Entrepreneurial Skills We Can Learn from Ray Donovan

Entrepreneurial Skills We Can Learn from Ray Donovan

Earlier this year, we said goodbye to Ray Donovan, in the movie finale of the long-running ShowTime crime drama series. Many of us are unsure whether it really is the last time we will see Ray (tears drop) in action.  


So much has been said about the complex ‘anti-hero’, however, with all his flaws, Ray’s character offers insights, as a self-made entrepreneur. If you're a ‘Donofan’, see if you picked up on these lessons that Ray has given us on how to become an entrepreneur.

1. Success is all about becoming a problem solver

Ray's job is best described as a “fixer," whether it's covering up a celebrity's indiscretions or protecting people from fellow criminal predators. From a young age, Ray found something he was good at (keeping a cool head under highly stressful situations) and carved out a niche for himself. Some might even call him a teen entrepreneur.


Lesson: The first step toward becoming an entrepreneur is figuring out what problems you can solve for others. What need is there in the market that you have a solution for? Once you've identified what you're good at, you can go out and share your talent with the world.


2. You may have to take some risks to get ahead

In the show, Ray takes his blue-collar Boston tough-guy roots with him to Hollywood and then ultimately to New York, upgrading his status and powerful network along the way.


Lesson: While you certainly don't want to cross the ethical and moral lines that Ray did throughout the series, you'll need to figure out not only how to earn money, but how to invest that money and make tough decisions throughout your entrepreneurial journey.



3. Multiple challenges call for resourcefulness.


At many points in the series, Ray's phone never seemed to stop ringing, with everyone calling about their problems simultaneously. It's in those moments that Ray had to focus and figure out how to best use his resources to put out multiple fires at once.


Lesson: Being able to think on your feet and pivot a plan when needed is an important skill for entrepreneurs. It’s good to have go-to contingency plans in place so that when disaster strikes, you know what to do.


4. Your reputation will precede you

What sets Ray apart is his ability to handle impossible (usually illegal) situations efficiently and discreetly. That's why everyone from Hollywood elites to rap stars to mayoral candidates wanted to hire Ray.

Lesson: Being an entrepreneur is all about building your personal brand. Figure out what you want your business reputation to be, and make sure you live up to it.


5. Surround yourself with a strong, dependable team

You can't do it all—not even Ray can. That's why he had key people in his organization like Lena and Avi to turn to when needed.


Lesson: Being a business leader means learning to delegate and finding people who complement your skills. Knowing your limits and findig people who can do what you can’t and help share the load, will make your business better. 


6. Action speaks louder than words

Ray is not a man of many words, behind his strong and silent exterior, his brain is always working to stay one step ahead of his rivals. His quietness also keeps his opponents guessing, which he uses to his advantage.


Lesson: Listening is a powerful skill and can help you learn more about your industry and what is needed from you to deliver results.



Are there better role models for your kids than Ray Donovan when it comes to entrepreneurial inspiration? Sure. However, finding inspiration from characters your kids watch on TV, in movies, books or even video games can make it easier to teach them about important financial concepts in ways they can relate to and engage with. 



What money lessons have you learned from TV or movies? Let us know with #letstalkmoney @gohenry on Facebook or Twitter.

Written by GoHenry Published May 23, 2022 ● 3 min. read