Defining Moments with Dustin
Defining Moments with Dustin Heise is where leadership meets high-performance sport. Dustin, CEO of Canada Snowboard, sits down with the athletes, coaches, and leaders who know what it takes to build strong teams and values-driven cultures. Expect real conversations, practical insights, and a closer look at the world of snowboarding, from Olympic drama to grassroots beginnings.
Defining Moments with Dustin
Daniel Oladejo - Professional Athlete, Business Development Representative at GameStrat
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What happens when failure becomes one of your greatest advantages?
In this episode of Defining Moments, Dustin Heise sits down with Daniel Oladejo to explore the experiences that shaped him as an athlete, leader, and business professional.
Daniel shares how being cut from teams, sitting on the sidelines for years, and facing pressure at the CFL Combine helped build the resilience and discipline that continue to guide him today. He also explains why learning how to respond to failure matters far beyond sport.
The conversation covers leadership under pressure, building trust through shared experiences, performing with freedom instead of fear, and why significant failure can be one of the most valuable experiences for young athletes.
Daniel also reflects on his transition from professional sport into business development and leadership coaching, and how the lessons he learned on the field continue to shape the next chapter of his career.
Uh so good to be here with you today, Daniel. Thanks for taking some time, my man. And you know it's uh it's never easy to get things calendared in, but we have finally both our connections, you know, lined up today. And today's guest is Daniel Olodejo, a professional Canadian Football League athlete, business development professional at GameStrat, and a leadership coach who is passionate about helping people perform at their best both on and off the field. Through football, speaking, leadership development. Daniel's built a career centered on resilience, discipline, and using sport as a vehicle to develop stronger leaders, stronger teams, and stronger communities. Holy smokes, does that ever align with what we're all about here? Thanks, man. Good to have you.
Daniel OladejoNo, it's a pleasure to be on. And just like you said, the alignment and the connection piece already looked through some of the things that you you're about, and definitely a lot of alignment and connection. So I'm I'm excited for this conversation for sure.
Dustin HeiseOh, very stoked, man. Thank you for being here. Well, you know what? Let's kick it off. You know, some of the biggest defining moments that have shaped you as both an athlete and a leader, where would you say that's come from? What are those moments?
Daniel OladejoYeah, I mean, the defining moments podcast is definitely very suiting or fitting for some of the things that I've experienced as an athlete, but then generally as a leader. So I would say the most, and it's kind of one of those like stories where you're like, well, how does that contribute? Or how did that, but this is really my origin story. So in middle school, played basketball in the sixth and seventh grade and the eighth grade, like I've played with the same guys for a couple years now. Um, thought I was pretty good, tried out for the basketball team in the eighth grade, got cut from the basketball team. So that's one of those things that as an athlete, because I've always identified with with the the tag of the athlete, as an athlete, getting rejected by a team that you really want to make is probably the most significant, one of those significant moments. And and it that was actually a precursor for what would go on to happen repeatedly throughout my athletic career. So it was funny that it started early, but that was really one of those defining moments where dealing with adversity and with overcoming and how I want to respond to it is something that, again, as an athlete, but also as a human being living this human experience, you got to get adept at. So got cut from the basketball team in the eighth grade, go to high school, try for the basketball team again in the ninth grade, get cut from the basketball team again in the ninth grade. So now I'm devastated, but that's really when it kind of clicked for me. Um in the ninth grade, got cut from the basketball team. Now it's been two years going on. And I made a decision like, what is it that I how do I want to react to this? How do I want to respond to it? You can either kind of cry, and I and I did have some shed some tears for sure. You can stay there, or you can try to get back up and try to make something out of it. So I try to make the best out of a of an unideal situation. And while my teammates and and peers were downstairs in the basketball gym practicing, I was upstairs in our weightlifting gym, lifting weights and making a decision on what I wanted to be as an athlete. So again, that rejection from the eighth grade and then into the ninth grade was something that was really the catalyst for my work ethic, which has contributed to some of my athletic, but also again, general career success that I've had thus far. So that was probably the biggest defining moment. Going to university, that was another defining moment there. Come in pretty highly recruited and then didn't play for two years, redshirt it for two years, which was very, again, one of those situations where you feel like you're being rejected. Those are probably my top two is is the high school experience, middle school experience, and then again at the university level, getting there and thinking I'm there and then being disappointed for two years back to back.
