Playing to Win, LLC - Love, Leadership, and the Courage to Begin Again with Melanie Kennemann

Melanie Owen Kennemann
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  • Entrepreneurship

Welcome to Playing to Win, LLC, where real conversations inspire real courage. Here, we believe every person has a story, every setback holds a lesson, and every ending can become the beginning of something extraordinary. Each week, you'll hear honest conversations with athletes, entrepreneurs, leaders, authors, and everyday people who chose courage over comfort and purpose over fear. Together, we'll explore love, leadership, and the courage to begin again. Because playing to win isn't about having the perfect life. It's about having the courage to live your own. It's never too late to come home to yourself. Welcome to the conversation!

  1. 1 day ago

    Episode 13- Your Story Ends Well-How Adversity Becomes Your Advantage with Dan Grieb

    What if the hardest chapters of your life were never meant to define you, but to launch you? In this powerful conversation, Melanie Kennemann and Dan Grieb explore the courage it takes to bet on yourself, rebuild after loss, and turn adversity into real advantage.Dan shares the story behind his new book My Adversity Advantage, and why he believes your story ends well even when the middle feels chaotic. He opens up about losing his badge as a police officer, rebuilding his life in real estate, getting his financial life back after collapse, and the redemption that came full circle years later. Along the way, he breaks down the hero’s journey, money DNA, fake pain versus real pain, and the three-part process of moving from adversity to acknowledgment, validation, and gratitude. Together, they get real about what it means to leave behind identities that no longer fit, reclaim confidence, and choose a life that feels aligned again.You’ll also hear the story of Dan’s world-record Iron Man journey with Chris Nikic, the first person with Down syndrome to complete an Iron Man, and how that experience reshaped his understanding of purpose, service, and human potential. From there, the conversation moves into legacy, leadership, healing, and the quiet power of telling the truth about what hurt you and using that to propel you forward in life rather than weigh you down. Extra time on this one full of great life lessons...A must listen!

  2. 22 Oct

    Episode 12- When Life Surprises you with Johana Gervais

    Some life events don’t just change your plans - they force you to rebuild your whole life in one single moment. Melanie Kennemann sits down with real estate agent Joanna Gervais for a raw, hopeful conversation about surviving unimaginable loss, navigating breast cancer, and learning how to begin again without losing yourself. Joanna opens up about moving from Mexico to the U.S. at 12, struggling to learn English, and the teacher who saw potential in her before she could see it herself. Joanna shares the moments that reshaped her family: the sudden loss of her brother, the emotional weight of her breast cancer diagnosis. This convo is an excellent reminder that courage, support, and self-belief can carry you through almost anything.

  3. 15 Oct

    Episode 11- Turning Hard Circumstances into an Unfair Advantage with Ben Kinney

    Most people think success starts with talent, money, or connections. Ben Kinney proves it starts with something far more powerful: learning how to turn hard circumstances into an unfair advantage.Melanie Kennemann sits down with the real estate legend and entrepreneur for a raw, practical conversation about growing up in a cabin with no electricity, working his way through cable installs and commission-only jobs, and building the mindset that later helped him scale companies, create opportunity for others, and stay grounded while doing it. You'll discover:How Ben learned the difference between being busy and being effectiveThe duplex story that changed everything and sparked his move into real estateThe “four fields” framework Ben uses to think about relationships, hiring, and long-term trustWhy he believes the fastest path to growth is not doing everything yourself, but helping other people winThe doubling mindset that shaped Place, Brivity, and the businesses he keeps buildingBen also opens up about the family lessons that shaped him, the leadership mistakes that made him wiser, and why generosity only becomes real when giving actually costs you something. Ben's message is simple but hard to ignore: focus on what you can control, double one thing, and keep moving. If you need a reset on money, leadership, growth, or courage, this conversation delivers it.Melanie brings out the stories, the frameworks, and the heart behind the builder, while Ben offers the kind of no-excuses wisdom that turns inspiration into action.

  4. 8 Oct

    Episode 10-Fierce Determination, Radical Resilience, & the Refusal to Stay Stuck with Clarissa Lopez

    Clarissa Lopez has built brands, raised a family, raised a quarter-million dollars for Make-A-Wish, had a long career in fitness and now she's in the most powerful transformation of her life.On this episode of Playing to Win LLC, host Melanie Kennemann sits down with Clarissa for an unfiltered conversation about the thread connecting every chapter of her life: fierce determination, radical resilience, and the refusal to stay stuck. From becoming the only freshman on varsity drill team to launching a clothing line that reached 155+ stores, Clarissa shares how she learned to trust her instincts, recover from costly business mistakes, and keep moving when life gets hard.

