Most of us get in the car, punch an address into Google Maps, and go. But when you’re driving an 80,000-pound truck, a wrong turn can become a very big problem. Today, we’re talking to Robert Philips, he is a part of a father-and-son team building Highway Miles, a free GPS app designed specifically for truckers. Robert recently got a CDL after retiring from the world of tech in order to help his son, Justin build out the app.

And I’ve got a special co-host joining me today: my 9-year-old son Sebastian, who’s going to help us find out whether these guys are building the future of trucking or just getting dad and son to agree on something for once.

And, with Pokemon cargo thefts on the rise, we get a special report from my 12-year old son Ronan.

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Andrew Donaldson has a pretty interesting history with Brad Jacobs: he worked at Con-way when Jacobs bought the company, and Andrew was fired in the aftermath. Now, more than a decade later, Jacobs’ RXO is being sold to C.H. Robinson for $5.8 billion. So what does Andrew make of the deal and the wild evolution of the freight industry since Con-way?

From there, we go way beyond freight: the death of the media monoculture, AI and the homogenization of everything, Trump and the political tribes, tariffs, West Virginia, outrage-driven news and why it has become so hard for people to simply talk to each other.

Thank you to our sponsors:

Load Secure:https://loadsecure.com/

Whimsy Intermodal: https://whimsyintermodal.com/

Become a guest or sponsor: https://timdooner.com/contact

Follow Tim and the Show on X

Tim: https://x.com/TimothyDooner

Show: https://x.com/DoonerShow

YouTube: https://www.youtube.com/@DoonerShow

Apple: https://podcasts.apple.com/us/podcast/dooner-show/id6805982168

Spotify: https://open.spotify.com/show/0mpzDhqiCUgSVU41WNIGHF