How This Dropout Created Massive Success as an Entrepreneur (with Olivier Roland): Episode 342

Olivier Roland was 19 year old drop out that created his first business and never looked back. He is now a serial entrepreneur, blogger, YouTuber, startup investor, bestselling author, amateur archaeologist, diver, amateur airplane pilot, globetrotter, international speaker and philanthropist among his many hats. He has built a global audience of more than 450,000 fans convinced by his method, while traveling the world 6 months a year for more than 10 years. Olivier is now on a mission to show that you don’t need to be brilliant in school to be brilliant in life.

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  • Early on, Olivier said he felt he was being held prisoner in his own business. He started the business to be free, but his business wasn’t giving him freedom, it was a jail.
  • Olivier says the key is to be a successful entrepreneur with balance between personal and professional life.
  • When Olivier first dropped out of high school to start a business, people thought he was crazy. But he said that before he made this life changing decision, he did an experiment to test to see if his business could work. He bought an ad in the newspaper and in 1 month he had $800 of sales. Sometimes life is all about taking risks and believing in your ideas. People might think you’re crazy.
  • Olivier’s philosophy is that if you want to do something life changing, what is a small experiment that you can do in your life that won’t disturb many things to see if it will work. What is a test that you can do that is a small amount of time, resources, and money that can be a trial before you launch.
  • An intelligent rebel is one who creates their own adventure in life. A lot of times people can have a good job, house, car, spouse, but inside they feel something is missing. Usually what is missing is creation: adventure, artistic creation, entrepreneurship. One of the things Olivier talks about in his book is that sometimes people aren’t taught through the education system this need for creation and adventure.
  • “There are millions of methods, but the principles are few.”
  • The 3 Vital Principles of an Intelligent Rebel:
    • 1. Understand in your guts that in every field, especially what you’re more interested in, you have more effective methods than others. Be open about the fact that everything around us is the result of our time and resources. Being an employee for example, is the worst way to make money. There is a difference between quitting your job, and quitting your business. The difference is that if you quit your job, you are a one man band. If you are building your business, you are orchestrating. The conductor doesn’t have to play every instrument, he’s just in charge of making it all go together.
    • Be a good skeptic. Salaries are skeptical. It can be good to be skeptical. It’s healthy. Instead of using your skepticisms to do experiments in your life. When you hear about a method too good to be true, instead of rejecting it, use the skepticism to fuel your curiosity to test to see if it works, if it’s true! This at the very least will allow you to try more things and get to know more about yourself and the world around you.
    • Once you identify good methods, follow Pareto Law: focus on the 20% causes that produce 80% of the outcome. It’s never exactly 20/80, but the thing is there are a small set of causes that make up most of the outcome! Focus on that 20%.
  • Olivier shares that one of the hardest things as an entrepreneur is finding out what that means. Entrepreneurs start with their skills often times, but in order to be an entrepreneur at the beginning, you need to do it all–business, marketing, etc. on top of your skills! He said he almost went bankrupt and he was ashamed because of the mistakes and loss of money. He said it’s better to face it and tell everyone of his mistakes. Honesty is key, and the center of growth.
  • Ikigai  is your mission in life. Olivier says that if your business is your Ikigai, things will be great. Think of it as your North Star. Not every business will be your mission and your passion, no. You might not start out like that. But the goal is to get there over time and to find your Ikigai in your lifetime.


  • (1:40) A little more about Olivier.
  • (2:50) Personal development books that changed everything for Olivier.
  • (3:58) Olivier’s current business.
  • (4:25) How Olivier went from a high school dropout to a successful entrepreneur.
  • (6:20) The power of taking risks.
  • (7:24) Olivier’s philosophy.
  • (8:05) What does it mean to be an intelligent rebel?
  • (13:22) The 3 Vital Principles of an Intelligent Rebel.
  • (16:30) Why it can be good to quit your job.
  • (19:01) Become a skeptic!
  • (20:45) Pareto Law.
  • (23:13) Mistakes Olivier has made along his entrepreneurial journey.
  • (28:55) What does it mean to Olivier to make an impact?
  • (30:21) What is your “Ikigai?”
  • (31:10) Where to connect with Olivier.


“The company I created to be free ended up being a jail.”

“If you want to do something life changing, what is a small experiment that you can do in your life that won’t disturb anything to see if it will work.”

“The system was not designed with you in mind.”

“The system can be a strength if you know how to play your cards right.”

“There are millions of methods, but the principles are few.”

“It’s good to quit your job.”

“You want to leave the world in better shape than when you arrived.”


Connect with Olivier:


Olivier’s Book: The Way of the Intelligent Rebel: Succeed Outside the System, Teach Yourself Anything, and Achieve Ultimate Freedom

Youtube Channels:

Olivier’s English Channel

Olivier’s French Channel

Book Recommendations:

4 Hour Work Week by Tim Ferris

The E-Myth by Michael Gerber

Watch Full Episode:

How This Dropout Created Massive Success as an Entrepreneur (with Olivier Roland): Episode 342

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Hey! I’m Rachel. I’m a former Big Ten volleyball player turned entrepreneur and professional cheese taster (kidding–but that would be a sweet job).

I’m a Pinterest strategist for female entrepreneurs who are sick of struggling on Facebook & Instagram and want to automate their traffic and get more leads on autopilot. I’ve used Pinterest to increase my blog traffic by 34,000/month…for free!

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