The Steady Leader: Interview with Schuyler Williamson

Summary

TheUPside Podcast

Episode: The Steady Leader – Interview with Schuyler Williamson

Host: Theresa Flood
Date: April 22, 2025

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Episode Overview

In this episode, Theresa Flood interviews Schuyler Williamson—former professional baseball player, West Point graduate, Army combat veteran, top Austin realtor, entrepreneur, and devoted family man. Together, they unravel the secrets behind Schuyler’s approach to “steady leadership,” exploring how his military experience shapes his success in business, family, and personal growth. The conversation delves into lessons on resilience, core values, stress management, purposeful leadership, and how clarity can emerge from chaos—in war and in daily life.

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Key Discussion Points & Insights

Schuyler’s Background and Journey (00:00 – 08:44)

• Origin Story:

  • Grew up in inner-city Pensacola, Florida, one of three brothers, raised by hardworking parents who encouraged self-sufficiency and achievement.
  • Used sports as a vehicle to access college, choosing West Point after being encouraged by his high school baseball coach.

• On Why West Point:

  • “I think it was just the head down approach... I was very goal focused and I wouldn’t quit. And a lot of that matters at these academies.” (Schuyler, 03:25)

• From Athlete to Military Service:

  • Played baseball for West Point; briefly part of the Detroit Tigers’ organization but felt compelled to serve after his brother’s difficult deployment.
  • Chose military service over baseball for a higher calling and family.
  • “The leader that was responsible for him didn’t step up... I would give it all I had. I wouldn’t let someone’s younger brother suffer the same way my brother did.” (Schuyler, 05:00)

• Choosing Family Over Career:

  • After serving tours in Iraq and Afghanistan, Schuyler faced a choice between advancing his Army career and being present for his family. He chose family, pursuing an MBA and a successful real estate career in Austin.
  • “It turns out I love my wife more than I love the military.” (Schuyler, 07:10)

• Clarity on Core Values:

  • Stresses the importance of being clear about personal priorities (“my God, my wife, my children, then everybody else”).
  • Playful family anecdote on always loving his wife first (08:06).

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Leadership Under Fire: Lessons from Combat (09:10 – 17:26)

• The Battlefield Story That Defines “The Steady Leader”:

  • Describes a life-or-death decision in Baghdad while responding to an ambush, where he had to choose between a fast, risky route or a safer, slower path to help fellow soldiers.
  • “You can choose the high risk, high reward route, or you can choose the low risk, sure reward, but low reward route... In that moment of chaos, what are some things you can do to lead your best?” (Schuyler, 09:51, 14:27)

• Preparation and Communication:

  • Detailed how leadership means preparing teams for contingency scenarios—the team rehearsed what to do if their vehicle was hit, so they could act swiftly under stress.
  • “The team knew before we even got there...you can say, okay, what’s the most probable thing that could happen in this scenario?” (Schuyler, 15:23)

• Transferable Lesson to Business:

  • “Military leaders always look at the situation first before they even start the plan... Look at the situation, right? We just look at real estate. What does the competition have that they’re better at me at?” (Schuyler, 17:09)

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Stress, Preparation, and Endurance (18:06 – 22:35)

• Managing Stress as a Leader:

  • Building mental, physical, and spiritual health as foundations for enduring stress and uncertainty.
  • “When you’re healthy, your endurance is so much stronger than someone that’s not... it’s a game of endurance to get through stress.” (Schuyler, 18:53)

• Energy Management:

  • True leadership energy is more than enthusiasm; it’s grit, endurance, and fortitude.
  • “To be the best leader, you gotta bring your best energy.” (Schuyler, 21:00)
  • Leaders have a responsibility to transfer energy to those they lead, whether family or teams: “In that moment, my son starts his day with his dad loves him, he misses him, he’s proud of him... I transferred that good energy into him and set him on this path of, hopefully, productivity.” (Schuyler, 23:13)

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Individualization and Pacing in Leadership (24:45 – 31:32)

• Not One Size Fits All:

  • Shares a hard lesson learned in Baghdad: not everyone has the same endurance or pace, and pushing A-players to match his speed led to burnout.
  • “Just because you can run fast and hard and long doesn’t mean that everyone else can. And it’s not fair for you to expect that from other people.” (Schuyler, 28:17)
  • “You want your motivations to be aligned... as the leader, you have to have a vision for their life. Everyone’s life is different and unique.” (Schuyler, 31:05)

• Tailoring Leadership for Different Team Members:

  • It’s about supporting individual strengths and visions, not cloning your approach for everyone.

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Decisiveness, Perspective, and Responding vs Reacting (31:48 – 34:17)

• Decisiveness vs Reflection:

  • From military urgency to business deliberation—a lesson in taking a breath before acting.
  • “We have more time than the world would tell us we do to make decisions... Leaders respond, they don’t react.” (Schuyler, 32:49, 32:51)

• The Who, Not the How:

  • Advocates for finding the right person (“who”) for the task rather than always defaulting to “how” you’ll do it yourself—referencing the book Who Not How.

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Fostering and Love-Centered Leadership (34:23 – 36:41)

• Parenting and Fostering:

  • With 10–15 foster children welcomed into their family, Schuyler and his wife prioritize love as the core of their home leadership model.
  • “They just need love. They don’t need somebody to teach them life lessons. Not when you get them… Start with love.” (Schuyler, 35:31)

• Family as a Business:

  • Vision, purpose, training, standards—all supported by an undercurrent of love.

