JT “Hollywood” Henderson has had one of the more unlikely career arcs in this show's history: college basketball operations under two legendary coaches, a pivot into nonprofit fundraising, and now Communications Director for a sitting Lieutenant Governor. In Episode 8 of Lessons From The Sidelines, JT joins Coach Greg Brown — a longtime friend and colleague — for a conversation packed with hard-won leadership lessons and a few stories that still make him wince.

From surviving a chartered-flight nightmare under Coach Dennis Felton to learning the difference between being responsible and being in control, JT walks through the through-line connecting a college locker room to a nonprofit boardroom to a state capitol — and makes the case that every stop along the way was a building block for the next.

In this episode:

• You're responsible for things you're not in control of — the core lesson of both coaching and politics

• Respond, don't react: the skill athletics teaches better than almost anything else

• The chartered-flight-gone-wrong story that still gets brought up twenty years later

• Quality over scarcity: what a faith-based nonprofit taught him about serving people well

• The Platinum Rule: leading people the way they need to be led, not the way you'd want to be led

• Why a blind spot isn't a weakness — it's the cost of doing what you're best at

• Lessons on working with nonprofit boards: filtering advice without dismissing it

• Adoption, identity, and "being where your feet are"

Whether you're coaching a team, leading a nonprofit, or working in a high-pressure office of any kind, this one's full of lessons you can use tomorrow.

Shame, guilt, and fear are highly effective coaching tools. Greg Armstrong won't pretend otherwise. But in Episode 7 of Lessons From The Sidelines, the cross-country coach, campus minister, and ultra-marathon record holder makes the case that effective isn't the same as right — and that Christian coaches, of all people, should know the difference.

Greg has spent 22 years as a campus minister at Friendship Christian School and built Run4Water, a nonprofit that has taken students from Tennessee to Uganda, Tanzania, Nicaragua, and Mexico to fight the global water crisis. He joins Coach Greg Brown for a conversation about what happens when youth sports becomes the end goal instead of a tool for building a whole person — spiritually, mentally, and physically.

In this episode:

• Why Greg's own athletic identity used to be entirely wrapped up in performance — and the moment that changed

• Spirit, mind, body: the order Greg believes coaches have flipped upside down

• Philippians 4:13, out of context: what “I can do all things” actually means for a coach or an athlete

• His research on bullying, harassment, and hazing in youth sports — and the "culture of silence" around it

• A father's answer to his daughter's softball struggles: “Your worth has nothing to do with your performance”

• Building a student-athlete handbook that sets real expectations for coaches, athletes, and parents

• Run4Water: how a love of running turned into wells in Uganda and a documentary premiering September 26th

Whether you're coaching, parenting, or leading a team of your own, this conversation will make you rethink what you're really building.

Jason Romano spent 17 years at ESPN producing some of the biggest shows in sports — Mike and Mike, SportsCenter, Monday Night Football, College GameDay — before walking away from a dream job with no guaranteed landing spot. Why? A question from Tony Dungy in a green room that he couldn't shake.

In Episode 6 of Lessons From The Sidelines, Coach Greg Brown sits down with Jason — now Executive Producer at Sports Spectrum and author of The Uniform of Leadership and Live to Forgive — for an honest conversation about identity, discernment, and what it looks like when sports (or your job, or anything else) quietly becomes your god.

In this episode:

• The Tony Dungy question that changed everything: “How do you live your faith out here?”

• Going from “an ESPN producer who happened to follow Jesus” to “a follower of Jesus who happened to work at ESPN”

• The Uniform of Leadership: why the best leaders put the team name on the front, not their own

• The “I Am Third” model — God first, others second, yourself third

• How to discern God's voice from your own — and why wise counsel matters more than a burning bush

• Earning the credibility to talk about faith at work by doing excellent work first

• Walking away from ESPN with no guaranteed contract — and why it made sense anyway

• Encouragement for anyone drifting from their faith: stay the course

Whether your world is sports, business, or somewhere in between, this one will make you rethink what — or who — you're really playing for.

At five years old, Drew Maddux drew himself in a Vanderbilt basketball uniform wearing his dad’s number. He went on to become a third-generation Commodore, a four-year starter, and an All-SEC honoree — and he’ll tell you that chasing that vision nearly cost him his identity.

In Episode 5 of Lessons From The Sidelines, Coach Greg Brown sits down with Drew — former head basketball coach at Christ Presbyterian Academy (CPA) in Nashville for 15 years, and now Chief Performance Officer at Fourteen Foods, the largest Dairy Queen franchisee in the country — for a deeply honest conversation about identity, pressure, and what it costs to let what you do define who you are.

In this episode:

• The lifelong wrestling match between identity and performance — and how it nearly hijacked his career

• Why he didn’t fully embrace “comprehensive excellence” until his junior year at Vanderbilt

• Coaching by fear and shame vs. coaching by freedom — and why the “toughest” coaches often have it backwards

• A CPA program with no cuts and no tryouts — and what it taught him about leading every single person in the gym

• “Death by a thousand cuts”: holding a standard without ever giving an inch

• His Three C's for scaling culture across a 10,000-person company: connection, clarity, commitment

• The Bible study on Psalm 23 he wrote with his daughter Ava

• His family's four core values and one lesson from the sideline

Whether you're leading a locker room, a classroom, or 250+ restaurants, this conversation has something that'll stick.

