How to Guarantee Failure

Marc Trestman is a three-time Grey Cup champion, two-time CFL Coach of the Year, former NFL head coach, and author whose coaching career spans more than four decades across professional and collegiate football.Throughout his career, Trestman has worked with some of football's most accomplished quarterbacks, including Steve Young, Rich Gannon, Bernie Kosar, and Anthony Calvillo. His coaching journey began at the University of Miami, where he helped the Hurricanes win the 1983 national championship. He later held coaching positions with numerous NFL organizations, including the San Francisco 49ers, Arizona Cardinals, and Oakland Raiders, where he served as offensive coordinator during their run to Super Bowl XXXVII.As head coach of the Montreal Alouettes, Trestman won back-to-back Grey Cup championships in 2009 and 2010. He subsequently became head coach of the Chicago Bears before returning to the CFL and leading the Toronto Argonauts to the 2017 Grey Cup championship. Most recently, he served as a senior offensive assistant with the Los Angeles Chargers under Jim Harbaugh.Beyond his coaching accomplishments, Trestman is the author of Perseverance: Life Lessons on Leadership and Teamwork and his latest book, Teaching the Game, which draws on decades of experience to explore football fundamentals, player development, and effective coaching.Here's some notable highlights from our conversation:[5:57] — Great Coaches Simplify Complexity[9:44] — Success Without Fulfillment[14:14] — Finding Joy in Coaching and Relationships[17:07] — A Coach's Lowest Point[19:16] — The Values Behind His Leadership[23:09] — Never Meet the Enemy on Your Own Sideline[29:20] — Leaders Are Developed, Not Born[34:40] — Vulnerability Builds Trust[37:00] — Invest In Your Assistant Coaches[39:58] — Surviving the Coaching Carousel[44:05] — Why Fundamentals Still Matter[48:05] — Lessons on Building Belief from Tom Moore[51:22] — A Letter to His Younger Self[54:05] — What Championship Teams Share[58:52] — Your Platform Isn't Your Purpose[1:02:02] — Beyond Football and ChampionshipsLearn More About Marc:Follow Marc's current work here.Purchase Marc's new book here.Learn More About Zach:Zach's Email -- [email protected] 1:1 coaching with Zach -- Schedule a free call here.You can watch the video recordings of the podcast on YouTube here.

What if one of the most powerful tools for holding people accountable had less to do with your expectations and more to do with their dreams? Drawing inspiration from Hall of Fame coaches, Tom Izzo and Nick Saban, this episode explores how coaches can connect an athlete's in-the-moment behaviors to their long-term goals for more meaningful accountability. We also discuss why great leadership requires both care and challenge and how to help people translate the future they envision into the behaviors they practice today.Learn More About Zach:Email Zach -- [email protected] Zach's new website here.You can watch the video recordings of the podcast on YouTube here.

Imagine opening a document with feedback about all your strengths and growth areas from dozens of people you spend time with regularly. Which comments would you fixate on? Which ones would you want to explain away or defend? Which ones do you think would show up, but internally you're hoping it doesn't? In this episode, Zach explores how to get better at receiving feedback and increasing your tolerance for it, especially the kind you don't want to hear. Learn More About Zach:Email Zach -- [email protected] Zach's new website here.You can watch the video recordings of the podcast on YouTube here.

What can penguins teach us about building stronger relationships? More than you might think. In this episode, Zach introduces a concept called pebbling and shares how something as simple as a thoughtful gesture can create opportunities for deeper connection and help others feel seen, heard, and valued.Learn More About Zach:Email Zach -- [email protected] Zach's new website here.You can watch the video recordings of the podcast on YouTube here.

Your team might have two very different cultures: The one you talk about and the one your people actually experience. Culture isn't simply shaped by the values you communicate or the standards you establish. It's shaped by the behaviors you consistently reinforce, reward, and tolerate. In this episode, Zach uses an everyday driving analogy to explore why consistency is essential to building culture and maintaining credibility as a leader. He also shares three practical questions to help coaches and leaders evaluate whether their actions are reinforcing the standards they expect others to uphold.Learn More About Zach:Email Zach -- [email protected] Zach's new website here.You can watch the video recordings of the podcast on YouTube here.

