#096 Cal Riley: Special Ops, Grief, and Why Your Business Needs a Heart

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Sep 30, 2025

Cal Riley, a former US Army Special Operations officer and CEO, discusses his transition to business leadership and how his military background informs his approach. He reveals the importance of compassionate leadership following personal grief, notably his brother's suicide. Cal shares insights on implementing the EOS framework to enhance business efficiency and personal well-being. He emphasizes self-care practices like journaling and meditation, highlighting the profound impact of compassion on employee morale and company culture.

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ANECDOTE

Preparing For The Unexpected

Cal describes developing a 'green on blue' battle drill to prevent insider attacks while partnered with Afghan forces.
The drill boosted team morale and likely prevented any green-on-blue incidents on that deployment.

ANECDOTE

Thrown Into Running The Family Firm

Cal joined his father's commercial construction firm and faced a sudden leadership void when his father died months after he joined.
He learned by trial-by-fire until EOS helped him step back and run the business instead of it running him.

ADVICE

Use EOS To Run The Business

Implement EOS to clarify vision, create discipline (traction), and build a healthy company culture.
Use rigid implementation: problems usually stem from not following EOS tools consistently.

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Topics:

(00:00:00) - Intro

(00:03:07) - Cal's military background

(00:13:59) - Transitioning into a family business

(00:19:35) - Implementing EOS

(00:25:08) - The journey to compassionate leadership

(00:36:16) - Prioritizing self-care and meditation

(00:37:19) - Journaling techniques and prompts

(00:39:02) - Mental health stigma and therapy

(00:40:16) - Daily intentions and successes

(00:42:28) - Leadership

(00:47:28) - Coaching and team building

(00:58:45) - Writing a book

(01:03:10) - Resources

Links:

Scribe — https://scribemedia.com

Entrepreneurial Compassion: An Entrepreneur’s Journey Through Combat, Suicide, and the Discovery of Compassionate Leadership - https://amzn.to/4nqH6AK

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We discuss:

How military battle drills shaped Cal’s approach to business leadership
How EOS changed about his company and personal life
Why compassion is both a moral imperative and a business advantage
Tactical ways Cal builds emotional awareness into his leadership habits
How journaling, meditation, and presence help fuel resilience and clarity

Quotes from Cal:

"The more compassion I showed my team, the more profit we made. It’s not soft—it’s smart."
"They’ll never care how much you know until they know how much you care."
"Every really good unit has this thing called a tactical SOP—just like your business has processes."
"EOS gave me the ability to step back, let the team lead, and focus on building the future."
"I went from working 90 hours a week in the business to now doing one meeting a week."
"The business stops running you, and you start running it."
"When we can be driven and compassionate, the sky’s the limit."
"As entrepreneurs, we’re good at putting out fires—and if there isn’t one, we’ll start one just to feel busy."
"My brother’s death has to mean something—this book is how I make sure something good comes from it."
"I want to create a million compassionate leaders and prevent a hundred thousand suicides."
"This isn't about monetizing trauma—every cent from the book goes to suicide prevention."

Important Quotes from the podcast on Business and Entrepreneurship

There is no skill called “business.” Avoid business magazines and business classes. - Naval Ravikant

You have to work up to the point where you can own equity in a business. You could own equity as a small shareholder where you bought stock. You could also own it as an owner where you started the company. Ownership is really important.

Everybody who really makes money at some point owns a piece of a product, a business, or some IP. That can be through stock options if you work at a tech company. That’s a fine way to start.