From childhood anxieties to executive leadership with Kyler Mason, part 1

Every leader eventually comes to a decision point. At some point you have to choose, am I gonna let this thing win or am I going to take control of it and become the leader I want to be? For Tiffany, that thing was fear. We heard to go through her fear journey and face her fear head on. For me, that thing is anxiety, and for years, I let it win until I had a choice to make.

I'm Kyler Mason and this is my takeover of scared confidence. I am a husband, father, friend, son, and I, I don't like to take things too serious. Love to joke around. I kind of the antithesis of the, like a corporate suit. I enjoy a lot of different things. I, uh, I'm kind of a collection of things you wouldn't probably put together commonly, like, enjoy gardening, sports betting, cryptocurrency.

A [00:01:00] lot of things that would be stereotypes of certain people that just like kind of end up as interests of mine. I'm a, a very curious person. There are a couple things that I think about as a kid. I like wanted to be an adult, which is weird. Maybe it's a like a firstborn thing, but I would sit at the top of the stairs and listen to my parents' conversations about, I don't know, the things they talk about as adults and sneak around to.

Just listened in on conversations. I remember them being like, don't you wanna go play with your cousins or whatever. And I would, um, at that stage, just want to know what the, the adults were talking about. I would've looked back at least as a young kid and considered myself entrepreneurial, probably would've toward high school.

Started to see that show up. My dad, he. He ran a handful of small businesses across like different industries, very much like, looked for opportunity in the marketplace and [00:02:00] didn't really care how sexy the industry was. So for example, he owned a dry cleaners, he had some websites that sold product, um, and a couple different industries and a few other things.

But I did find with, with my dad and what he was doing, he was trying to like get me to help, like I'm free labor pretty much. Um, but the help wasn't. Probably what you would expect a typical high schooler to be doing. It wasn't like manual labor. I had to learn how to host websites and um, run paid media.

I had spreadsheets that I started to put together that demonstrated the funnel and how many leads we were getting and the, the sales per product and stuff like that, I had no idea at the time was gonna be a valuable skill. Um, I don't know that I would call that even entrepreneurial until I started to have an opinion about, hey, you could.

Make more money with doing these things cuz I was starting to learn stuff and had an opinion about the products that he had that would sell better. This is funny [00:03:00] because Tiffany, Back in the early days, she said that I was a few decisions away from being a drug dealer. Kyler. Um, he is this hard to describe combination of your classic, highly responsible, highly aware, very accountable firstborn, and this.

Reckless idiot that like gets himself into a profound number of completely avoidable situations. I went to a lot of concerts in high school and so I gotta tie this back to my dad's businesses. One of his websites sold like personalized, personalized, like merchandise. So the way that you would personalize it with is with this like laser engraver.

I, so I went to these concerts and I was talking to one of my buddies. I was like, We could probably put some of the band's logos on these like dog tags and stuff like that. And, um, and slang some of this, I think sometimes he's just like, I [00:04:00] don't know, decides he's gonna take a risk and just test it. So, uh, we, I went, figured out how to like gear this laser up, learned Photoshop to like crop out the band images and stuff like that.

So we took all this stuff and walked up and down the. Tailgate aisles at, um, different venues across the Midwest. We like traveled around to do this. I, there were no like, set prices for what we were selling, so we would like size up the situation, estimate how big of a fan they were, and then price those things on the spot.

Something about him is just like, I think he has to have a place in his life where there's a little bit of recklessness for him to feel like it's all working for him. We were in Michigan at a Dave Matthew's concert and the security like started to like kind of hover around like, what is going on here?

Um, and we realized, This is [00:05:00] not allowed. Uh, and they started chasing us and we ran and hid behind cars in the, um, in the parking lot and decided this is probably not something we should be doing. So I, that's why I said that. Like I do think he's a couple of choices. In his past self away from being a drug dealer, where like if something would've tipped wrong, he's so loyal that he would've been like, I'm here now.