Shonda Stanton is the head softball coach at Indiana University and one of the most accomplished coaches in collegiate softball, with nearly three decades of head coaching experience and more than 890 career victories.Since taking over Indiana's program in 2017, Stanton has helped transform the Hoosiers into a consistent Big Ten contender, leading the program to four consecutive NCAA Tournament appearances from 2023–2026, including its first NCAA Tournament berth since 2011. Her tenure has also featured multiple 40-win seasons and a program-record 23-game winning streak in 2023.Before arriving at Indiana, Stanton spent 18 seasons as the head coach at Marshall University, where she became the winningest coach in program history. During her tenure, she led the Thundering Herd to multiple conference championships and NCAA Tournament appearances, establishing Marshall as one of Conference USA's most competitive programs. In recognition of her contributions, she was inducted into the Marshall Athletics Hall of Fame in 2024.Stanton's coaching experience also extends to the professional ranks. She previously coached with the Akron Racers and, in 2026, served as head coach of the Chicago Bandits in the Athletes Unlimited Softball League (AUSL), working with some of the sport's top professional players.Here's some notable highlights from our conversation:[6:00] — Become an Engineer of Belief[8:53] — No Surprises in Our Program[13:08] — Confidence Isn't Built Through Perfection[18:11] — The Baton of Leadership[24:49] — Energy Giving Behaviors (EGB's)[30:38] — Adjust Your Leadership, Not Yourself[34:05] — Love Who They're Becoming[38:20] — Love Goes First[41:35] — Let Them Make Mistakes[45:32] — Stop Trying to Please Everyone[49:43] — Winning Doesn't Always Define Great Coaching[52:46] — Know What You Value[56:15] — Sustaining Yourself in the Coaching Profession[1:00:21] — "Honoring the Pause"[1:03:16] — The Family Behind the CoachLearn More About Zach:Zach's Email -- [email protected] 1:1 coaching with Zach -- Schedule a free call here.Download my free Win More, Live Better Leadership Playbook here.You can watch the video recordings of the podcast on YouTube here.

What makes someone the best coach or leader you've ever had? Harvard leadership instructor Margaret Andrews has spent nearly two decades asking people a similar question. Her findings reveal that approximately 85% of the reasons people identify have little to do with intelligence or technical expertise. In this episode, we explore what these findings can teach us about coaching and why the way people experience your leadership matters.Learn More About Zach:Email Zach -- [email protected] Zach's new website here.Download my free Win More, Live Better Leadership Playbook here.You can watch the video recordings of the podcast on YouTube here.

We spend a lot of time thinking about what it takes to succeed, but what if identifying the behaviors that guarantee failure could be just as valuable?  Drawing on lessons from UCLA head football coach Bob Chesney and Charlie Munger's famous prescriptions for a life of misery, we examine how identifying destructive behaviors can help us clarify our values and avoid becoming someone we never intended to be.Learn More About Zach:Email Zach -- [email protected] Zach's new website here.Download my free Win More, Live Better Leadership Playbook here.You can watch the video recordings of the podcast on YouTube here.

Jamion Christian is the head men's basketball coach at Bryant University, bringing more than a decade of Division I head coaching experience and an international championship to the Bulldogs.Christian began his head coaching career in 2012 at his alma mater, Mount St. Mary's, becoming one of the youngest Division I head coaches in the country at just 29 years old. During his six seasons leading the Mountaineers, he guided the program to two Northeast Conference Tournament championships and NCAA Tournament appearances in 2014 and 2017.He went on to serve as head coach at Siena College, where he earned MAAC Coach of the Year honors in 2019, before spending three seasons leading the program at George Washington University.Christian's coaching journey also took him overseas to Italy, where he led Pallacanestro Trieste to promotion back to the country's top professional basketball division.Before becoming a head coach, Christian held assistant coaching positions at William & Mary, Bucknell, and VCU.Here's some notable highlights from our conversation:[5:48] — Creating "Forever Relationships"[9:22] — Turning Love Into Daily Behaviors[13:54] — Asking Better Questions[18:43] — Building Confidence By Reinforcing Strengths[23:24] — Accountability Doesn't Require Yelling[27:42] — From Young Tyrant to Intentional Leader[31:12] — Supporting Athlete's Well-being[35:03] — Demand More, React Less[38:36] — What Getting Fired Taught Me[44:12] — Build A Culture Worth Staying For[48:48] — Winning Beyond BasketballLearn More About Zach:Zach's Email -- [email protected] 1:1 coaching with Zach -- Schedule a free call here.Download my free Win More, Live Better Leadership Playbook here.You can watch the video recordings of the podcast on YouTube here.

What if one of your greatest competitive advantages is being willing to look where others won't? Gil Brandt helped revolutionize NFL scouting by finding extraordinary talent in places other organizations overlooked, but his success wasn't simply about thinking differently. It was about knowing exactly what he was looking for, while remaining open-minded about where he might find it. In this episode, we explore what Brandt's unconventional approach can teach us about recognizing potential and finding valuable lessons beyond our own profession.Learn More About Zach:Email Zach -- [email protected] Zach's new website here.Download my free Win More, Live Better Leadership Playbook here.You can watch the video recordings of the podcast on YouTube here.