The First 17 Years: Don’t make yourself small so others feel comfortable with Kyler Mason

Building a business, when done correctly, should create incredible opportunities for worthy individuals. There is no one more worthy for this next opportunity than Kyler Mason.

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Chapter 1: Dedicated to Kyler Mason

Kyler Mason—the once-22-year-old “basically intern” who joined E3 at a time in his life that was filled with grief and uncertainty. The same Kyler who Tiffany is now entrusting with an incredibly important role in the future of the company she built.

What did it take to get here? This chapter explores the incredible story of the young man who had an incredible impact on Element Three from a very young age, and continues to see the fruits of his labors as he takes on this next chapter.

For more exclusive content and a deeper look into Tiffany and Kyler’s story, follow @ScaredConfident on Instagram.

Tiffany: You quit. That was like one of the worst days of my life.

Kyler: I was like, she was cool as a cucumber. Tiffany: I don't remember how I rolled it back, but I was like, well, now I wanna vomit chapter one, Kyler, Mason, this is the story of how a 22 year old young man and a very new leader come together on an almost eight year journey where we worked really closely together.

We had. I would say really exceptional highs. We sort of crashed into the wall and we had a choice to make about whether or not we were gonna pick the pieces up together, or if we were gonna do that separately. And, um, I'm really excited that. We chose to do that together and, um, have worked really hard to gain a level of trust where Kyler is gonna be stepping in, uh, to some really important roles at element three.

As I look across the characters that built my character, we can't possibly tell the story without including Kyler these

people, these voices, these experiences. They were my mentors. They are the people who help build and refine and grow me into the leader that I have the opportunity to be today. This is the first 17 years.

Kyler: I always believed that we were building something unique. I think that we had this approach to solving problems for our clients that, uh, went deeper into understanding the, the way our clients business operated and functioned and. Taking that knowledge and translating it into marketing recommendations, that really felt tied to something real and experiencing that I think was a gravitational pull for me to, to stay and see, see something through that I thought could become something big.

We were generating revenue. Like we had never before. I think that she was riding this like winning train. And I think, I, I don't know if I said, said this to her, but I had thought it and I was like, this revenue was covering up all of the problems. So we weren't facing the brutal facts. She wasn't as disciplined as.

She had been in the past about being engaged and making hard decisions all the time, even when you're crushing it. And the mountaintop came and we fell I pretty much, I walked in one day. I was like, Hey TIFF, I think I'm done. I was like, I'm not quitting today, but I think I just need to be done with this.

Tiffany: You were hard on me. And I think that was a really important part of my growth. I'm very likable. And that is helpful and also sometimes not helpful. Yeah. Because people want me to like them, but I need also to be told things that I'm not doing right. Or truth inside the organization. And you are usually the tip of the spear on that.

And it was the thing that is your X factor it's because the values were starting to get to a place where you're like, I can't follow this anymore. Mm-hmm I, I think the essence of Kyler is. The same. I think his spirit has always been like him as a person has always been very mature. I think he's always had a clear understanding of the direction he was headed.

Maybe the ingredients of exactly what that was. He was sort of open to some variability, but I he's always known the direction. I think that. Part of what has led me to a place where I trust him so much is that I have seen him over time. You really learn people's behaviors, their character, when you watch over a long period of time, and he's genuinely motivated by being successful simply so that he can enable people around him to do things that are important to them.

He's also intrinsically had a high sense of responsibility, like personal responsibility. Does things because he said he would, and only commits to the things like his body, physically repulses, when he says he's gonna, he can't say he's gonna do something he's not gonna do. Um, and so that intrinsic sense of responsibility, even when he was like more of a 22 year old.

I'll say punk, not really, but just sort of like not making life decisions. His mom would probably prefer on the, on the off time, you know, on the off season, he was, he was always really responsible and was able to like code switch really hard with that. And so I think knowing that I could attract talent like you at 22, create an opportunity.

