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Driven To Win

Driven To Win

著者: Chaz Wolfe
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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.


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.

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  • He Didn't Start Playing Until 14. Then He Went Pro for 10 Years | Dre Baldwin
    2026/10/19

    Connect With Chaz

    Dre Baldwin did not start playing basketball until he was 14. He played one year of high school ball, mostly from the bench. He walked on at a Division III school, a level that almost never sends anyone to the pros.

    After college he sold gym memberships and worked at Foot Locker. Then he paid his own way into an exposure camp in the summer of 2005, played well, signed with an agent, and was playing pro ball in Lithuania a few weeks later. He played professionally for almost 10 years.

    Today Dre runs Work On Your Game. He has written 11 books, spoken at TEDx four times, and built more than 48 million views on YouTube. In this conversation with Chaz Wolfe, he breaks down the mental toughness behind all of it, and how a business owner can use the same playbook.

    KEY TAKEAWAYS

    1. Quitting and pivoting are not the same thing. Dre walked away from baseball because he did not have the talent. He kept the goal and changed the vehicle. Owners do the same when a service line or a market stops working.
    2. If it is not working, your formula may be wrong. When a business stalls, Dre says the strategy itself may be off. Find someone who already has the right information and learn from them.
    3. Review your habits like employees. Every habit gets a review. Keep it, adjust it, or let it go.
    4. Work backward from the goal. Dre calls it a reverse roadmap. Start with the result, then decide what has to be true at each step to get there.
    5. Moderation is average. Dre says there is no neutral in life. You are either getting better or getting worse. Clear yes or no rules make hard decisions easy.
    6. Invest in yourself early. His advice to his younger self is to start investing in himself as soon as possible, in what he learns and in who he spends time with.

    If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you.

    Go to gatheringthekings.com and apply for a GTK Growth Audit. We will show you exactly where you are leaking time, profit, and opportunity, and what it would take to fix it.

    Connect with Chaz Wolfe (Host):

    Website

    Facebook

    Instagram

    LinkedIn

    YouTube

    Connect With Dre Baldwin:
    Website: https://dreallday.com

    Support the show

    Like what you heard?

    Share this episode with a friend and leave us a review on Apple Podcasts or Spotify!

    Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

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    49 分
  • 451 | His Company Lost $7 Million on One Job. Here's What He Did Next with Ryan Schmitt
    2026/10/12

    Connect With Chaz

    In 2018, Ryan Schmitt thought he was having a heart attack. He was cutting every dollar he could find in the business, and he was trying to decide whether to cancel the key man life insurance policy. He kept it. Because he was not sure he was going to make it.

    The company he had built over a decade had just lost $7 million on one job. They had lost their bonding. He had borrowed $2 million from a colleague. He was staring at the ceiling every night.

    He never had a single employee leave.

    Today, 230 people work for Petticoat-Schmitt. They hear the financials every Monday at 3:30. They share in the profits. And Ryan is in the middle of converting the company to an ESOP so his people can own it.

    That is where a valley of darkness can take you, if you walk into the punch every morning and refuse to stop.

    KEY TAKEAWAYS

    1. The most impactful project is often the one that nearly kills you. When Ryan was asked at a conference what his most impactful project was, he immediately named the one that lost $7 million. Not because it was successful. Because it changed everything about how he leads.
    2. Tell your spouse first. Ryan's business group told him to go home and tell his wife before anyone else. She said, "as long as we're together, that's all that matters." That sentence became fuel for everything that came after.
    3. Relationship capital is real capital. Two people showed up with money and resources when Ryan needed them. They said yes because they knew his character, not because the numbers looked good. That is what you are building when you build genuine relationships.
    4. Transparency did not cause a stampede. Ryan shared the full financial picture with his team during the worst of it. Nobody left. In a good market where every other company was hiring, his people stayed. That is what a people-first culture actually produces under pressure.
    5. Stop hiding in your office. Pre-crisis Ryan was head-down at his desk. He thought that was where he was most valuable. He was wrong. Post-crisis Ryan has no office. He shows up on job sites at sunrise with biscuits and questions.
    6. Profit sharing changes the conversation. When employees see exactly how the company is doing and share in the upside when it performs, they stop being workers and start being partners. That shift is what made the rebuild possible and is what the ESOP is formalizing.

    If you are a contractor business owner and you want to make more money, work less, and win at home, we built something for you.

    Go to gatheringthekings.com and apply for a GTK Growth Audit. We will show you exactly where you are leaking time, profit, and opportunity, and what it would take to fix it.

    Connect with Chaz Wolfe (Host):

    Website

    Facebook

    Instagram

    LinkedIn

    YouTube

    Connect With Ryan Schmitt:
    LinkedIn: https://www.linkedin.com/in/ryan-schmitt-14866587/
    Website: https://www.petticoatschmitt.com/
    Facebook: https://www.facebook.com/petticoatschmitt
    Instagram: https://www.instagram.com/petticoatschmitt/
    YouTube: https://www.youtube.com/channel/UCPPhiL7wjPWpFPH30VqMcbQ

    Profit Starts with Better Books!
    Clean books. Clear reports. Monthly bookkeeping built by business owners, for business owners.

    Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.

    Support the show

    Like what you heard?

    Share this episode with a friend and leave us a review on Apple Podcasts or Spotify!

    Join the conversation by visiting GatheringTheKings.com and apply to connect with other high-performing entrepreneurs and their families.

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    43 分
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