Best Brandon Held Podcasts (2025)

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Episode 35: Boots to Boardrooms: My Unexpected Career Evolution 50:53

2d ago50:53

50:53

Send us a text Brandon shares his professional journey from military service to project management and consulting, revealing how early experiences shaped his leadership abilities and career trajectory. • Joining the Air Force at 17 taught crucial foundations of discipline, resilience, structure, and accountability • Military experience provided ear…

1
#108 - Case Study: Real Estate Professional Status That Held Up in Court with Brandon Hall 21:04

8d ago21:04

21:04

In this episode, Tait Duryea flies solo to spotlight a powerful tax strategy many high-income earners overlook: real estate professional status. Featuring Brandon Hall from Hall CPA, this episode breaks down a real tax court victory by a harbor pilot who leveraged a flexible W-2 job schedule to claim REP status and unlock massive tax savings. Disco…

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Episode 34: Six Steps to SEO Success That Anyone Can Follow 18:36

3d ago18:36

18:36

Send us a text In this practical guide to SEO for small businesses, Brandon breaks down search engine optimization into simple, actionable steps anyone can implement without technical expertise or large budgets. He explains how SEO works as a digital visibility tool that levels the playing field for small businesses, allowing them to compete effect…

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#109 - The Flight Plan for Syndications: Risk, Returns, and Real Wealth 39:19

2d ago39:19

39:19

In this episode, hosts Tait Duryea and Ryan Gibson deliver an in-depth, pilot-friendly primer on syndications and passive real estate investing. They break down the risk spectrum from core to opportunistic deals, while sharing real-world analogies and experiences from their own projects, like the Canyon City land entitlement. Learn how to properly …

1
Episode 33: Three Sons, Countless Lessons: The Unexpected Education of Fatherhood 35:10

9d ago35:10

35:10

Send us a text Brandon explores the transformative impact of fatherhood and shares the key lessons he's learned raising three distinctly different sons throughout their lives and after divorce. • Finding balance between being present for your children and maintaining self-care • Leading by example and creating a judgment-free environment for open c…

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Episode 32: The Power of Self-Awareness 17:07

13d ago17:07

17:07

Send us a text Self-awareness is the key to unlocking your potential and improving relationships, allowing you to see yourself clearly through reflection and understanding how you impact others. Both internal self-awareness (understanding your inner world) and external self-awareness (understanding how others perceive you) are crucial for personal …

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Episode 31: Uncover Your Purpose: 10 Life-Changing Questions 39:32

17d ago39:32

39:32

Send us a text Powerful questions can fundamentally change the trajectory of our lives, helping us reconnect with what truly matters when we've lost sight of our purpose in the daily hustle. I share ten transformative questions that can help you break through barriers and create meaningful change. • What do you truly desire to achieve in your life,…

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#107 - Take Control of Your Capital: Infinite Banking Strategy With Brent Kesler 38:43

17d ago38:43

38:43

Host Tait Duryea sits down with Brent Kesler, a seasoned life insurance strategist, to explore how pilots and high-income earners can build wealth by turning whole life insurance into a personal banking system. Brent breaks down the misunderstood "infinite banking" concept and how it can be used for real estate, debt payoff, or high-return lending—…

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Episode 30: Is Finding Love Abroad Worth the Price? 51:08

21d ago51:08

51:08

Send us a text Brandon Held shares his personal journey of finding love internationally and marrying a woman from Brazil, discussing the realities that dating shows like 90 Day Fiancé don't fully capture. He explores the challenges and rewards of cross-cultural relationships with honesty and vulnerability based on his own experience. • Dating inter…

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Episode 29: Divorce: The TRUTH They Don't Tell You Pt. 2 29:47

27d ago29:47

29:47

Send us a text Brandon reflects on the lessons he's learned from his divorces, exploring how good communication and understanding are essential for lasting relationships. • Communication is absolutely critical - especially about your feelings and mental state • Nobody is perfect, so allowing grace for mistakes is essential for both partners • Discu…

