Share The Struggle

A missing laptop charger, a freezing parking lot, and a crowd of costumed kids shouldn’t add up to a breakthrough—but that’s exactly where the weekend took us. What started as a simple pair of charity DJ gigs turned into a lesson on composure, community, and the kind of closure you don’t plan for but desperately need. We kick off with a trunk-or-treat at Arundel Ford a local Ford dealership, where...

What if the thing you’re missing is the very thing that could make you unstoppable? We dig into the uncomfortable truth that scarcity can be a strategic advantage and explore how to turn setbacks into a springboard for action, growth, and grit-fueled wins. Pulling from 50 Cent’s The 50th Law, we break down why “every negative situation contains the possibility for something positive,” and then put...

Grief doesn’t keep a tidy calendar. After months of waiting, closed doors, and a family pulled in different directions, we finally laid a mother to rest beside her dad and felt the first real breath of relief. The next morning, we did something brand new together: we walked into church as a family, not for ceremony or obligation, but for hope. What unfolded was honest and unscripted—tears in the f...

Grief can flatten you—or forge you. On Charlie Kirk’s first heavenly birthday, we sit with the weight of loss and the power of witness as Erica Kirk accepts the Presidential Medal of Freedom and models a fearless, faith-first path forward. That moment reframed our day and our decisions, pulling a simple prayer—“Thy will be done”—from ink on skin into the center of our work, our words, and our home...

The season finale came with bigger stakes and sharper edges: we expanded our Fryeburg Fair booth by 10 feet, doubled down on Made in USA quality, and walked straight into the kind of attention that tests your backbone. We break down the real numbers—rent jumps, tent upgrades, inventory bets—and how an opening surge leveled into a week that finished a hair shy of our all-time record. Second best ev...

When everything that can break decides to break—bus, budget, and belief—you find out what you’re really building. We pushed into our biggest Fryeburg Fair ever by tripling our booth size, stretching every dollar, and betting on our community. Then the week erupted: the bus died at a gas station, the camper lights quit at dusk, and the last credit card barely covered a rental truck. We turned wrenc...

Left-wing lunatics hoped for a funeral. America got a revival.  Sunday's Charlie Kirk memorial service transformed into something extraordinary - a spiritual awakening that reached far beyond the 100,000 people physically present in Arizona. Viewers worldwide witnessed not just remembrances of a remarkable 31-year-old conservative leader, but testimonies that sparked what many are calling a t...

The brutal assassination of Charlie Kirk has left America reeling, forcing us to confront the devastating reality of political violence in our nation. In this raw, emotional episode, we process this tragedy together, examining not just what happened, but what it means for our collective future. Charlie Kirk embodied something rare in today's political landscape—a willingness to engage with op...

Life gets hectic at the Liberty household as we prepare for Fryeburg Fair, work weddings, and navigate a major career change that could transform our family's work-life balance. • Fryeburg Fair approaches with significant business preparation, requiring us to bring in about 2,000 items in the coming weeks • We successfully DJed Jake and Sage's wedding despite last-minute challenges and a...

We celebrate our daughter's first birthday while reflecting on a challenging yet rewarding year at Windsor Fair and the struggles that shape our entrepreneurial journey. The road isn't always smooth, but finding joy and purpose through difficulties has become our greatest strength. • Overcoming bus mechanical failures with the help of "redneck mechanics" who found creative solu...

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...

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-journ...

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 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 Skow...

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 enth...

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 temperame...

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 da...

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 wo...

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...

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 build...

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,...

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 Mat...

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 imp...

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. Desp...

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),...