TheUPside Podcast

Episode: The Steady Leader – Interview with Schuyler Williamson

Host: Theresa Flood
Date: April 22, 2025

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.

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).

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)

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)

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.

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.

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.

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)

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

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)

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)

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)

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

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.