I'm gonna be the best. I'm finishing it out. This is what I'm doing. And that's what would've happened. So that was a, um, an odd angle at entrepreneurship. I'm probably gonna like go to jail for copyright infringement.

Baseball was, baseball was life. I spent a lot of time in like the, the structured environment, practicing getting better, and also a lot of time on my own. Um, like from weightlifting and, um, training on that end to just the, the skills of what's needed. I was a catcher, so [00:06:00] a lot of drills involved in that.

Um, and then working to become a, A better hitter. I probably played a hundred games a year through junior high to high school. I remember we were in a, just a big game in high school, um, probably the largest like crowd that I had played in front of. And, um, I just like could not get over this feeling. I had no idea what it was at the time.

Um, and I. I like, forgot how to even throw the ball back to the pitcher, so I was like so anxious about it. Um, and that like came and went really fast. Um, and it didn't present itself again until college. Um, where if you're familiar with sports, that's called the yips, it is a very embarrassing thing to have to do a thing probably millions of times, throw the ball back to the pitcher and then be overcome with anxiety that.

Like shuts your brain down [00:07:00] is a very frustrating thing. The feelings were all over the place. Uh, I remember just being like, please, just take me outta the game. Please take me outta the game. I remember like trying a lot of things, um, like trying to trick my brain out of it. I remember being incredibly, like, disappointed in myself.

Um, embarrassed. Uh, It's ultimately what led me to stop playing baseball. Like I don't know that I've actually ever said that before. Um, I did not want to go through another season as a catcher having to deal with, or am I gonna have the yips again? Um, and um, so I just was like, I'll, I'll move on. So my senior year of college, my dad passed away, um, which was like a, a huge event for me in my family.

He and I were very, very close. I would talk to him about, about all [00:08:00] things all the time. I, um, probably talk to him every day on the phone at least, and. You know, talk to him about the presentations I'm giving, the decisions I was contemplating making about, you know, even, um, right before he died, I made the decision to come work at Ailment three.

Um, so that was some like final advice he got to give me. I. I, I was pretty mature and responsible for my age, but the, the rate at which I had to grow up and be a new role for my family was fairly profound, I guess. Um, I needed to show up in different ways for my mom. I like moved back in with my mom for a little while just to, to be there.

Um, and my two brothers, I'm the oldest of three, so that presented just like a new challenge and identity that I had to process. I think that it brought us. Closer. Um, unfortunately, cause each of us, they're like roughly three years apart. So like, just enough time to be in very different life stages.

Growing up my dad had cancer. Uh, so, [00:09:00] um, during it and after, uh, I think definitely brought us closer. I think we all also recognized that we had a particular role to play with my mom. People talk about this, but my memory during that time is so terrible. It's such a blur. I don't know how, but I still found a way to be productive and ambitious, which I, I think I like, had told myself stories like, this is what my dad would say to me.

Like, do these things, um, act this way, prioritize these things. So I, I think all things considered my, my mental state was pretty damn good. Um, uh, I think helped me stay on the right track. I also talked about losing my dad all of the time. Um, it was something I enjoyed when people would ask me about, uh, you [00:10:00] know, it's kind of sounds weird, but I, I enjoyed talking about the things that, that I admired in him and things he taught me and stuff like that.

He, uh, Had a, had a very, very abundant mindset, which I think mostly transferred to me. He's very optimistic and had a, like a view on the world that you can accomplish so much in life that you should dream big and take the chances that you want. Um, I remember him saying something along the lines of like, you could, you could have five.

Different professional careers easily in the span of your full career. Like, it's like if you wanted to decide to go be a doctor after doing, um, what you're doing now, like you could make that choice. So he had a view on the, on the world in your life in a way that was very abundant. Dad passed away like right at the end of my [00:11:00] senior year, and then from there, I.

