We were lucky to catch up with Jay Graves recently and have shared our conversation below.

Jay, appreciate you joining us today. So, let’s imagine that you were advising someone who wanted to start something similar to you and they asked you what you would do differently in the startup-process knowing what you know now. How would you respond?

If I could hit rewind on my entrepreneurial journey, armed with the wisdom I’ve picked up along the way, I’d fail faster and ditch playing it safe. I’d dive headfirst into risks and invest in a coach or mastermind group from day one. That intimidating upfront cost is nothing compared to the growth when you’re on fire for what you do. I’d pitch my story to everyone I met, making sure no one missed what I’m all about. My social presence? I’d crank it up with daily videos, weekly ‘Go Lives,’ and posts that scream the value I bring to those who need it. I’d show how I could take them to the next level by sharing the ‘what’ and letting them crave the ‘how.’
Bottom line? I’d rewind, redo, and rock it with fierce confidence, knowing every stumble gets me closer to the success I’m chasing.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I have a strong foundation in training and development, and there’s nothing I love more than facilitating the growth of a hungry, open mind! I spent 15 years in corporate learning and development, moving from trainer to Capability Development Director, before stepping out to start my own leadership training and consulting business. Today, I bring that experience to both corporate and non-profit organizations, offering dynamic leadership training that covers everything from emotional intelligence and Altitude Training to 5 Voices Workshops. My secret sauce? Customizing every training to fit each client’s unique needs, helping them grow personally, professionally, and relationally.

I’m a huge sports fan, and just like in sports, I believe in playing to win. That’s why I wrote “You Got This: 6 Principles to Win in the Game of Life.” Here’s the deal: most of us play too small, focusing on not losing instead of going all in for the win. We settle for less than God’s best because we’re afraid to fail. But I challenge everyone to flip that script.

What if it’s not too late to get that degree? What if you can still save that relationship? What if you can reach your goals despite life’s hurts, hang-ups, and habits? I’m here to tell you: you can still win! So, stop playing it safe, lean into the challenges, and let’s make winning a habit.

What’s a lesson you had to unlearn and what’s the backstory?

A Lesson I Had to Unlearn:
One of the biggest lessons I had to unlearn was the belief that “playing it safe” was the smartest way to succeed. For years, I thought that staying in my comfort zone, avoiding risks, and following a predictable path would lead to stability and success. But what I found was that playing it safe was actually holding me back from achieving my full potential.

The Backstory:
Early in my career, I spent 15 years in corporate training and development, moving up the ladder from a trainer to a Capability Development Director. I loved my work, but I always had this nagging feeling that there was more out there for me. There was more impact to make, more lives to touch, and more room to grow. But I kept telling myself to play it safe, to stay in the lane that felt comfortable and secure.

Then, a few years ago, I had a realization: the “safe” path wasn’t fulfilling my true passion. I was stuck in a loop of caution, missing out on opportunities because I was too afraid of failing. I knew I needed to take a leap of faith. I decided to step out on my own, launching my coaching, training, and speaking business. I wrote my book, “You Got This,” with one mission in mind: to inspire others to stop playing small and start playing to win.

The Unlearning:
I had to unlearn the idea that safety equals success. Instead, I learned that real growth and fulfillment come from taking risks, embracing failure, and trusting the process. I realized that when you take risks, you open yourself up to new possibilities and experiences that you never would have encountered if you’d stayed comfortable.

Now, I challenge my clients and myself to lean into discomfort, to see failure not as a stop sign but as a steppingstone. Because playing it safe might keep you from losing, but playing to win? That’s how you create a life that’s truly worth living.

Any advice for growing your clientele? What’s been most effective for you?

Hands down, the fastest and most effective way I’ve grown my clientele has been through the power of word of mouth. When one client experiences my approach, my commitment to their goals, the accountability I bring, I become an extension of their team. They’re eager to share my name with others. One happy client leads to another, and then another, creating a ripple effect that’s been the backbone of my business growth.
But it’s not just luck. It’s because I make it all about them. I dive deep into understanding their needs, challenges, and goals, and I prioritize delivering value that far exceeds what they pay me. I believe that when you put your clients first, treat their success as your own, and show up fully every single time, they become your biggest advocates. That’s been my secret sauce: providing value that speaks for itself and clients who can’t help but spread the word.

Contact Info:

• Website: https://www.thejaygraves.com
• Instagram: @the_jay_graves
• Facebook: https://www.facebook.com/jay.graves2
• Linkedin: https://www.linkedin.com/in/jay-graves