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A map on my phone might be a good start.

He would be familiar with maps so that would be something we could build off of.

Show George Washington a smart phone. He'll know all he needs to know about modern people with some time browsing Twitter and Pornhub.
The web, with all its warts, idiosyncrasies, and repercussions as a mature medium dominated by the very few. Maybe he'd find a way to let it thrive again, as knowledgable he was about human nature.