In this deep-dive conversation, Dustin sits down with business coach Winston Payne, a seasoned entrepreneur who sold his company, retooled his career, and now helps other business owners navigate their own pivotal transitions.

Together, they explore what’s really holding entrepreneurs back from growth—and it's not the market, the team, or the economy. It’s often themselves.

From the technician who can’t let go of the day-to-day to the owner wrestling with succession and legacy, Winston unpacks the most common mindset gaps he sees in 2025. He shares the tools he uses in his coaching—including values clarification, DISC profiling, and the simple question: "What are the top three things you want to achieve right now?"

They also dive into:

• The difference between mentoring and coaching
• Why small business owners need space to think, not just hustle harder
• How to recognize the performance gap between what you're doing and what you're capable of
• And the power of mastermind groups for accelerated growth and accountability

Whether you're building your first team or wondering how to step away from a business you built from scratch, this episode will help you see the blind spots, upgrade your thinking, and move with more intention.

Resources Mentioned:

• The 7 Habits of Highly Effective People by Stephen Covey
• Think and Grow Rich by Napoleon Hill
• 🧭 DISC Personality Profile
• Wheel of Life self-assessment

Connect with Winston Pain:

Website: www.wpcoachingservices.ca

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