Bad Boss Confessional

Speakeasy Podcast Network
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Bad Boss Confessional is the podcast where entrepreneurs, founders, and leaders fess up to their most cringeworthy management moments—the times they micromanaged, blew up in meetings, or simply got it dead wrong. With names changed (to protect the innocent...and guilty), guests walk us through their “bad boss” moment in all its messy glory. But this isn’t just a cringe-fest—it’s a redemption story.

  1. 31: Building a Business Without Burning Out

    2D AGO

    31: Building a Business Without Burning Out

    In this episode of Bad Boss Confessional, Beth sits down with EOS Implementer Robert Hartline to explore the difference between being the firefighter and becoming the fire chief. After years of scaling businesses and chasing growth, Robert shares the moment he realized he was addicted to chaos and operating from scarcity rather than structure. From exponential growth to sobriety to launching Scaling Sober, Robert reflects on how awareness, breathwork, and EOS helped him move from reaction to intention. The conversation dives into why sober leadership matters and how entrepreneurs can build businesses that are driven by purpose rather than pressure. Timestamps 00:00 Introduction to Bad Boss Confessional 02:50 Robert’s Entrepreneurial Journey 07:38 The Firefighter Realization 12:51 From Firefighting to Purpose 17:10 Discovering the ‘Why’ 21:29 Learning from a ‘Bad Boss’ Moment 26:54 Scaling Sober: Entrepreneurial Wellness 33:11 Redefining Sobriety and Leadership 39:07 The QR Code Tattoo 43:04 The Importance of EOS Rollouts   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Website: https://implementer.eosworldwide.com/robert-hartline/ Robert Hartline is an EOS Implementer, serial entrepreneur, and founder of Scaling Sober, a wellness community for growth-minded entrepreneurs. After scaling Absolute Wireless to over $100 million in sales, he shifted his focus to helping leaders build businesses that operate without chaos, burnout, or dependence on the owner. Today, he blends structure, purpose, and personal growth to help entrepreneurs lead with clarity and design lives that feel as good as they perform. Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.

    46 min
  2. 30: The High Price of Saying Yes

    FEB 18

    30: The High Price of Saying Yes

    In this episode of Bad Boss Confessional, Beth talks with serial entrepreneur and coach Jill Salzman about the early mistakes that shape stronger leaders. From quick-start decisions to client-pleasing habits, Jill reflects on how saying yes too fast and avoiding boundaries can quietly erode confidence and clarity. The conversation expands into coaching, asking better questions, and resisting the urge to solve everything for others. The real lesson is not about one bad decision. It is about learning to trust experience over ego, service over approval, and patience over speed.  Timestamps 00:00 Introduction to Bad Boss Confessional 02:16 Meet Jill Salzman 05:05 Music and Personal Outlets 06:51 The Black Crows Concert Fiasco 12:15 Lessons from the Cancellation Fee 17:29 Influences and Coaching Philosophy 21:09 The Quick Start Challenge in Coaching 24:45 Human Connection vs. AI in Coaching 28:30 Detox from Social Media 32:57 The Big But Book 35:35 Tattoos and Final Thoughts About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Jill Salzman isn’t your ordinary business coach. She’s a serial entrepreneur, a thinking partner, and a musician who rarely misses a beat. Jill brings humor, heart, and strategic clarity to every conversation. She thrives on collaboration, sparks creativity, and makes the hard parts of entrepreneurship feel a little lighter. LinkedIn: https://www.linkedin.com/in/jillll Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.

    39 min
  3. 29: Rollout: A Book Born From Bad Boss Moments

    FEB 11

    29: Rollout: A Book Born From Bad Boss Moments

    In this episode of Bad Boss Confessional, Beth Fahey is joined by EOS Implementer and Rollout co-author Marisa Smith for a different kind of confession. Together, they unpack the leadership mistakes that inspired the book in the first place. Both Beth and Marisa share what it was like to implement EOS in their own companies and realize that simply using the tools was not the same as rolling them out effectively. Marisa reflects on moving too fast, skipping context, and assuming her team would automatically understand what she understood. Transparency without education created confusion, not clarity. EOS worked best only after slowing down, following the process, and aligning the leadership team before expecting the rest of the organization to follow. The lesson is clear. Great leadership is not about speed or certainty. It is about humility, repetition, and teaching others how to think, not just what to do. Rollout is not an event. It is a discipline that turns vision into shared ownership across the organization. Learn more about "Rollout" here!: https://www.rolloutbook.com/ Timestamps 00:00 – Intro and book preview 00:29 – Why this podcast exists 02:05 – Writing the book together 03:09 – Marisa’s early business days 04:48 – Breaking EOS on rollout 06:35 – Learning to slow down 08:52 – The rollout roadmap 10:08 – Client success lessons 14:07 – Mid managers matter 16:18 – From student to teacher About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.

