Intro

Most people fail at leadership because they complicate what should be simple. Greg Osborn’s approach is different. After leading in Vietnam, raising a family with old-school work ethic, and building businesses in Silicon Valley as the tech boom took off, he learned that success comes from two things: giving people the right training and keeping them motivated.

In this conversation, Greg breaks down why teams succeed or fail based on this simple principle — and how you can apply it in business, family, and life. You’ll hear how his leadership lessons from the Vietnam battlefield translated into managing people, teaching his kids, and running companies.

This is timeless advice that still works today — practical, proven, and refreshingly clear.

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Timestamps:

00:00 - Introduction to Greg Osborne and His Garage

05:01 - Camping Adventures with Greg Osborne's Family

10:01 - The Joy of Making and Solving Problems

15:00 - Early Life, Education, and Military Background

20:01 - College Basketball Career at Stanford

25:01 - Physical Challenges and Surgeries Over the Years

30:01 - Reflections on Basketball and Life Experiences

35:01 - Military Training and Assignment to Vietnam

40:02 - Experiences in Vietnam and Impact of War

45:01 - Teaching GED to Soldiers and Life Lessons

50:01 - 54 Years of Marriage and Family Life

55:00 - Raising Children and Teaching Responsibility

01:00:00 - Reflections on Joy and Family

01:05:00 - Personal Anecdotes and Life Lessons

01:10:00 - Challenges and Sacrifices in Life

01:15:02 - Real Estate Experiences and Business Ventures

01:20:01 - Encounters with Tech Industry Leaders

01:25:00 - Growth of Silicon Valley and Early Tech Companies

01:30:01 - Closing Thoughts and Final Conversations

Episode Partners:

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