Become a better person and build a better business.



Ashley Winston's Unstoppable Coaching and business training help you identify any limiting beliefs that keep you and your business back from operating at peak performance. Ashley focuses on assisting individuals in developing a winning attitude and abundance mindset needed to create wealth and improve the overall quality of each business. Her coaching and reflective exercises address every aspect of starting, building, and growing a business. She helps executive leaders discover and take the necessary steps to achieve unrivaled results and explosive growth. In addition, Ashley helps companies transform inside out by providing counsel and efforts to increase productivity. Ultimately, she equips and empowers individuals with the necessary tools to become better people who build better businesses.








Entry Level Entrepreneurs

Are you thinking about starting a business? Have you recently started one? Are you stuck in the wild adventures of entrepreneurship trying to figure it all out and feel a little stuck because you don't know how to take what you have to the next level? Do you sell services, information, advice, or products? Whether you're a coach, author, owner-operator, or consultant, unstoppable coaching can help develop the mindset, systems, and structures to increase your business's quality and bottom line.

Successful Entrepreneurs

Do you feel stuck in your business? Do you feel like you can't seem to break the ceiling on a certain level of revenue? Are you tapped out on the level you've been doing business on, and you know there's more, but you don't know what to do next, but you're ready to learn? Are you running your business alone, and you know it's time to scale? Or maybe you have a team, but it needs to become more efficient. 
Unstoppable Coaching will help you bridge the gap between where you are and where you want to be.

Executive Leaders

Whether you are looking to improve your company's overall organization or communication, Ashley's insight and training are essential in your business reaching its full potential. Suppose you're looking to boost your company morale, systems, quality of work, or revenue. In that case, Unstoppable Coaching will analyze your unique situation and provide customized solutions and strategies that will move your business forward at warp speed. If you're hungry for growth, the core of Ashley's philosophies and business coaching is designed to help you do just that.

Why Choose Ashley? Ashley Winston is a multi-passionate entrepreneur, speaker and author. With over fifteen years of experience in teaching and coaching in both personal and business settings, she helps people win and provides them with the necessary keys to unlock their peak performance. Her gifts and unique skill set have landed her a wide range of opportunities both here and abroad. She has served on the mission field in Port Au Prince, Haiti and Hyderabad, India. She has been featured in commercials, films, and on television including the popular daytime talk show, Rachael Ray, and worked behind-the scenes of major productions. From classrooms to churches to corporations, Ashley Winston has worked with over 15,000 women & youth, 50 Chicago Public Schools, and more than 90 organizations including The Lyric Opera of Chicago and McDonald’s Corporation. Ashley Winston is the Founder and Creative Director of BREAK FREE BE UNSTOPPABLE, where she teaches people how to show up, tell the truth, and do the work so that they can live God’s best for their lives. She is the author of Break Free: Unlock Your God Given Potential & Unleash Your UnstoppableYou Are Enough, and her most recently published book, 7 Secrets to Living Your Best Life, a guide to help you overcome your obstacles and create a life you love.

A Note From Ashley

You're probably wondering how I got here.  When I started my business, I had just been fired from my job. Yikes! I didn't have any financial resources, I was depressed, and I had no clue what to do next. After I got let go, I started a small group for women across the street from my house at this coffee shop. I didn't know how I would pay for the room rental each week and if anybody would even show up to my sessions. I started the group anyway and just took it one week at a time. After a few weeks of the women consistently showing up, I was like, I guess this is my new job now - drinking coffee and coaching people, lol. I had been casually advising strangers for years, but I had no idea that it would lead to me having my own business. I just knew that I wanted to make the world a better place, as cliche as it sounds, and improve the quality of life for people. I knew I was a good communicator, and I knew I didn't want to work in a cubicle! I discovered that several years prior, during my graduate school internship, lol.

Eventually, I got serious, invested in myself, signed up for a few programs, traveled to a few conferences, and grew my business. I took the risk and decided not to listen to the naysayers. I had no experience with starting a business. I had no money to do it, and I had no connections. In addition, it was a completely different world from what I was doing previously. After a few weeks turned months, turned years into coaching programs and books, I knew that I was officially an entrepreneur. How scary and unpredictable, right? The complete opposite of what I had in mind for my life. Anyway, 98 organizations, 15,000 women and children, and 50 schools later, fast forward, and here I am with you!



Entrepreneur, Women's Pastor

Evan Plummer

Director of Arts Education
Department of Arts Education /
Chicago Public Schools

Angela Johnson

Entrepreneur, Business Owner

Jordan LaSalle

Vice President of Education
The John F. Kennedy Center 
for the Performing Arts

"Get Clear. Get Going."

"Those are two results I can always count on getting when I speak to Ashley. Whether we are talking about growing in God, in business or as a person, her questions and counsel help me get clear on what is holding me back, get past it and move forward at warp speed. Ashley helped me do, in less than 24 hrs, what I had been trying to do in my business for more than two months. And I was able to bring in new money because I did what she said. Whatever she tells you to do, do it. You WILL get results."

- Rebecca Watson, Entrepreneur and Leadership Coach



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"Your Remedy
to Get Unstuck"

Ashley brings real talk with spiritual revelation that sets listeners on a path to real success in every area of life.

"Inspirational Podcast
for Entrepreneurs"

This podcast is a necessary weapon to have in your arsenal as an entrepreneur or if you're looking to discover your purpose. 

Life-changing, Relevant"

It has changed the way I approach entrepreneurship and my day to day life and encourages me to do the inner work.