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.
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 have him on the pod!
7 Oct 2026
#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.
Resources:
What makes a great over the road trucker??
https://www.google.com/search?q=what+makes+a+good+over+the+road+trucker%3F&rlz=1C5OZZY_enUS1225US1226&oq=what+makes+a+good+over+the+road+trucker%3F&gs_lcrp=EgZjaHJvbWUyBggAEEUYOdIBCTEwMDQ0ajBqN6gCCLACAQ&sourceid=chrome&source=chrome.ob&ie=UTF-8
23 Jul 2026
#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 face have remained steady over the years.
Resources: (mostly fun looks back)
Earliest Days! : https://www.youtube.com/watch?v=iBo05spYleg
The 70's: https://www.youtube.com/watch?v=kAkLazvGWOg&list=PL03dM5mTrjVFPtq_Y-mj1tHiCvsmnF50G
1976: Oregon to Arizona: https://www.youtube.com/watch?v=2h3opFiKX4k
The crappy side of much (most) of trucking jobs today. I am glad I work for a small family run outfits that treats us well and pays by the hour and NOT the mile. https://www.youtube.com/watch?v=yIZRffLA294
28 Jun 2026
# 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 women in trucking in the US.
10 Jun 2026
#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 operations. Clint explores the whats, whys and predicted whens for autonomous truck adoption in the trucking industry. What will this mean for truck drivers and the rest of us? Relax . . . Clint thinks he will have a job for a good while longer!
Resources:
If you want to see what these things look like, here you go:
https://kodiak.ai/technology
https://ir.aurora.tech
As always, please share Ivy League Trucker with family and friends! Thanks - Clint
26 Apr 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.
6 Apr 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 (https://www.everygoodgift.org/). 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 (https://www.everygoodgift.org/). (https://www.everygoodgift.org/)
Christ Kitchen: Loving Women Out of Poverty (https://www.amazon.com/Christ-Kitchen-Jan-Martinez/dp/1937756920/ref=sr_1_1?crid=1GF0BDZNS8B90&dib=eyJ2IjoiMSJ9.VrA0OrnbRhXgQFnYnZQCfA.2nS2g2I_kynEaZTzkyQJ4r_FEbAVGHA3CcfMPQf2yS0&dib_tag=se&keywords=jan+martinez+christ+kitchen&qid=1773759780&s=books&sprefix=jan+martinez+christ+kitchen%2Cstripbooks%2C141&sr=1-1); 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 (https://www.amazon.com/Bridges-Out-Poverty-Professional-Communities/dp/1934583359/ref=sr_1_2?crid=1GUWOGKU6MOPA&dib=eyJ2IjoiMSJ9.F62PNFNrS96yDYrvJtSSNvy-WOw9DREF0UtrMkyoWn_e-70AbP-T36JXac6IDKCKdlRx5tuNk16OtCi4e6VkY_dtYcrOfqD3nN6nI_3I-Tmm3bJ8qbAlWWyEQsd6lY8WMzQ50SG0DHWRH9v3zCuONL_goRGdimRhxbmyJK8UkJgxEjMs9DQ4NPsmgKUxFzx8Ul7QPQ5rKQRyuu9IkFtlHljiM44-nLGRy1CiovDD2Ts.4oZudL4M0taVt76dSGIN5qv4Y0wkS1Fn-M7ebjsXxdM&dib_tag=se&keywords=bridges+out+of+poverty+book&qid=1773762269&sprefix=bridges+out+of+p%2Caps%2C186&sr=8-2). by Terri D. Smith, Ruby K. Payne, Philip E.. DeVol. The book jill referred to that helps us help the poor without hurting.
22 Mar 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
6 Mar 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/ (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
22 Feb 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.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 (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
12 Feb 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/
25 Jan 2026
#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 generation. Good Stuff!!
Resources:
Somewhat relatedly . . . . Great pod interview with Loretta Ross on “Leaning In” to people we would rather cancel.
https://podcasts.apple.com/us/podcast/clear-vivid-with-alan-alda/id1400082430?i=1000745843394 (https://podcasts.apple.com/us/podcast/clear-vivid-with-alan-alda/id1400082430?i=1000745843394)
If you like this stuff - please hit the “Share” button on your podcast player and send to friends, colleagues and family! We want to grow a community of those seeking to connect and understand. Also “Follow” the show to get us in your regular feed.
Direct feedback is always welcome. What would you like to hear on the show? - - and always - helpful critiques to: ivyleaguetrucker@gmail.com
18 Jan 2026
#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 use the "Judgement of Charity".
How Truck Brakes Work:
https://auto.howstuffworks.com/auto-parts/brakes/brake-types/truck-brakes.htm
Runaway Truck Ramps!
https://www.youtube.com/shorts/bJMK6ErcAGw
What's a Tank Wash?
https://www.youtube.com/watch?v=9dAM3tU51eM
We love feedback! Please send comments and requests for future show content to: ivyleaguetrucker@gmail.com
10 Jan 2026
#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 regular box trailers you see behind most tractor trailers going down the road)
Resources for making meaninful connections - especially if you “aren’t good at it” .
Orion Taraban; 6 minute video on connecting
"Ideas divide, emotions unite"
"They only remember how you made them feel"
https://youtu.be/J6aZhfj9NVM (https://youtu.be/J6aZhfj9NVM)
Brene’ Brown on Empathy (short video)
https://youtu.be/1Evwgu369Jw (https://youtu.be/1Evwgu369Jw)
A Book Recommendation:
Daniel Goleman; Emotional Intelligence
https://www.amazon.com/s?k=daniel+goleman+emotional+intelligence&crid=1QOC7FGQSU21D&sprefix=daniel+goleme%2Caps%2C262&ref=nb_sb_ss_p13n-expert-pd-ops-ranker_3_13
Feedback! Please email any (useful) thoughts to: ivyleaguetrucker@gmail.com
4 Jan 2026
#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:
https://www.google.com/search?q=history+of+china+tibet+oppression&oq=history+of+china+tibet+oppression&gs_lcrp=EgZjaHJvbWUyBggAEEUYOTIHCAEQIRigATIHCAIQIRigATIHCAMQIRiPAtIBCDgyNDlqMGo3qAIIsAIB8QWfRPm0UPmxqw&sourceid=chrome&ie=UTF-8
What We Can Learn From Immigrants:
https://jimdaly.focusonthefamily.com/four-things-learn-immigrants/
27 Dec 2025
#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.
15 Dec 2025
#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 road about seeing folks we might miss altogether.
(Also, my wife kindly noted that I use the business jargon of "P&L" in this episode. That means "Profit and Loss" of a business.)
7 Dec 2025
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 the educated and working-class, as well as connecting generational divides. Clint's journey from the corporate boardroom to the trucking life serves as a backdrop for interviews and stories to challenge us, foster empathy - and help us understand and connect with all sorts of people. We also explore themes of personal challenge, loss, reinvention and grace. This podcast is ideal for those curious about understanding, empathy and human connection to counter today's divisive environment.
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Apple Podcasts (US)
5.0 / 5
6 ratings
Spotify
5.0 / 5
8 ratings
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