Episodes

The struggle is real, but so is the strength that emerges from it. This raw, unfiltered episode takes you behind the scenes of entrepreneurship when everything that can go wrong, does. Windsor Fair season brings both celebration and chaos as we mark my daughter Paisley's first birthday while simultaneously dealing with our third consecutive year of vehicle disasters at this event. The bus is leaking brake fluid faster than I thought possible, the shifter linkage disconnected, and we're stranded...

Ever feel like you're putting everything into your business only to fall short of expectations? That's exactly where I found myself at the Skowhegan Fair this year. After days of watching people walk past my booth, enduring stretches of 5-6 hours without a single sale, I had to make a critical mental shift that entrepreneurs rarely talk about: redefining what success looks like mid-journey. When my original sales goals became clearly unattainable, I set new targets that would still represent...

Sometimes the hardest moments reveal our greatest blessings. From the comfort of my wife's camper instead of the school bus I planned to sleep in, this episode takes you on the raw, unfiltered journey of a small business owner fighting for survival at the Skowhegan State Fair. What does it feel like to open your booth in 95-degree heat, wait five hours for your first sale, and end a 10-hour day with just $120 in your pocket? I'm holding nothing back as I share the mental battle between the d...

We explore the transformative impact of appreciation in both personal and professional settings while preparing for a new adventure at the Skowhegan Fair. • Appreciation makes a significant difference in how we feel about our work and relationships • A stark contrast between DJing at an unappreciative biker bar versus a 9-year-old's birthday party • Living in a school bus for 11 days at Skowhegan Fair while missing family milestones • The "crunch season" of running back-to-back fairs and managi...

Faced with balancing career and family, DJ Keith makes a life-changing decision to step away from his longtime gig at Bentley Saloon to focus on fatherhood and more profitable ventures. • Reflecting on a successful final "Mullets and Daisy Dukes" night with strong crowd participation • Struggling with staff tensions around playing past the scheduled 11 PM end time • Entertaining an enthusiastic bachelorette party that inspired extending the night • Delivering an unplanned, emotional farewell sp...

The journey to Syracuse Nationals wasn't just another road trip – it was a testament to resilience in the face of adversity for Loud Proud American. What began with a production nightmare when our custom racing t-shirt design arrived completely wrong quickly cascaded into a series of challenges that would test our limits. Picture this: six hours on the road in 100-degree heat with a temperamental air conditioner that alternated between cool and hot air every 20 minutes. Our 10-month-old daug...

Resilient optimism isn't just a trendy concept—it's the beating heart of entrepreneurship. After exploring this powerful mindset last week, we immediately faced the perfect opportunity to put it into practice at our first fair of the season. The results? A much-needed victory that confirmed we're trending in the right direction after a challenging start to the year. Every single day of our four-day event outperformed its counterpart from last year, and our brand-new "Midnight Hammer" t...

Ever feel like you're drowning in challenges while trying to stay positive? That tension between acknowledging reality and maintaining hope is exactly what this episode explores through the lens of resilient optimism. We dive deep into the entrepreneurial journey — not the glamorized social media version, but the raw reality of sitting in 95-degree heat for hours to make $40, losing $1,200 worth of merchandise before a major event, and somehow maintaining belief that better days are ahead. T...

Breaking a streak of bad luck doesn't require perfect circumstances – it demands a perspective shift that transforms how we experience life's inevitable challenges. As I celebrate the milestone of 260 episodes spanning five consecutive years of Share the Struggle, I find myself reflecting on a chaotic 24-hour period that perfectly illustrates this truth. From malfunctioning equipment and surprise mortgage payments to vehicle breakdowns, the universe seemed determined to test my resilience. Y...

Ever notice how that familiar routine you once loved suddenly feels like a prison? That's exactly what hit me this week as I found myself sweating in my garage, recording this episode while contemplating one of life's hardest truths: I've outgrown my comfort zone. After 13 years of entertaining crowds at Bentley Saloon's bike week—hosting pinup contests, DJing events, and building my brand—I faced an uncomfortable realization. What once felt like my safety net had transformed into a source o...

Have you ever felt that pit in your stomach when you realize a relationship you once cherished has evolved into something that drains rather than sustains you? That moment when it dawns on you that your time, energy, and goodwill are being taken for granted? This raw, vulnerable episode dives deep into the murky waters of exploitation in relationships – whether business partnerships, friendships, or professional connections. We begin by examining the subtle evolution from mutual benefit to one-...

We explore how unexpected blessings can become powerful catalysts for change when we recognize and embrace them with gratitude. • Life often tests us hardest right before sending the solutions we need • Comparing ourselves to ducks – calm on the surface but paddling frantically beneath • The challenge of running a business without reliable transportation for our family and camper • How friends Matt and Sarah from Ledgeway Farm blessed us with their farm truck, plow, and trailer • The spiritual ...

