Brandon Estep and Tim Waybright

The Awkward Pastor

Religion EN ↓ 28 episodes

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.

Author

Brandon Estep and Tim Waybright

Category

Religion

Podcast website

www.theawkwardpastor.com

Latest episode

Jul 9, 2026

Where to listen?

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Episodes

(Ep. #26) Lead Well: God's Not Impressed With Your Resume 09.07.2026

What does God actually look for in a leader? In Episode 3 of Lead Well, our Christian leadership podcast teaching series, we are tackling one of the most important questions in biblical leadership: does your private life match your public one? A lot of leaders have an impressive resume. Not many have the character to back it up. We are diving deep into 1 Timothy 3, breaking down the Greek word &#3...

(Ep. #25) Lead Well: Good Leaders Are Rooted In The Right Stuff 25.06.2026

Most leaders get evaluated on decisions and confidence — but what actually determines whether you survive pressure is what's underneath: your roots. Brandon breaks down Psalm 1, 1 Corinthians 3, and the fruit of the Spirit as a leadership framework, backed by research on self-awareness, empathy, and integrity in leadership...with the humor (and conviction) you'd expect from The Awkward Pastor.

(Ep. #24) Lead Well: Leading From A Solid Foundation 11.06.2026

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 iden...

(Ep. #23) After Taps: The Legacy of SGT. Derek Banks 28.05.2026

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....

(Ep. #22) The Night Everything Changed: The Story of Jon Holt 14.05.2026

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...

(Ep. #21) If Your Gospel Requires Your Help...It's Fake 29.04.2026

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…...

(Ep. #20) Why Did Jesus Have To Die? (The Cross Explained) 25.03.2026

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? I...

(Ep. #19) When The Phone Rings at 2AM: Dealing with Tragedy 11.03.2026

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 wrest...

(Ep. #18) We Got A Letter from Son of Sam (Live) 18.02.2026

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...

(Ep. #17) Burned or Buried? God's View on Cremation 11.02.2026

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...

(Ep. #16) Angels Don't Smoke: Hollywood vs. Heaven 28.01.2026

This is a installment in a periodical series called 90's Movies That Made God Cringe. Hollywood cast John Travolta as a chain-smoking, beer-drinking archangel… so we brought that hot mess to the podcast, opened the Scriptures, and asked, “Okay, but what are real angels actually like?” Spoiler: they’re not middle aged mall Santas in trench coats — they’re holy, terrifying, battle-tested servants of...

(Ep. #15) Why Do I Feel So Guilty? 14.01.2026

Do you ever ask: “Why do I still feel guilty as a Christian?” or “If God forgives me, why can’t I forgive myself?” In this Season 2 launch of The Awkward Pastor , Brandon and Tim tackle Christian guilt, shame, and regret through biblical truth, humor, and real talk. They answer common questions believers search for online, like: What is the conscience and how does it work biblically? Can a Christi...

Season 2 Trailer 30.12.2025

When the Lord returns, will He find folks who are operating in real faith?

(Ep. 14 - Season 1 Finale) How to Lead Like Jesus...In A World That Acts Like Hell 01.12.2025

What does real leadership look like when faith isn’t a slogan and mistakes cost lives? In this episode of The Awkward Pastor, Brandon and Tim sit down with two men who shaped Brandon’s life long before he ever held a microphone. Major Matthew Swanson, Brandon’s former Platoon Leader, and Platoon Sergeant Harvey Blow, his Platoon Sergeant, led a route clearance team in Iraq in 2007—driving straight...

(Ep. #13) Bombhunters Anonymous: Confessions of a Route Clearance Patrol 11.11.2025

A Veterans Day Special TRIGGER WARNING: The content therein discusses real war trauma, has sounds from an actual firefight, and may be disturbing for some. You don’t look for God the same way when you’re driving five miles an hour through Baghdad, scanning for bombs that could erase you in a blink. You don’t pray politely when a sniper round passes close enough to heat your skin. And you don’t tal...

