The Awkward Pastor

Brandon Estep and Tim Waybright
  • 5.0 (2)
  • Christianity
  • Updated Biweekly

The Awkward Pastor is a savage Christian podcast for people exhausted by fake religion, shallow answers, and plastic faith. Hosted by Brandon—a pastor and Iraq war combat vet—and Tim, a seasoned believer with real ministry scars, this show confronts chaos with biblical truth, satire, and zero concern for religious comfort. From grace for the worst sinners to exposing church hypocrisy, nothing is off-limits. If you’re tired, skeptical, or done pretending—hit play.

  1. (Ep. #24) Lead Well: Leading From A Solid Foundation

    2d ago

    (Ep. #24) Lead Well: Leading From A Solid Foundation

    Why do some leaders inspire trust while others leave a trail of frustration, division, and burnout? Before we talk about leadership skills, influence, vision, or strategy, we have to start with something deeper: identity. In this first episode of our Lead Well series, we explore a truth many leaders miss: leadership problems are often identity problems wearing a leadership costume. When your identity is built on titles, applause, positions, or the approval of others, leadership becomes a never-ending quest to prove yourself. But when your identity is rooted in Christ, you can lead from security instead of insecurity, service instead of self-promotion, and conviction instead of fear. In this episode, we'll discuss: • Why character matters more than charisma• The connection between insecurity and unhealthy leadership• The difference between Saul's leadership and David's leadership• Why titles don't create leaders• Practical questions every leader should ask themselves• How a secure identity produces healthy leadership Whether you're a pastor, parent, business owner, coach, teacher, ministry worker, or simply someone who influences others, this episode will challenge you to examine the foundation beneath your leadership. Because leadership isn't about becoming somebody. It's about knowing whose you already are.

    32 min
  2. (Ep. #23) After Taps: The Legacy of SGT. Derek Banks

    May 28

    (Ep. #23) After Taps: The Legacy of SGT. Derek Banks

    On November 14th, 2007, SGT. Derek Banks passed from injuries sustained during combat in Iraq. The folded flag was presented. Taps was played. The ceremonies ended. But for the families left behind…the grief did not. This episode is deeply personal. In 2007, Brandon deployed to Iraq alongside Derek. They trained together, shared laughs, and attended church together before war changed everything. Nearly two decades later, Derek’s mother, Renee Person, opens her heart to share the story behind the uniform...not simply of a soldier, but of her son. Together, we honor Derek’s life and legacy while listening to the perspective of a Gold Star mother who has carried grief, faith, questions, memories, and hope through the long years that followed. This is a conversation about sacrifice. About grief that does not run on a schedule. About the people we love and the memories we carry. And about trusting God when life leaves wounds that never fully disappear. This episode also honors Gold Star families, including Derek’s son, DJ...a living extension of his father’s legacy and a reminder that while death may interrupt a life, love and influence often continue long after. Some stories entertain. Some stories challenge. And some stories deserve to be remembered. This one aims to remember.

    53 min
  3. (Ep. #22) The Night Everything Changed: The Story of Jon Holt

    May 14

    (Ep. #22) The Night Everything Changed: The Story of Jon Holt

    What happens when a man survives the kind of night that should’ve killed him? In this powerful episode of The Awkward Pastor, we sit down with Jon Holt — an Iraq War veteran that Brandon served with, Purple Heart recipient, and law enforcement officer whose story sounds more like a movie than real life. After surviving a devastating EFP roadside bomb attack in Iraq that killed two of his brothers-in-arms and left him severely wounded, Jon was told he may never walk normally again. But that wasn’t the end of his story. It was the beginning. By the grace of God, Jon went from the battlefields of Iraq to a life spent serving and rescuing others as a police officer — pulling people from burning homes, responding to horrific crashes, and walking through trauma most people could never imagine. His journey is one of pain, resilience, brotherhood, faith, survival, and purpose. This episode dives deep into: The reality of combat trauma and PTSDSurvivor’s guilt and grief after warBrotherhood forged in combatThe mental and emotional cost of law enforcementFaith in the middle of sufferingHow God can bring purpose out of devastationOvercoming impossible oddsRedemption, resilience, and hope after painThis is not a polished Hollywood war story. It’s raw.It’s human.And it’s unforgettable.

    2h 3m
  4. (Ep. #21) If Your Gospel Requires Your Help...It's Fake

    Apr 29

    (Ep. #21) If Your Gospel Requires Your Help...It's Fake

    What if the most dangerous false gospel isn’t outside the church…but sounds almost exactly like the truth? In this episode of The Awkward Pastor, we expose the “Jesus + something” gospel...a subtle, soul-crushing lie that started with the Judaizers and still shows up in churches, sermons, and social media feeds today. They didn’t reject Jesus.They just made Him… insufficient. “Jesus saves you… but you better perform.”“Grace starts it… but you better maintain it.”“Faith matters… but your effort proves everything.” It sounds spiritual.It sounds serious.It sounds right. But it’s poison. In this episode, we break down: What the Judaizers were really teaching (and why it spread so easily) Why adding anything to the gospel doesn’t strengthen it—it destroys itHow performance-based Christianity quietly replaces peace with pressureThe difference between real obedience and religious exhaustionHow to finally rest in a gospel that doesn’t depend on youIf your faith has ever felt like a constant test you’re failing…If you’ve been stuck trying to prove something God already settled…If Christianity feels more like a burden than freedom… This episode is going to hit you right where you live.

