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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this powerful episode, Charles sits down with Navy SEAL combat veteran, bestselling author, and leadership expert Brent Gleeson to explore the transition from elite military operations to high-performance business leadership. (01:22) Gleeson opens up about his deployments in Iraq and Africa while sharing how combat experiences forged the leadership philosophy he now teaches worldwide. (05:44) The conversation delves deep into the emotional weight of reintegration and identity transformation that veterans face after returning home. (10:18) Together, they examine what elite teams get right about culture, why most organizational change fails, and how the principles that drive success on the battlefield directly translate to building resilient businesses and meaningful relationships.
Brent Gleeson is a Navy SEAL combat veteran who served with SEAL Team 5 on deployments in Iraq and Africa. After leaving military service, he became a successful tech entrepreneur and founded Accelerate, a hybrid management consulting and enterprise software company. He is a two-time bestselling author, with his latest book "All In: The Pathway to Personal Growth and Professional Excellence" releasing December 2, 2025.
Charles is the host of the Proven Podcast, focusing on actionable insights and proven strategies for ambitious professionals. He emphasizes execution over planning and has experience in business coaching and organizational development.
The biggest trap for high performers transitioning from elite environments is trying to do too many things simultaneously. (05:33) Gleeson explains that successful operators often become their own worst enemy by chasing multiple opportunities instead of narrowing their focus to one or two key areas with intentional strategic overlap. The key is identifying a few core relationships, business practices, and personal goals rather than practicing "the fine art of mediocrity" across multiple projects. Practical Application: Create systems where all your projects strategically support each other rather than operating in separate silos.
Sustainable transformation requires changing who you believe yourself to be before attempting to change behaviors. (23:23) When Gleeson eliminated alcohol from his life, it wasn't just about breaking a habit—it was about becoming someone who shows up differently for his family and business. He emphasizes that without deep emotional connection to your desired identity, you'll backslide to old patterns when distractions arise. Practical Application: Instead of saying "I want to stop X behavior," declare "I am someone who does Y" and then ask how that person would operate daily.
High-performing organizations don't just list core values—they operationalize them into every system, process, and daily ritual. (39:57) Gleeson teaches clients to define exactly what each value means, how to measure meeting the standard, exceeding it, and missing it. This removes ambiguity from performance management and creates accountability through clear behavioral expectations rather than subjective interpretations. Practical Application: For each core value, document specific behaviors that demonstrate meeting, exceeding, and falling short of the standard, then integrate these into all performance conversations.
Elite teams thrive on a culture of caring personally while challenging directly—what Gleeson calls radical candor. (44:20) This means having performance conversations in real-time rather than waiting for scheduled reviews, creating an environment where trust enables immediate feedback without ruffled feathers. Leaders must eliminate toxic team members quickly, regardless of tenure or rank, because one underperformer impacts five to ten other people and damages trust in leadership. Practical Application: Establish regular debrief sessions where team members can challenge each other's performance immediately after projects or meetings, focusing on continuous improvement rather than blame.
True resilience comes from maintaining emotional connection to long-term purpose while simultaneously leaning into obstacles rather than avoiding them. (59:18) Gleeson learned from fallen teammates that the most resilient people don't just accept adversity—they use it as fuel, understanding that suffering is part of the journey toward meaningful outcomes. This requires both accepting current reality and staying focused on the mission that drives you. Practical Application: When facing setbacks, immediately reconnect with your deeper "why" while taking one concrete action toward your goal, treating obstacles as data rather than reasons to quit.