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PODCAST

Bad Boss Confessional

Speakeasy Podcast Network

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.

business management

All Episodes

31:14

36: The Culture You Create When You're Not Looking

Bad Boss Confessional ·

2026/04/01

In this episode of Bad Boss Confessional, Beth Fahey sits down with Rocco Cozza, a business attorney, TEDx speaker, and founder of Cozza Law Group, a multi-seven-figure firm he built from the ground up in Pittsburgh. Rocco shares what happened when rapid growth pulled his focus inward and someone close to him began quietly reshaping the culture he had worked hard to build.The conversation explores what it costs a leader to keep their head down, why intuition matters even when the numbers look

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31:24

35: When Your Team Tells You The Truth

Bad Boss Confessional ·

2026/03/25

In this episode of Bad Boss Confessional, Beth Fahey sits down with Shea Peffly, a former CEO and integrator who now guides other leaders through EOS as a certified implementer. Shea shares the moment a Vistage exercise forced her to sit in silence while her own team told her the direct truth: that her constant questions and close involvement weren't landing as support; they were landing as distrust.The conversation explores what happens when a leader's intentions and their impact are completely

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55:49

34: When a Star Player Stops Being a Teammate

Bad Boss Confessional ·

2026/03/18

In this episode of Bad Boss Confessional, Beth Fahey talks with David Kolbe, CEO of Kolbe Corp and co-developer of the Kolbe A™ Index, about the complicated decisions leaders face when values, performance, and people collide. David shares lessons from running a values-driven company and the leadership mistakes that taught him the most along the way.The conversation explores what happens when high performers fall out of alignment with company culture, why leadership communication matters just as

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43:37

33: The Cost of Skipping the Details

Bad Boss Confessional ·

2026/03/11

In this episode of Bad Boss Confessional, Beth Fahey sits down with Chris Beer, founder of Wizard of Ops and a fractional Integrator. Chris shares a leadership mistake that shows up in many growing companies: assuming communication has happened when it hasn’t. After years of working in the fast-paced trading pits of Chicago, she developed a shorthand style of thinking and speaking that often skipped the context others needed.The result was confusion, missed expectations, and conversations that

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41:03

32: Letting Go of the Vine

Bad Boss Confessional ·

2026/03/04

In this special group episode of Bad Boss Confessional, Beth Fahey sits down with fellow EOS Implementers Erik Dodier, Megan Piper, and Patrick Metzger fresh off a Great Boss workshop. Together, they unpack the leadership missteps that still linger in memory, from surprise firings and unclear feedback to micromanaging and holding too tightly to the vine.The conversation explores the weight of responsibility that comes with leading others and the humility required to admit when the problem is not

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45:51

31: Building a Business Without Burning Out

Bad Boss Confessional ·

2026/02/25

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

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39:15

30: The High Price of Saying Yes

Bad Boss Confessional ·

2026/02/18

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

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44:11

29: Rollout: A Book Born From Bad Boss Moments

Bad Boss Confessional ·

2026/02/11

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

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37:02

28: Getting Out of Your Own Way

Bad Boss Confessional ·

2026/02/04

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

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38:35

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

Bad Boss Confessional ·

2026/01/28

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,

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30:50

26. When Good Intentions Go Wrong

Bad Boss Confessional ·

2026/01/21

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

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36:19

25. The Hidden Cost of Doing the Right Thing

Bad Boss Confessional ·

2026/01/14

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

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28:56

24. The Shift from Peer to Boss with Jessenia...

Bad Boss Confessional ·

2026/01/07

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

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21:20

23. Owning It: A Year of Leadership Confessions

Bad Boss Confessional ·

2025/12/31

This year-end episode of Bad Boss Confessional is a look back, a deep breath, and a heartfelt thank you. After launching the show in July, Beth reflects on what it has meant to create a space where leaders tell the truth about the moments they got it wrong. Across the year, listeners heard confessions about emotional outbursts, fear-driven decisions, people pleasing, missed conversations, and leadership mistakes that still linger. They also heard redemption stories, hard-earned self-awareness, and

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32:43

22. The Role of Honest Dialogue in Healthy Leadership...

Bad Boss Confessional ·

2025/12/17

This week on Bad Boss Confessional, Beth Fahey welcomes Dennis Purcell, Chief Human Resources Officer at Skidmore Sales & Distributing Co., Inc., for a conversation about what happens when leaders develop talent without asking the questions that matter most. Dennis shares the painful lesson he learned after mentoring a high potential team member for years, only to discover in a heated leadership meeting that others had been struggling with that relationship all along.What began as a well

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43:29

21: Be Their Boss, Not Their Buddy

Bad Boss Confessional ·

2025/12/10

On this episode of Bad Boss Confessional, Beth Fahey sits down with lifelong entrepreneur and EOS Implementer Dan Heuretz to share a story about betrayal, accountability, and healing. Dan explains how he handed full control of a multimillion dollar real estate project to his trusted right hand, only to discover that the person he supported and believed in had been stealing from him. The fallout was immediate. The financial records were wiped. Investors were furious. Dan felt alone and

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39:19

20: From Positional Power to Humanized Leadership

Bad Boss Confessional ·

2025/12/03

On this episode of Bad Boss Confessional, host Beth Fahey sits down with Mary Pat Knight, author of The Humanized Leader, to unpack a career-defining moment of shame. Mary Pat tells how, at 19 and newly promoted in a troupe of performers, she lost control, hurled objects, and verbally exploded at a colleague. She reflects on how that moment taught her the limits of positional power and the lifelong work of emotional regulation. Conversation moves from the sting of shame to practical repair: naming

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32:12

19: Empathetic Leadership Without Compromising...

Bad Boss Confessional ·

2025/11/26

This week on Bad Boss Confessional, Beth Fahey welcomes Dominic Sergi, CEO of Clear Height Properties, for a conversation about how unchecked empathy almost held his company back. Dominic shares the hard lesson he learned from keeping the wrong people in the wrong seats for too long, all because he cared too much.What began as a culture built on patience and compassion evolved into one grounded in clarity, accountability, and authentic care. Dominic reveals how a mindset shift from fear to candor

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42:20

18: Startup Fails, Shark Tank Tales, and Bad Boss...

Bad Boss Confessional ·

2025/11/19

This week on Bad Boss Confessional, host and EOS Implementor Beth Fahey sits down with Mike Shannon, CEO of Impruve and author of Sweaty Equity. From surviving Shark Tank to opening his first businesses, Mike opens up about his cringiest leadership missteps, the chaos of scaling to 120 employees, and how embracing systems thinking (and a few bad boss moments) helped him grow as a leader. Expect startup war stories, EOS insights, and a fresh look at how AI is transforming financial advising.00:00

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38:51

17: Perfectionism, Pivoting, and Perseverance

Bad Boss Confessional ·

2025/11/12

In this episode of Bad Boss Confessional, Beth Fahey welcomes Kathy Bresler, founder of Altar Community, a Chicago-based hub for connection, wellness, and growth. Kathy shares her journey from corporate strategist to reluctant boss and accidental entrepreneur. After years of envisioning a gathering space, she opened Altar in early 2020, just as the pandemic shut everything down. Forced to pivot, she and her community shifted online, building resilience through shared purpose.Kathy reflects on her

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