For someone who has the vision for their lives, that what success looks like, the expectation of success in their life, to be able to create a career path to keep you was me proving it. Wasn't I didn't just build a company that I could attract, build, and keep leaders that were worth leading. And I, I think that became.

a personal challenge of mine. And in some ways I think the experiment that I had to run about whether or not I was a leader with following in people who didn't have to follow me. Um, and, and so I think that's been the same. I've I've seen him continue to mature as you just get smarter and wiser, and you've been in more situations, but the essence of Kyler, I would say is more the same than D.

Kyler: When we met, I agree, like been the same, like values wise forever. Um, the way you've helped shape me is providing the opportunity and the space for growth and challenges and failure, and the ability to, I don't know, find my own boundaries, um, within the like framework of my values.

Tiffany: I've just learned that is like the most critical thing you are smart.

but smart without the other pieces of it. I don't know that I could have grown to trust you with as much as I have, and we've seen each other in really high temperature situations. Mm-hmm and I think we both have walked through those in a way where we feel really proud of the way that we've honored our values first.

And I see, I have seen you do that. Make good character decisions. Even when you didn't have to, or nobody was watching so to speak. And I just think that that is important. And like you, you would get so angry when the work wasn't good. Mm-hmm, not because we couldn't sell it, but because it's just like viscerally, it just should have been good.

Kyler: It should have been good.

Tiffany: Yeah. And it wasn't okay with you. And those are things that innate to you that I think as a leader, as a business owner, , you know, having those people close to you will make you better. You know, having those people in your organizations will make everybody else better. I, I think at our core, you and I are both fiercely loyal individuals.

Mm-hmm and I think truth, the size of the truth that like the other parties willing to put on the table sort of continues to extend or not the rope of loyalty. And. I can't ever remember a time where one of us stepped into sort of the danger zone of truth, where it wasn't met equally at the same sort of pace and energy mm-hmm with, like, here is my full truth on that.

And I think that just extended the rope of truth, like three more months, six more months, one more year

Kyler: mm-hmm in a way where like, and now here we are communication and honesty. All that good stuff are the parts of really solid relationship. And I think that our personalities commit to that. And then that has let us develop a relationship that I think is a really strong one that somehow got me back here.

Yeah. After I that's free, I believed and believe in what we're doing, what led to quitting was I stopped believing that we were gonna do what I thought we were gonna do. Because of some of the things that I had described about getting complacent and not staying disciplined and Tiffany and I really, that was probably the weakest our relationship ever was mm-hmm I,

Tiffany: I think he knew with my personality either consciously or unconsciously, like he was gonna have to throw the nuclear bomb in front of me to get my attention, to like understand.

And you didn't give me an ultimatum, which I actually think is very mature. It was like, I just, I can't be part of this. I need to make that decision. I think in an environment where our relationship was closer, that conversation would've played out mm-hmm in nuggets. You know what I mean? So I don't, I don't sit in fear that like, this is a cycle we're gonna go through lots of times.

Like at all, I think that it was a symptom of where I was at as a leader. Some things I rightly believed or not, and him having a different vantage point into the organization about where the culture was at. What was getting prioritized, what was getting resourced. Um, and knowing that that was not actually probably congruent with my own DNA, but if I was gonna allow those decisions to be made in the organization, I was condoning it just by default.

And so I think he needed to know in so many words, like who, how is this ship gonna be driven forward? Because I can't be part of this. I always value people who are willing to tell me a hundred percent the. And like in spite of the fact that I've literally never overreacted to information that is bad.

People continue to believe that leaders are gonna overreact to information that is bad. Like it's just not how I react, but it's so important that you have really bad news. And so how do you create an environment of people who when they have, it will bring it to you courageously, cuz it's really important that, you know, mm-hmm, , I've always known he will lead a company.

Um, and I feel grateful that it's going to be this one that I built and that we've built together for a long time. I think when I saw over the last 12 to 18 months, as he has accepted the responsibility of. Understanding he needs to lead. What, who were his peers? And he's always been younger than the table.