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Purpose and the Will Not to Quit (36:41 – 39:04)

• Purpose as Anti-Quit Fuel:
  • Distinguishes between the ever-present drive to stay in life-or-death situations (combat) and the frequent desire to quit in grueling, ego-driven experiences (Ranger School).
  • “Purpose is the one thing in life that’s evergreen if you get it right... It has to be about others.” (Schuyler, 37:27)
  • “If your purpose is about you, at some point you’ll be like, this ain’t worth it. It’s not worth it.” (Schuyler, 39:02)

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The Steady Leader – Book Details & Leadership Models (39:04 – 41:49)

• Who the Book is For:

  • The “rookie leader in business” with ambition, seeking practical frameworks to build stability and success; structured by models for leading self, teams, and business.
  • Advice: “You are always writing your book for yourself ten years ago.” (Schuyler, 39:33)

• How to Get The Book:

  • The Steady Leader: Leadership Models That Bring Clarity to Chaos
    • Releases April 29, 2025
    • Pre-order: Thesteadyleader.com

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Daily Habits, Personal Growth, and Final Leadership Challenge (41:49 – 43:00)

• Daily Reading & Journaling:

  • Schuyler journals and posts daily on LinkedIn, sharing what he’s reading and learning.
  • “A book comes when you do the stuff every day.” (Theresa, 41:41)

• Challenge to Listeners:

  • “Make your first hours of the day super intentional... What are you doing in the first two hours of the day to take care of yourself mentally, physically and spiritually? If you could do that... you are going to fire out of a cannon to be the best that you can be.” (Schuyler, 42:30)

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Notable Quotes & Memorable Moments

• Schuyler Williamson:

  • “You want your motivations to be aligned... as the leader, you have to have a vision for their life. Everyone’s life is different and unique.” (31:05)
  • “Purpose is the one thing in life that’s evergreen if you get it right... It has to be about others.” (37:27)
  • “Leaders respond, they don’t react.” (32:51)
  • “If your purpose is about you, at some point you’ll be like, this ain’t worth it.” (39:02)
  • “To be the best leader, you gotta bring your best energy.” (21:00)

• Theresa Flood:

  • “Parenting is the greatest leadership lab of all time, because they will try you more than anybody else.” (23:59)
  • “At the higher level you get within a company, you really are paid to think. Other people are paid to do.” (34:14)

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Important Timestamps & Segments

• Background & Military Foundations (00:00–08:44)
• Combat Leadership Story (09:10–17:26)
• Managing Stress & Transferring Energy (18:06–23:59)
• Hard Leadership Lessons—Pacing & A-Players (24:45–31:32)
• Perspective on Decisiveness & Reactions (31:48–34:17)
• Leading Family & Fostering (34:23–36:41)
• Purpose & Not Quitting (36:41–39:04)
• About ‘The Steady Leader’ Book (39:04–41:49)
• Morning Routines & Growth Challenge (41:49–43:00)

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Resources & Further Learning

• Book: The Steady Leader: Leadership Models That Bring Clarity to Chaos (Released April 29, 2025)
• Website: skylarwilliamson.com for newsletter and daily insights
• Host Site: teresaflood.com

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Summary

This episode is a blend of deeply personal stories and actionable leadership insights, from leading men in combat to nurturing teams and family. Schuyler Williamson embodies the “steady leader” who brings order to chaos through preparation, clarity on purpose, tailoring his approach to individual strengths, and operating from love and service. Whether you’re leading in business, at home, or both, the episode urges you to be intentional, align your actions with enduring purpose, and invest daily in your own and others’ growth.

Transcript

[Teresa Flood]

Welcome to the Upside Podcast, where we help you get unstuck in your life and your business by elevating your thinking and provoking meaningful change from the inside out. Y' all are in for a treat today because I have a guest with me. So if I told you that I was bringing you a former professional baseball player, would that maybe be an interesting conversation? And if I told you I was bringing you a decorated military veteran, graduate of West Point, Bronze star medal recipient, did tours in Iraq and Afghanistan, A top producing realtor running a team out of Austin, Texas, owner of many investment properties, over 55 investment properties. He owns multiple businesses, including Laundry Love. And if you heard my previous episode with Ken Wimberley, you, you know that Ken is one of the owners of Laundry Love. If you haven't heard that episode, I'd encourage you to go back and listen to it. It was great. And a father, a husband, a foster parent. What did I miss? Oh, my goodness. I have Skylar Williamson in the house. And if you don't know his name, you do now. And literally all of that talent wrapped up into one human being. I'm trying to figure out what I've been doing with my life. So happy to have you with me today.

[Skylar Williamson]

Oh, I'm grateful to be here.

[Teresa Flood]

Oh, my gosh. So we just got out of our market center and you came and talked to my agents. We filled up the room, we had a great conversation, and now we're just gonna continue it here, but we gotta start from the beginning for everybody. So I know I gave a few high points. Yeah, we're talking about all your low points from now on. No, I'm kidding. Okay, so just tell us in your own words, just who are you? A little bit about you. And we are gonna get into the study leader, which I'm really. I'm excited to read it cover to cover once it's out. But you tell us about you.

[Skylar Williamson]

Yeah, I'm one of three brothers from Pensacola, Florida. And not the beach part of Florida or Pensacola, the inner city part. I played sports my whole life. My parents had me very young, and they were wonderful parents. They were loving, and, man, they set an example for such hard work that all three of us, all three brothers are hard workers. But it was pretty clear early that my parents weren't just going to cut us a check for school after the public school. So if we wanted to go to college, we had to pick either academics or sports to get there. And I chose sports. That was my decision. And I started to refine my craft of Just earning my way to achievements at a very young age. And so I did have fun playing sports, but I was always intentional with it. I knew that it was going to take me to the next step in life. And, and so I worked real hard to be the best football and baseball player that I could be, the best athlete that I could be, and was rewarded for that. I applied to a bunch of schools, was accepted by a bunch of schools, invited to play on scholarship at a bunch of schools. And my high school baseball coach said, hey Skyler, you remind me of academy guy. You ought to apply to the academy. And I knew nothing about that. Interesting. So I wasn't.

[Teresa Flood]

And what do you think he saw in you? Like what made him say that? What character trait or what, what quality?