And made the decision to go work at Element three and that was a wild time to change jobs. Like I couldn't have been like less productive for the first few months. Um, and super thankful for Tiffany and Karen at the time cuz I let them know what was going on and they were very helpful. Um, and then it would've been probably three years into working at Element three when Morgan and I met.

I am Morgan and I am Kyla's wife. Uh, we've been together, gosh, eight years now, almost three years married. We met through just like mutual friends. She likes to say that she tried to introduce herself and that I blew her off and I don't remember it. I believe her. Um, but she, she tells me that story and others that story every once in a while.

And then, [00:12:00] um, actually, Same group of friends was hanging out on New Year's because we met on New Year's Eve, we had mutual friends. We ended up at the same party and, um, we talked all night. We talked about our, our families, our jobs, all that fun stuff. And then exchanged phone numbers. And he called me to ask me out on a date.

Like, I have never, never had a guy call me to ask me out on a date. So right then I was like, I think he's, he's different. He's different from other guys that I've been with or, um, even guys that I've hung out with. Um, so I knew right away that, that there was something unique about him. He was also so much more mature, I feel like, than a lot of guys his age.

A lot of guys that I'd spent time with, I knew right away that he was different. And that is when I actually like talked to her and then she and I spent, um, I dunno, many hours, like getting to know each other for the first time on New Year's. However, many years ago, probably, [00:13:00] uh, seven-ish years ago, we dated for, I, I wanna say four or five years.

I always said, I was like, I am gonna marry a guy that's just like my dad. And when I met Kyler, I was like, oh, okay. We're good. We're good there. He is the most hardworking, the most loyal, the most. Passionate person that I've ever met. Um, and he's also, he's so goofy and fun and I feel like a lot of people don't get to see that side of him.

Like I get to see that and we, we'll joke sometimes, like he'll do something really weird at home and I'm like, you run a company. He makes me want to be the best ver version of myself too. Sometimes it drives me nuts when he pushes me and I'm like, back off. But he wants to be the best version of himself and so he pushes everyone around him to also be the best version of themselves.

And then I proposed and we had a fairly long engagement that, um, went into Covid. So we were trying to plan a wedding through Covid, which [00:14:00] was, um, an event I do remember. When we were getting married, like it was leading up to our wedding, there was a lot going on. The pandemic was happening cause we got married in 2020.

A lot of like big things were happening in my life and I, I was, I think coming out of an executive team meeting, like just got added to the team. Nothing like intense that I can remember was like going on during that meeting. But I just got added to the executive team. Um, I. Was taking on some new responsibilities at work.

And I also was, um, planning my wedding with Morgan. So big life changes in, in job and life. Uh, we also had just moved, so like, just a lot of big things. I didn't realize this until afterward, so I had been having, I would just call like, [00:15:00] Subtle panic attacks. I don't even know if that's a thing, but just have moments where I would be either in a meeting or at home.

It wasn't like some big event. It def it definitely wasn't when I was like presenting and would have just like a tight chest and sweaty hands and be like, just get over it. And that would work. Usually I was like, are you having doubts? Like, what's going on? And um, he was like, no, no, not at all. It's just a lot.

And we were navigating. Can we have a wedding? Can we not have a wedding? We're paying for the wedding. We're about to get married, have this, have this really serious thing happen. Um, so that was when I noticed it, is just those, that physical response to like the not sleeping well and the. Um, waking up, sweating, or having a panic attack.

Um, and then he would, um, withdraw a little bit. I came out of an executive meeting one day and just went and sat at [00:16:00] my desk and started just, I was like feeling dizzy. My chest was tight. I was like super sweaty and I was like, this is not normal. Next time I'm scared, confident. He had an episode where he went to the hospital.

That was really scary for me because, I mean, how do you hope besides just getting him there? I said, Tiffany, if I were you, I would not let me be the president or an owner until I get this like anxiety thing figured out. I think that, you know, he had a choice to make.

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