Why aren’t you getting the results you want? Coach Dan Holland has a blunt answer: you’re perfectly designed to get exactly the results you’re getting right now — because your results are just your rhythms, thoughts, and systems showing their work.

In Episode 4 of Lessons From The Sidelines, Coach Greg Brown sits down with Dan Holland — a leadership coach, CEO, and former pastor of 30 years who now coaches executives, pastors, and coaches through his framework, The Genesis Way. Dan combines the heart of a pastor with the systems of a CEO, and this conversation is packed with frameworks you can use the same day you hear them: how to actually have a hard conversation, how to identify your own blind spots, and why confidence is simply a result of predictability.

In this episode:

• “You’re perfectly designed to get the results you’re getting” — and what to do about it

• Focus, Pace, Listen: the three-part discipline that took Dan from busy to effective

• Wise, foolish, and evil: Henry Cloud’s framework for knowing who you’re really dealing with

• A five-minute process for having the hard conversation you’ve been avoiding

• Thoughts → actions → habits → character → destiny: the flow that builds (or breaks) a leader

• Why “stay in your lane” might be the best leadership advice you’ll hear this year

• The three-step coaching process: what do you want, design the system, then submit to it

• Understanding your DISC blend — and finding your “left tackle” to guard your blind side

This one’s for leaders in business, ministry, sports, or anywhere people are involved — which is everywhere.

Jason Kuhn was a Division 1 pitcher at MTSU on the verge of professional baseball when he woke up one morning and couldn’t throw a strike. Six wild pitches in a single inning later, his baseball career was over. So he became a Navy SEAL.

In Episode 3 of Lessons From The Sidelines, Coach Greg Brown sits down with Jason — decorated SEAL operator and sniper, founder of Stonewall Solutions, and the performance coach who helped Tyler Matzek beat the yips and win a World Series — for a tactical conversation about identity, failure, and what it actually takes to perform under pressure. Jason takes the systems forged in BUD/S, Hell Week, and combat and translates them into a framework usable by anyone who competes — in sport, in business, or in their own head.

In this episode:

• Why combat eliminates the clutter — and why the principles that win in war are the same ones that win anywhere else

• The yips story: career-ending injury that became his life’s work

• Why your identity can’t be your outcome — and what to anchor it to instead

• The tactical approach to failure: controllable corrections, uncontrollable workarounds, and the part high achievers skip

• The Three Defeaters: distraction, others’ beliefs, and failure

• Why team-first isn’t self-sacrifice — it’s self-interest done right

• When decentralized leadership works (and when it absolutely doesn’t)

• Why he hates the phrase “surrender the outcome”

• And the one lesson he’d give from the sideline

This one will reach the high achievers, the coaches, the operators, and the parents trying to raise kids who can compete without losing themselves.

What does it look like when somebody who coached Michael Jordan, Isaiah Thomas, and Joe Dumars — and won back-to-back titles with the Detroit Pistons “Bad Boys” — finishes a 50-year career and says the most important thing in coaching is love?

Brendan Suhr joins Coach Greg Brown for Episode 2 of Lessons From The Sidelines. Brendan was Chuck Daly’s right hand on two championship Pistons teams and the 1992 Dream Team, learned under Hubie Brown and Lenny Wilkens, and now runs Coaching U — a global coaching, leadership, and performance company reaching 140+ countries. He’s unfiltered, opinionated, and genuinely funny about what it actually takes to lead — in a locker room, a boardroom, or anywhere else.

In this episode:

• Why courage is the #1 leadership trait — and why most people in leadership positions don’t have it

• The three Cs: Competence, Credibility, Connection — how players (and employees) actually decide to follow you

• Lead up, lead sideways, lead down — the assistant coach’s framework for leading from any seat

• Why championship teams keep their staffs small (the Pistons won with three coaches; the modern NBA has fourteen)

• Define roles, not just systems — what Dennis Rodman and Ben Wallace taught him

• Why your best people are business partners, not employees

• The Chuck Daly story about Joe Dumars that he never forgot — and the one lesson he’d give every coach

Whether you’re running a team, building a business, or sitting one chair away from the top, Brendan’s got something for you.

What does it take to lead when you’re not the one in charge? In the debut episode of Lessons From The Sidelines, Coach Greg Brown sits down with Bob Starkey — associate head coach for LSU women’s basketball and one of the most respected lifelong assistants in the game — for a candid conversation about leading from the middle.

Over four-plus decades alongside Hall of Famers like Dale Brown, Sue Gunter, and Kim Mulkey, Bob has built a career on a rare idea: that the best leaders aren’t always the ones with their name on the door. He and Greg get into the hard conversations most leaders avoid, why he attaches his emotions to the process instead of the result, how he builds a staff the way he’d recruit a team, and the difference between coaching a team and running a program.