(Ep. #12) The Devil Was A Worship Leader 29.10.2025

What if the music in your headphones isn’t just background noise—but formation? What if the songs you repeat are shaping your loves, discipling your emotions, and quietly training your soul long before a sermon ever does? In this episode of The Awkward Pastor, Brandon and Tim step into a conversation most Christians sense but rarely name: music isn’t neutral. It moves us. Forms us. Opens us. Somet...

(Ep. #11) 15 Signs You're Probably A Church Drama Queen 15.10.2025

If you’ve ever left church thinking, “Was that sermon about me?” … or watched church gossip turn a sanctuary into a comment section—this episode is for you. Not to shame you, but to help you tell the difference between real church hurt and manufactured church drama—because both can quietly destroy your joy, your relationships, and your witness. Welcome to The Awkward Pastor, a bold Christian podca...

(Ep. #10) Live Q and A with Undercover Matt From Ep. #9 24.09.2025

Ever feel like you’re holding it together in church… but one honest moment away from unraveling? If you’ve been to the edge—and God pulled you back—this one’s for you. This episode is a LIVE Q&A follow-up with Undercover Matt—the undercover police officer featured in Episode 9, one of our heaviest conversations yet. It isn’t polished. It isn’t scripted. It’s real people, real questions, real l...

(Ep. #9) The Shot He'll Never Forget 09.09.2025

WARNING: This episode discusses disturbing and sensitive concepts. What happens when faith is tested in real time—when grace collides with gunfire and survival leaves scars that don’t fade? In this episode of The Awkward Pastor, Brandon and Tim sit down with Matt, a retired Kentucky State Trooper and follower of Christ, who faced a moment every believer hopes they’ll never encounter: kill or be ki...

The Shots He'll Never Forget Trailer 06.09.2025

A retired Kentucky State Trooper shares his story of a shootout, faith, and God's work in the midst of the chaos.

(Ep. #8) Are We All God's Children? 01.09.2025

“We’re all God’s children.” It sounds comforting. It sounds inclusive. It sounds like something you’d print on a mug or post after church. But what if it isn’t true? In this episode of The Awkward Pastor , Brandon tackles one of the most popular—and most misunderstood—beliefs in modern Christianity. With clarity, compassion, and bold biblical honesty, he draws a crucial distinction the church ofte...

(Ep. #7) Church Hurt: Legit or Bruised Ego? Part 1 26.08.2025

What if the thing you call “church hurt” isn’t what you think it is? What if some wounds came from real sin—and others from pride that never got challenged? In this episode of The Awkward Pastor , Brandon and Tim step into one of the most emotionally charged conversations in modern Christianity: church hurt vs. bruised ego. With honesty, humor, and pastoral clarity, they wrestle with the differenc...

(Ep. #6) No Lights, No Camera, Just Action, Part 2 12.08.2025

Somewhere along the way, a lot of us learned how to sound like Christians… without actually loving like Christ. We can quote verses, post sunsets with a scripture, and say “praying for you”… while a real person bleeds out ten feet away in silence. This episode of The Awkward Pastor is a Part 2 rope-drop into that hard question again: Do we love people—or do we love being seen loving people? Becaus...

(Ep. #5) No Lights, No Camera, Just Action, Part 1 29.07.2025

Some of you are tired—not because you’ve done too much, but because you’ve been disappointed too many times. You’ve heard “love you, brother” in church… then felt invisible when life got heavy. And if we’re honest, we’ve all been on both sides of that. In this episode of The Awkward Pastor (“Talk Is Cheap”), we chase one uncomfortable question: Do we love people—or do we love people seeing us love...

(Ep. #4) Serial Killers Who Professed Christ, Part 2 15.07.2025

If you’ve ever heard a story so dark you thought, “God can’t reach that,” this episode is going to confront you—in the most necessary way. In this episode of The Awkward Pastor, we wrestle with one of the most uncomfortable questions in faith and real life: Can the grace of Jesus Christ truly redeem someone like David Berkowitz—the “Son of Sam”? Not as shock value, and not as a theological stunt,...

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