Um, the only piece of advice I really remember giving you Kyler is when you first I think became a VP or manager, I forget which it was. I said like, don't make yourself small so that other people are comfortable. Mm-hmm, , he's very respectful in the best way about that. Like not want. And sort of not wanting to be the like stereotypical mag magnanimous leader of like, ah, like it's just not his style.

Kyler: No attention please.

Tiffany: Yeah. And so part of that is it can come across as sort of making him like him making himself small, even though he does know the right answer. And so I've really seen him grow a ton in introducing conflict where they're starting, starting to be decision, making him being like, I don't see it that way and challenging.

You know, other leaders in the company. I just, I, I began to see, like, he can, he can really do this. And I think honestly, in ways he has clarity of vision forward in parts of our business that I don't even hold. And so that's exciting to be able to collaborate, not just on like operating and moving the like things around, but he has.

His own independent perspective of where marketing is going, what it's gonna take to deliver that at a really high level. Cause I really believed it is hard to start at a place effectively as an intern. I mean, you weren't an intern, but you're 22 years old.

Kyler: I was pretty much an intern.

Tiffany: Yeah, you, but you weren't that, but kind of, and then to get to the place where he's now gonna be the president, that's, it's really hard to do to.

Leadership and authority by influence and to have people have watched you work for eight years and then choose to want to follow you. Like that's incredible. And that's him. that's his style is like, my work will speak for my capability and that's how I'll grain your respect. And once you respect me, you'll begin to hear me.

And once you hear me, you'll start to understand I'm here to make you better. And once you understand that, then you start to invite me into the process. And once you invite me into the process, you have the, you understand my vision. And then once you understand my vision, then we can sort of all start rowing in the same direction.

It's like his, his style. It's his formula. And. It's very rare and that's really special

Kyler: earning the respective of leaders. This might be a flaw, but I feel that I have never actually earned it. I think that it's always my responsibility to, to continue to renew it. Um, and re-earn it. And that's probably a part of what like gives me anxiety and makes me nervous all of the time.

Is that. Assessing myself am. Am I good enough? And I don't know, maybe that humility is a part of what makes people feel safe around me.

Tiffany: I think that my natural bend is to like cheerlead myself to the finish line and like everybody who's following me and in that world, it can be very fun, but it can be devoid of the brutal facts.

And I think I know working beside Kyler and his. like critical first way. And I say that in the best way possible, like we're such an unlikely pair. Cause I literally am like, you know what? We should do throw a party. And he's like, you know what? We should do audit everything we think is great and make it bad.

and so it's like, so we just come at it so different. He's a bottom-up thinker. I'm a top-down thinker. Like there's, there's just so many different. We have such complimentary ways that we view the world. Both visual though, in the way that we learn, which is very helpful in the way that we communicate with each other.

Kyler: We do both externalize as well.

Tiffany: Uhhuh that's true. Mm-hmm um, but I think it's, I have learned to be more comfortable and courageous in the words of Jim Collins, um, like in this productive paranoia, in that. That is not something that's natural to me. It's not something I would like wish to learn in my natural sort of state of life.

And I have really learned that there's a wisdom in, in that, in assessing the risk of understanding that there is a next level, every place you are and continuing to push and sort of have this serial. Unsatisfaction with the way that things are. I've learned to really get excited about those things. That, again, naturally I wouldn't sort of spend my time on

Kyler: mm-hmm I would sort of a tangent talking to my wife Morgan last night.

And you just mentioned like, Like get it out and audit how bad it is and whatever you said. And with Wells, our, our boy that we just had three months ago, I was like, I am scared of how critical I am. I was like, this dude cannot grow up feeling like he's never good enough for me. I was like, I need your help, Morgan.

and. Making sure. He knows that I'm always proud, um, but have really high expectations. And I was like, that is how I am at work. I always want to be better. I need to take more time to celebrate, but it's interesting how reflecting on that just very recently translated to the, the kid we just had. Mm.

Tiffany: I'll say this on the microphone so he can listen to it back on bad days, but know that the people that you love know that you love them.