  5. 2 Oct

    Episode 9- The 500-Mile Walk That Reshaped Her Faith, Business, and Purpose with Mallory Mundy

    Most people think a successful life has to look conventional, yet Mallory Mundy built the opposite on purpose. From waiting tables and launching a real estate career to co-owning a pizza shop with her husband in remote West Texas, working across multiple businesses, and walking 500 miles across Spain, Mallory shares the mindset that turned risk into a life she loves. Host Melanie Kennemann sits down with her longtime chosen sister for a heartfelt conversation about reinvention, faith, sobriety, leadership, and building a life by design. If you’ve ever felt drawn to a path that doesn’t fit the usual script, this episode is for you. Mallory also shares how sobriety, time outdoors, and the quiet of the West Texas landscape helped her find clarity—and how the 500-mile walk across Spain became one of the most challenging and meaningful experiences of her life. Mallory’s story is a reminder that you can shape a life around what matters to you—and that you’re worth going after it.

  6. 25 Sept

    Episode 8- From Business Leader to Community Builder- Marybeth Olive and the Power of Showing Up.

    In this episode, host Melanie Kennemann talks with longtime friend and leader Marybeth Olive about developing people, serving others, and building a legacy that reaches far beyond business.Marybeth shares how leadership showed up early in her life, why authenticity and accountability matter, and what she looks for in people ready to grow. The conversation also explores the story behind Sheltered Hearts, the nonprofit Marybeth founded to provide food, shelter, and hope. She recounts how cooking alongside her father grew into a community effort serving thousands of meals, and shares the experiences that shaped her work supporting people in need, including a lasting connection to children and families in Tanzania.Together, Melanie and Marybeth discuss leading with love and courage, finding purpose in the season you’re in, and taking the first step even when the path feels uncertain. Marybeth’s reminder is simple: show up, know your why, and believe that you can make a difference.

  7. 16 Sept

    Episode 7- Turning Pain into Purpose and Potential into Action with Coach Jesse Coleman

    Most people wait for a breakthrough. Jesse Coleman shows why it usually starts with a breakdown, a small decision, and the courage to stop proving the wrong people right. In this powerful conversation, Melanie Kennemann sits down with Jesse, a 19-year real estate veteran, vice president of career development at KW1 Chicago, keynote speaker, trainer, and host of the Breakthrough Blueprint Podcast, to unpack the mindset shifts that turn pain into purpose and potential into action. Jesse shares how growing up on Chicago’s South Side shaped his instinct to protect the underdog, why a single step-in moment as a trainer changed the course of his career, and how losing 110 pounds taught him the same lesson he now teaches others: consistency beats hype every time. From real estate coaching to personal transformation, he reveals the difference between knowing what to do and actually changing, and why the best coaches don’t give answers—they help people discover their own. He also opens up about Quantum Leap for Young Adults, the program he’s taught for seven years to help young people define their mission, rethink their future, and stop shrinking to fit other people’s expectations. Along the way, he shares the unforgettable moments that remind him why this work matters, including helping a young person through a dark mental health struggle and seeing an athlete in one of his trainings go on to win silver at the 2024 Olympics. If you need a reminder that authenticity, action, and self-belief can change your entire trajectory, this conversation delivers it!

  8. 8 Sept

    Episode 6- In Purpose On Purpose with Singer/ Songwriter Sherree Patrice

    Sherree Patrice, the voice behind dozens of iconic records and a career spanning more than 30 years, reveals why reinvention gets easier when you stop tying your identity to applause, labels, or the music industry’s approval. Host Melanie Owen Kennemann sits down with the songwriter, vocalist, arranger, mentor, and recording artist to explore Sherree’s journey—from growing up on the South Side of Chicago and finding music as a refuge to working with artists including Jamie Foxx, Brandy, Babyface, Queen Latifah, Whitney Houston, Usher, Pink, Celine Dion, and Toni Braxton just to name a few. Sherree opens up about the difference between being gifted and understanding the business, the role family and faith played in shaping her success, and how healing helped her reclaim her voice and break generational patterns. Together, Melanie and Sherree discuss identity, purpose, protecting your peace, and the courage to begin again—including Sherree’s new song, “Love Has.” If you’ve ever felt overlooked, underestimated, or ready for a reset, this conversation will remind you that your best years are not behind you. Stay free, trust your assignment, and move forward without waiting for permission. Join in on he conversation!

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About

Welcome to Playing to Win, LLC, where real conversations inspire real courage. Here, we believe every person has a story, every setback holds a lesson, and every ending can become the beginning of something extraordinary. Each week, you'll hear honest conversations with athletes, entrepreneurs, leaders, authors, and everyday people who chose courage over comfort and purpose over fear. Together, we'll explore love, leadership, and the courage to begin again. Because playing to win isn't about having the perfect life. It's about having the courage to live your own. It's never too late to come home to yourself. Welcome to the conversation!

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