Entrepreneurship is all about solving problems—but what happens when you’ve built nine businesses, experienced both success and failure, and learned the hard lessons along the way? In this episode of Outsmart the Hustle, we’re bringing back Ray Myers, a seasoned entrepreneur, business coach, and visionary behind multiple successful ventures. Ray dives deep into his journey of scaling businesses, overcoming setbacks, and knowing when it’s time to let go. One of his guiding principles? “Always teach what you wish you had known.” This conversation is packed with wisdom for anyone looking to grow smarter, not harder—whether you’re in the early stages of entrepreneurship or scaling toward your next big milestone.
Key Takeaways:
- How Ray started his first business at the age of 14
- The mindset shifts required to scale your business
- Key lessons learned from scaling and selling multiple businesses
- The importance of hiring the right people and delegating effectively
- How to break free from burnout and keep pushing forward
- Tips on knowing when to sell and how to exit gracefully
- Why emotional honesty is the foundation of real growth
Outsmart the Hustle helps creative entrepreneurs build brands that convert—through strategy, storytelling, and high-impact content.
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What is Outsmart the Hustle?
Does your creative business struggle to bring in the right clientele and financial leverage, leaving you feeling stuck and frustrated? The Outsmart the Hustle podcast will show you how to turn hard work into smart work! I'm your host, Hannah McGinty, helping you focus on the high-impact moves that drive your business forward without the endless grind. Whether you've been running your business for 20 years or 20 minutes, I'm here to bring you clear, practical strategies from industry experts and successful entrepreneurs who know how to create a sustainable business. I've been running my creative video production business since 2019, where I primarily work in the wedding and event space. And since 2021, my business has continued to hit six figures in revenue. Now imagine that for yourself. What would it help you achieve in life if that meant your passion could turn into a consistent paycheck? Tune in each Tuesday for fresh insights, tools, and ideas to help you streamline, scale, and find freedom in your work—so you can build the business and life you truly want to live.