team. Employees that see their leader invested in the project will be inspired to do their best work as well as improving the team’s motivation, creativity, and collaboration. Good leaders in the corporate world lead their employees by example. Employees will respect their supervisor a lot more if they are relatable and make themselves approachable to the staff.

Supervisors at any level are only as good as the employees that work for them. If a supervisor does not respect their employees and treat them well, the employees will not perform to the best of their ability, and this will reflect poorly on that supervisor and the project they are in charge of.

6 leadership lessons I learned from running an organic meal delivery company

StrategyDriven Management and Leadership Article |Leadership|6 leadership lessons I learned from running an organic meal delivery companyCooking the perfect meal takes time, planning and foresight — and so does great leadership.

My journey as CEO of Fresh n’ Lean, the country’s largest organic pre-prepped meal delivery company, began in 2010 when I was 18 years old.

The early years were the hardest. I consistently worked 20-hour days, tackling any task that was required, including cooking meals, washing dishes and customer service.

There were other challenges, too. I’d be sitting in meetings with older men, and they’d ask me my age (I’d feel compelled to lie and say I was 27). Or they would direct questions to my male colleagues instead of me.

People would question my decisions or my tone or my voice or my demeanor or the way I dressed. Constructive feedback can be so valuable! But much of the feedback I received wasn’t constructive and came from a place of insecurity — people’s own issues working for a young, female leader. It took me years to block out the negativity. And I was so much happier when I did.

Here are some of the other lessons I’ve learned while running Fresh n’ Lean, takeaways for other women navigating the corporate culture to become strong leaders themselves.

Find your deeper calling.

I was inspired to start Fresh n’ Lean after my father faced a life-threatening health battle. He was eating for convenience, so his diet was full of heavily processed foods. He recovered after shifting his eating habits to nutrient-rich, organic meals. His journey motivated me to find a balance between nourishment and convenience — and to help busy people lead healthier lives.


It’s stressful being a boss — you’re inevitably going to encounter difficult situations.

But instead of showing how overwhelmed you are, make sure to keep your emotions in check. Employees will look to you for guidance and stability, and if you’re visibly stressed, everyone else is going to be stressed, too. Be the steady presence guiding the team forward.

Be patient.

As a boss, it’s natural to want to make changes. But how will those changes impact your company’s day-to-day operations?

You may need to wait months — or even years — before your staffing, workflow or facilities changes are implemented. That was the scenario we faced when building our own kitchen and manufacturing area, a goal that had been in the works for a long time. Since Fresh n’ Lean didn’t rely on outside capital, we had to be pragmatic about growth opportunities and only moved forward when the timing was right.

It was so meaningful to fulfill that dream, and I’m glad we didn’t rush the process.

Trust your employees and empower them.

Believing in your employees and giving them opportunities to succeed will give them — and the team — a better chance of reaching full potential.

Too many people second-guess themselves, afraid to fail or worried about taking risks.

Employees should trust their judgment and follow their instincts. That culture of trust begins with the boss.

Lift up other women.

Women too often try to tear each other down in workplace settings instead of building each other up.
Look for growth opportunities for women, and empower younger women to be entrepreneurs and leaders. Go out of your way to showcase their talent. And help them recognize the leader within.

Don’t let the naysayers get to you.

As a strong female leader, it’s frustrating to face labels. Difficult. Loud. Moody. A man can act the same way and it’s celebrated. He’s passionate.

But don’t feel like you need to compromise your leadership style in order to get your point across.

If I’m in a meeting, I’ll often sit quietly and observe and wait for the right moment to speak up. Being the loudest person in the room doesn’t make you the most powerful. You’ll find the right moment, and the right way, to ensure that your voice is heard.

About the Author
StrategyDriven Expert Contributor | Laureen AsseoLaureen Asseo is only 27-years-old, yet she has become a pioneer in leading the nation’s organic food craze. She’s the CEO and founder of LA-based Fresh n’ Lean, the largest nationwide organic meal delivery service in the country. It’s her mission to make eating organic easy, affordable and accessible – reclaiming the phrase “fast food”. She was inspired by her father’s ailing health due to his eating habits, and started the company from her one bedroom apartment.