Episodes

Holidays have a way of turning up the volume on everything—joy, grief, pressure, and hope. This week, we follow a small family errand that became a marker moment: a dad, his daughter, his brother home after 15 years, and thei...

A snow globe of a day turns into a reunion years in the making as we welcome my brother home and share our first Thanksgiving together in decades. We open about addiction, boundaries, small business stress, and the hope that ...

Holidays bring glitter and gravity at the same time. We’re laughing about hot coffee and bulldogs one minute, then staring down the second anniversary of my dad’s passing the next. That’s real life at our place: farm chores, ...

The kind of moment that keeps a dream alive doesn’t always arrive with a banner; sometimes it’s a quiet ping at the register and a lump in your throat. We finally crossed the sales number we set five years ago—through shutdow...

The holiday rush came roaring back and, for a weekend, the mall felt alive again. We landed a two-week pop-up at the Bangor Mall, solved a tough layout challenge, and ended up with a space that felt like our own shop—clean si...

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 le...

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...

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 mornin...

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...

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 bre...

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 ...

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 rem…

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, examinin...

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 bus...

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…

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 celebrat...

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 ment…

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 lik…

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...

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 "Mul...

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 tha…

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 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 v…

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 chao…