Leonardo DiCaprio: Hollywood Rebel, Entrepreneurial Badass

Leonardo DiCaprio: Hollywood Rebel, Entrepreneurial Badass


There’s no question that Leo is an unbelievable actor. His track record is impeccable, he’s a household name, and he’s known for jaw-dropping performances and seamlessly jumping between genres. He’s had some of the most notable roles in Hollywood over the past 15–20 years and has been full steam ahead with his career since he entered the game.

For the millennial generation, he’s one of the best actors we’ve known.

He’s also been under-recognized, I think, for being a great role model. He does what he loves, he does it extremely well, and he does it regardless of whether anyone else thinks he is worthy of awards. He’s a real life, mainstream, celebrity example of how we should all try to show up in the world — he’s also a distinct parallel to what it takes to be a successful entrepreneur outside of Hollywood.

Leonardo DiCaprio is also his own version of a positive disruptor. He’s never been appropriately lauded for his work, namely he’s never won an Academy Award, although he has been nominated for Best Actor three times. Admirably, he consistently states in interviews that the reason he’s an actor is not for the recognition — it’s the passionate love of the work itself, and the art of cinema.

It’s an unfortunate reality that many people are driven by external validation, material gain, and toppling their competition — exclusively for the sake of ticking these boxes. While there’s no argument that these aspects of success are great, the real value is in finding true fulfillment in the work that you do. DiCaprio is an exemplary representation of exactly how to show up for the grind with complete integrity, tenacity, and authenticity.

When your mind is right, the motivation behind your hard work is the fact that you want to consistently hold your focus on what moves you to be inspired, not stacking millions.

In my personal experience, one of the greatest lessons I’ve been fortunate to learn and share is that material wealth is no match for the complete gift of doing what you love and changing people’s lives. I have no doubt that DiCaprio is an inspiration to many other actors, and that he is an encouraging point of reference for those who truly believe in their craft above all else.

Whether Leo wins an Oscar or not is a moot point now, because his career is a testament to what it means to be fully in alignment with being a stand-up human. He’s dedicated, passionate, and unconcerned (seemingly) about whether anyone else validates his performances.

I firmly believe that embodying these characteristics in any career or walk of life are what can be the difference between tremendous sustainable success and short-lived empty material gain.

I see DiCaprio as a rebel in this way — there are plenty of actors, entrepreneurs, and people everywhere who see financial gain as the only goal. They want to be known, to be famous, but not always for reasons that come from a deeper, meaningful place. Most of us do want to be recognized. Most of us do desire financial freedom. But both of these things are so much better when you’ve handled your rise to the top with enough badassery to do it simply because you love it, and the kind of positive rebellion that sets you apart because you’re doing great work without worrying about what others have to say.

We need more great role models like this.

Speaking to the millennial generation, we’re all starved to make our own unique impact. If we can align our minds to consistently and dedicatedly work on our passions and transform them into our incomes, the world will be a hell of a lot more honest, satisfied, and meaningfully creative.

Back to Blog