Lessons Ron Loveless Taught Me On Life & Business

When you reflect on your life you can see pivot points that changed everything. Within those pivot points are people and for me one of those people was Ron Loveless a former Walmart executive who helped to create Sam’s Club. As I write these words I am filled with gratitude and grief as Ron’s funeral has just recently happened. Since meeting him in 2008 much has changed in my life because of his influence and the leadership lessons he imparted to me over that time. This is my story of an unlikely meeting between a seasoned well-connected and respected executive for one of the world’s largest brands, a young technical professional in Canada and how you should never underestimate the impact of your own ripple effect.

THE MEETING – 2008 Boomer Summit in Arkansas

It all started when Ron decided to host a weekend summit with some of his friends in Arkansas in 2008. I was invited because I had written a whitepaper on Digital Signage and the group wanted to learn about this up and coming new technology. The night before, I landed in Bentonville and drove a few hours through rolling mountainsides that twisted and curved. I was a little nervous (especially at night on unknown roads) and little did I know that these same roads would end up teaching me a valuable lesson and creating a memory later on with Ron. The next morning I arrived into a beautiful and serene building and entered into a boardroom filled with a small group of men.

They were all kind, generous, and humble as they introduced themselves (Ron, Jim, Larry, David, Bill…) Down to earth – they immediately put me at ease. Over the course of the day I learned I was sitting amongst some of the brightest minds in America. Some were directly linked to huge deals responsible for real-estate development and projects like ushering in the age of cell phone cards. While others were associated with massive brands like the gentleman who’s business plan was the foundation of Home Depot, another associated with Marriott, a family member of the Halls of Hallmark, the founder of American Outdoorsman, Ron of Walmart – and me.

I was acutely aware that I did not “fit” in this room (and not because I was a female if you are wondering) but rather because at the time I was only a Director of a rather unknown brand. I made my presentation and was fully prepared to make my exit during the break that followed when Ron approached and invited me to stay on for the day.

These men were meeting to explore business deals together and I was being invited to stay! I had enjoyed my morning with all of them and I blurted out “Well I’d love to but I have to ask, why? I mean you don’t know me and you don’t know if you can even trust me. How do you know I won’t leave here and steal all these ideas?”

Ron chuckled and then smiled. I didn’t know it yet but he was about to give me my first mentoring lesson. With his gentle southern accent he explained to me that after reviewing the agenda they felt digital signage would be something that could be a part of a few of their other projects so it be useful for me to stay as a resource. The way he explained the next part left a lasting impression on me. My first lesson on friendship and loyalty was beginning, “Everyone has great ideas, that’s not hard, but their are very few people who can implement, and fewer yet who could implement these projects. That and if you tried to take our ideas and bring them to others, you could, but then you would have breached the trust of all of us and we’d simply never work with you again.” I remember we chuckled together and over the course of the day, sitting in that room as the outsider I learned my first valuable lesson:

Use business as the excuse to build relationships and friendships as opposed to using relationships and friendships to build your business.

It’s a slight but important difference that changes everything. So many people try to play the friendship game but it’s all just manipulation, a means to an end, to make money. Ron explained to me that they all really liked each other and so found ways to spend time together and sometimes business came out of it. I remember one of the men laughing that he had been trying to do business with another gentleman in the room for over a decade to no avail. They shared a goodhearted laugh as they bantered and poked fun at the amount of referrals they had passed back and forth but had yet to worked directly. The camaraderie, affection and respect that I witnessed was an amazing lesson and one that has stayed with me over the last eight years. Just embracing this truth of making good friends and being a good friend above all else has brought me the greatest of joy.

THE QUESTION – How can we help you?

That night these same group of wonderful men invited me to join them all for dinner. We were ushered into an absolutely gorgeous private room and since they insisted I sit in the middle of the table I decided I was not going to miss the opportunity to glean as much knowledge as I could. I figured I would never see these men again so I began to ask questions. (For those that know me and my propensity to ask questions this comes as no surprise.)

During the course of conversation the topic of betrayal came up. Those times in business when someone you trust takes your goodwill and breaks it to pieces is a difficult time to walk through. I had recently had my first real taste of this and thought it was because of my inexperience at the time. I’d lost some money in the process and it stung. When I shared my story the entire group laughed sympathetically shaking their heads. One kind gentleman leaned over and promptly informed me that was my “initiation fee” and to consider it my tuition. He explained it would be the best training I could receive in business for I was now smarter for having been burnt and it would be invaluable.

One after one they shared their different stories. They laughed when after listening for some time I replied “Well, in comparison to those stories I suppose I got off easy.” Then the moment arrived that would change my life. One of the gentlemen sitting across from me said: “Karolyn, we like you. You’ve got an entrepreneurial spirit. You have all of our attention. So how can we help you?”

True story. The moment he asked me that question I heard the lyrics from Eminem blasting in my head. There I was in Arkansas, surrounded by all these powerful professionals and all I could hear in my head was the intro to Lose Yourself “Look, if you had one shot or one opportunity. To seize everything you ever wanted in one moment. Would you capture it or just let it slip? Yo.”

