Casual conversations with founders, technologists, investors, and artists about building a brighter future, together. Welcome to our digital living room.
With science, technology and entrepreneurship we can *continue* to create unfathomable leaps in quality of life. We show you how to find, apply, build, and invest in technologies to change your life and the world.
When we have smart friends, we do smart things. When we do smart things, we save the world.
No matter who, where, or when you are – now you have smart friends, too.
Outside this podcast, I’m the author of The Almanack of Naval Ravikant and The Anthology of Balaji. Connect at ejorgenson.com
Laugh and learn with people like Balaji Srinivasan, Naval Ravikant, Andrew Wilkinson, Austen Allred, David Senra, Josh Storrs Hall, Ashley Rindsberg, Zach Pettet, Bret Kugelmass, Omar ElNaggar, Grace Guo, Brett Kopf, Max Olson, Chris Williamson, Shane Mac, Tim Hwang, David Perell, Jason Hitchcock, Natalia Karayaneva, Sebastian Marshall, Taylor Pearson, Mitchell Baldridge and more.
Join conversations with my partners in early-stage tech investing, Bo Fishback and Al Doan. Our Rolling Fun Episodes cover our investments and escapades as angel investors and startup helpers. We invest in startups creating the *next* industrial revolution. Learn more at rolling.fun
“Surround yourself with people who remind you more of your future than of your past.”
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Casual conversations with founders, technologists, investors, and artists about building a brighter future, together. Welcome to our digital living room.
With science, technology and entrepreneurship we can *continue* to create unfathomable leaps in quality of life. We show you how to find, apply, build, and invest in technologies to change your life and the world.
When we have smart friends, we do smart things. When we do smart things, we save the world.
No matter who, where, or when you are – now you have smart friends, too.
Outside this podcast, I’m the author of The Almanack of Naval Ravikant and The Anthology of Balaji. Connect at ejorgenson.com
Laugh and learn with people like Balaji Srinivasan, Naval Ravikant, Andrew Wilkinson, Austen Allred, David Senra, Josh Storrs Hall, Ashley Rindsberg, Zach Pettet, Bret Kugelmass, Omar ElNaggar, Grace Guo, Brett Kopf, Max Olson, Chris Williamson, Shane Mac, Tim Hwang, David Perell, Jason Hitchcock, Natalia Karayaneva, Sebastian Marshall, Taylor Pearson, Mitchell Baldridge and more.
Join conversations with my partners in early-stage tech investing, Bo Fishback and Al Doan. Our Rolling Fun Episodes cover our investments and escapades as angel investors and startup helpers. We invest in startups creating the *next* industrial revolution. Learn more at rolling.fun
“Surround yourself with people who remind you more of your future than of your past.”
#096 Cal Riley: Special Ops, Grief, and Why Your Business Needs a Heart
Smart Friends
1 hour 5 minutes
1 month ago
#096 Cal Riley: Special Ops, Grief, and Why Your Business Needs a Heart
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
>> Text the podcast to a friend
>> 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.
Smart Friends
Casual conversations with founders, technologists, investors, and artists about building a brighter future, together. Welcome to our digital living room.
With science, technology and entrepreneurship we can *continue* to create unfathomable leaps in quality of life. We show you how to find, apply, build, and invest in technologies to change your life and the world.
When we have smart friends, we do smart things. When we do smart things, we save the world.
No matter who, where, or when you are – now you have smart friends, too.
Outside this podcast, I’m the author of The Almanack of Naval Ravikant and The Anthology of Balaji. Connect at ejorgenson.com
Laugh and learn with people like Balaji Srinivasan, Naval Ravikant, Andrew Wilkinson, Austen Allred, David Senra, Josh Storrs Hall, Ashley Rindsberg, Zach Pettet, Bret Kugelmass, Omar ElNaggar, Grace Guo, Brett Kopf, Max Olson, Chris Williamson, Shane Mac, Tim Hwang, David Perell, Jason Hitchcock, Natalia Karayaneva, Sebastian Marshall, Taylor Pearson, Mitchell Baldridge and more.
Join conversations with my partners in early-stage tech investing, Bo Fishback and Al Doan. Our Rolling Fun Episodes cover our investments and escapades as angel investors and startup helpers. We invest in startups creating the *next* industrial revolution. Learn more at rolling.fun
“Surround yourself with people who remind you more of your future than of your past.”