Welcome to the WINNING INSIDE with Cheddy and Michelle Podcast website!

What is the Winning Inside Podcast About?

Life is a roller coaster; ups, downs, unexpected bumps, and turns are all part of the journey. How we handle those ups and downs impacts who we are, who we become and how we see ourselves. And many times, there are life situations that throw us for a loop and it impacts us in ways seen and unseen. These can have us feeling defeated, stuck, alone and wondering how to move forward. Cheddy Matthews and Michelle Wickman are joining forces to share interviews, chats, and their own journeys riding this roller coaster that we call “life.” If you are working through some of the ups and downs, loop de loops and corkscrews, then this is the podcast for you!

About the Hosts

Cheddy W. MatthewsProfile Photo

Cheddy W. Matthews

Founder/Speaker/Leadership Coach


Making good, great, and great exceptional is what Cheddy Matthews does for individuals and organizations alike. This is not only his passion, but it is his gift, calling, and profession.

As an inspired, conscious-raising, eternally optimistic and faithful lover of people and life, Cheddy believes his work at HED Space Coaching is fulfillment of his life’s purpose. He is a motivational and keynote speaker, transformational leadership coach, Winning Inside Podcast host, business growth strategist, serial entrepreneur, retired U.S. Marine Corps Officer, and most importantly proud father. His purpose for being on this planet, he says, is to leave the Earth better than he found it. Cheddy does this by empowering Business owners and leaders to increase revenues by taking precise actions that yield significant results. He also helps the leaders to better connect, inspire, and support their employees for sustained company satisfaction, growth and an overall improved quality of life. This in turn results in transformative leadership and significant business growth. He calls this powerful skillset his “superpower.” 

“Do it. Do it now. What are you waiting for?”

This quote, from his beloved, late sister Annette Smith, is Cheddy’s inner motto.

Of Jamaican descent, Cheddy was raised in London, England, grew up in New York, traveled the world during his military career, and considers himself a New Yorker. His ethnic, cultural, and global richness contribute to his unique perspective and approach. 

Cheddy now resides in beautiful San Diego, California. As he would say, “Stay Amazing!”

Michelle WickmanProfile Photo

Michelle Wickman

Founder/Life Coach/Speaker


Having the exceptional ability to inspire significant results from herself and others has been a superpower of Michelle Wickman for decades. As a Certified High-Performance Life Coach, she finds great success in helping people to discover the best version of themselves. Michelle coaches people to peak performance in all areas of their life.

As a former Collegiate Division 1 and European League athlete, Michelle’s competitive and team-oriented approach have been great assets. Whether as a senior manager or while collaborating with people at all levels within an organization, she knows how winning is done! Michelle pairs this ability with a focus on improving performance and efficiency, while focusing on the stated and implied goals of the business or organization. Michelle is a master training-course creator and facilitator who knows how to connect and challenge for great impact. 

As the Founder of Wickman Wellness, and host of the Wining Inside Podcast, Michelle has been called “The Soul Whisperer” because of her keen ability to guide people to identify the real issues, challenges and blocks in their lives. Inevitably, this leads to tremendous breakthroughs and significant life changes. Her focus is always on the client’s success and it shows.

“This story is not about me, it’s about you; it’s your story and what brought you here?”

Michelle is a graduate of the University of California at Berkeley with a degree in Social Welfare.  She is a proud mom, Life Coach, national speaker and an incredible asset in the lives of those she interacts with.

Michelle resides in sunny San Diego, California.