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Episode 28: Divorce: The TRUTH They Don't Tell You Pt.1 29:02

27d ago29:02

29:02

Send us a text Brandon Held shares profound insights from his three divorces and how these experiences have shaped his approach to his current marriage. He explores the evolution of his self-awareness and the lessons that failure taught him about relationship success. • First marriage at 19 while in the Air Force was driven by practicality and lone…

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#106 – Time Freedom and Cash Strategies with Brian Herriot 39:31

25d ago39:31

39:31

Hosts Tait Duryea and Ryan Gibson welcome financial strategist Brian Herriot for a thought-provoking conversation on redefining retirement and wealth. Explore the power of time freedom, why cash might be your most underappreciated asset, and how to build passive income streams that work for pilots and professionals alike. Brian shares practical tac…

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Episode 27: Air Force vs. Army: My Experience and Comparison 28:18

30d ago28:18

28:18

Send us a text Brandon Held shares his unique perspective on the differences between the Air Force and Army based on his personal experience serving in both branches. Drawing from his time as an Air Force security policeman at 17 and later joining the Army at 29, he offers candid insights into the contrasting cultures, benefits, and challenges each…

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Episode 26: Owning Your Truth: The Power of Self-Acceptance 30:40

1M ago30:40

30:40

Send us a text Owning who you are means embracing your unique qualities and imperfections without feeling pressure to conform to others' expectations. This liberating mindset allows you to set boundaries, live authentically, and find genuine happiness without constant people-pleasing. I implore you to please start at Episode 1 if you're downloading…

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#105 - Buying and Building a Profitable Aviation Business with James Spearman 46:05

1M ago46:05

46:05

In this episode, Tait Duryea and Ryan Gibson are joined by James Spearman, owner of Spearman Aircraft and Iconic Rides. James walks through his journey of acquiring and scaling an aircraft maintenance business through seller financing, boosting its value through streamlined systems and strategic marketing. He shares the mindset and steps that helpe…

1
Episode 25: Last One 22:23

1M ago22:23

22:23

Send us a text Brandon Held wraps up his life story by sharing significant recent events including his grandmother's passing, estrangement from his son, and health challenges that derailed his fitness journey at age 50. Despite experiencing profound grief, relationship uncertainties, and medical issues, he continues moving forward with a new home, …

1
Episode 24: Can You Control Who Breaks Your Heart? 29:11

1M ago29:11

29:11

Send us a text I share the emotional journey of being separated from my Brazilian wife for nine months after marriage and how we finally reunited when her visa was approved. The perfect timing of my new work-from-home consulting position allowed me to be present as she adjusted to life in America while also regaining shared custody of my children. …

1
Episode 23: Life Across Continents 27:51

1M ago27:51

27:51

Send us a text Brandon continues his journey of meeting, marrying, and working to reunite with his Brazilian wife Juliana, detailing the challenges and triumphs of maintaining a cross-continental relationship. From navigating Bahamian bureaucracy to passing crucial visa interviews, this episode captures the emotional rollercoaster of building a lif…

1
Episode 22: What Would You Endure for Love? 24:12

1M ago24:12

24:12

Send us a text Brandon continues his love story where he left off, dealing with the heartache of separation from Juliana and navigating the challenging process of bringing her from Brazil to America during COVID-19 travel restrictions. Please start with Episode 1. Go to my site BrandonHeld.com • Discovering that spousal visas process much faster th…

1
Episode 21: When You Know, You Know: A Cross-Continental Love Story 27:33

1M ago27:33

27:33

Send us a text I share the story of meeting and falling in love with Juliana from Brazil after months of online conversations, culminating in an eight-day trip that changed my life forever. What began as a skeptical first meeting transformed into the most magical experience of my life when I spontaneously proposed marriage. Please start with Episod…

1
Episode 20: When American Dating Fails, Go Global 26:19

1M ago26:19

26:19

Send us a text I'm navigating new beginnings while reflecting on past relationships and helping my adult children find their paths. Please start with Episode 1. Go to my site BrandonHeld.com • Website brandonheld.com now launched with podcasts being uploaded incrementally • Memory challenges affecting creative process and retention of episode ideas…

