Tales From The Back Porch with Woody and Brady

Woody and Brady
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🎙️ Two retired United States Air Force Chief Master Sergeants take you behind the scenes of their extraordinary careers—sharing powerful stories, hard-earned lessons, and timeless wisdom. From leadership and management insights to career guidance tailored for both active-duty military and private-sector professionals, they deliver practical advice with authenticity and humor. Each episode is infused with lively commentary on pop culture, sports, politics, and current events—making it as entertaining as it is enlightening.

Episodes

  1. Aug 8

    Bunker BS #3 - Dylan Westmoreland

    # A Journey from Antlers to the Military: Dylan's Story > Discover the experiences that shaped Dylan Westmoreland's path. Dylan Westmoreland shares his journey from a small town in Oklahoma to the military, shedding light on his early life, military experiences, and the people who have influenced him along the way. ## From Small Town Roots Dylan hails from Antlers, Oklahoma, a town with a population of around 2,000. Before joining the military at 21, he worked various jobs, including in the oil field and at a call center. He fondly recalls his high school days filled with basketball, influenced by his family's teaching background. ## The Call to Serve In 2014, as the oil industry faced challenges, Dylan realized he needed a better plan for his future. After an inspiring encounter with a recruiter, he signed up and embarked on a military journey that would change his life. > "You’re going to lay there in your bunk... and be like, what did I get myself into?" > — Dylan Westmoreland Dylan's experience in boot camp was both challenging and transformative. He remembers the intense heat of San Antonio during training and the amusing moments, like realizing he was part of the band flight during graduation. ## Memorable Mentors Throughout his military career, certain individuals left a lasting impact on Dylan. He recalls Technical Sergeants Ortiz and King, who pushed him to succeed and helped shape his perspective on leadership. ## A Twist of Fate Dylan's journey took an unexpected turn when he traded orders to be stationed at F.E. Warren, a decision he believes was pivotal for his career. > "Looking back, it was the best move I could have done." > — Dylan Westmoreland His time there introduced him to key experiences that pushed him beyond his comfort zone and prepared him for future challenges. ## Facing the Elements Dylan recounts his arrival at F.E. Warren in December, where he faced the harsh winter conditions head-on, contrasting sharply with his summer boot camp experience. This change tested his resilience but also made for memorable stories. ## The Journey Continues After serving at F.E. Warren, Dylan transitioned to base security and later deployed to PSAB, where he helped stand up a new base amidst the challenges of COVID-19. Dylan's story is one of determination, growth, and the connections formed along the way. His journey from Antlers to the military is a testament to the impact of mentorship and the importance of seizing opportunities. --- Reflecting on his path, Dylan encourages others to embrace their journeys, no matter how unexpected they may be. To hear more about Dylan's experiences and insights, tune into the full episode.

    Bunker BS #3 - Dylan Westmoreland

  2. Mar 19

    S1 E6 Guest: SMSgt (Ret) Jason Hallmon

    In this episode we hosted retired Defender and First Sergeant, SMSgt Jason Hallmon. Jason shared highlights, insight, and lessons learned from from his early years a young defender and then transitions to a few of the more 'extraordinary' tales from his time as a First Sergeant. Through his brand of story telling and ability to add levity to otherwise difficult situations, it is easy to see why Jason is such a great people person and why he was such a valuable 'Shirt.'

  3. Feb 22

    S1 E5 Guest: CMSgt (Ret) Michelle Thorsteinson-Richards

    In this episode Brady and Woody host retired MAJCOM Command Chief, Michelle Thorsteinson-Richards, aka "Chief TR". Michelle shares insight and perspective from her 30 years of service. She reflects on how a handful defining moments as a young Airman provided some powerful lessons that she continued to leverage throughout her career. And of course, with 30 years of service and a stint as a First Sergeant, she shares a few stories form the "You Can't Make This Stuff Up File".

  4. Jan 11

    S1 E4 The Hard Conversations

    In this episode, Brady and Woody review Blanton's Burbon, Delirium Belgian Ale, and Leinenkugel's White Mocha Stout. Later, in the heart of the episode, they discuss and share stories of personnel issues (disciplinary, growth and feed back, dealing with death, among others) from throughout their careers both good and bad and navigating the associated pitfalls from a supervisor's perspective.

  5. 11/16/2025

    S1 E3 Why Can't I Get Promoted?

    During this session, Brady and Woody let their hair down a bit with new segment where they sample and comment on a new beer and bourbon, before answering the question a lot of Airmen have, "Why can't I get promoted?" After providing some experience-based perspective, the guys get a few things off their chests with "Random Rants."

  6. 10/06/2025

    S1 E2 Demystifying USAFA

    In this episode, Brady and Woody recap their recent travels, touch on SecWar's new standards and policy, and spend the majority of the episode talking through and annual cycle at the United States Air Force Academy and the challenges faced by cadets.

  7. 09/01/2025

    S1 E1 Standards & Expectations

    In our first episode Brady and Woody discuss the importance of standards and expectations and the gray area on the sliding scale of enforcement. Although the guys share experiences from their military careers and examine the topic through that lens the importance of upholding standards transcends into the civilian world and private industry.

  • 7 Episodes

About

🎙️ Two retired United States Air Force Chief Master Sergeants take you behind the scenes of their extraordinary careers—sharing powerful stories, hard-earned lessons, and timeless wisdom. From leadership and management insights to career guidance tailored for both active-duty military and private-sector professionals, they deliver practical advice with authenticity and humor. Each episode is infused with lively commentary on pop culture, sports, politics, and current events—making it as entertaining as it is enlightening.

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