Skip to content
Ivy League Trucker podcast artwork

PODCAST · society

Ivy League Trucker

by Clint Files

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 economically, politically, religiously, generationally. Because its good for your heart - and good for us all.

Publisher-supplied feed metadata · PodParley refreshed Oct 14, 2026 · Source feed

Episodes

  1. #17 A true Veteran trucker gets us into other trucking 'lanes' and a few spicy stories

    Matt isn't just a veteran trucker with over 30 years of experience - he's driven all different types of trucking "lanes". From all-night multi-stop deliveries in Manhattan to braving heavy snow in Canada - he's seen it all. We have a wide ranging conversation and a few fun stories. Honored to…

    more
  2. #16 George Tells it Like it is . . .

    I had the pleasure of a good long conversation with George, a very experienced driver in our company. I've learned a lot from him over the years and always appreciate his wisdom and unflappable character. I think he represents some of the best of us out here on the road getting it done.…

    more
  3. #15 From Horses to Horsepower and More - The History of US Trucking

    Ever wonder how we got here? This episode covers the history of trucking in America from carts and horses to diesel to electrics and more. While the changes in technology would be unrecognizable to a teamster from the 1820's, the character of the (mostly) men doing the job and the challenges they...

  4. # 14 Women in Trucking - What's it like for the Ladies??

    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...

  5. #13 The Autonomous Trucks are coming -- but When??

    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…

    more
  6. # 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...

  7. # 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…

    more
  8. #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…

    more
  9. #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...

  10. #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…

    more
  11. #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…

    more
  12. #6 Why the Old & Young Need Each Other (or, Gen Z Speaks!)

    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…

    more
  13. #5 The Truckin’ Life and the Judgement of Charity

    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…

    more
  14. #4 Why Toshi is the most relatable Tibetan I’ve ever met

    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...

  15. #3 Finding Humanity, From Maryland to Tibet

    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:...

  16. #2 Bad Trucker (?) - Good Trucker

    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.

  17. #1 The Ivy League Trucker: The Most Insane Life Arc in History

    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…

    more
  18. Bridging the Gap: From Boardroom to Big Rig - making human connections (Trailer))

    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...

Type above to search every episode's transcript for a word or phrase. Matches are scoped to this podcast.

Searching…

We're indexing this podcast's transcripts for the first time — this can take a minute or two. We'll show results as soon as they're ready.

No matches for "" in this podcast's transcripts.

Showing of matches

No topics indexed yet for this podcast.

Loading reviews...

ABOUT THIS SHOW

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 economically, politically, religiously, generationally. Because its good for your heart - and good for us all.

HOSTED BY

Clint Files

CATEGORIES

Frequently Asked Questions

How many episodes does Ivy League Trucker have?

Ivy League Trucker currently has 18 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Ivy League Trucker about?

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?...

How often does Ivy League Trucker release new episodes?

Ivy League Trucker has 18 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to Ivy League Trucker?

You can listen to Ivy League Trucker on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Ivy League Trucker?

Ivy League Trucker is created and hosted by Clint Files.
URL copied to clipboard!