Freedom of expression comes with responsibility, and when our nation's independence celebrations are targeted for cancellation, we need to examine what this means for our shared values and identity as Americans. • TikTok trends attempting to cancel July 4th celebrations have gained national attention • Celebrating Independence Day transcends political differences and administrations • The importance of maintaining patriotic traditions even during politically divisive times • Media narratives...

What happens when life forces you to confront deep-seated negativity? My wife joins me to share her transformative journey in this powerful episode that examines how removing toxicity creates space for unexpected blessings. After losing her mother to suicide, my wife began evaluating every aspect of her life—relationships, possessions, and most significantly, her increasingly toxic workplace. Despite creating her referral department position from scratch and investing five years with the compan...

Ever find yourself questioning whether the entrepreneurial journey is worth it? That moment when you look at the calendar, realize half the year has passed, and your goals seem further away than ever? You're not alone. After a transformative weekend of back-to-back events kicking off our busy "selly season" (that perfect blend of selling and silly that defines entrepreneurial life), I'm sharing the raw truth about what keeps me going after nearly five years in business. This Memorial Weekend ma...

What happens when your business is growing 92% but you're still struggling with doubt, guilt, and anxiety? Welcome to the entrepreneur's paradox. Ever feel like you're being pulled in multiple directions at once? In this revealing solo episode, I dive into the complex emotions that come with balancing new fatherhood, business expansion, and pursuing the American dream on my own terms. After sharing some heartfelt appreciation for my wife's recent vulnerability on the podcast, I explore how our ...

Alli joins us again to share the conclusion of her healing journey through shamanic Reiki sessions, focusing on finding closure after her biological mother's passing due to addiction. • Appreciating listeners who reached out with support and sharing similar experiences • Describing the experience of loving an addict as a roller coaster of ups and downs • Importance of setting boundaries despite others' opinions about family relationships • Significance of angel numbers, particularly 555 repr...

Alli returns to share her healing journey after opening up about her mother's tragic loss to addiction and suicide last week. • Sharing raw, vulnerable stories in real-time speeds up healing and can help others find their own path forward • Multiple listeners reached out after last week's episode to share their own struggles and some even requested to share their stories on the podcast • Alli explains she's "good" because the hard part - the constant worry about her mother - is over, allowing h...

The grip of addiction tears through families like a silent hurricane, leaving behind shattered relationships and broken promises. In this raw, vulnerable episode, we dive deep into what it truly means to love someone battling addiction – and the impossible choices that love sometimes demands. Through a daughter's heartbreaking journey growing up with addicted parents, we witness the devastating ripple effects that spread through generations. From enduring physical abuse as a child to protect he...

"Maine continues to cater to transgenders at the expense of women." This powerful statement opens a raw, honest conversation about a growing controversy in Maine's social landscape. Following the state's decisions about transgender policies in women's sports and prisons, attention now turns to the Miss Maine pageant, where the first-ever transgender contestant will compete in the traditionally female competition. The episode features deeply personal insights from a former Miss Maine contestant ...

Maine's transgender policies have cast the state into an unwelcome national spotlight, creating ripple effects that reach from schoolyards to prison cells and ultimately into living rooms of everyday families like mine. The federal government recently pulled $1.5 million in funding from Maine's Department of Corrections over its policy allowing transgender inmates to be housed according to their gender identity rather than biological sex. At the center of this controversy is a biological male w...

I explore whether social media can actually increase productivity, sharing surprising results from a challenge my wife gave me to do TikTok Lives while working. This counterintuitive approach completely transformed my perspective on how social platforms can benefit my business. • My struggle with social media as both necessary for business and a massive distraction • How dopamine addiction creates a cycle of unproductivity and guilt • My wife's challenge to use TikTok Lives while working on hat...

The moment you notice something isn't right with your child, your entire world shifts on its axis. For us, that moment came when our six-month-old daughter Paisley began experiencing strange head-dropping episodes that would ultimately lead us on an unexpected 72-hour journey through fear, uncertainty, and eventually, profound relief. What started as a routine Friday quickly spiraled into a whirlwind of medical consultations that left us caught between two drastically different opinions. Our tr...

After our Daytona Bike Week adventure, we face the hard truth about whether the financial outcome justified the personal sacrifices made to attend the event. The tension between leaving family behind and achieving business results creates a powerful backdrop for exploring what "success" really means. • Financial results fell short of expectations despite positive relationship-building • Leaving a 5-month-old daughter behind created significant emotional struggle • Being positioned off the main ...