An entrepreneur always looking for new hats (and sometimes helmets) to wear, Courtney Stephen is someone that definitely doesn’t like to be put into a box.

When not playing professional football with the Hamilton Tiger-Cats, he works as a motivational speaker, runs the youth football camp Overtime Football Club and co-hosts The Come Up podcast – which focuses on success stories and the lessons that can be learned from them.

We spoke with Stephen about raising the bar, leadership, strengthening your brand with social media content and got some predictions for the CFL season too!

GO MAGAZINE: You often talk about raising the bar and pushing your limits. Why are those ideas important to you?

COURTNEY STEPHEN: I think people underestimate what they’re capable of. We often just need that one person to nudge us over the edge and give us a vote of confidence so that we can actually try something new and do those great things that we’re all capable of. That’s why I’m about always raising the bar because I think we all have so much talent inside of us, but it’s untapped and not polished yet.

You seem to be continually raising the bar in your own career. Where do you generate the energy for your passion and drive to keep pushing yourself to continually improve, give back, mentor and explore new opportunities?

I would have to say that it’s in me because I get to operate in this space where I’m doing what I love and I’m living my truth. When you do what comes naturally to you, at the end of the day you’re not excited to go to bed. I work hard and I get tired and the disappointment for me is that I don’t have more juice in the tank, and that I actually do have to rest. If it was up to me, I would just do what I do all day long 24/7 because I genuinely love it. I love public speaking. I love working with youth. I love the grind and the struggle of figuring out things in the entrepreneurial world. And of course I love football. I love pushing my physical limits so I don’t really need much outside motivation because this is who I am.

What motivated you to start The Come Up podcast? Why did you want to speak with not only athletes, but also artists, authors and entrepreneurs?

I have a pretty busy schedule, so I didn’t think I’d have time to dive into another project. But a friend of mine convinced me that we should do this together. We’re both into branding, building businesses and digital marketing and we’re always interested in the journey people took to get places as opposed to the end result. So we decided to talk to people about the brands, reputations and companies they built and get the inside scoop on what their steps to success were.

The podcast has connected us with so many amazing people from all different walks of life operating in different realms and doing different things. I’ve spoken to people from all over the world and realized that one thing they all have in common is an unrelenting will to do what makes them happy. The podcast has taught me that there’s so much value to be gained from conversations and that you never know how valuable the next person you talk to might be for your life.

Leadership is a concept mentioned multiple times on your website and social media channels. What do you think makes a great leader?

I think a great leader is somebody who seeks first to understand and is okay with not being completely in control. An efficient and effective leader will take the time to go through an iterations cycle of understanding what the problem is, how you’re approaching it, what the results you’re getting are and how you can improve that process for the next time. So a great leader is always trying to expand themselves, learn, understand and get to know their team. Leadership is helping other people be the best that they can be.

Mentorship seems extremely important to you. Why do you want to give back to the community and help others improve themselves?

Simply put, no man is an island. I didn’t get here by myself and it would be completely selfish to think that I can have all of these things given to me and then take them with me to the grave. One of my coaches once told me, “What you keep will die with you, but what you give will live on forever.” And so for me it’s just a part of my legacy. I want to be somebody who gave and I want to be somebody who helped others.

What’s keeping you up at night these days whether it’s on or off the field?

I have some macro issues and I have some micro challenges. Right now, I’m really trying to figure out how I can produce a daily vlog without having someone follow me around all the time because I want to produce a lot more information for people. I don’t want to just entertain the world. I want to produce. I think there’s a lot of opportunities for learning especially for the younger people who are watching me. I want to be able to show them how to take your name and make it into a brand. But I have apprehensions about doing things that aren’t all the way polished and up to the standard that I think they should be.

Do you think that’s hindering or helping you with creating content? Is it more important for things to meet your level of standard right now or do you need to simply start getting some things out?

Well I’m definitely putting some things out now. But for me to become an authority, I need the quality of the things that I’m creating to be at a much higher level. Instead of giving you a tidbit, I want to give you a textbook. The things I’m doing now are good learning experiences and are helping me improve. A year ago, I did 13 weeks of Facebook live videos. It was just an experiment but it helped me with public speaking and video presentation skills.

The Tiger-Cats were 6 – 12 last year. How are you guys going to do this season?

We’re going to win the Grey Cup.

Aiming high! We like that.

That’s the only way you can approach it. If I sit down here and talk about “It will be a good year and we’re going to try and do this and that,” well you know what, that’s easy. We did that already. We did the mediocre thing. So now it’s time to shoot for the stars.

Before you go, we’d love to ask you an insurance question. How did you last purchase insurance? Is there anything you’d like changed about the process of buying insurance?

I purchased my life insurance through an insurance broker. They came to my house for a consultation and we began the transaction there. It was great. When I bought my car insurance, I had to drive into the broker’s office to fill out paperwork. I’d love to be able to buy car Insurance more immediately. Maybe you can, but I personally don’t know how!

Courtney Stephen plays defensive back for the Hamilton Tiger-Cats. You can check out his official website here. You can listen to his The Come Up podcast here and learn more about his Overtime Football Club here.

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