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At The End of the Day, Relationships Matter Most

Posted on March 30, 2023 by James Harold Webb
At The End of the Day, Relationships Matter Most

In business, relationships are more important than capital, ideas, infrastructure, or profitability. Relationships have unlocked opportunity after opportunity in my career. Strong relationships with banks have gotten me loans when I probably didn’t qualify for them. Relationships with mentors and customers have helped me to overcome temporary shortfalls. Relationships with partners and competitors have allowed me to take risks, try new things, and view strategy through a different lens. Relationships with employers and employees have multiplied my output and brought meaning to my work. In life, relationships are the reason for working. Family, friends, communities—without these, life would be hollow and empty.

But not relationships are easy – some even come with major roadblocks and heartache. It’s from some of the hardest ones that I’ve learned the most about myself.  In 1990, a man named Barry O’Brien became extremely important to me; he was my mentor. Long before I began my entrepreneurial journey, he took me under his wing and got me out of hospitals and into business. I adored Barry, and I think he saw in me the kind of person he wanted to help. Working with him was an adventure, learning from him was a gift, and calling him a friend was a treasure. Until I screwed up. 

Our relationship, which had been something I could count on when so much of my life was in question—ended almost overnight. Barry and I had a fight. I was wrong. I had hurt him, and abused his trust. While I was happy to leave elements of this time of my life in the rearview mirror, this failed relationship with Barry stung. 

Years later, I had been in Boca Raton when I got a phone call from a mutual acquaintance and former coworker. Barry was going to be in Florida, and he wanted to know if I’d meet him for dinner. What started out awkwardly, ended in a lightness I hadn’t experienced in a long time. We laughed and told stories about the old days. We caught up on family stuff and work and even made plans to get together for golf.

I couldn’t undo the past, but it felt like the chance to rewrite the future and include Barry in it had been dropped into my lap. The relationship could never be the same, but it could still be good, and that created a sense of release and happiness in me that I could never have expected.

It was only a couple of days later when I got the call that Barry had been skiing with his son not far from their Connecticut home and died. I was floored, devastated. Our relationship had been built over years of working together, had come close to a permanent ending in a matter of moments, and, after three years of stagnation, had just begun to show promise … then this. Just as quickly as he had come back into my life, he was gone, and the sadness was overwhelming. The funny thing about sadness is that it’s temporary. Once the fog started to clear, I realized that the grief had morphed into an overwhelming sense of gratitude. I was grateful to have had Barry in my life, grateful for the opportunity to make up and to be able to look back on the good memories, not the bad ones. I felt extreme gratitude for my relationship with Barry—not the money we made together, the sales, or the impact on my career. No, I was grateful for him.

The relationships you have, the ones you try to salvage are worth more than anything. People are always more valuable than money; memories mean more than money ever could. I have found that the greatest accomplishments of my life and career are defined by the relationships with the people who have been a part of it every step of the way.


In my book, I share with you fundamental principles that have helped me triumph personally and professionally. You’ll learn about amazing wins and devastating losses, about sin and redemption, recovery, and forward momentum that can help you spur your own growth, profitability, and success. Attain your own copy of Redneck Resilience: A Country Boy’s Journey to Prosperity today!