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Driven To Win
Driven To Win episodes
- 134 | Lessons Learned from Losing 2 Businesses in the 2008 Crash W/ Tyler PrattIn this episode, Chaz Wolfe sits down with entrepreneur Tyler Pratt to discuss his journey. They delve into the importance of balance in ambition, Pratt's experience with bankruptcy, and the growth of High Voltage Inc. They also touch on Pratt's views on money, a significant lawsuit, and his inspiration from Teddy Roosevelt. The episode closes with a book recommendation and tips on balancing business with family life.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.55 min - 133 | The Obsession with Growth: Strategies for Expanding Your Business W/ Dennis SteinIn this episode, Chaz Wolfe chats with Dennis Stein, a former corporate retail worker turned business owner. They discuss Dennis's career transition, the importance of building the right team, and the impact of a thorough interview process. Dennis also shares insights on investing back into business and the effectiveness of guerrilla marketing.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.45 min - 132 | From Firing To Presidency: The Comeback Story of Jerry JehnIn this episode, guest Jerry Jehn joins Chaz Wolfe to discuss the influence of AI on industries, the importance of a joyful workplace culture, and his personal entrepreneurial journey. They delve into personal growth, the impact of bold business decisions, and the significance of lessons from past experiences. The discussion also covers the importance of cash flow and networking, maintaining life balance, and concludes with Jerry's advice for his younger self.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.53 min - 131 |The Jobs Not Finished W/ Matthew McReynoldsIn this episode, Chaz Wolfe chats with Matthew McReynolds about his entrepreneurial journey, the dynamics of family business, and the importance of self-growth and accountability. They delve into the challenges of owner-reliant businesses, discuss the key roles in business, and share insights on business growth strategies. Matthew also emphasizes profitability over revenue and shares valuable resource recommendations.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.57 min - 130 | Faith, Family, Then Financial W/ Rick ButlerIn this episode, Chaz Wolfe is joined by Rick Butler to discuss how he incorporated Christ-like behavior into his business. They delve into Rick's family business evolution, the role of family in decision-making, and lessons from past mistakes. The episode wraps up with a speed round about business tracking, book recommendations, and contact information for Rick.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.27 min - 129 | Raising Up Leaders W/ Dean BradyIn this episode, Chaz Wolfe engages with entrepreneur Dean Brady on his business journey, the importance of company culture, and the role of personal growth in business. They explore overcoming delegation fears, handling employee performance issues, and the implications of trust in decision-making. The discussion also covers stress management, maintaining business principles, and the benefits of team diversity. Dean finishes with advice to his younger self and insights on emotional control.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.44 min - 128 | Organize Your Life & Business W/ Tina O’KeeffeIn this episode, Chaz Wolfe sits down with Tina O'Keeffe, a professional organizer. They discuss the psychological aspect of organizing, the importance of trust-building, and how to address client fears. Tina shares lessons from bad decisions, maintaining boundaries, and how to properly value services. They also discuss task prioritization, decision-making, and the role of an organizer for clients.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.46 min - 127 | Building A Beauty Business W/ Richard KostickIn this episode, Chaz Wolfe welcomes Richard Kostick, who shares his journey of creating a successful beauty brand. They delve into strategies for balancing risk and growth, navigating business during the pandemic, and decision-making under uncertainty. The discussion also covers building a high-performance remote team, leadership, key performance indicators, and networking. Kostick concludes with advice for young entrepreneurs.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.51 min - 126 | Boom & Bust W/ John SharpeIn this episode, Chaz Wolfe welcomes guest John Sharpe. They dive into John's entrepreneurial journey, exploring his backstory, first business, and transition into a recession business. John shares his reflections on adversity, global challenges, and the importance of sobriety for success. Through the lens of self-awareness and decision-making, they discuss overcoming obsessions and the role of reading in business growth. The episode concludes with a call to action to join the Gathering The Kings community.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.39 min - 125 | Building a Media Empire: Strategies from Emmy Winner Vinnie PotestivoIn this episode, Chaz Wolfe chats with Vinnie Potestivo, discussing his career journey and insights into business. They explore the power of podcasting for networking, leveraging awards, and the importance of an intentional entrepreneurial mindset. The chat concludes with advice for younger self and strategies for visibility.
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Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.59 min
About Driven To Win
From the publisher's feed
Driven To Win is the podcast for entrepreneurs who refuse to choose between building a successful business and building a strong family.
Hosted by serial entrepreneur Chaz Wolfe,…
the show is built for business owners who want to scale their companies, lead stronger teams, and create a life that wins both at work and at home. Chaz built and scaled multiple businesses by his late twenties, becoming a millionaire by 29 and a multi-millionaire soon after through ventures in franchising, home services, real estate, and online education. His approach centers on leadership, systems, and structure that allow businesses to grow without the owner carrying all the weight.
On Driven To Win, Chaz sits down with elite entrepreneurs, business leaders, authors, and operators to break down the real strategies behind growth. These are not surface level conversations. Each episode focuses on the practical disciplines required to build companies that run through strong leadership, clear structure, and effective sales systems.
On Driven To Win, Chaz sits down with elite entrepreneurs, business leaders, authors, and operators to break down the real strategies behind growth. These are not surface level conversations. Each episode focuses on the practical disciplines required to build companies that run through strong leadership, clear structure, and effective sales systems.
But business success is only half the conversation.
Driven To Win is built around the belief that true success means winning in all areas of life. That includes business, family, health, faith, and lifestyle. Through honest conversations and practical insights, the show challenges entrepreneurs to build businesses that support their family life instead of competing with it.
Listeners will learn how to:
• Scale a business through leadership and systems
• Develop stronger sales and operational discipline
• Build teams that reduce owner dependence
• Lead their family with the same intentionality they lead their company
• Create a legacy that lasts beyond the business
Whether you are building your first company or scaling an established business, Driven To Win delivers clear strategies and real conversations with leaders who are committed to growth in every area of life.
If you are serious about building a business that creates freedom instead of pressure, this podcast is for you.