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Episode 19: The Unexpected Blessings Behind My Professional Rebirth 26:55

1M ago26:55

26:55

Send us a text Brandon reflects on his journey from nearly four years of unemployment to finding stability in his career and personal life despite significant challenges along the way. Please start with Episode 1. Go to my site BrandonHeld.com • Taking a temporary healthcare position over a permanent aerospace job based on intuition and long-term i…

1
Episode 18: Sometimes Life Forces You to Start Over 26:46

1M ago26:46

26:46

Send us a text I share the progress of my podcast journey and my attempts to rebuild a relationship with my oldest son Ethan during a challenging period of unemployment in Arizona. Please start with Episode 1. Go to my site BrandonHeld.com • Creating a website to build community around the podcast, primarily aimed at men based on my life experience…

1
Episode 17: What Happens When You Lose Everything at Once? 25:55

1M ago25:55

25:55

Send us a text Brandon shares his journey through his third divorce, which became the lowest point of his life as he simultaneously lost his job, home, and faced financial ruin while fighting for custody of his children. Please start with Episode 1. Go to my site BrandonHeld.com • Third marriage ended after 12 years together, 10 years married with …

1
Episode 16: When Your Past Shapes But Doesn't Define You 28:44

1M ago28:44

28:44

Send us a text Brandon reflects on his life journey, sharing how past mistakes and difficult experiences have shaped him into the person he is today while emphasizing his commitment to growth and learning from both his own errors and those of others. Please start with Episode 1. Go to my site BrandonHeld.com • Growing up surrounded by alcohol abuse…

1
Episode 15: Finding Myself After Job Loss: A Story of Resilience and Transformation 21:48

1M ago21:48

21:48

Send us a text Brandon continues his life story, detailing the aftermath of being let go from Raytheon and discovering it was partly because he was a white male with "no recourse" according to insider information from a Puerto Rican colleague in management. Please start with Episode 1. Go to my site BrandonHeld.com • Finding a new position through …

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Episode 14: The Dream Job That Turned Into a Nightmare: My Raytheon Story 26:51

1M ago26:51

26:51

Send us a text Brandon reflects on his transition from military life to a civilian career and the rollercoaster of personal and professional challenges that followed his Army service. Please start with Episode 1. Go to my site BrandonHeld.com • Built strength through intramural sports and weightlifting during military service • Met and married 3rd,…

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Episode 13: The Toxic Army Experience: Navigating Leadership, Love, and Mental Health Challenges 25:27

1M ago25:27

25:27

Send us a text Brandon reflects on his challenging transition from Air Force, to civilian life and then to Army service, revealing how toxic leadership and workplace politics severely impacted his military experience and mental health. Please start with Episode 1. Go to my site BrandonHeld.com • Joining the Army as a food inspector to challenge him…

1
Episode 12: The Hard Restart 26:11

1M ago26:11

26:11

Send us a text Brandon shares his journey from struggling with post-college jobs and a toxic relationship to finding stability by rejoining the military, this time as an Army food inspector. Please start with Episode 1. Go to my site BrandonHeld.com • Attempted to become an Air Force officer, only to have his application abandoned when recruiter wa…

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Episode 11: What They Don't Teach You: Navigating the Murky Waters of Early Employment 28:52

1M ago28:52

28:52

Send us a text After graduating college, I navigated a series of unexpected career turns that took me from a lucrative accountant sales representative role to multiple jobs with broken promises and ethical challenges. This journey highlights how early career paths often involve setbacks, difficult choices, and learning experiences that shape your p…

1
Episode 10: Hair Today, Gone Tomorrow: My Journey to Embracing the Bald Life 25:35

1M ago25:35

25:35

Send us a text Brandon shares a missing piece of his previous relationship story and reveals how his journey through college at Wright State transformed his confidence and self-image. Please start with Episode 1. Go to my site BrandonHeld.com • Recalls a moment when his girlfriend's attractiveness to other gym-goers affected how he perceived their …

