Ivy League Trucker

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! 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

23 July 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

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28 June 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.

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52:24

10 June 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

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26 April 2026

# 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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