Driven To Win
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.
Driven To Win
506 | Why Only 2% Will Ever Win — A Conversation With Carson Porter
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In this powerful conversation, Chaz Wolfe sits down with insurance and financial services leader Carson Porter, a builder of community, a sharp thinker, and a coach who’s helped thousands of agents level up both their mindset and their income. Carson shares openly about the internal battles he’s fought, the identity shifts he’s made, and why helping others has been the key to his own success.
Carson breaks down the mindset patterns holding most people back — fear of investing in themselves, hesitation, lack of clarity, and the story loops that keep entrepreneurs “stuck” even when they know what they should do. He dives deep into what he calls “value without expectations,” the belief that true abundance only comes when you stop guarding your value and start giving it away freely.
Together, Chaz and Carson unpack the real reason most entrepreneurs don’t take action, the difference between knowing something and actually doing it, and how stepping into community removes blind spots you could never fix alone. Carson shares stories from his massive insurance community, where new agents, million-dollar producers, and everyone in between grow together in a culture built on honesty, commitment, and doing the work no one else wants to do.
They explore the power of deep thinking, teaching as a tool for mastery, freedom through remote work, leveling up family life through intentional decisions, and the ripple effect leaders create — a butterfly effect that impacts clients, families, and future generations.
If you are an entrepreneur who wants to think bigger, act faster, and surround yourself with people who hold you to a higher standard, this episode will light you up.
Carson’s community: Winning at Insurance (free group on Facebook)
Carson on social: @cporter389
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