Successfully Unsuccessful

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 We...

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...

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 mob...

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 appr...

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, pro...

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...

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 uniqu...

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 th...

In this episode of Successfully Unsuccessful, I sit down with my good friend Skip Johnson to unpack his incredible journey from building a billion-dollar wealth management firm to discovering what true success really means. Skip shares openly about his drive for achievement, the identity struggles that came with it, and the moment he realized that outward success wasn’t bringing the fulfillment he...

In this milestone 40th episode of Successfully Unsuccessful, we take a different approach as I sit down with my co-host and producer, Chris Barrett. We reflect on our shared journey, the impact of radical transformation through faith, and the power of walking the path together rather than alone. Success, as defined by the world, often revolves around financial milestones and personal achievements....

In this episode, I sit down with my good friend Dave Barton, a man whose story is a powerful testament to the transformative journey of faith, intentionality, and relentless pursuit of growth. We dive into Dave's background in corporate America, where he's spent over 20 years navigating roles in banking, retail, and healthcare. Dave shares how his career evolved alongside his passion for mentorshi...

In this heartfelt episode of *Successfully Unsuccessful*, I sit down with my mentor and friend, Ric Olson, a man whose journey through leadership, faith, and resilience has profoundly shaped my own. Ric shares his incredible story, starting with his transformation from a reluctant CPA to a nationally influential leader in healthcare and non-profits. He opens up about the pivotal role faith played...

In this episode of Successfully Unsuccessful, I sit down with Rashad Kennedy, a client, entrepreneur, and friend who has transformed his passion for improvement into a thriving real estate and construction business. From his beginnings as a collegiate wrestler to becoming a multi-faceted real estate developer, Rashad shares his journey of faith, growth, and the power of relentless determination. W...

In this episode of “Successfully Unsuccessful”. I sat down with my good friend, Jordan Olmscheid, who has carved out a unique path as a solopreneur in the cleaning industry. Jordan shares his journey from teaching to managing a window cleaning business, initially started as a side income. Through trial and error, hard work, and a spirit of adaptability, he found his niche in the commercial cleanin...

In this episode, I had an insightful conversation with Jake Stank, diving into his journey through banking, faith, and leadership. Jake shared how his return to the banking world revealed a renewed perspective on purpose, shifting his fulfillment from the technical aspects of finance to the profound impact he has on his team and peers. We discussed how his passion for seeing "the light bulb" come...

In this episode of “Successfully Unsuccessful”, I sit down with Kevin Johnson, a long-time tech lead and entrepreneur at heart. We start by reminiscing about how our connection began at a recent event where Christian entrepreneurs gathered, highlighting the power of community and shared passions. Kevin shares his background as a tech lead, discussing his journey in building world-class software ap...

For this episode of Successfully Unsuccessful, I sat down with Pete Tavernier, a man whose journey has taken him from building a successful auto repair business to following God’s calling all the way to Haiti. Pete's story is one of faith, perseverance, and finding purpose in places and moments where others might see only uncertainty. He shared how a mission trip turned into a life-changing experi...

In this episode of Successfully Unsuccessful, I sat down with Kyle Miller, a dynamic entrepreneur with a background in construction, sales, and leadership. Kyle shared his journey from working in his father's remodeling business to becoming a successful leader in the construction industry. We discussed his early career experiences, including how skepticism about traditional education led him to fi...

In this episode of Successfully Unsuccessful, I had the pleasure of welcoming Jason Paris, founder and partner of Aleph Holdings, to our studio. Our conversation began with a look at Jason's entrepreneurial journey, which started with Paris Painting. Jason shared how his company evolved into a holdings company focused on transforming trade businesses, specifically house painting companies, into sc...

In this episode of "Successfully Unsuccessful," I had the pleasure of sitting down with Jadde Rowe, a dynamic young real estate professional who has navigated the complexities of faith, business, and personal growth. Jade shared his journey from corporate America to the thriving real estate market, emphasizing the significance of taking risks and following one's passion. His story is a testament t...

In this episode of "Successfully Unsuccessful," I had the pleasure of sitting down with Danny Greene in his studio in Long Lake, Minnesota. We explored Danny's multifaceted identity, from his roles as an entrepreneur, content creator, and endurance athlete, to his unexpected musical talents. Danny shared his journey of transitioning from city life to embracing the peaceful countryside, highlightin...

In this episode of Successfully Unsuccessful, I had the pleasure of sitting down with my good friend Matt Eklund. Matt's journey is nothing short of inspiring, from his early days in construction to becoming a project manager overseeing massive developments. But what truly stands out is his personal transformation over the past six years. Matt shared the pivotal moment when he decided to attend ch...

Welcome back to "Successfully Unsuccessful," hosted by me, Josh Dittrich. In today’s episode, I had the pleasure of sitting down with Jordan Crockett, a remarkable individual mastering the art of real estate investment while balancing family life in suburban Eagan. Jordan’s journey from software sales to real estate investment provides a wealth of inspiration for anyone looking to pivot their care...

In today's episode of Successfully Unsuccessful, I had the pleasure of sitting down with Connor Schmidt right here in my home studio in St. Michael. Connor, who is not just a colleague but a friend, delved into his journey of faith, marriage, and career development. We discussed how his life shifted from his bachelor days to becoming a husband and a father, emphasizing the roles of spirituality an...

In today's episode of Successfully Unsuccessful, I had the distinct pleasure of sitting down with Kyle Lanzen, a passionate entrepreneur with deep roots in the retail industry, aiming to revolutionize product marketing. Our discussion, enriched by our mutual connections through a Christian business group, veered into the transformative power of living a life dedicated to a higher purpose. Kyle sha...