[Skylar Williamson]

I think it was just the head down approach. And I didn't make a whole lot of bad decisions. You know, I kept myself under control and I was very goal focused and, and I wouldn't quit. You know, it didn't matter what it was, I wouldn't quit. And, and a lot of that matters at these academies.

[Teresa Flood]

Sure.

[Skylar Williamson]

But I, but because I didn't know the academy lifestyle or what it was, I only applied to West Point cause that's what he told me to apply for.

[Teresa Flood]

Okay. So.

[Skylar Williamson]

So I didn't know to apply to Annapolis for the Navy Academy or the Air Force. I just didn't.

[Teresa Flood]

This was West Point.

[Skylar Williamson]

That was, didn't research it. Yeah, they had a ball team there. So I applied and met with my congressman to get that nomination, got all that stuff done and met with the football and baseball coaches there and got in and really hard to get in. And my grades probably shouldn't have been approved compared to all of my classmates, but I was, I was the best ballplayer.

[Teresa Flood]

There we go.

[Skylar Williamson]

And so, you know, my, my plan of using ball to get me to college came true in that moment where I was accepted from West Point to basically be a part of their baseball team. I played well there. They changed the rules actually while I was at the school to make it so that you could be classified an Olympic athlete.

[Teresa Flood]

Interesting.

[Skylar Williamson]

And then go play sports. So I was still in the army, but I was an Olympic athlete while I was playing for the Detroit Titans.

[Teresa Flood]

Okay, I add that to the list. Olympic athlete.

[Skylar Williamson]

Well, I was a baseball player.

[Teresa Flood]

Yeah.

[Skylar Williamson]

But that's how the army approved it because I was an active duty officer while I was playing baseball. And all my buddies from West Point, all my classmates, my younger brother, they all deployed overseas while I was playing baseball. And it just didn't sit well with me. And when my brother came back, he really struggled. And that's a whole story in its own there. But when he was telling me stories about his leadership, that was the first time in our life that I wasn't able to protect my younger brother. And the leader that was responsible for him didn't step up to do it. And I didn't think that I was going to be this special leader in the military, but I would give it all I had. I wouldn't let someone's younger brother suffer the same way my brother did. And so I called Detroit and I told him I wasn't going to come back. They had invited me back to spring training to continue on with the. With the ball team. But I. I went into the military. I did all the ranging.

[Teresa Flood]

So really, it was a calling for you.

[Skylar Williamson]

It was a.

[Teresa Flood]

You felt like it was a calling.

[Skylar Williamson]

Yeah. You know, they teach at West Point to the desire to serve. And so, you know, they want us all to be servant leaders. And that, you know, that resonated with me. So I've always had this servant heart. And, yeah, I mean, it just pulled on me the whole time. And then my brother's stories were where the. With the last bit that I needed to motivate me to go do it. And so I did the whole Ranger, Airborne, all that stuff. I fought in Iraq and Afghanistan and then.

[Teresa Flood]

Thank you for your service.

[Skylar Williamson]

Well, the honor is all mine. It's truly been a blessing. But I. I wanted to have children, and I wasn't doing this job that was safe. The job that I was doing was dangerous. And my wife knew that through some situations that we went through in the military. And, you know, look, she. She laid it out for me. She's like, I'm never going to leave you. I love you. I want to be with you for the rest of my life, but I'm not going to have a child and you not come home from war. And. And. And then she kind of went on, we talked more about it, and she. She essentially said, this wasn't the life that I thought we were going to have together. And so I came to a point where I had to decide, am I going to be this general in the army that I was kind of working toward, or am I going to be the family man? And it turns out I love my wife more than I love the military.

[Teresa Flood]

I get a call for you.

[Skylar Williamson]

Yeah. So I chose her. And in that, I applied to UT to go to their MBA program because my undergraduate's in engineering. And I knew I wasn't going to be an engineer, so I had to go to the MBA school to figure out what I was going to do next, and graduated from there and went into real estate, and I've been in real estate ever since.

[Teresa Flood]

Well, you built an impressive career. And I think it's interesting when you talked about your wife expressing her desires, and it's easy to say, so then I made the decision. Right. And it's not always so cut and dry, except for when you're really clear on core values, it guides those decisions. Right. And so you having a core value of family being so key and so pivotal and more important. Right. Than those other things know, it makes it a clear. Maybe not an easy decision, but it makes it clear, which I know in your book, it's all about bringing clarity to chaos.

[Skylar Williamson]

That's right.

[Teresa Flood]

That's right. So.

[Skylar Williamson]

Well, just a fun thing on that. Let me just tell you, this is fun at the house. I have two children now. And, you know, and every once in a while we have an extra. Right. We have a little foster child. But my two children, they'll always ask me, well, daddy, who do you love more? And it's kind of a game that we play now, because they know what the answer is. I love mommy first, and then I love you two equal. But it's always been, my God, my wife, and then everybody else. You know, I have children now, so it's my children, then everybody else. But I'm real clear, like, where my priority is in life. And it's my wife.

[Teresa Flood]

It makes the decision so much easier. So we have the same conversation, except with the kids. We say it depends on the day.

[Skylar Williamson]

Yeah.

[Teresa Flood]

And who's behaving. No, I'm kidding. We don't really do that.

[Skylar Williamson]

Yeah. We don't ask mom who she. Because I think she'd pick the kids.

[Teresa Flood]

Okay. So. So you told a story, a battlefield story to our. To our office earlier. And I. I think it was a great depiction, really, of what steady. The steady leader is.

[Skylar Williamson]

Yeah.

[Teresa Flood]

And how wartime and battlefield leadership was really cultivating you. I'd love you to share that story. And then just a little bit about kind of some of the lessons that you learned through war and through battle and how that has made you. You know, in real estate, we feel often like it's a battlefield and yet not quite the same as getting actually shot at. But leadership is chaotic, and it's challenging and it's stressful, and it can feel life or death to some degree. Right. So I would love you to just share that story and kind of dive into some of those models.

