Successfully Unsuccessful

About Successfully Unsuccessful

Introducing "Successfully Unsuccessful" - the podcast that redefines success for executive, entrepreneurial, and professional men who aim to live their fullest lives. In a world fixated on achievements, this show challenges the norm by delving into the uncharted territories of failure, weakness, and imperfection. Join us on a transformative journey where we spotlight the world's most accomplished men—individuals who've scaled great heights while stumbling through setbacks. Unmasking their trials and tribulations, our podcast shatters the illusion of flawlessness. We confront head-on the very facets our culture prefers to avoid, addressing the intricate interplay of ambition, relationships, and self-indulgence that shape our lives. Diving deep, we dissect the blueprints of success—their goals, priorities, habits, and systems—laid bare by their colossal blunders. These luminaries humbly share their personal struggles, exposing the fractures beneath the polished surface. This candid exchange serves as a guiding light, illuminating a path for others to forge enduring change. "Successfully Unsuccessful" is a quest to unravel the enigma of achievement. We embrace the messy art of crafting an honorable life—one that leaves an indelible mark on the world, transcending generations. It's about leveraging our time on Earth to unearth our true purpose. By aligning our gifts, societal needs, and compensation, we catalyze profound transformation while unburdening ourselves from the past. Through unvarnished conversations, our guests paint a vivid portrait of their journey. We traverse the highs, lows, and shadows they've encountered, plumbing the depths of body, heart, soul, and mind. This raw vulnerability compels introspection—directing our gaze inward, upward, and outward. It's a clarion call to contemplate our existence, forge connections, and transcend our limitations. "Successfully Unsuccessful" challenges convention and champions authenticity. It's a sanctuary for men who seek more than surface triumphs, who dare to navigate the tumultuous seas of vulnerability to rewrite their narrative. Join us as we unravel the paradox of triumph through failure, embarking on a mission to sculpt lives of significance and leave an enduring legacy.

Publisher

Josh Dittrich

Category

business · religion & spirituality

Language

en

Explicit

No

First episode

11 Oct 2023

Latest episode

10 Jun 2025

Latest episodes

50 episodes in the feed.

1. 

   10 Jun 2025

   From Weed Ponds to Kingdom Purpose

   As business owners and leaders, we’re often laser-focused on metrics—revenue, growth, headcount, scale. But every now and then, I get the privilege of having a conversation that shakes those definitions of success to the core. That’s exactly what happened in this episode of Successfully Unsuccessful, when I sat down with my good friend and CBMC peer, Connor Pichet. Connor’s the founder of Scuba Weed Control, a company that started as a scrappy college side hustle and has grown into a multi-location operation cleaning lakes and ponds across Minnesota. What struck me wasn’t just how he’s scaled a niche service—it’s how he’s done it while raising four kids, building a team from the ground up, and learning to lead with vision, faith, and intentionality. But the real gold of our conversation was what you won’t find on a P&L. Connor opened up about a transformative moment in his life—a late-night conversation with his cousin that led to a powerful encounter with God. It was raw, it was real, and it was the start of something eternal. He wasn’t in a church pew or a boardroom; he was in the middle of a personal storm, and yet God showed up with clarity, comfort, and conviction. That moment shifted everything: how he leads his company, how he loves his family, and how he sees success. And if you’ve ever wrestled with burnout, identity, or whether you’re building something that really matters, Connor’s story will meet you right there.

2. 

   3 Jun 2025

   Built to Rise: Redefining Success Through Faith and Leadership

   In this episode of Successfully Unsuccessful, I sat down with my good friend Eric Robinson, co-owner of Rise Realty, for an honest and refreshing conversation that went far beyond real estate. From his early years in Wisconsin to his journey through car sales and eventually into real estate, Eric shares the transformative moments that shaped both his professional and personal life. We explore the deep motivation behind founding Rise Realty—not as a profit engine, but as a community built on the right people, structure, and support. Eric unpacks how this model has allowed agents to thrive in their own way, embracing the “be more, do more” mindset that’s foundational to his mission. But we didn’t stop at business. We dove deep into what success really means for Eric—a concept measured not in dollar signs but in dinners at home with family, open conversations with his wife, and the consistent effort to remain fully present. He speaks candidly about how his phone, a vital business tool, often becomes the biggest distraction in his marriage, and the systems he and his wife use to stay aligned. We touched on parenting styles, the balancing act of fatherhood, and the importance of guardrails to avoid drifting off course in life. His transparency on these challenges is both relatable and encouraging. Perhaps most powerfully, Eric opened up about a deeply humbling season in 2023 when everything he thought was stable—relationships, finances, plans—was stripped away. He describes this time as a “sweet cut of the surgeon,” a painful but necessary realignment of heart and purpose. We ended by reflecting on the intersection of faith, work, and calling, and how Eric uses his position in the real estate world as a platform for meaningful conversations and lasting impact. Whether you’re in ministry, business, or navigating personal growth, there’s something in Eric’s journey that will resonate with you.

3. 

   6 May 2025

   Dad Awesome vs. Dad Angry: Leading with Legacy

   What a joy it was to welcome Jeff Zaugg, founder of Dad Awesome, to the Successfully Unsuccessful podcast. From the moment we hit record, Jeff brought his signature high-energy presence and deep insights into what it means to be a father who shows up with intentionality and heart. His journey from being a reluctant kids' ministry leader to launching a podcast that has released 375 episodes and mobilized over a thousand men through events like Fathers for the Fatherless is a powerful testament to what happens when passion meets purpose. We unpacked his transition into full-time ministry, the importance of making the role of dad a delight, not a duty, and how delighting in our kids can shape their sense of identity in a world filled with lies. This conversation hit me in a personal way. Jeff talked about the difference between dad angry and dad awesome—how we're called not to perfection but to a posture of curiosity, cheerleading, and consistency. He shared practical tools, from candlelight blessings to specific affirmations that light up our kids’ eyes. He reminded us that being a great dad starts with going upstream—dealing with our own wounds, finding healing, and surrounding ourselves with brotherhood. His metaphor of the RV showerhead versus a waterfall of God’s love brought to life the difference between living as orphans, hustling for worth, and living as beloved sons, overflowing with purpose and presence. I’m still chewing on the impact of simply “getting low and getting slow” with my own kids, and I hope it hits you like it hit me. What I loved most about this episode is how Jeff reminded us that fatherhood is a story—our story. And when we zoom out, we realize that today’s decisions shape generations. Jeff’s vulnerable moment of running out of ministry funding wasn’t a failure—it was formation. And that spoke volumes to me about trust, stewardship, and living fully aligned with what God is calling us to do. If you’re a dad, if you’re a leader, or just someone searching for purpose beyond a paycheck, this episode will stir your heart. Let it be a spark that flips the switch from surviving to thriving.

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

6 ratings

Spotify

5.0 / 5

2 ratings

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.