Sam is joined by Dean, an ex football player who was sadly forced to abandon his professional career, but couldn’t leave behind his expensive lifestyle until the day he realised he had lost everything. Dean shares how he realised he wanted to pursue entrepreneurship and the rides that came with it. Dean and Sam discussed the reality of earning 100k a year, the lessons they learnt from earning a lot and having nothing. The reality of what being CEO means and questions such as how we should educate children on personal finance, does money bring true happiness and more.

Dean was picked up by a professional football team with the ambition to be a professional football player until he was 21 where he damaged his disks and ended up taking a job in sales. He realized that the lifestyle that he had as a footballer was far different from the one in the corporate world. With people telling him when he could go to lunch and permission to go home as well as when he could take holidays. He knew the lifestyle wasn’t for him.

Dean lasted six months at that company. When his family holiday was disapproved of by his company, he started to think about missing out on family and social events unless he did something about it. He went on the holiday and received a warning when he returned. Dean realised he couldn’t live by other people’s rule sets.

He found out that one of his friends who used to play for the same football team left and started a business. So Dean reached out to him and joined in. This was the start to his entrepreneurial venture at the age of 23. The business was about going into secondhand shops for designer items and selling them double the price on eBay. Dean was earning more and working less. “ It just gave me that taste to say, okay, I can see why people start businesses and why being an entrepreneur is appealing to people, because then you can start to design your own life and work.”

What does it mean to be wealthy?

Entrepreneurship allowed Dean to get paid and have a lot of free time. His definition of wealth  is how much time they have. He talked about his friends who work in Investment banking, earning loads but feeling miserable and working for the weekend. They have a better car and house but no time to enjoy it.

Dean now lives in Spain. He can just flip his laptop and go sit on the beach whenever he felt like it. So for him, he feels like he has the wealth and the money.

What does being CEO really mean?

As an entrepreneur, Dean focuses on execution. “The way I try to live my life is I would run the things that I want to do then succeed at things I don’t.” and not a lot of people have that mentality. And it took me a while to say we need to not keep up with the Joneses. And also you are governed by your peers to a degree, especially when you’re younger, because you want to have a nice car and a nice house. So people on the outside can look at you and think this guy is successful, but inside you’re dying, they don’t know how you’re feeling inside.”

Dean went to work for a recruitment company and became a manager in two years, he then went on to set up a business in recruitment so Dean, who hated jobs, started an entire business  to help give jobs to people. It did really well for a period of time. They started to hire senior people who have worked with the investor to create a board. So Dean was the CEO who had to report to the board and then received a lot of pressure to deliver results.

Dean felt like he was back to square one when he realised he couldn’t take his honeymoon. And it was at that point he told his son there’s no way out of this type of lifestyle. No matter what it is, if you are employed or even if you think that you’re a CEO with a percentage of a company you’re still working for people. After years of putting blood, sweat and tears into his business, Dean described his CEO role as “basically HR” which he described as “terrible.”

Dean felt like he was trying to manage the staff and upwardly manage the board. It’s tough to be CEO, you’re working more hours than your staff. Dean’s work was seasonal, so he had really booming summers, but then winters, he had to really retract and be careful what he spent.

Dean stated that the experience will tell you if you really are entrepreneurial, you can thrive on stuff like that,” that stuff never affected me.”  But in hindsight, Dean advises that you have to look at yourself and identify what you could have done differently and change it.

“Before I went on, on my venture into the corporate world, I should’ve just taken a moment, take a breath and try to forget about what my friends, my family, and all my peers are going to think of me and just figure out what I want to do, and then try to make that into a business.”

What does success mean?

Dean thinks how much money you make is deemed ‘ successful ‘ is personal. How people judge how successful you are is how much money you make. But we should all be looking at the individual definition of success by different people.

Dean’s friend who is earning seven plus figures in his investment banking job hates his life. His other friend who works in a bar in Spain literally loves his life. He finishes his shift. He goes and lays on the beach for a few hours, meets his girlfriend after work and rinses and repeats. We have to realize that success has to come from within how we measure it. Once you can get your head around that, then you just become free and life just becomes fun.

Dean listens to compliments and criticisms equally. “ I just do things that I want to do. And once you do it, I can’t describe how liberating you feel. “

To check out more of Dean’s story, his failures and successes, check out the podcast episode here!