Ray Dalio calls Sean ‘Diddy’ Combs his hero

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Ray Dalio is an American billionaire investor, hedge fund manager, and philanthropist. He is the founder, co-chairman and co-chief investment officer of Bridgewater Associates, the world’s largest hedge fund.

After posting Part II of his mentoring session with the hip-hop icon, Dalio explains why ”Sean ‘Diddy’ Combs is a hero of his.”

Diddy said in the video when he started his ‘paper boy franchise’, it gave him a sense of pride. At the time he was making about $500/week enough to really make a difference in his family’s life.

His worth ethic came from his mother after seeing her work 4 jobs to support his family. Diddy’s journey as an entrepreneur began working multiple different jobs doing the paper route, was a gas station attendant and worked in a Mexican restaurant. This is how the hip-hop icon discovered concepts of hard work and what it would take in order to be successful.

Dalio said that Diddy’s family background and upbringing helped lay the foundation for his success in life.

”When I think about your background, in terms of your dad, and all of that journey, I think your roots of what you want and value came from there” – Dalio

What Does ‘Can’t Stop Won’t Stop’ Mean?

Sean ‘Diddy’ Combs: ”Theres so many times where you want to quite and the odds are so much against you. When you get knocked down 10 times, get back up 11”

Diddy talks to Dalio about his journey as a hip-hop icon, record producer, actor and entrepreneur. He said that individuals should focus on personal growth, keep learning and progressing. He also says that we should embrace both the good times and bad times. Without this, it will make it much more difficult to keep moving forward when obstacles come our way.

Dalio’s Mantra In Life

”Dreams + Reality + Determination = A successful life”

Inside A Meeting Part I – Sean ‘Diddy’ Combs Questions

Question 1: ”What is your definition of being radically open-minded?”

Answer: To simultaneously have an opinion, while also considering any variables that may compromise your thesis. Dalio explains that it is your ”capacity to hear and then challenge”

It is being open-minded and assertive at the same time. There must be a balance because being too assertive can lead to arrogance. This is one of Dalio’s principles that he constantly reiterates that lead to his success in business and life. His ability to apply this principle in his hedge fund, Bridgewater Associates, has been an important component to his success.

Question 2: ”What advice would you give me to help me find the best people to build my team?”

Answer: Have a specification sheet for each particular job. Every job requires a person with particular ”essential elements and traits”. These jobs are very specific and people with specific talents must be picked to do the right one.

Ray Dalio’s Reverse 360 Criteria:

3 Most Important Things In Hiring Process: Value, Ability & Skills

If your values do not align with the individual, that is where the disconnect comes into play. Each person has natural abilities that make them who they are. People also develop skills that are innate or learned.

The most important thing is making sure their values align with yours. Dalio emphasizes in the reverse 360 process that contacting people who have known them in the past and working backwards is very important part of the hiring process.

He also explains that apart of the journey when the hiring process is done is constantly testing these people’s skills and abilities every single day.

Question 3: ”What advice would you give for someone coming from a history of success, what steps did you take to reset and become the best person you could be?

Answer: Pain + Reflection = Progress

Dalio says that if you’re in this position where you have already seen success, focus on what really matters to you. This is apart of the reflection stage. He also says that if you don’t have great talent around you it can be a very miserable time. Great talent and great individuals often leads to great results. Finding this great talent and having individuals that can be ”radically openminded” is a very important part of the process.

”Your have to sort through the people that keep the bar high” – Dalio

He says to Diddy that an easy way to fix his problem and find people to work with that are at the same level that he is at is to find a partner. This partner may have certain characteristics or traits that you don’t have or value that could be very useful to the success and the milestones that you’re trying to reach.

Dalio uses the analogy of a basketball team and how a basketball organization is formed. You as the CEO and leader don’t necessarily have to have all the skills to build a great business. But you need to have good pieces i.e. basketball players, scouts, managers, coaches etc. in order to be successful.

Question 4: ”Who are some of the leaders you look up to, why?”


  1. Mohamad Yunus is a Bangladeshi social entrepreneur, banker, economist. He was awarded the Nobel Peace Prize for founding the Grameen Bank and pioneering the concepts of microcredit and microfinance.
  2. Geoffrey Canada is an African American educator, social activist and author. Canada has been president of the Harlem Children’s Zone in Harlem, New York, since 1990. The organization’s goal is to increase high school and college graduation rates among students in Harlem.

Question 5: ”Why did you write the book Principles?”

Answer: Dalio says that he is a transition phase in his life where he has seen success and learned things in different areas of his life. His goal when writing the book ‘Principles’ is to guide others through the trials and tribulations in the journey called ‘life’ and help them be successful. He wanted to pass these same principles along to others so he can have peace. This will allow him to leave this earth knowing that the lessons he taught others could apply to their own lives to reach their full potential.

Dalio explains that his ability to mentor Diddy is important because he will be able to pass along those same principles to others that he learned and it will ”reverberate.”

For more information,

Visit Diddy & His Mentor Ray Dalio | Inside a Meeting

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