    1h 11m
  5. (Ep. #20) Why Did Jesus Have To Die? (The Cross Explained)

    Mar 25

    (Ep. #20) Why Did Jesus Have To Die? (The Cross Explained)

    With Good Friday approaching, we’re forced to confront a question most people avoid—why did Jesus have to die? The cross of Jesus Christ is the center of the Christian gospel. Without His death and resurrection, there is no forgiveness, no peace with God, and no hope of salvation. But if God is good, why didn’t He simply forgive sin and move on? Why the cross? Why did Jesus have to be crucified? In this episode of The Awkward Pastor, we go deep into the why behind the cross—exploring God’s holiness, justice, and mercy, and what was really happening when darkness fell and the earth shook. We also examine the supernatural events surrounding the crucifixion and unpack the powerful symbolism behind them, revealing that the cross was not just an execution, but a divine act of redemption. Joining us is A.T. Stewart, a seasoned Bible expositor, and former pastor with over 50 years of ministry experience bringing clarity, depth, and biblical truth to one of the most important questions in Christianity. Check out Dr. Stewart's sermons here: https://podcasts.apple.com/us/podcast/a-t-stewart-ministries/id82454198

    1h 9m
  6. (Ep. #19) When The Phone Rings at 2AM: Dealing with Tragedy

    Mar 11

    (Ep. #19) When The Phone Rings at 2AM: Dealing with Tragedy

    Tragedy is something every person will face eventually. A sudden death. A devastating accident. Suicide. Violence. Loss that makes no sense. In this episode, Brandon and Tim step into an honest, raw conversation about tragedy in a broken world. This episode was motivated by the recent sudden and tragic death of Brandon’s close friend, which forced a deeper reflection on questions many people wrestle with but rarely say out loud: Why does tragedy happen? Where is God in the middle of it all? With biblical truth, real-life experience, and the occasional dark humor that life sometimes requires, Brandon and Tim talk openly about the reality of living in a fallen world while still holding on to hope. In this episode, they discuss: • Why tragedy exists in a broken world • Why suffering and loss are part of the human experience • How hope and meaning can still emerge from painful moments This conversation isn’t about giving easy answers or pretending tragedy is simple. It’s about facing the hard realities of life with honesty, faith, and the kind of discussion that happens when friends sit down and talk about the things that actually matter. If you’ve ever struggled to understand suffering, wrestled with grief, or wondered how faith survives real-life tragedy, this episode is for you. Because sometimes the most honest conversations about faith begin in the darkest moments.

    1h 10m
  7. (Ep. #18) We Got A Letter from Son of Sam (Live)

    Feb 18

    (Ep. #18) We Got A Letter from Son of Sam (Live)

    We went live with Investigator Eric Smith (featured in our previous episode series “Serial Killers That Received Christ”) to talk about one of the most controversial questions in true crime and Christianity: 👉 Can a serial killer truly be saved? After those episodes, we reached out to David Berkowitz...also known as the “Son of Sam.” He wrote us back. In this episode, we read his letter live and wrestle with what it means for the power of the Gospel to transform even the darkest lives. But this didn’t stay theoretical. This live stream turned into a powerful moment of conviction and response ending in a clear Gospel presentation and an altar call for anyone ready to stop playing games and come to Christ. This isn’t about sensational true crime...it’s about whether we actually believe the Gospel is powerful enough to save anyone...and we do.

    57 min
  8. (Ep. #17) Burned or Buried? God's View on Cremation

    Feb 11

    (Ep. #17) Burned or Buried? God's View on Cremation

    Cremation or burial — does it matter? Is one more biblical than the other? And why does this question hit so deep in our hearts? In this episode, we step into a conversation most people avoid but everyone will face. We explore what Scripture actually says, what it doesn’t say, and how Christian hope goes far beyond the method of laying a body to rest. This isn’t just theology — it’s personal. It’s about grief, dignity, resurrection, and the unshakable promise that for the believer, the grave is not the end of the story. With biblical clarity, pastoral honesty, and a few awkward moments along the way, we separate tradition from truth and fear from faith. If you’ve ever wrestled with end-of-life questions, funeral decisions, or what honors God most, this episode will steady your heart and point you back to the gospel. Because in Christ, whether buried or burned, the promise still stands: raised incorruptible, reunited in glory, and held forever by the One who conquered the grave.

    1h 11m
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Ratings & Reviews

5
out of 5
2 Ratings

About

The Awkward Pastor is a savage Christian podcast for people exhausted by fake religion, shallow answers, and plastic faith. Hosted by Brandon—a pastor and Iraq war combat vet—and Tim, a seasoned believer with real ministry scars, this show confronts chaos with biblical truth, satire, and zero concern for religious comfort. From grace for the worst sinners to exposing church hypocrisy, nothing is off-limits. If you’re tired, skeptical, or done pretending—hit play.

Information

  • Creator
    Brandon Estep and Tim Waybright
  • Years Active
    2025 - 2026
  • Episodes
    26
  • Rating
    Clean
  • Copyright
    © Brandon Estep and Tim Waybright
  • Show Website
    The Awkward Pastor