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Episode 9: The Magnetic Pull of a Toxic Relationship 24:08

1M ago24:08

24:08

Send us a text Brandon opens up about his conflicted feelings while recounting the story of his second significant relationship, expressing love and consideration for his current wife while sharing this challenging chapter of his past. Please start with Episode 1. Go to my site BrandonHeld.com • Meeting a beautiful redheaded woman at the gym who in…

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Episode 8: The Transformative Years: From Military Spouse to Single College Student 20:02

1M ago20:02

20:02

Send us a text Brandon reflects on his journey through college after the Air Force, exploring the complex choices around dating, fatherhood, and personal transformation that shaped his character during a pivotal time in his life. Please start with Episode 1. Go to my site BrandonHeld.com • Remaining in a failing marriage while attending college par…

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Episode 7: The Air Force Files: Four Years I Still Can't Believe 20:14

1M ago20:14

20:14

Send us a text I take you behind the scenes of my four years in the Air Force, sharing the wild personal stories and intense human drama that defined my military experience beyond the uniform and duties. Please start with Episode 1. Go to my site BrandonHeld.com • Strong military camaraderie formed with friends like John Copado, Dan Malone, and Dav…

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#104 - Active vs. Passive: Storage Strategies from the Flight Deck with Michael Meylor 49:01

1M ago49:01

49:01

In this episode, Tait Duryea and Ryan Gibson sit down with Michael Meylor, a seasoned pilot and self-storage investor who has built an impressive portfolio without raising outside capital. Michael shares how he transitioned from military to commercial flying, how he and his wife started investing in single-family rentals, and why they pivoted to co…

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Episode 6: Breaking Formation: How Betrayal Led to a New Beginning 21:27

1M ago21:27

21:27

Send us a text Brandon Held recounts his Air Force career trajectory and the pivotal moment that led him to abandon his original plan of military retirement for a completely different path. A false report from a vindictive master sergeant and subsequent lack of support from leadership sparked a series of events that ultimately led Brandon to pursue…

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Episode 5: When Life Forces You to Grow Up 21:55

1M ago21:55

21:55

Send us a text Brandon continues his life story, transitioning from a mental health crisis back to military service as a missile security cop and eventually into an unexpected journey to fatherhood that changes everything. Please start with Episode 1. Go to my site BrandonHeld.com • Returning to missile security duty after his mental health facilit…

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Episode 4: From Military Service to Mental Health Crisis: A Raw Personal Account 27:39

1M ago27:39

27:39

Send us a text Brandon shares how his life dramatically changed after joining the Air Force, from women suddenly showing interest in him to facing a mental health crisis following a relationship breakdown. His journey from Ohio to North Dakota reveals both the external transformations and internal struggles that shaped his early military experience…

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Episode 3: Tidy Whities and Trash Cans: My Shocking Introduction to Military Life 26:41

1M ago26:41

26:41

Send us a text Brandon Held recounts his transformative four years in the Air Force, a period that changed his life trajectory and helped him escape a troubled upbringing with minimal guidance and support. Please start with Episode 1. Go to my site BrandonHeld.com • Graduating high school early with a 1.5 GPA to join the Air Force at age 17 • Strug…

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Episode 2: How I Smiled Through the Chaos: Planning My Escape 24:20

1M ago24:20

24:20

Send us a text From poverty to purpose, Brandon shares how his brother's birth sparked a transformation in his outlook on life during a childhood marked by neglect, hunger, and searching for guidance amidst family dysfunction. Please start with Episode 1. Go to my site BrandonHeld.com • Experiencing a new sense of responsibility and protectiveness …

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Episode 1: Introduction and My First Memory 21:13

1M ago21:13

21:13

Send us a text Brandon Held shares his first memory—witnessing his father's brutal assault on his mother when he was just two years old—and how this traumatic experience shaped his identity as a protector for the next 50 years. This raw, unfiltered introduction to Brandon's life story begins his journey through childhood trauma, abandonment, and fi…

