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 excha

Successfully Unsuccessful is a business podcast hosted by Josh Dittrich, with 50 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Josh Dittrich hosts Successfully Unsuccessful, a business show with 50 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #49

  From Weed Ponds to Kingdom Purpose

  Jun 10, 20251 hourS1

  <p >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 scale...

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  Episode #48

  Built to Rise: Redefining Success Through Faith and Leadership

  Jun 3, 20251h 13mS1

  <p >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 ow...

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  Episode #47

  Dad Awesome vs. Dad Angry: Leading with Legacy

  May 6, 202555 minS1

  <p >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...

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  Episode #46

  From Comfort to Calling: Jake Howes' Leap of Faith

  Apr 29, 202543 minS1

  <p >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 w...

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  Episode #45

  Exclaim Jesus: Branding, Belief & Bold Purpose

  Apr 22, 202555 minS1

  <p >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...

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