[Skylar Williamson]

Yeah, you know, I tell the military stories because they're extreme. They make it crystal clear.

[Teresa Flood]

Right.

[Skylar Williamson]

When you, when you tell a war story, it's crystal clear where the principle is and where the life and death, right or wrong, you know, it's real clear. So, you know, in the book, we tell a lot of war stories because it just makes the leadership point so clear. Yeah, the story I told was we were, we were in Baghdad and the. Listen, Al Qaeda's. Which I was in a Sunni area of Baghdad, Baghdad's a big city. I was in the Sunni area and Al Qaeda was the one that ruled the Sunni area. And their weapon of choice was the ied. And we all knew that. I mean, it happened hundreds of times to us personally, whether we found it or it detonated on us. It was something that was normal in our day to day. And we were out on a patrol and my sister platoon that was just in the sector beside us pulling a very similar mission to us, had an effective IED blow up on them. They had casualties and then there was small arm fire after the ied. So they were under attack and it was a sustained attack. They needed help and they were very clear on the radio that they needed help. And listen, no better army in the world than the US Army. I've fought next to all the armies that are out there that are willing to fight, and there's no better army than the U.S. army. So we quickly as a unit were mobilizing air support. But it takes time, right? This pilot's got to get to the vehicle, the aircraft, and they got to get up and they got to get to the unit. We were close, right? And so I didn't wait for anybody to tell me what to do. We started moving toward my sister platoon. And it's kind of like in business you have a choice. You can choose the high risk, high reward route or you can choose the low risk, kind of sure reward, but low reward route. And so the way it played out in this scenario in combat was there was a dangerous route that we could get there fast and where I know we could probably save lives and maybe, you know, take the fight to the enemy. But it was, it was the quick route, but it was the most dangerous route. Then there was a longer route that was more safe, but who knows who would have been hurt between now and the time that it took us to get there. There wouldn't have been that much value because the aircraft would have shown up soon after me. And so we took the high risk route and, you know, the end.

[Teresa Flood]

How fast did you have to make that decision?

[Skylar Williamson]

I mean, there was plenty of time to make that decision. But, you know, as a soldier, I think where your heart first lies is the brotherhood of protecting one another. You know, look, we want to search and destroy the enemy, and we're kind of doing it under this umbrella of we're fighting for our country, for freedoms, and for the way that we live our life, and we believe it's a great way for others to live. So there's like these overarching things, but at the core of the heart of the soldier, we fight for one another. And that makes that decision a little bit easier. You know, I'm going to go save their lives, just like I'd hoped that they would save my life. And so we started maneuvering there and we took the dangerous route and the enemy was effective. They blew an IED up on my vehicle personally, and it disabled my vehicle. It disabled two other vehicles as well. And every soldier in my truck was. Was injured. And the reason why I tell the story is because it was the one time where I had this fog of war moment that you see on the movies, the good movies, where my ears were ringing. I don't think I was knocked out, but it sure felt like I was coming to. So my brain was at least shook. The people behind me were screaming because they had suffered shrapnel impact. My gunner that was in the turret was completely knocked out from the concussion. And then my driver who was trying to start the vehicle, you know, he was bleeding from his ear. I mean, he was, he was hurt. And there was so much dust in our vehicle, we couldn't see anything. And I heard on the radio soldiers screaming, you know, for the lt, what should we do? I mean, they were asking their leader to make the next decision. And I usually stop right there because, you know, the rest of the story is good, but like, that is chaos. And just because I suffered a direct impact from an IED didn't mean that I get to call T, right? I told my son does jiu jitsu and he wants to fight non stop. Sometimes I just be like, dude, I need a timeout, okay? I couldn't call a timeout. Not in combat. We can't call timeout in our business just because we're a little disrupted or it's chaotic. I mean, we got to keep leading. And in that moment of chaos, what are some things that you can do to make sure. That you can lead your best. I'm not saying perfect. Right. Perfection is unachievable. But what can we do to be our best to achieve the excellence in that moment? And there are some things that we can do ahead of time. There are some things that we can do in the moment. And certainly there's some learning that we can always do after experiences.

[Teresa Flood]

But, yeah, that's a great point. Well, and I think if you don't do the learning ahead, you'll never be able to do the action in the moment. Right. It's, like, too late to prepare once you're there. You've got to pay the price ahead of time.

[Skylar Williamson]

Well, and so the part of the story that I didn't tell was, as a leader, when we were taking the dangerous route, we knew where it was most dangerous. It channeled our traffic into one specific funnel, and there was guardrails, which the enemy loved to just put bombs right up on the guardrail. And so we had already talked through what were we gonna do if we were detonated in IED on that point. And so the team knew before we even got there. The team knew what we were gonna do. Whatever truck was hit and disabled, the one behind it was gonna push it through, and we weren't gonna get out of our vehicles until we were through the kill zone. So we knew. We knew. And that's one of those things that you can do ahead. Like, you can say, okay, what's the most probable thing that could happen in this scenario?

[Teresa Flood]

Right.

[Skylar Williamson]

Military leaders always look at the situation first before they even start the plan. So what's the most probable thing that happens here? What's the most dangerous thing that could happen? And we talk those out, and then we start to plan. Right? And I think that's a great lesson that the military blessed me with, is before you start to plan an activity, you look at the situation, right? I mean, we just look at real estate. You know, what does the competition have that they're better at me at? Yeah, Right. I mean, there's brokerages we got to deal with, but then there's individual agents that if we find out that we're competing against them individually, they may have an edge on us one way or another, Right. If I was competing against another agent on my team who has the same team value proposition, well, I'm competing person to person.