Dustin HeiseSo I just think like what a foundation though, because of the resilience and the determination that's required as a foundation. And not everyone gets that gift, you know, given to them or is able to look at it as that. And of course, you've used that as a foundation. And, you know, you've spoken about you know being overlooked in some of those early stages of your of your athletic career, but also, you know, before NFL Combine, you know, how did you providing people, you know, and showing them the way that you challenge yourself and the way that you were able to overcome all of that? You know, how did proving people wrong change the way that you now approach and challenge everything in your life today?
Daniel OladejoYeah, and Dustin, that's a great question because um we talk about defining moments again. The CFL Combine was definitely one of those defining moments where going into the CFL Combine, I wasn't, again, wasn't very I'm not very high on the ranks in the CFL draft boards. I think projections had me going maybe sixth or seventh round, pretty late. Going into that, I'm aware of that, but again, it's all auxiliary. It's just all noise. Um, this is I was very confident in myself at this point. And part of the confidence that I had was having to deal with these significant adversities growing up, but then also early into my athletic career. One thing that we faced early, I was born in Nigeria, we moved to New Orleans, Louisiana, and then Hurricane Katrina hit within eight months of us moving there. So again, a significant adversity, but that along with some of the adversities I I faced athletically, helped me to build this thick skin. You said the word, and it was perfect. It's resilience. This resilience that regardless of what it, whatever the situation I'm facing is, I've overcome adversity in the past, and that gives me confidence to overcome adversity in the present and in the future. So at the CFL Combine, faced with significant adversity, not being very highly touted, go to the CFL Combine, I test. I tested well in in most regards. My 40, 40 yard dash, which is what they look at is terrible. I ran a 4-8 as a receiver. So again, going through that, now it's like, ah, well, I wasn't highly touted. I ran a 4-8, which is not good. But the good thing about that specific combine is we had three days of just football after testing. So again, facing adversity, being in a situation where this isn't how I planned for things to go, but I gotta respond. And I went on to have three days of probably the best football I've played in my life. Amazing. Every day was a coach's picker, recognized it as one of the all-stars of the combine, had one of the what have some reporters in the CFL have called one of the best uh CFL combine performances of all time. Got drafted in the second round, 17th overall. So again, none of this was supposed to happen. And it looking at it before, it wasn't looking like that's what was gonna happen. But having dealt with adversity in the past, having dealt with those defining moments and been able to catalyze that into performance, that was something that was very significant for me and something that propels me even today when I fix that.
Dustin HeiseYeah, well, again, that body of evidence that just shows what you're capable of doing. I I want to dig in what what were you able to tap into? Like I know you had the fuel from the knowing what you didn't do that you felt like maybe you could have had a different result in the 40 or whatever, but like how did you tap in to make sure that you had the gameplay the way that you did on this on the coming days after that?
Daniel OladejoYeah. And again, great question. And and it was really it was, I want to say reckless abandon because the day before I flew out for the combine, it was in Edmonton, my agent called me and says, if you don't run a 4-5, you're probably not gonna get drafted. And I ran 4-8. So after I run, I'm like, I got nothing else to lose. At this point, it's it's like I was supposed to run a certain number, I didn't hit that number. I felt like I tested well and everything else. But if the 40 is what's gonna stop me from getting drafted, well, I'm gonna go out here and just play and have fun. If it's my last time playing football, I'll just go out and have fun. So, and that's when we perform our best, just as human beings. We don't perform our best when we pile the weight of the world on our shoulders or we feel like, oh, I have to make this happen. Like when you're tight and you're tense and you're stressed. You perform your best when you're free. That's when you hit flow state. That's when you get your highest uh peak of performances when you're free and relaxed. So it was a situation where I was like, well, my back's against the wall, got nothing else to lose, so let's just lay it all out there. And that was the attitude that I had. And I felt really good, like I had so much fun because I was just playing, and that's when you play your best.
