Operation Pineapple Express: Saving the Heroes of Afghanistan from the Taliban

With Scott MannEP 121

Creating deep human connections and building a high-trust culture is crucial to truly thrive as a leader. In this episode, our guest is Scott Mann; he spent 23 years in the United States Army, 18 of them as a Green Beret, where he specialized in unconventional, high-impact missions in places like Afghanistan, Iraq, and Colombia. He is a storyteller and the founder of Rooftop Leadership, where he helps leaders make better human connections in high-stakes, low-trust environments. He also empowers people – both in warfare and in business – to stand up for themselves and develop a strong voice. He is the author of Operation Pineapple Express: The Incredible Story of a Group of Americans Who Undertook One Last Mission and Honored a Promise in Afghanistan.

In our conversation, Scott shares some of his experiences from his time in Afghanistan and how he was able to use his relationships to help save people and build deep relationships with them. He digs into the importance of leadership, social capital, and accountability and how polarization can be dangerous and counterproductive. Scott remarks on why relationships are essential for building successful organizations. Listen and enjoy!


[00:01 – 07:32] Opening Segment

• Leadership lessons learned from a war zone

• How to build relationships of trust with the local population to rescue people in high-risk situations

• Check out his book Operation Pineapple Express

A story of this rescue mission and the inspirational lessons that can be learned from it
[07:33 – 22:15] The Problems with the US Withdrawal from Afghanistan

• The problems with the U.S. withdrawal from Afghanistan

No public hearings on what happened and no accountability
• Look at the situations that as a leader you face and ask yourself what’s your pineapple express

• Afghan special operations forces and the veteran volunteers who stood on their shoulders and honored a promise

• Why it’s key to focus on local solutions, such as helping tribal leaders stand up to terrorists and training select special operations units

[22:16 – 36:36] If America Abandoned Its Allies, What Would Happen?

• What has led to increased conflict and instability in Afghanistan

A political decision made without input from military leaders
• Why the division between left and right in America is a major obstacle to effective policymaking on issues like Afghanistan

• The importance of opening public hearings by Congress to allow for a more informed discussion of policy options for Afghanistan

There is still potential for the United States to support its allies, but it needs to do so in a more transparent and effective way
[36:37 – 40:38] Closing Segment

• How to make decisions as a leader

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Guest Bio
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Scott Mann

Lt. Col. Scott Mann is a retired Green Beret with over twenty-two years of Army and Special Operations experience around the world. He has deployed to Ecuador, Colombia, Peru, Iraq, and Afghanistan. He is the CEO of Rooftop Leadership and the founder of a 501c3 committed to helping veterans tell their stories in transition. Scott regularly speaks to and trains corporate leaders, law enforcement, and special operations forces on best practices for going local and making better human connections. Scott has frequent appearances on Fox News, CNN, and other national platforms as a thought leader on countering violent extremism, building organizational relationships, and restoring trust in our communities. He is also an actor and playwright who has written a play about the war called Last Out—Elegy of a Green Beret on Amazon Prime.

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