[Teresa Flood]

Person to person, right?

[Skylar Williamson]

And there's some things that I could sell, and obviously they can sell against me too. But, you know, you gotta understand the situation of the competitors. You gotta understand the Situation of what you have at your assets, your uniques, the landscape, right. We got high interest rates, we got low supply, you know, we got all these things that we're dealing with right now. You gotta think about all of that so that you can put together the best plan. And I, you know, military gave me that knowledge of how to do that.

[Teresa Flood]

No doubt. So it must, I would imagine, and you just can't feel free to tell me. I don't wanna make assumptions here, but I would imagine that having the perspective of true life and death helps you manage stress in what's not actually life and death. I would imagine that there's a unique perspective when you're been in situations where you have human beings whose lives you're physically protecting. That it gives perspectives, perspective. But how does a steady leader manage stress? How do they get through the chaos and manage just challenges in business, going through seasons of losing people, problems?

[Skylar Williamson]

Yeah, yeah, it's a, it's a really big question. I do think that there's some work you can do ahead of stress to make sure that you're in the best condition to handle it. And so for me, I, you know, I talk about being healthy and that's being healthy mentally, physically and spiritually. And when you're healthy, you know those three areas, your endurance is so much stronger than someone that's not. And you know, listen, a lot of things that stress us out in the moment, we'll get past it. Like if you just, like if we just talk about something that you're stressed out about and we say, hey, look, Theresa, a year from now, do you think you're gonna be worried about this? I mean, more times, not more press.

[Teresa Flood]

Than not more times not. We're like, no, we don't even remember it happened. That's right.

[Skylar Williamson]

And so really it's a game of endurance to get through stress. So what are the things that we do? So mentally, I think you have to have a growth mindset and that's how you're healthy mentally. And so you got to be hungry to be better than you were yesterday. Today, physically, I mean, that's literally taking care of your body physically. So sleep, good nutrition, exercise. And I tell people, is your body telling you what to do or can you tell your body what to do? So just my day today, I woke up very early to get here to Dallas. I left Austin. Yeah, my pleasure. Right away I had a low tire, so I have a nail on my tire, but I gotta blow that. So I had to do all the great stuff to fill the tire up, so I was behind, so I didn't have a chance to eat because of the tire. But I got here, turned it on so that I could be a great opportunity for your market center. We back these things back to back. So we came straight here and we're having this conversation. And so am I going to let my body tell me like, oh, you're tired and you're hungry and this and that, or am I going to say, hey, body, step up, get all this stuff done, be sharp, deliver value. And I think, you know, your body's either an asset or a liability. So if it's an asset, you can tell it what to do and it'll perform for you to an extent.

[Teresa Flood]

Well, I think you become so much more conscious of that as you age and get older. But then the flip side of it is also, you know, this morning my daughter was just so tired. She's 13 and she was just unglued this morning. It was not a typical morning. She was just so tired. And I'm thinking this child, if she doesn't flip it, if she doesn't get in control of this emotion, this is not going to be a great day for her. And there's a maturity aspect of that, but also of conditioning.

[Skylar Williamson]

Oh yeah, well there, yeah, certainly it's conditioning and making good decisions the night before. But I'll just say, like we didn't talk about it today at your Marcus center, but I believe in, to be the best leader, you gotta bring your best energy.

[Teresa Flood]

Yes.

[Skylar Williamson]

And so what you were doing with your daughter was trying to transfer good energy into her so that she could have, you know, a better chance at the day.

[Teresa Flood]

Right.

[Skylar Williamson]

And I think that, that, you know, I have my own way of doing that with my children. But I think leaders also recognize opportunities to transfer good energy, good productive energy. And that's another, like, if you're not prepared to do that, you're not going to be as effective as a leader as you could be.

[Teresa Flood]

But I think sometimes people mistake being a high energy leader for being legitimately jumping up and down in front of a room and being a rah rah. And that's not what it is. It's grit, it's endurance, it's mental fortitude. Energy is so much more than just those obvious things. That's really the kind of energy that transfers, is that deep character of that.

[Skylar Williamson]

And there's so many leadership books that talk about innovation shows up when your employees feel safe and feel empowered and. Right. And so a lot of what we try to do as leaders is make our team feel safe and feel empowered and supported and affirmed. You know, when you can teach them how to think and then you give them those feelings, you know, you energize them in that way. They're going to perform, they're going to bring great value. And. Yeah, I mean, for my children, I'll just tell you, I got this whole morning routine that's a bit extreme, but let's just say I'm energized by the end of it. Okay. And so I have.

[Teresa Flood]

Are you as extreme as Ken?

[Skylar Williamson]

We're cut from the same cloth, right? Yeah. No, we. I mean, we share life together. We're partners.

[Teresa Flood]

Yeah.

[Skylar Williamson]

So I go. I go wake up my. My. My son. He's younger.

[Teresa Flood]

He's old.

[Skylar Williamson]

He's eight.

[Teresa Flood]

Eight.

[Skylar Williamson]

So he wakes up. So I wake my son up, and I'm like, hey, man. He's, hey, Dad. I go, I love you. And he goes, love you, too. I was like, I've been missing you all morning.

[Teresa Flood]

He goes, you've been up for, like, four hours.

[Skylar Williamson]

Yeah, yeah, yeah. Well. And so my son, he's young, so he just thinks repeating it back is polite. So he repeats, I've been missing you, too. He just woke up.

[Teresa Flood]

So sweet.

[Skylar Williamson]

And I tell him, I'm just so proud of you. And I was like, you ready? He goes, yeah. I go, let's go. Have a good day. So in that moment, my son starts his day with his dad loves him, he misses him, he's proud of him. And I didn't give him a choice. I said, we're gonna have a great day. And so his mindset is set, and so I transferred that good energy into him and set him on this path of, hopefully, productivity, you know, and then I go do it with my daughter, and the script changes a little bit with my wife, you know, but, you know, then I go show her how much I'm grateful for her. But I. It's the first chance as a leader that I get to practice transferring energy for that day.

