Successfully Unsuccessful

Josh Dittrich
  • 5.0 (6)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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.

  1. 06/10/2025

    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.

    1 hr

  2. 06/03/2025

    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.

    1h 13m

  3. 05/06/2025

    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.

    55 min

  4. 04/29/2025

    From Comfort to Calling: Jake Howes' Leap of Faith

    What a powerful conversation with Jake Howes—entrepreneur, founder of Pioneer Golf Company, and a man on fire for purpose. I’ve had a front-row seat to watch Jake’s transformation from a corporate guy in the golf simulator industry to a bold, faith-driven founder ready to shake up the game. Jake's journey started with a dissatisfaction in his W-2 life, but what set him apart was his proactive approach. From proposing an innovative national video marketing campaign at his old job to boldly stepping out and launching his own company months ahead of schedule, Jake is living proof that when you're called to something, you go. We talk about the fears, the mental gymnastics of waiting for the “perfect time,” and how our core council helped him make the leap. What stood out most to me is Jake's clarity on his mission—not just in business, but in life. He’s not only building top-tier golf simulators for homeowners and commercial facilities alike, but he's also driven by deeper values: mentoring, community, and excellence through Christ. His approach is deeply relational. He responds to clients the same day, customizes solutions down to the studs, and shows up with passion and purpose. Jake isn’t just building simulators—he’s building trust, freedom, and experiences that make a lasting impact. And he’s doing it while learning how to be a husband, supporting his wife’s food truck launch, and living out his faith in a way that truly inspires. This episode reminded me of what it really means to pursue freedom—freedom of time, freedom in Christ, and the freedom to create something meaningful. Jake’s story is a masterclass in patience, obedience, and the power of community. It’s a testimony to what happens when you stop waiting and start building. I’m proud to know Jake, to watch him grow, and to learn from his fearless pursuit of what matters. Whether you're considering a side hustle or wrestling with your next move, this episode is for you. Let Jake’s journey be your wake-up call—because if he can do it, you can too.

    43 min

  5. 04/22/2025

    Exclaim Jesus: Branding, Belief & Bold Purpose

    On this episode of the Successfully Unsuccessful podcast, I had the pleasure of sitting down with Nash Faulk, a man whose journey from a non-believing, basketball-obsessed kid to a faith-filled entrepreneur is both raw and inspiring. We talked through his early years marked by dysfunction at home and a singular focus on basketball, which ultimately gave way to a winding road of self-discovery, professional experimentation, and deep spiritual transformation. Nash shared how his initial years in sales and tech eventually led him to question the purpose of it all, sparking a spiritual hunger that was finally satisfied when he encountered the truth of God’s Word, starting with the book of James. What really stood out to me was how Nash's entrepreneurial path became an extension of his faith journey. He went from chasing worldly definitions of success to embracing his calling through brand building and fractional marketing. His story about the birth of the “Exclaim Jesus” brand—scribbling spiritual truths on a notepad and watching that turn into a bold faith-forward apparel line—was powerful. What I loved most was his perspective on branding as a unique reflection of personal story and values. In a world of noise and sameness, Nash is helping others stand out by anchoring their business identities in what matters most. We also talked about integrated living—how community, business, and faith aren’t meant to be compartmentalized. Nash challenged the idea that marketing is just tactics and ROI; instead, he believes that belief systems shape brands. He brings that to his clients, helping them unpack their unique story so their messaging is authentic and enduring. His insights into the long game of building something meaningful, especially in a culture obsessed with instant results, hit home. This episode was a real one, full of truth, testimony, and reminders of what matters most when walking in purpose.

