What I learned on my road trip across the country about politics & technology

Charlie L
The Startup
Published in
6 min readJul 6, 2019

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I drove from Portland, OR to Chicago, IL last weekend (technically 3 days) with my friend Dima and my dad (Simon). I am not sure what I was expecting to talk about for 35 hours but somehow there was never a quiet moment which made the emptiness of Montana, Wyoming and South Dakota a little more entertaining (and irritating). As much as I was hoping the drive would be like Zen and the Art of Motorcycle Maintenance meets Wes Anderson, it ended up being a lot less profound and with a lot more Applebees, Outback, Econolodge and Culver’s. Even though we didn’t solve all of the worlds intellectual problems like characters in a Wim Wenders or Ingmar Bergman movie might or have any coming of age moments (except my dad asking the waiter for too many details about the “nature, flavors and aroma” of the mashed potatoes at Applebees and me politely asking him to “shut the fuck up”), we had plenty of time to talk about politics. It ended up being a very illuminating discussion for me in a way I didn’t expect.

Dima, the lucky third passenger on our trip, is from Ukraine, not the United States originally. He was very curious to hear about how our election process for President works and my dad was more than willing to share his opinion on the matter (arguably too willing if measured by the time he spent talking). Ukraine also…

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