    44 min
  4. 28: Getting Out of Your Own Way

    FEB 4

    28: Getting Out of Your Own Way

    In this episode of Bad Boss Confessional, Beth Fahey sits down with EOS Implementer Amanda Matthews to unpack a painfully relatable leadership moment driven by ego, insecurity, and a lack of self-awareness. After years of corporate leadership training, Amanda found herself out of her depth while managing in a high-volume restaurant environment. What she thought was confident leadership quickly turned into public shaming. Even experienced leaders can lose their way when ego and self-doubt take over. Great leadership requires pausing, reading the room, and remembering that praise belongs in public while criticism belongs in private. Growth begins when leaders learn to get out of their own way.   Timestamps 00:00 Introduction to Amanda Matthews 01:45 Amanda’s Love for Swing Dancing 04:36 Corporate to Restaurant World Shift 09:02 The Tobacco Chewer Incident 16:11 Lessons from the Incident 22:55 Recommended Management Books 26:08 The Simplicity of Direct Feedback 31:57 A Tattoo for Ego Check   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Amanda Matthews coaches entrepreneurs on how to be wildly successful while also having time for what matters most in their lives using the Entrepreneurial Operating System (EOS). She describes herself as a dance enthusiast, book nerd and interpersonal knot detangler.  Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.

    37 min
  5. 27: Paying Attention to the Red Flags | Bad Boss Confessional

    JAN 28

    27: Paying Attention to the Red Flags | Bad Boss Confessional

    In this episode of Bad Boss Confessional, Beth Fahey sits down with EOS Implementer Ken DeWitt, also known as “Hurricane,” to unpack a leadership lesson that quite literally required warning flags. Early in his career, Ken’s intensity and drive created an environment where employees tracked his moods to protect themselves. What he didn't realize was that his passion was being met with fear and anxiety. Leaders are always on stage, whether they realize it or not. Self-awareness, emotional control, and humility matter as much as vision and results. Successful managers will never stop growing, even if it means facing some painful gut checks. Timestamps 00:00 Introduction to Ken ‘Hurricane’ DeWitt 02:27 From Accountant to EOS Implementer 05:08 The Psychologist’s Revelation 07:22 The ‘Hurricane’ Nickname 10:55 Dealing with the ‘Hurricane’ 14:58 Learning Calmness and Self-Awareness 19:04 The Impact of Personal Change 23:55 Understanding Different Communication Styles 28:59 Trust, Care, and Excellence in Leadership 32:56 Legacy and Learning: The Hurricane Tattoo   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Over the past 40 plus years, Ken DeWitt has built, grown, and successfully exited companies across multiple industries, including accounting, agriculture, consumer finance, real estate, and consulting. He has worked with more than 100 owners and leadership teams to install EOS across seven states, helping them gain control, strengthen leadership, and build businesses that work for them rather than because of them. Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.

    39 min
  6. 26. When Good Intentions Go Wrong

    JAN 21

    26. When Good Intentions Go Wrong

    In this episode of Bad Boss Confessional, Beth Fahey sits down with EOS Implementer Carolyn Mitchell for an honest conversation about leadership, ego, and the hidden cost of trying to help too much. Carolyn shares a moment many leaders will recognize. As the unofficial “company therapist,” she believed stepping in and sharing sensitive information was for the greater good. Instead, it backfired. The employee she tried to protect walked it back, leaving Carolyn exposed, frustrated, and humbled. What felt like service was actually ego at work. The need to fix, to be needed, and to save the day created more dysfunction, not less. The lesson is simple and hard-earned. Great leaders coach people to speak for themselves instead of carrying their burdens. Growth happens when leaders pause, listen, and ask whether the problem is truly theirs to solve. Sometimes the best leadership move is letting go and letting it be easy.   Timestamps 00:00 Introduction to Carolyn Mitchell 02:08 Career Journey: Engineer to EOS Implementer 08:39 The Unofficial Company Therapist 12:09 Ego and the Hero Complex 19:02 Learning to Pause and Listen 23:33 Coaching vs. Fixing, and Tattoos   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links: Website:  https://implementer.eosworldwide.com/carolyn-mitchell/ LinkedIn:  https://www.linkedin.com/in/carolyn-mitchell-coach Carolyn Mitchell is an EOS® Implementer, business coach, and speaker with a background in sales and marketing leadership. She’s been in the founder and leadership seats, implemented EOS, and now helps teams build clarity, accountability, and trust. She’s also a personal development junkie, a certified yoga teacher and believer in leadership that grows people, not just results. Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.