[Teresa Flood]

I love that. And I think it's the purposefulness of it. And I think I've always said that parenting is the greatest leadership lab of all time, because they will try you more than anybody else. You're in it. It's the most important one. So you have the most at stake, right, with your family. But it is truly the greatest leadership lab. My girls are 13, so we're about to go into teenage years where it is less about managing a lot more about leading. So, yeah, you can say a prayer. I would love to know what is the most surprising thing you learned in the military? Like what would what surprised you going in that you walked out thinking I had no idea this experience would change me in this way or the.

[Skylar Williamson]

I think the story that comes to mind is my hardest leadership lesson. I don't know if I was, I mean, I guess I was drastically surprised by it, but I view it more as a lesson learned. Yeah, when we were overseas again, it was very nasty. Right? We don't have to expand on that anymore. We spent some time on a story, but it was a very high tempo environment. And about three months into the deployment to Baghdad, my second in command just kind of hit his breaking point. And it's a very sad story and I'll spare the details, but I lost my second in command to distress. We had to send him home and so I lost him. Then I lost another higher ranking enlisted gentleman who was what you would have called my toughest soldier prior to deployment. And he's still a tough guy, but like, you know, stress gets you. And then I went to this. Then we, then we kind of figured it out, right? I started giving people breaks. But then in the deployment, my guy, that was my first truck, he came to me, he's like, hey, sir, I can't be the first truck. Every time, you know, like all three of the guys in the vehicle, they were just, they felt terrible about telling me they couldn't do it. And right when he said it, I was like, of course, like this whole burden, this whole IED burden has been yours to carry. By being an elite truck, your responsibility is to identify him. And I just poured all that on one team and never gave them any kind of break from it. I was like, man, of course. And so I started cycling the vehicles through and then my, then my soldiers started coming to me, other trucks, and saying like, sir, we can't be in the first vehicle. It's just too stressful. I'm like, all right, well you know what, my truck will be the first vehicle. And we went with my truck as the first vehicle for a while. And I just thought, like, I can control the mindset in the truck. Know I've got great soldiers in my vehicle. Well, about a month after us just being the only one being in the front, my guys came to me and they hit their knees and they cried and they just said, sir, we can't do it anymore. And, and then finally, like the fifth time through all this, I, it finally resonated with me what the Lesson learned was. And that's not everyone has the same pace that you do. And so just because you can run fast and hard and long doesn't mean that everyone else can. And it's not fair for you to expect that from other people. And I don't think I. I don't know that as a young soldier that I expected my soldiers to soldier as hard as me. I don't know that that's what I was saying, but that's what my actions were doing. And, and it's played out in my professional career where when you hire an A player, they try to match your tempo. And I'm a hard worker and I'm not normal in that way. It's my superpower to be able to focus and to work hard for a long time. Other people try to match me because they're my team. They don't want me to do it all on my own. And then it just wears them out and they lose their joy in what they're doing. And I've got to tell them, like, hey, I never had an expectation of you doing the same thing that I'm doing.

[Teresa Flood]

That's really, really.

[Skylar Williamson]

I'm grateful. I'm grateful for you as an A player trying to step up and do. But like, you just be great at your job. You let me do my job my way, you do it your way. You know what the expectations are. This is what I expect of you. If you do more, awesome. But not, not at the sacrifice of your health or your family time or any of that. And you know, the end of the story is I ended up just cycling everyone through and I just stayed in the first truck because I could do it. God gave me an ability, leadership. Well, but even the leaders that can't do that though, Teresa, like, it's not everyone has a breaking point. Everyone does. I just didn't happen to run in the mine yet and, and I'm grateful for that. That was a supernatural strength in that moment, I believe. But that, but that lesson on pace and being aware of your A players that are trying to measure up to what you're doing. If you don't pay attention to that, you'll lose your A player.

[Teresa Flood]

And they're just need to hear that today. No doubt.

[Skylar Williamson]

Yeah. And they're just trying to be the best employee they can be. And it doesn't matter how many times you affirm them or give them an atta boy like, they will work themselves into resenting the job and they'll leave.

[Teresa Flood]

That is wise. Very, very wise. So. And two, I think you've, you learn through leadership that it's not one size fits all. What makes a leader great is that they're able to lead Joe this way and Susie this way and. Right. And it's not about creating a bunch of mini Teresa's or mini Skylers. It's about helping people become their very best. Determining their superp.

[Skylar Williamson]

Yeah.

[Teresa Flood]

And that's also what makes great team.

[Skylar Williamson]

Oh, yeah.

[Teresa Flood]

Right. When we can bring that out in people. But yeah, that is, that's, that's really, that's really interesting.

[Skylar Williamson]

Yeah. You want your, you want your motivations to be aligned.

[Teresa Flood]

Yeah.

[Skylar Williamson]

Right. Because you want to ask somebody to go have their best life and that actually help you get yours as the leader. So you, you want to be completely aligned on motivations and values. But as the leader, you have to have a vision for their life. Okay. And everyone's life is different and unique. And so I have a vision of how I'm going to help you live your best life. And then this employee, it's going to be different. It's not a one size fits all. Everybody has their own unique life and it's different than yours. We're all trying to make this one big thing get accomplished. But in doing that, if you've got a mom of three that would love to be there when their kids get off the bus and then you got a young man who just wants a bunch of money to save up so that he can do whatever. Right. Like they're both motivated to get to the same goal as you and have a similar life, but they need different things. Right. Like you need to let that mom.

[Teresa Flood]

Gotta slow down to determine those things.

[Skylar Williamson]

That's right. The second that I asked that mother to run her business the same way that I asked that young man to run hit is the second I lose her.

