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! 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 ec...
Author
Clint Files
Category
Podcast website
Latest episode
Jun 28, 2026
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Episodes
# 14 Women in Trucking - What's it like for the Ladies?? 28.06.2026 52:24
Though it is a male dominated industry, there are a number of women driving big rigs out there. What is it like for them? We talk with a lady trucker in Clint's company to get the scoop. Resources: Women in Trucking https://www.womenintrucking.org/ is the leading organization advocating for more women in trucking in the US.
#13 The Autonomous Trucks are coming -- but When?? 10.06.2026 37:32
We have all heard of, and some of us ridden in, autonomous cars. Tesla and Waymo are bringing self-driving cars and autonomous taxis to American streets. What about autonomous big rig trucks moving our freight? This is actually happening now in the first pilots and very small commercial operations. Clint explores the whats, whys and predicted whens for autonomous truck adoption in the trucking ind...
# 12: A New Direction for Ivy League Trucker 26.04.2026 15:39
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 truc...
# 11: Radically Improving the lives of Struggling Families 06.04.2026 49:27
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...
#10 The Power of Vulnerability plus Curiosity in making Connections 22.03.2026 1:07:44
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 t...
#9 A Family Man lives a Life of Connection and Care 06.03.2026 1:10:49
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 effec...
#8 A young Pastor Shares How She makes connections through Service 22.02.2026 55:17
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 follo...
#7 How a Creative Mind makes Human Connections 12.02.2026 47:15
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:/...
#6 Why the Old & Young Need Each Other (or, Gen Z Speaks!) 25.01.2026 44:51
What happens when an older guy and a younger guy actually listen to each other? Today Clint interviews Robert, a Gen Z law student. Robert has great insights about Gen Z, including what's good and bad about his generation - and what they've learned from - and have beef with - the older generation. Good Stuff!! Resources: Somewhat relatedly . . . . Great pod interview with Loretta Ross on “Leaning...
#5 The Truckin’ Life and the Judgement of Charity 18.01.2026 24:01
What about the 'trucking' in Ivy League Trucker? Clint shares some trucking insider info and the search for lost America. He also shares a point of connection with one of the guys at the tank wash (A very dirty job that is necessary for the liquid tankers Clint hauls) where he gets a chance to use the "Judgement of Charity". How Truck Brakes Work: https://auto.howstuffworks.com/auto-parts/brakes/b...
#4 Why Toshi is the most relatable Tibetan I’ve ever met 10.01.2026 33:56
It's all about connecting. Clint shares some ideas on that - - and an interview with someone from another part of the world who is good at making connections. I've learned a lot from him. Also, see the show notes below for some good resources on connecting with others. (Also "Dry Van" means the regular box trailers you see behind most tractor trailers going down the road) Resources for making mean...
#3 Finding Humanity, From Maryland to Tibet 04.01.2026 19:17
A long, uncomfortable night leads to some serious reflection - followed by conversation with folks making a living in an interesting way. In another segment Clint shares what he has learned from his conversations with a trucker friend from very far away. History of Repression of Tibet by China: https://www.google.com/search?q=history+of+china+tibet+oppression&oq=history+of+china+tibet+oppressi...
#2 Bad Trucker (?) - Good Trucker 27.12.2025 35:19
It takes all kinds! Clint meets a very interesting fellow trucker (bad trucker) who may or may not be like him. And we hear from a brother trucker (good trucker) on insights from the road.
#1 The Ivy League Trucker: The Most Insane Life Arc in History 15.12.2025 35:48
Clint shares how he got here. From an Ivy League education, military and corporate life - to the road. It's not a typical story! We explore themes of pride, perormance, getting seriously humbled, real loss and picking yourself up off the floor and starting all over again. Also a story from the road about seeing folks we might miss altogether. (Also, my wife kindly noted that I use the business jar...
Bridging the Gap: From Boardroom to Big Rig - making human connections (Trailer)) 07.12.2025 1:25
Ivy League Trucker offers a unique blend of broad educational and life experience - and school of hard knocks - insight. Hosted by Clint, a big tig trucker with an Ivy League, military, corporate and small company background. We explore the often unseen connections between diverse worlds—bridging the educated and working-class, as well as connecting generational divides. Clint's journey from the c...
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