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Share The Struggle
Over 250 Weekly Episodes

Share The Struggle

If you find strength in the struggle then this podcast is for you!

Everyone struggles the difference is some of us go through it and some of us grow through it, the choice is yours.

Share The Struggle Podcast is a raw real-time response to life from a Patriotic S.O.B with an entrepreneurial mindset and a leadership obsession.

In this podcast, Keith Liberty shares a collection of life lessons that led him to bet on himself, wins losses, and funny F-ups in between. Leaving a career to chase his American dream, follow along as he builds a brand. His transparent and explicit approach to life and storytelling will keep you entertained.

Often joined by his wife and best friend Allison or an occasional guest STS is a weekly show with diverse topics that always end with a positive message.

Keith strives to build strength by sharing his struggles and encouraging you to grow through your struggle.

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Recent Episodes

Sept. 3, 2025

When Life Changes, We Choose How to Grow

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…

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Aug. 27, 2025

When Everything Goes Wrong, Keep Moving Forward

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...

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Aug. 20, 2025

The Courage To Take One More Step

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…

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Aug. 13, 2025

Camper Confessions: Finding Faith at the Fair

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…

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Aug. 6, 2025

What a Difference Appreciation Makes

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...

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July 30, 2025

Good Parenting Or Bad Business? You Tell Me

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...

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July 23, 2025

When Your First Time Is Your Worst Time, Keep Going Anyway

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…

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July 16, 2025

First Fair Success: Business Challenges and Family Memories

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…

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July 9, 2025

Resilient Optimism

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…

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July 2, 2025

Finding Grace When Everything Goes Wrong: Lessons in Gratitude

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…

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June 25, 2025

When Loyalty Becomes a Barrier to Growth

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 cro…

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June 18, 2025

Are They Taking Advantage? Actionable Steps to Reclaim Your Worth

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 good...

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Recent Blog Posts

Aug. 19, 2025

Camper Confessions: Finding Faith at the Fair

The Journey of a Small Business Owner: Counting Blessings Amidst Struggles Running a small business is often romanticized as the ultimate freedom—being your own boss, setting your own hours, and building something from nothing. What's rarely …

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Aug. 19, 2025

What a Difference Appreciation Makes

The transformative power of appreciation cannot be overstated, whether in personal relationships or professional settings. In this week's Share the Struggle podcast episode, I explore this concept through a simple yet profound experience that perfec…

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Aug. 19, 2025

Good Parenting Or Bad Business? You Tell Me

  The age-old struggle between career and family took center stage at Bentley Saloon last weekend when longtime DJ and podcast host Keith made an unexpected announcement during his final set of the season. What began as a typical "Mullets and …

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Reviews

Motivation that is fun!

"Been a loyal listener since day one and it keeps getting better and better. Keith (and sometimes Alli) do not hold back about the real life struggles they have. Keith is always sharing self help an…"

Jen Barnes | April 20, 2022

Must Listen to Episode 86

"Episode 86 is a must listen to....if you are an American and you are working this episodes breaks down what is wrong with the leaders of our wonderful country...."

Jen Barnes | April 29, 2022