[Teresa Flood]

Yeah.

[Skylar Williamson]

Because her life's different.

[Teresa Flood]

Yeah. It's not cookie cutter.

[Skylar Williamson]

Yeah. I mean, know who you're leading, have a vision for that.

[Teresa Flood]

So this may be. You maybe kind of answered this already, but is there anything you believe to be true about leadership in the past that you'd say I feel differently about leadership than I did previously?

[Skylar Williamson]

Yeah. Actually there's something that comes to mind. You know, in combat and as a young leader, you are very much rewarded for decisiveness. And look, you have to be decisive as a leader. If you're going to achieve massive success and you have a big job, you have to be decisive. What I know now, after years of experience is we have more time than the world would tell us we do to make decisions. I mean, every time that you feel urgency pushing you to decide on something, whether it be for our family or for our business or for our personal health or whatever, if you, if you really took a step back and said, am I letting all these other influences drive me to, to make a quick decision or am I making this decision on my own timeline? I mean, usually it's the world telling you to make a quick decision and. Because they need something. Right.

[Teresa Flood]

And so it's more reactive than intentional.

[Skylar Williamson]

That's right. Yeah. I say it all the time. Leaders respond, they don't react. And so I love taking more time than naturally. I feel like I want to because I am a, I'm a, I'm an urgent person, personality type. But I love taking an extra step of thinking so that I can respond and just not react. Maybe my reaction is still the right answer, but I'm still going to give it some thought. Yeah. And so I want to be thoughtful. That's what I want a part of my brand to be as a thoughtful leader.

[Teresa Flood]

I like that. And sometimes there are some problems, I think actually self resolve some of them. If you wait too long, they get worse.

[Skylar Williamson]

Yeah. Well. And I read a book, who not how.

[Teresa Flood]

Yes. Great book.

[Skylar Williamson]

Yeah. A lot of people just think, you know, how I need to solve that. Well, if you, if you take an extra second to think about the problem, that extra second will give you the opportunity to think, well, who do I have that can take care of that? And you save that time. But if you just get it right into action, you lose that time because you're going to do it right. Leaders are doers. That's why you got into your leadership role, is because you were able to do right. So, you know, you need to. I know now you could take another minute.

[Teresa Flood]

Yeah. You also have to think. Yeah. And really, you know, at the higher level you get within a company, you really are paid to think. Other people are paid to do.

[Skylar Williamson]

Oh, yeah, yeah.

[Teresa Flood]

You get to hire somebody to do all the things so that you can.

[Skylar Williamson]

Yeah. The doing is all working in the business. You know, the thinking's working on the business.

[Teresa Flood]

Okay, so you and your wife are foster parents.

[Skylar Williamson]

Yeah.

[Teresa Flood]

And you told me you have had, you have two of your own biological children. You've had 15 to 20, 10 to 15, 10 to 15 children come through your home, which I think is a beautiful thing. Just an unconditional love. And obviously has to have a huge set of challenges for you two as parents and even for Your own children. Right. Because it's disruption into your normal routine. And I'm sure all the children you get, I'm sure there's unique needs every time somebody new comes through. So what have you learned from that experience? Just give me one major lesson on leadership that you have learned. Fostering just really vulnerable little humans.

[Skylar Williamson]

Yeah, well, I mean, love conquers all. I mean, that's. You know, if there was. If there was ever anything that you could make a priority or start with, with leading, you just start with love. And. And that's what those kids need. They just need love. They don't need somebody to teach them life lessons. Not. Not when you get them.

[Teresa Flood]

Yeah.

[Skylar Williamson]

You know, if they stay with you a very long time and then they become a permanent part of your family, then, yeah, we're going to teach them how to succeed in the world. But in the foster world, it's just love. You know, they come into your life, and then the way you lead your family is you make sure that your wife feels supported and safe and that she's loving. Then you make sure that the kids feel safe and supported and that they're loving. And then you love yourself, everybody. And then keep control. And the more that you can make that foster child feel safe and love, the more they're just going to fit right in with the rest of the crew. They just will. And some need more love than others. But, yeah, my family, we run it like a business. I have a vision. We have purpose, we have training. We have standards. We have all the things. But it's love. Right. And so I tackle everything every day with love in the family. And I think that that's just been driven even more home with the foster experience.

[Teresa Flood]

That's really, really awesome. So one of the things you mentioned when you were speaking earlier was that never once did you think about quitting. When you were in Iraq.

[Skylar Williamson]

Yeah.

[Teresa Flood]

And yet at Ranger school, you thought about quitting every. I don't know what you said every five minutes. I don't think it was.

[Skylar Williamson]

Oh, shoot. It wasn't that long.

[Teresa Flood]

Okay, okay, okay. Every moment of the day, you were thinking of quitting, which is so interesting. Cause you're the same human being, two very different scenarios, but yet very challenging. And yet. I'm pretty sure you weren't being shot at in Ranger school.

[Skylar Williamson]

No.

[Teresa Flood]

So what's the key to not wanting to quit? Like, talk to the person that wants to quit or is having things in life where they're considering. What's the key to not quitting?

[Skylar Williamson]

Yeah, it all Comes back to purpose. Right? And purpose is the one thing in life that's evergreen if you get it right. And it's the thing that can drive you to be the best that you can be or the most that you can be in this life. And for the purpose to be evergreen and to be an impactful one, it has to be about others. It has to be about others. If you have a purpose in your business or if you have a purpose in life that's about something that you're going to get for yourself or something that you want that's not going to last and you'll quit on it. And so my story about not quitting combat and being willing to quit Ranger School if I just had the right moment to do it was to be.

[Teresa Flood]

Clear, he didn't quit. He didn't actually quit.

[Skylar Williamson]

But no, thank you.

[Teresa Flood]

The thought was there.