    55 min

  6. 04/15/2025

    Grace Over Grind: Redefining Success Through Surrender

    In this powerful and deeply personal episode, I had the honor of sitting down with Jim Walczak—an incredibly resilient, faith-filled man who’s navigated intense challenges, transformation, and wild success in the world of sales. What struck me most was his openness about the journey from a works-based faith to one rooted in grace, and how that revelation transformed not only his relationship with God but also the way he parents, mentors, and lives every day. Jim reminded me how critical it is to simplify our understanding of Jesus—how grace, not performance, is the foundation—and how that clarity opens the door to true freedom. We talked about his transformation from a performance-driven persona to someone who fully embraces his identity in Christ. His story of addiction at a young age, his battle to overcome shame, and his path into a high-powered sales career while staying grounded in faith is incredibly inspiring. Jim's candid reflection on parenting, the pain of a 40-year marriage ending, and how he found restoration in vulnerability speaks to the real struggles so many of us face behind closed doors. He also shared how intentional disciplines like reading Proverbs daily and praying for wisdom have helped him stay centered and move forward with purpose. What I love about Jim’s story is how it's both raw and redemptive. Even with all his professional achievements, his heart is focused on serving others and pointing people to Jesus. He’s a man who has truly lived the “successfully unsuccessful” mantra—owning his past, embracing his calling, and choosing to live in the moment with passion and faith. This conversation reminded me that the goal isn’t perfection, but joyful discontent—the constant pursuit of becoming more like Christ, even through hardship. Jim’s vulnerability will stick with me, and I hope it encourages others to embrace their own stories and walk more boldly in grace.

    58 min

  7. 04/08/2025

    Excellence Over Success: Leading with Eternal Purpose

    I had the chance to sit down with my friend Alex Wilson, a man I deeply respect and admire, for this powerful episode. Alex is a husband, father of three boys, and a Chick-fil-A owner/operator of two thriving locations. But behind the accolades and business success is a story of perseverance, obedience, and faith. We reflected on the early days—our time in a peer advisory group together, his unique journey from consulting to fast food, and how God used seemingly unrelated experiences to prepare him for this season. His path wasn't linear, but it was divinely ordered. Alex's heart for excellence over success really stood out. We talked about how Chick-fil-A’s values, particularly their commitment to glorify God, shape the way he leads his stores and teams. He opened up about the ongoing tension between competitiveness and surrender—between chasing wins and pursuing the will of God. I loved how he put it: excellence is doing your best unto the Lord, not chasing recognition. His insights into running a business while keeping Christ at the center challenged me. He’s not just building stores; he’s building culture, legacy, and discipleship opportunities. But maybe the most impactful part of our conversation was the honest back-and-forth about fatherhood, marriage, and identity in Christ. We dug into what it means to truly die to self, to trust God with our time and influence, and to live out our faith authentically in every area—home, work, and beyond. Alex shared how his intentionality has created margin to invest deeply in his family and community. For both of us, this episode was more than a conversation—it was a moment of sharpening, reminding us that success is defined by obedience and that our lives are best lived when surrendered to Him.

    49 min

  8. 03/18/2025

    Belief, Business & Legacy: Leading with Purpose

    As business owners and executives, we often measure success in numbers—profit margins, revenue growth, and market share. But what if true success isn’t just about financial gain? What if it’s about something much deeper—about faith, about purpose, about how we steward the opportunities and gifts we’ve been given? In this episode of Successfully Unsuccessful, my co-host Chris Baird and I explore the foundation of the BEAST framework: belief. Because belief is what shapes everything—our leadership, our businesses, our relationships, and ultimately, our legacy. One of the most powerful illustrations of this is the parable of the talents. Each of us has been entrusted with something—skills, resources, influence—not to be buried, but to be cultivated. In the same way that a business grows through innovation, vision, and strategic decisions, so does our faith and our purpose. But here’s the challenge: too often, we separate our faith from our work. We assume that doing God’s work is reserved for pastors, missionaries, or church leaders. The reality? Every single one of us is called to be a disciple and make disciples—right where we are. Whether you’re a CEO, an entrepreneur, or a team leader, your workplace is your mission field. Leading with integrity, treating employees with respect, and serving customers with excellence aren’t just good business principles—they’re ways to glorify God in what we do every day. But the purpose isn’t just about business—it’s personal too. Toward the end of our conversation, I shared something that’s been weighing on me: my marriage. It’s easy to prioritize work over relationships, to chase career success while neglecting the people who matter most. But what’s the point of professional growth if our personal lives crumble? Transformation starts with belief—believing that change is necessary, possible, and worth pursuing. Whether it’s improving our marriages, becoming more intentional with our families, or deepening our faith, we have to ask: What’s holding me back? What fears, excuses, or limiting beliefs are keeping me from stepping into my God-given purpose? This episode is an invitation—to reflect, to realign, and to take action. Because success isn’t just about what we build, but about who we become in the process.

    33 min
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5
out of 5
6 Ratings

About

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.

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