By: K.H. Koehler
Cal Riley believes that compassion isn’t just a warm, fuzzy feeling. A US Army officer, successful entrepreneur, seasoned business coach, and author, Riley views compassion as a reliable and repeatable system of soft skills for leadership that’s crucial for any organization to function effectively. He has led teams in intense situations, from the battlefield to the boardroom, and his unique take on leadership with integrity comes from a profoundly personal place. He lost his brother to suicide in 2023, a tragedy that significantly changed his entire approach to leadership.
“His death devastated me,” Riley shares. “It completely changed the lens through which I viewed my life and all my experiences as a successful coach and entrepreneur. That was the beginning of my journey to entrepreneurial compassion and the reason why I wrote this book.”
The Roots of Entrepreneurial Compassion
Riley presents his leadership approach in his book, Entrepreneurial Compassion. He views this concept as a way to lead with integrity and address common leadership mistakes. It is not some gentle, fleeting ideal, but rather a practical skill that leaders can learn, practice, and improve upon. It encompasses compassion in the workplace and, more broadly, compassion in professional settings. It’s structured, it’s all about actions, and it’s vital for any business that wants to grow.
As a business strategy coach, he wisely puts it, “Empathy without structure leads to chaos. Structure without empathy leads to turnover. Compassion is the bridge.”
Riley’s approach to business, which is deeply rooted in his military background, is that of a dedicated business coach. He sees a clear connection between battle drills and business coaching and mentoring. Even as elite military teams practice to protect their members, they also need leaders to actively build systems of safety and human connection in how they operate.
Lessons from the Battlefield
The business coach from Cary, North Carolina, tells of how he would face “green-on-blue” attacks during his time in Afghanistan, where allies would turn on coalition forces. Riley developed a battle drill focused on 360-degree security, where soldiers would face each other, constantly watching each other’s backs and looking out for one another. The simple act made a significant difference in morale.
It was a way for the leader of a team to show he cares for his unit. Riley reflects on how he would tell his soldiers, “This will not happen to you. Not on my watch.” He sees a direct link between this attitude and running a business. And his book, Entrepreneurial Compassion, includes practical frameworks, checklists, and exercises that work like a playbook for compassionate leadership.
Business Beyond Profits
Riley’s ambitions extend beyond profits. By 2035, he hopes to inspire a million leaders who, by embracing his ideas, will potentially help prevent at least 100K suicides. All of the money from his book goes to charity, driven by his belief that if his brother had felt more cared for at work, he might still be alive.
Riley reminds us, “In combat, you don’t leave someone exposed; you build a system to protect them. That’s what leaders need to do for their teams, too.”
For busy entrepreneurs who are always “doing” instead of “being,” Riley offers what he feels is a life-altering path. It’s not about being perfect, but about being intentional and disciplined. His journey through war, building businesses, and personal heartache has shaped a powerful message: Leading with compassion isn’t just good for people; it’s good for business, and it might even save lives.
To learn more and to become part of Riley’s movement, visit Riley’s Blog.