[Skylar Williamson]

Yeah, the thought was there. And I was humbled in that moment. Right. Like everybody's got a. They got a point. And so the reason why I never thought about quitting in combat is because I was there for the other soldiers. I was there for them and I was there for our country. And it wasn't about me. Nothing about risking my life was about me.

[Teresa Flood]

Yeah.

[Skylar Williamson]

In Ranger School, 100% of that achievement was for me. It was for my career. It was a badge that I got to wear. It was something that would build my ego, and it was all about me. And yes, when things got hard, I thought about quitting. It ain't worth it if something's about you. If your purpose is about you. At some point you'll be like, this ain't worth it. It's not worth it.

[Teresa Flood]

That'll preach.

[Skylar Williamson]

Yeah.

[Teresa Flood]

Okay, So I am so excited to get a copy of this book. When does it come out?

[Skylar Williamson]

April 29th.

[Teresa Flood]

April 29th, it's going to be on the shelves. It's a beautiful book. The Steady Leader leadership models that bring clarity to chaos.

[Skylar Williamson]

And you can pre order it [e-mail] the steadyleader.com.

[Teresa Flood]

So we'll put that all in the show notes. Why should somebody who should. Who's your. Who should needs to read this book?

[Skylar Williamson]

Well, let me give you a book hack.

[Teresa Flood]

Yes.

[Skylar Williamson]

You are always writing your book for yourself. Ten years ago. Okay, okay. So if you were to write a book, you got to write it for yourself 10 years ago. And 10 years ago, I was this rookie leader in business that had an idea that I had a leader profile and that I wanted to do big things, but I needed Some models. I needed some models to go build my empire with. And so this book is an accumulation of all the models that I use to run my business, or, excuse me, all the models that I use to lead myself, lead my team, and lead my business. And so the book is broken up into those three sections, and there's models in each section that you can, if you deploy them, you'll be steady.

[Teresa Flood]

I love this. And I think steady leadership. I don't know that there's any other books maybe specifically talking about that.

[Skylar Williamson]

There's not.

[Teresa Flood]

I'm sure you've checked. We've checked if there is that we haven't determined this one will be the best. I would encourage anybody listening to Grab to pre order this book and to get it shipped to you. I already have mine on the way and I've bought it for several other people. So I'm just very excited for you and I think you have a real message to tell. You have a very impressive resume. Thank you. Of success. But what I love the most is you're a good human. And I can just see that just in our conversations. You're the real deal.

[Skylar Williamson]

Thank you.

[Teresa Flood]

And I love how purposeful you are. And, you know, there's a. There's. There are people who achieve success that can't exactly articulate how they got there or why they do what they do. They maybe have just some good gut intuition or what have you. But you're very, very clear on what your journey has been about, what you've learned all along the way. And one of the things you shared that I thought was so great is every day you read in the morning.

[Skylar Williamson]

That's right.

[Teresa Flood]

Which I do as well.

[Skylar Williamson]

Yeah.

[Teresa Flood]

And you and Ken are both challenging me. I don't journal. But you write a blog or what do you. What do you call it?

[Skylar Williamson]

I post on LinkedIn. My journal post every day.

[Teresa Flood]

Just a journal post?

[Skylar Williamson]

Yeah.

[Teresa Flood]

Okay.

[Skylar Williamson]

Yeah. So if you follow me on LinkedIn, you'll see what I'm reading and you'll just get the hacks there. And then we have a newsletter that we send out once a week that's just a leader newsletter.

[Teresa Flood]

And they can get that if they go to your website.

[Skylar Williamson]

Yeah, go to skylarwilliamson.com.

[Teresa Flood]

Okay, perfect. But a book comes when you do the stuff every day. Right. So you've been reading and writing and learning and growing. This doesn't happen overnight. This is. I get blood, sweat, and tears of figuring this out. And I can already tell you, I know you have a great team around. You as I've dealt with a couple of them as we've scheduled all of this, but yeah. All right. Just leave us with one more challenge to grow leadership. If you were to tell people to go from where you're at to where you want to be, what's one purposeful thing Intentional. Besides, of course, buy the book and read the book.

[Skylar Williamson]

Yeah, I think make your first hours of the day super intentional, you know, So I talked about being healthy mentally, physically and spiritually. Well, what are you doing in the first two hours of the day to take care of yourself mentally, physically and spiritually? If you could do that in the first two hours of the day, you are going to fire out of a cannon to be the best that you can be. And you, you won't achieve excellence for yourself unless you're taking care of yourself like that in the morning.

[Teresa Flood]

Love that.

[Skylar Williamson]

Yeah.

[Teresa Flood]

Completely agree.

[Skylar Williamson]

Yeah.

[Teresa Flood]

Thank you for coming on with us.

[Skylar Williamson]

Oh, it was my pleasure.

[Teresa Flood]

Enjoyed the conversation. Please the steady leader and tell them.

[Skylar Williamson]

Again the website thesteadyleader.com oh, that was pretty simple.

[Teresa Flood]

Thesteadyleader.com Got it. By the way, I've also was noticed I was holding for those of you who watch this whole thing and notice that my Upside podcast cards were upside down the whole time. I do, yeah. It's the downside. Halfway through, though, I changed my mentality and we went back to the Upside. So just noted that I noticed and fixed it. It's fine. All right. As always, thank you for joining us on the Upside podcast where we believe if you invest in your growth every single day, it will yield you great returns in your life and in your business. I encourage you to grow your leadership. Please go to teresaflood.com as well if you're not a subscriber. And one of the things that I send out is we drop an episode every Tuesday and then on Thursday I will send you a leadership and teaching guide to go along with that episode. And because I do believe one of the best ways to grow personally and in your leadership is to turn around and teach what you are learning. So that is a resource that's available to you if you go to teresaflood.com but we appreciate you tuning in, Skyler. Thank you so much. And y' all keep living on the Upside.