From Driven Operator to Compassionate Leader

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

To support the costs of producing this podcast: 

>> Buy a copy of the Navalmanack: www.navalmanack.com/ 

>> Buy a copy of The Anthology of Balaji: https://balajianthology.com/

>> Sign up for my online course and community about building your Personal Leverage: https://www.ejorgenson.com/leverage 

>> Invest in early-stage companies alongside Eric and his partners at Rolling Fun: https://angel.co/v/back/rolling-fun

>> Join the free weekly email list at ejorgenson.com/newsletter

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>> Or at least give the podcast a positive review to help us reach new listeners!

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.