    31 min
  7. 25. The Hidden Cost of Doing the Right Thing

    JAN 14

    25. The Hidden Cost of Doing the Right Thing

    In this episode of Bad Boss Confessional, Beth Fahey talks with EOS Implementer Michael Deutsch about a leadership failure that tested his ethics, his systems, and his gut. After landing the biggest client in his electronics recycling business, Michael discovered that valuable materials were being stolen somewhere in the supply chain. The mistake was not driven by bad intent, but by gaps in people and process that he ultimately owned as the leader. Michael shares the uncomfortable moment of choosing to proactively tell a Fortune 500 client the truth, knowing it could cost the relationship. Looking back, Michael points to right person, wrong seat decisions, weak project oversight, and the danger of trusting without the right structure in place. The lesson is clear: Core values are not words on a wall. They are tools that guide decisions when things go wrong. Doing the right thing does not always protect the outcome, but it protects who you are as a leader. Timestamps 00:00 Introduction to Bad Boss Confessional 01:28 Michael Deutsch’s Diverse Career Path 05:51 The Electronics Recycling Business 07:46 The Biggest Client Scandal 12:54 Owning the Mistake and Lessons 16:32 People, Process, and System Building 21:31 Applying Core Values and EOS 27:53 Personal Core Values and Self-Reflection 33:09 The ‘Let Them’ Tattoo and Farewell About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links: Website:  https://implementer.eosworldwide.com/michael-deutsch/ LinkedIn:  https://www.linkedin.com/in/michaeldeutsch/ Michael has been part of senior management for over 25 years - first as a leader for several high-growth organizations and then as a business owner. Now, as an EOS Implementer, he helps other business owners avoid the mistakes he made and get what they want from their business that they're not getting right now. Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.

    36 min
  8. 24. The Shift from Peer to Boss with Jessenia Flores-Gayle

    JAN 7

    24. The Shift from Peer to Boss with Jessenia Flores-Gayle

    On this episode of Bad Boss Confessional, Beth Fahey sits down with marketing executive and general manager Jessenia Flores-Gayle to explore what happens when you suddenly become the boss of people who used to be your peers. Jessenia describes the emotional and practical challenges of stepping into an integrator role inside a close-knit, all-female leadership team. She talks about the pressure to be liked, the discomfort of holding friends accountable, and the self-doubt that surfaces when you feel caught between belonging and leading. Jessenia shares how her background in dance shaped her natural ability to bring people together and build strong relationships that support collective goals. She and Beth discuss boundaries, decision making, and the importance of vulnerability when the demands of leadership feel heavy. Jessenia stays grounded with a personal mantra that guides her work: forgive, learn, and move forward with intention. Timestamps 00:00 Introduction to Bad Boss Confessional 01:56 Jessenia’s Career Journey and Integrator Role 06:36 Challenges of Leading Friends 12:12 The Skill of Relationship Building 15:35 Vulnerability and Saying No 20:18 Influences and Decision-Making 24:08 Tattoos and Leadership Lessons   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links Jessenia Flores-Gayle is a marketing executive and General Manager with over 13 years of experience in the haircare industry, recognized for building impactful brands and leading philanthropic campaigns, including a Shorty Award for her work with nonprofit partners. Throughout her career, she has championed culture, language, and representation, creating inclusive experiences that resonate with diverse audiences. She is also the co-creator of Mighty Big Love, a bilingual children’s brand designed to celebrate identity and heritage from an early age. Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.

    29 min
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About

Bad Boss Confessional is the podcast where entrepreneurs, founders, and leaders fess up to their most cringeworthy management moments—the times they micromanaged, blew up in meetings, or simply got it dead wrong. With names changed (to protect the innocent...and guilty), guests walk us through their “bad boss” moment in all its messy glory. But this isn’t just a cringe-fest—it’s a redemption story.

Information

  • Creator
    Speakeasy Podcast Network
  • Years Active
    2025 - 2026
  • Episodes
    31
  • Rating
    Clean
  • Copyright
    © Copyright Speakeasy Podcast Network
  • Show Website
    Bad Boss Confessional