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#103 - Multifamily Mastery: Building Cashflow and Legacy with Gino Barbaro 45:35

2M ago45:35

45:35

In this episode, Tait Duryea welcomes Gino Barbaro of Jake & Gino to unpack the mindset and mechanics behind building lasting wealth through multifamily real estate. Gino shares his journey from running a family restaurant to becoming a real estate investor with over 1,800 units. They explore topics like values-based decision-making, creating "happ…

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#102 - Creating True Passive Income Through Note Investing with Tom Force 49:39

2M ago49:39

49:39

In this episode, Tait Duryea and Ryan Gibson sit down with retired airline captain and seasoned investor Tom Force to discuss a real estate strategy many overlook—note investing. They cover tax strategies, risk management, and how to get started in note investing. If you’re tired of tenant headaches and want to invest like a bank, this episode is f…

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#101 - Airbnb for Aircraft: Hangar Investing & Aviation Real Estate with Trenton Ray 41:21

2M ago41:21

41:21

Hangar space is in short supply, but Trenton Ray is changing that. In this episode, Tait Duryea and Ryan Gibson chat with Trenton about Hangar Direct, his platform that’s like Airbnb for hangars—making it easier for pilots to find and rent space. They dive into the supply shortage, investment potential, and what to know about leasing, financing, or…

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#100 - Getting to Know Tait & Ryan 51:12

2M ago51:12

51:12

In this special 100th episode of Passive Income Pilots, Tait Duryea and Ryan Gibson take listeners behind the scenes of the podcast, sharing how it all started and what goes into creating each episode. They also dive into their personal journeys in aviation, investing, and entrepreneurship. From buying their first rental properties to scaling multi…

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#99 - Turnkey Real Estate: Passive or Problematic? A Deep Dive with Zach Lemaster 52:24

3M ago52:24

52:24

In this episode, Tait Duryea and Ryan Gibson connect with Zach Lemaster to explore the world of turnkey real estate and build-to-rent properties. They discuss the benefits and challenges of owning physical real estate, the tax advantages of rental properties, and how busy professionals can invest without becoming full-time landlords. Zach shares in…

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#98 - The Right Coverage: Property Insurance Strategies with Valerie Cusano 49:46

3M ago49:46

49:46

In this episode of Passive Income Pilots, Tait Duryea and Ryan Gibson sit down with Valerie Cusano, an insurance expert with a background in law and decades of experience in commercial and residential insurance. Val dives deep into the critical aspects of real estate insurance, particularly for condo and rental property owners. She explains the dif…

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#97 - Creative Deal Structuring: Smart Real Estate Strategies with Chris Prefontaine 53:27

3M ago53:27

53:27

In this episode, Tait Duryea and Ryan Gibson dive into creative real estate financing with Chris Prefontaine, founder of Smart Real Estate Coach. Chris shares powerful strategies like seller financing, subject-to deals, and lease purchases, revealing how investors can acquire properties without banks—even in today’s high-interest rate environment. …

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#96 - Airplane Write-Offs, IRS Audits, and Smart Tax Planning with Ryan DeMoor 49:44

3M ago49:44

49:44

Have you ever wondered how you could write off an airplane? In this episode, Ryan DeMoor joins hosts Tait Duryea and Ryan Gibson to break down the tax benefits of aircraft ownership. Ryan shares how pilots and business owners can strategically use aircraft purchases for tax deductions, the IRS rules around business use, and why proper record-keepin…

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#95 - Franchise Investing 101: Insights and Opportunities with Cliff Nonnenmacher 53:31

3M ago53:31

53:31

In this episode of Passive Income Pilots, hosts Tait Duryea and Ryan Gibson explore the world of franchise ownership with franchise expert Cliff Nonnenmacher. Cliff brings decades of experience as a franchise consultant and serial entrepreneur, sharing insights into how pilots and professionals can invest in or operate franchises to build wealth. T…

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