Ivy League Trucker

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Podcast by Clint Files

Ivy League Trucker

Ivy League Trucker, where stories and conversations bridge the gaps to connect people with different backgrounds and lived experiences. Hosted by Clint Files, a big rig trucker with an Ivy League education. How do we connect with those unlike us, challenge our own perspective and foster empathy? Join us on a journey to build understanding in a world desperately needing it! A perfect show for those who are tired of the divisions, polarization and rage-baiting tearing us apart - who want to reverse the tide and move toward others. Who want to heal our social fabric and restore empathy, understanding and tolerance. Who want to embrace the humanity in their fellow man and woman, no matter where they stand. Who understand that valuing the other person does not require you to surrender your values. Clint’s personal journey from Ivy League educated corporate executive to big rig trucker has given him an empathy for those different from him. Join Clint, as he explores how to find community with those different from us economically, politically, religiously, generationally. Because its good for your heart - and good for us all.
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Latest episodes

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26 April 2026

EP 12: A New Direction for Ivy League Trucker

We are making a change with the podcast. Getting back to the core of Ivy League Trucker, which is the observations of an Ivy League educated guy with broad corporate and small company experience - living the life of a big rig over the road trucker.

Future episodes will cover everything from self-driving trucks to the immigrant experience in trucking to truck safety, crashes and the history of trucking. We will speak with people involved in all this along the way.

Resources:

Why most trucker Owner-Operators Fail. https://www.truckclub.com/trucking-news/owner-operator-failure-prevention-guide

Please remember to "like" the show and press "Follow" in your pod player to get each episode.

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06 April 2026

# 11: Radically Improving the lives of Struggling Families

Can a single white woman really help struggling single moms of color break generational cycles of poverty? Yes, it's possilbe! Jill Page Goss of Every Good Gift tells a story of personal bridge building and connection that is really making a difference for moms and their children.

Resources:

Every Good Gift. Jill's non-profit ministry to single mothers in crisis, through job training and personal interaction, giving them job and life skills to break the cycles of poverty. Follow the link to learn and also support this 501c3 non-profit.

Christ Kitchen: Loving Women Out of Poverty; by Jan Martinez. This book is about the ministry that inspired Jill to start Every Good Gift

Bridges Out of Poverty: Strategies for Professionals and Communities. by Terri D. Smith, Ruby K. Payne, Philip E.. DeVol. The book jill referred to that helps us help the poor without hurting.

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22 March 2026

#10 The Power of Vulnerability plus Curiosity in making Connections

We have all heard it before. Be 'more vulnerable' with people to better connect with them. But man, it's hard and not what we want to do! A friend shares how this has actually been a connection game changer for him - - And a pathway to really seeing other people.

10 episodes in . . . so what do you want to see more or less of?? Check out our poll below - we need to hear from you!

Be sure to like the show and give a podcast player review. This makes the show easier for others to find - - and share the show with your peeps! Thx! - Clint

Resources:

In the TED talk that made her famous, Brene' Brown discusses The Power of Vulnerability (TED Talk; 2011)

https://www.youtube.com/watch?v=iCvmsMzlF7o

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01:07:44

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06 March 2026

#9 A Family Man lives a Life of Connection and Care

Clint has some musings about life and human flourishing - and we have a great interview with Josh Chapman, a friend who was shaped for relationship in his family of origin and is intentionally building a relational family with his wife. He also serves as a deacon in our church, which is where the practical needs of our folks are met with love and care. Lastly, some good stuff on the negative effects of social media and phones on kids and how Josh and his wife are effectlvely managing it. Good Stuff!

Please continue to share the pod and give a rating to help others find it. Thx!!

Resources:

Link to Article: "Finding the Good Life in an Age of Designer Babies and High Achievers" (Dispatch Faith; Feb 15, 2026). https://thedispatch.com/newsletter/dispatch-faith/designer-babies-down-syndrome-christianity/

What are Deacons?:

https://www.google.com/search?sca_esv=99ae616f7fa66d58&q=Presbyterian+deacons&sa=X&ved=2ahUKEwiKqre7jIWTAxVQC3kGHeTTBI4Q1QJ6BAhIEAE&biw=1280&bih=678&dpr=2

Josh referenced this book about helping people:

Ministries of Mercy: The Call of the Jericho Road; by Tim Keller

https://a.co/d/066itWon

Everyone should read this book!

The Anxious Generation: How the Great Rewiring of Childhood Is Causing an Epidemic of Mental Illness; by Jonathan Haidt

https://a.co/d/06lCodIr

Details of Facebook's Mark Zuckerberg testifying in the Feb 2026 California trial about Facebook targeting youth with potentially very addictive social media - and harms to children - a landmark legal case:

https://www.cnn.com/2026/02/18/tech/meta-mark-zuckerberg-testifies-social-media-addiction-trial

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01:10:49

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22 February 2026

#8 A young Pastor Shares How She makes connections through Service

I think you will really enjoy this interview with Addie, a young female pastor in the Anglican Church. She combines her heart for people and innate curiosity to serve people in and out of her congregation. A young mother of 2, she is fully engaged in life at work and at home. Themes of compassion, respect and empathy undergird her ability to make connections without judgment.

Don’t forget to follow the show to get the latest! And share with anyone who would like this stuff - thanks - - Clint :)

Resources:

What is an Anglican Church??

https://anglicanchurch.net/anglicanism/

How are pastors different than 'regular' (lay) folks?

https://learn.ligonier.org/qas/are-preachers-and-pastors-more-important-than-other-christians

Jargon decoder: The word 'ordain' means "to set aside for special use". An ordination ceremony is where this is applied to a person in a formal, publicly recognized way.

What is driving this national housing shortage that is affecting Millenials and Gen Z so much? (or, it's not your father's Housing market)

https://www.bankrate.com/real-estate/low-inventory-housing-shortage/

https://www.npr.org/2024/12/11/nx-s1-5223561/the-u-s-is-facing-a-severe-housing-shortage-will-trumps-proposals-help

ttps://www.npr.org/2024/12/11/nx-s1-5223561/the-u-s-is-facing-a-severe-h

Feedback please in your pod player comments or directly to me at: ivyleaguetrucker@gmail.com

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12 February 2026

#7 How a Creative Mind makes Human Connections

How does creativity relate to our ability to connect with others? Are the artistic types better at it, or not? My good friend Elaine is a trained artist who also has an innate curiosity about her fellow man. In this interview she links her artistic curiosity with a practice of helping people create AND connect.

Here is a cool article about why creativity is important to all, by Brene Brown

https://www.shortform.com/blog/brene-brown-creativity/

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