The Cowboy In You

Who Am I to Write This?

I'm no prophet. I'm no philosopher.

I'm not selling anything.

I've been broke enough to sell my daughters' dollhouse.

I built companies and watched them collapse.

But every rebuild was bigger.

And I learned more sleeping on concrete than you ever will in an Ivy League classroom.

I wrote this for my children. I'm sharing it in case it's useful to you.

The Survival Manual

Ten lessons from a life lived at the extremes.

This document is free. It is not commercial. It is meant to be shared.

Read onlineRead the manual (PDF)

The words are always free.

The Book

Ten lessons, and the stories they came from. The stories are not illustrations of the lessons. They are what the lessons cost.

• OpeningPrologue
• OpeningHow We Got Here
• StoryThe Cowboys Who Raised Me
• Lesson 1You Are Going to Die
• Lesson 2More Cowboys… Less Bureaucrats
• StoryThe Grinder
• Lesson 3Become Unbreakable
• StoryThe Doll House
• Lesson 4Foundation in God & the Truth
• Lesson 5Things Aren't Complicated
• Lesson 6Entrepreneurship, Business, Money & Career
• Lesson 7Marriage, Family/Kids & Community
• Lesson 8You Never Know What Will Happen
• StoryThe Colonel
• Lesson 9Don't Say It, Show It
• StoryThe Exit
• Lesson 10Enjoy the Ride… Live with Joy
• StoryThe Jungle and the Joy
• ClosingThe Future Is Yours to Ride
• ClosingLast Words
• StoryThe Quiet Cowboy
• StoryBack to the Frontier

About the Author

Greg Keough has received the CIA's Intelligence Star for extraordinary heroism, and been reduced to a number in a federal cell. He built companies worth hundreds of millions and lost it all. But every rebuild was bigger. He wrote this manual from a prison cell in Alabama. He lives in El Salvador with his wife of thirty years and their five children.

He was early to five successive waves of financial technology. Today he backs the people building artificial intelligence and autonomous systems. Competence over credentials. He's the coach now. Not the quarterback.

More at gregkeough.com

Questions

What is The Cowboy In You?

The Cowboy In You is a free survival manual by Greg Keough. Ten lessons from a life lived at the extremes, on freedom, money, death, marriage and faith, told alongside the stories they came from. Keough wrote it for his five children and gives it away free.

Who is Greg Keough?

Greg Keough served as a covert operations officer in the CIA’s Directorate of Operations and received the Agency’s Intelligence Star for extraordinary heroism. He has built companies worth hundreds of millions and lost it all. But every rebuild was bigger. He wrote The Cowboy In You in a federal prison cell in Alabama. He lives in El Salvador with his wife of thirty years and their five children.

Is the book really free?

Yes. The whole book can be read on one page, or downloaded as a PDF, at no cost. There is nothing to buy, nothing to subscribe to, and no email address required. A paperback and hardcover are coming, for anyone who wants to put a copy in someone’s hands. In Keough’s words: I wrote this for my children. I’m sharing it in case it’s useful to you.

Can I get a physical copy?

A paperback and hardcover are coming. The words are always free. Paper is not. The printed edition exists so a copy can sit on a table, or go to someone who will never open a PDF.

What are the ten lessons?

1. You Are Going to Die. 2. More Cowboys, Less Bureaucrats. 3. Become Unbreakable. 4. Foundation in God and the Truth. 5. Things Aren’t Complicated. 6. Entrepreneurship, Business, Money and Career. 7. Marriage, Family, Kids and Community. 8. You Never Know What Will Happen. 9. Don’t Say It, Show It. 10. Enjoy the Ride, Live with Joy.

What does More Cowboys, Less Bureaucrats mean?

It is Lesson 2, and it comes from Keough’s years in the CIA. His line is: I’ve seen bureaucrats in silk ties do more damage than the enemies we fought overseas. A Cowboy is anyone who takes real risk and accepts responsibility for it. A Bureaucrat is anyone whose instinct is to avoid both. Keough frames it as a war of values with no middle ground.

Why did he write it?

He wrote it for his five children. He published it because he thought it might be useful to anyone else standing somewhere similar.

What is Greg Keough’s legal history?

The loan applications in this case were made in 2020, under the pandemic relief programs. In December 2022, nearly eight months before any charge was filed, he repaid the $500,000 loan principal to the Small Business Administration, with no agreement or compromise attached. He was charged in August 2023, pleaded guilty, and served a federal sentence. The restitution was paid before he was sentenced, not after. The judgment states: “The restitution has been PAID IN FULL directly to the victim.” He writes about this period in the book. The full record, with the court documents, is at gregorykeough.com.