It is incredibly important to me that no matter who is leading this company, that it always be from a place of service first. Our purpose is to foster growth in people and business, other people and other businesses. And when we do that, we then reap the benefits of individual growth. We grow as people we grow as leaders in our business by extension grows, but first it's a service first leadership role.

Um, it's in our, it's my, in my DNA and it's in. Our DNA is a company. And in walking so closely, this journey of element three with Kyler over eight years, eight plus years, I, I know that his DNA is that it's complete selfless leadership. I've seen him when he is tired. I've seen him when he is happy. I've seen him when he is lost.

I've seen him when he is won. I've seen him in valleys in his life. Um, and his character has been completely consistent. And so it's it's with that, that I'm really excited to sort of move to the next chapter for me and for him where he will move into the president spot the role for element three, he'll begin kind of shaping the vision alongside me as CEO and, um, really beginning to take.

The reigns of the day to day. And he's been doing that for the last year and kind of like practicing it. Um, but it's special to be at this place where Element Three is not only exceeded my own dreams and ambitions, but to know that it is such an important puzzle piece in Kyler's life when our lives are peaceful and there's so much.

that happens to us that if we can keep life simple, the things that we can control, then we have energy for the things that really matter. So I feel really proud of this moment personally. Um, I feel really grateful. I feel like I'm redeeming the trust that Kyle. Put in me, um, along the way, I think there were seasons, I deserved it and had earned it.

And there were seasons that I was really learning and probably didn't, uh, deserve it. And I know that there's been seasons, he's extended a lot of grace to me. I've learned a lot from him and it's meaningful to me to be able to mature as people. Um, beside each other for a long time. So thanks for trusting me Kyler and I am excited to operate with you in this capacity as we look forward to the next eight years.

Likewise. And like I said, a little bit ago, I'll feel like I have to keep earning.

As we begin to weave this journey of my life for 17 years in growing and building this company. I'm so incredibly proud of getting to a place where I'm handing some of the reigns over to Kyler to continue to lead and run with that. You don't live a life of, and you don't get to a place where as we talk about and scare confident where you can add new things into your life without strategically intentionally finding out how you're gonna make space for those.

And I have found almost always that space comes when you find incredible people who too have big dreams of, and, and in helping Kyler, you know, sort of opening the door and allowing him to step through, to accept and take that life of, and it creates more space for me to give and serve and give him my time and talents in different ways.

And EOS has this language that they use called letting go of the vine. And this is definitely a moment where I'm letting go of the vine, where I am letting go of things that I've had a lot of comfort leading for the first 17 years and trusting Kyler, giving him the space to lead and to become who he was born to be.

So it may seem sort of weird that we started this like memoir sort of jam, um, was really the end of the story. And we decided actually to start this project before we knew totally that Kyler was gonna be stepping into this role, but it seemed so apropo that we would sort of draw the story arc of all of this led to a place where I'm hand.

You know, a real shared responsibility in the leadership at element three over to Kyler. And this is a, a way to kind of memorialize what I've learned so that I don't forget. And he doesn't forget, and that we can lead knowing some of the same stories and knowing some of the same lessons and that the character that I've led from, hopefully he also will continue to like lead and grow and, and move forward from here.

But I do think it makes sense to sort of start back at the beginning. So the next episode, we're actually gonna talk to my parents. Um, they have been, you know, all of our parents were instrumental in our lives. Let's not be weird and pretend like I'm the only one. Um, but my parents were really instrumental in this journey.

It was really scary, you know, starting at 25, my dad is an entrepreneur. And so a lot of what I was facing, he had seen before and they were such guides through this journey. And my mom, you know, as I was becoming a mom in the journey as well, Um, was there as I was unwrapping that part of life too. So, um, in many ways I think my life is a true, like braided story of their two talents.

I am equal parts, my mom and my dad. And so I'm excited for you all to get to know them a little bit and the great impact they've had on my life in this company. This is the first 17 years a production in partnership with Sherry.

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