My palms WERE sweaty and I took a quick moment. Even writing this, all these years later, I can still recall with clarity how I felt and the words I said. “Well,” I started slowly ” The way I see it is that you all have more success in your baby finger than I’ve ever had, so…” I continued cautiously. “…if I were to ask for anything it would be for you to mentor me.”

I remember feeling like it was very quiet at the able for a very long time which I am sure was only seconds.

“Mentor you?” the gentleman across raised his eyebrows up.

“Yes. You know, take my phone calls, advise me, help me with the things I am working on so I can learn.”

He broke out in a wide smile and said “Well now, I think that is just about the best answer I’ve ever heard!”

I let out a huge sigh of relief. Three of the men immediately agreed to my request and one of those men was Ron. When I look back I consider how extraordinary it is that these men (after having just explained how they had experienced betrayals) were still open to making new friends and even mentoring a person they had only just met.

That night I learned this lesson:

Just because you have been betrayed does not mean you cannot learn to trust again. In fact, you will be smarter for it. Remember: You will also make your own mistakes and that does not mean it is the end of your story. You can learn from your mistakes and the mistakes of others and write a new story.


The next day I had to drive back through the mountains and Ron asked if I’d like to follow him back since we were driving the same way. I remember coming around a bend in the road and seeing an unusual sight – it looked like someone had built a campfire out on a cliff jutting near the road. “That’s odd.” I remember thinking. Within a few moments, I could hardly see the tail lights of Ron’s due to smoke. We were in the middle of a forest fire on both sides of us.

I remember he slowed right down and together we carefully winded our way through until we made our way clear. The whole time I was assuming that Ron probably had experience in this and so felt a measure of peace as I carefully followed him.

Once we finally got to Bentonville we pulled into a parking lot and he jumped out of his car and walked back to mine “Wasn’t that something else!” he said. We laughed as I revealed I thought he’d encountered that before and he had no problem admitting he was nervous to driving through hills and trees that were on fire. If this isn’t an analogy on leadership I don’t know what is! The lesson he taught me in that moment was:

Leaders have no problem leading their people through fires and there is nothing wrong with admitting to your people that you don’t have all the answers.


Ron’s mentorship remained constant over the years through phone calls and emails. He always took my calls but I remember the first time he sought my advice. He sent me over a business proposal and asked for my “gut instinct”. That marked the beginning of a friendship. I remember when he sent me a copy of his book “Walmart Inside Out: From Stockboy to Stockholder” before it was released. I felt so incredibly honoured that he did that.

We would spend time talking about leadership, about projects, and advising back and forth. I remember when I asked for advice on a particular professional challenge that was difficult and messy (to say the least) and he made me feel better by cracking a joke about how it was even outside of his professional experience: “Glad it’s not me!” I remember how hard we laughed when I sarcastically thanked him for his “mentoring”. His affirmation that the situation I was experiencing was “extraordinary” in all the worst ways was actually validating. Sometimes, as leaders, we can assume that others have gone through worse fires and that’s not necessarily the case. In a way we were back driving through the mountains with fire all around and simply having his leadership near helped me navigate my way through. He couldn’t provide me answers but not being alone in the situation I faced helped me get through.

When we chatted we would have discussions on life and business that always left me thinking and reflecting. We even developed a show treatment we designed called “Hindsight” that was based on leaders sharing the lessons from some of their biggest mistakes. I can still hear the excitement in his voice as he arranged an introduction to yet another friend of his on this particular project. He did this often for me and I in turn introduced him to people as well but it’s fair to say he gave more than I could return. In fact, the whole reason I am doing the job I have today, with the people I do, is because of Ron’s decision to gather his friends into a room in Arkansas.

Now, ironically in hindsight, I find myself reflecting on my friendship with Ron after all these years. My heart is sad at the loss of my mentor and friend. I look at some of the projects we had wanted to do together. He’s had other health issues and while we paused our projects we never cancelled them. We always left with the anticipation of continuing and when I spoke with him last month I couldn’t comprehend that he would find another way to get out of this one too. Ultimately, that was not to be the case but even in how he left this earth Ron had one final lesson for me and it is this:

Don’t stop. Don’t stop choosing to invest in people. Don’t stop chasing new horizons. Don’t stop – for the rock that has slipped beneath the surface can no longer be seen but the ripples it creates carry on long after. Invest in others and the ripple effect of your life (like Ron’s) will carry on long after.

Karolyn Hart
About the author: 

Karolyn Hart is the Chief Operating Officer of InspireHUB Technologies, the creator the IHUBApp a Progressive Web App that helps small business owners and entrepreneurs simply engage. Karolyn’s twenty year technology career has spanned multiple industries including financial services, healthcare and automotive. She also has the distinction of being the first female appointed executive to one of Canada’s oldest economic development agencies. Follow her on Twitter.