Dustin HeiseIsn't that the truth? Is perfect transition into the career that you've built in football business leadership coaching. You know, what lessons from the locker room have you learned or on the field and in that combine that you know you can lean on, you know, as a business leader through that experience?
Daniel OladejoYeah, and again, it it's really all my story and all that I talk about comes comes back to how you respond to difficulty because that's one of the guarantees in life. You you can't go through this life in any capacity, whether it's academically, whether it's professionally, athletically, you can't go through this life without without dealing with difficult things, without dealing with failure. So what I come back to in every aspect is, well, again, now I've dealt with failure in perhaps some of the most stressful environments. You're playing in front of 25,000 people, playing in front of 30,000, 40,000 people in the stadium, maybe 100,000 people watching across the country. If you make a mistake, there's nothing you can do but respond. You have no other alternative. You know everybody's just seen it, but that's what it's gonna be like in life. You're gonna make mistakes in business, you're gonna make mistakes with relationships, you're gonna make all types of mistakes, and there's gonna be scrutiny. But the learning point is you have to have a mechanism of responding to failure, um to responding to difficulty. And that's something that I try to cultivate on a day-to-day basis, even in the littlest things. I'm telling you, like, I don't want to wake up in the morning and go on a run, or I don't want to, whatever the case may be. It's I I want to be comfortable. Like there has to be something in me that can break through that need for comfort and familiarity and deal with when things don't go how I planned, deal with when people don't do what I want them to do. That's that's what makes or breaks us as people, but also a business and life.
Dustin HeiseI just also loved how earlier on you also tied it to being able to operate with that freedom and just knowing that you can get after it and building that momentum because you're dead right. Yeah, absolutely. You that foundation that you just mentioned around overcoming that that challenge or the failure and just constantly coming back from it. And then was as you come back from it, being able to tap into that freedom and that mindset that just like allows you to keep building off of that goal and and you know what's continued to fuel you. And I know like for for you, you you you spend a lot of time speaking to students and developing future leaders. You know, what do you believe sport has such a unique ability to build people and bring people together from such different backgrounds?
Daniel OladejoYeah, I mean, I mean, sport's probably I think the greatest tool um for doing that, for uniting people across nations. We see it um with I mean, just team support. We see it at the World Cup level with soccer, we see it and in all different types of facets is is it unites people. And and what part of it is you feel the joys of victory, but you also feel the despair of losing. So doing that in a community setting is just there's there's no replacement for it. There's no there's nothing like it in life, really. And so the lessons that I've learned playing sport, but also in these communities, are really what has empowered me to do some of the things that I'm doing now. So networking's huge for me. So the ability to network coming from my ability to relate to my teammates, my ability to relate to my coaches, uh, my ability to relate to the fans. Like had to do a lot of growing in that in my early years in the sport. Sure. But those are things that are really foundational to everything that I'm doing now. So that's just one aspect of it. I'm there's hundreds of it, but just the connection piece with with your teammates, with a fan base, with the organization, those are things that are very, very important and you you find value in in real life when you have to connect with people as well.
Dustin HeiseWell, there's no question that you're gifted in that. Uh, I've looked at some of the videos that you have you have online with you know, speaking to students and just engaging and you bring in energy and and you know, you're so well spoken and articulate, and and and no doubt you you are able to reach uh whatever audience you choose to operate in. Daniel, there's no question about that.
Daniel OladejoUm Thank you very much, Destiny.
Dustin HeiseIt's just uh it's obvious, so it's it's really cool. When you're part of a high-performing team, you know, what's what creates that genuine trust between people just beyond winning the games?
Daniel OladejoThat's a great question. And I think it's one of those things that was very important that I learned actually for the most part in my time in Montreal with the Alouettes. Awesome. Um, so our head coach, uh Coach Moss, had one of these things that, or some of these things that he would repeat to us, and one of those things was connection, um, how we connect as a team. And so we would do non-football related things. The day before games, we'd play ping pong, we'd play racquetball, we'd play cornhole, just things to connect as teammates. And it would be offensive guys with defensive guys, starters with backups, practice roster was active, like it was just everybody and the coaches included as well. So, to answer your question, that's one of those things that when you have shared experiences, it develops that trust. You don't have to try, you don't have to force it, but when you have shared experiences, and again, back to the adversity point, as a team, when you go through significant adversity together and you have to bind together to overcome it, that's one of those things that naturally just builds trust. Like you're gonna trust each other because you helped each other through difficult times. I've been in situations at the university level where we lost two teammates across two or three years. And the the bonds that were formed in those times, obviously significant adversity like losing a brother, but we had to become closer to fill the void, but also to overcome this adversity because we had a in one situation, we had a game uh the next week. So significant adversity, but having that shared experience of binding together, it develops trust. And that trust goes beyond just your team performance. That trust goes on for life. There's guys that I can call at any time because we went through those situations together. So um, yeah.
Dustin HeiseLove that. Hey, if you could design one experience that every young athlete would go through before entering the professional world, what would that be and why?
Daniel OladejoAnd I'm gonna sound like like I'm beating a dead horse, but hey, let's do it. Significant failure. That's the experience that I that I want for every young athlete is to face, is to really want something, feel like you put your all into it, and to fail and to not get it. And it sounds counterintuitive, but when you do when you deal with something like that at a young age, there's a gear that has to start working in your head that's like, okay, I deal with this, but I know that I still want it. So I gotta go back to square one, go back to the drawing board, reevaluate, and find a way to get it. And I'm telling you, when you know you faced significant failure, when you know you have a goal in mind and you fell short of it, if you can find a way to repurpose that experience into success and to reach that goal, it's gonna propel you to levels that no success independently could. And I face that again at the university level for two years, wanting to be a starter, not even getting a chance to put the jersey on. And getting getting my sliver of opportunity, my third year, and I had been preparing for two years for this, and I knew that because I failed these first two years, I had to give everything to get it. And I was able to do that by third year, I was able to start. Fourth year, COVID happened, but the perfect thing was now I've been in university for four years, I've only played one season, but I know that in my head, again, to come back to the this confidence you build from facing difficult things, I know in my head I had to wait for two years. So, what's one more year? So, again, being able to do that, and then my last two years at in university was have able to have great success and win awards and get drafted, but significant failure early on was the catalyst for that. So that'd be what I want every young athlete to go through is try, try, try and fail. And then sit at the drawing board and be like, okay, what am I gonna do to get this goal that I still have?
Dustin HeiseAbsolutely brilliant, man. And those are so true in a business context as well. And just know I'm sure you know. Oh, we uh we've learned lots. We're gonna continue to learn lots, we're gonna continue to drunk to grow lots. Um that's how you you you build that that confidence like you shared, uh, but that that body of evidence that just shows from a results perspective, but also, hey, it wasn't always all just results. It was so much, you know, blood, sweat, and tears and glass that had to get chewed in order to get there, you know?
Daniel OladejoYeah. That's a perfect way to describe it.
Dustin HeiseOh yeah, man. But uh, you know, as we kind of look to shape, you know, in one year's time, what is one defining moment that you hope to be able to look back on and realize it's changed everything for you in one year's time?
Daniel OladejoGreat question. And again, life is just a compilation of these defining moments. And right now I'm in a transitionary period, transitioning out of sport into um the working world. And and again, like you mentioned, uh, doing business development at GameStrat, which is still a sports software company, so I get to be around the sport, which is great. But this transitionary period is something that I know that in a year's time, how I navigate this will will definitely set the standard for what the rest of my life after after football is gonna be like. So there's a couple things that are in the air, like just with business, and then now with with working and and coaching, seeing what I'm gonna do there. And and it's it's a lot, it's a lot that's on my plate, but I love it. So I just know that finding a way to navigate these times, do the right things, invest in the right areas, I know that in a year from now and five years from now, this point in time is gonna be very critical. So I'm hoping that when I look back on it a year from now, it's gonna be it's gonna be with a smile on my face.
Dustin HeiseWell, no doubt it will be. No doubt that because of your relentlessness, you will also be successful. And in that example that you shared with the listeners and viewers today, it's gonna be a really, really cool journey when we circle back any years or so time from now and do this again, you know, how we can continue to to shape the message and and also see how things have continued to progress as we we hope to share those learnings with with others around us. Daniel, thanks so much, man.
Daniel OladejoThank you, man. It's been a pleasure.