What Would the Founders Ask an AI?

America turns 250 this Saturday, and I’ve been carrying a dinner-party question around all week: if you handed the Founders a laptop running a modern AI, what would each of them ask it? I keep coming back to it because the Founders were, as a group, the best question-askers ever assembled on this side of the Atlantic (no playbook to inherit, so they interrogated one into existence), and asking good questions is kinda my whole thing… it’s the podcast, it’s the sign-off, it’s probably going on my tombstone.

(Edward, you just measured four of history’s most consequential minds against your own podcast tagline, and now you’re going to grade their imaginary homework in public. Three of them ran newspapers and any one of them would’ve out-written you by Tuesday… although none of them had a blog, so technically you’re up one on Jefferson, which is a sentence nobody should ever say. Moving on.)

Franklin’s the easy one, so we’ll start there. He was a printer before he was anything else, and his whole career was one long bet that making knowledge cheaper makes people freer… the almanac, the lending library, the post office, the bifocals so older readers could keep reading, you name it. Hand him an AI and I don’t think he wastes one minute on consciousness or the singularity. He asks what just happened to the price of knowing things, and the answer would make him giggle: the cost of a decent first draft of almost anything (a contract, a lesson plan, a business case, a diagnosis) has fallen further in 3 years than in the previous 300, and Franklin, being Franklin, would have a business running on top of it by Thursday and the profits pledged to a library by Friday. Honestly, he’d probably skip the rest of the dinner party to keep playing with it. Of the four, he’s the one I’d most want to watch meet the machine, and the only one whose credit card I’d worry about.

Jefferson’s my favorite of the bunch (lets just say the feeling is well-documented around my house), and his question is the one we still can’t answer: who controls it? He distrusted concentrated power the way the rest of us distrust gas-station sushi, so he’d want to know who owns the thing, who can read what you ask it, and who decides what it refuses to say, and today’s honest answer (“a handful of companies, and it depends”) would send him straight up a wall. He’d want the tools in as many hands as possible and every citizen educated enough to argue about them… which happens to be roughly the mission of the free AI meetups we run in Puerto Rico, so at least somebody’s on it, Tom.

Adams and Washington I’d sit at the same end of the table, cause their questions are two halves of one worry. Adams believed the republic ran on the quality of its arguments (his “Thoughts on Government” is basically an argument about how to argue, and the Federalist Papers from his era ran 85 essays written on brutal deadlines by 3 men sharing one pen name… wait, I had a point. The point: he’d ask whether a machine that writes fluently makes our arguments better or just more numerous, and having run AI companies, I’ll give the honest answer, which is both, in whatever ratio we choose). Washington would barely need the laptop. The man won a war, held absolute power in his hands, and gave it back… twice?!? So he’d skip right past what the AI can do and ask the question I now put to every executive I work with: which decisions stay human on purpose? Somebody has to own the outcome, and owning an outcome isn’t something you can delegate to an API, no matter how good the API gets.

And the thing that actually holds up after 250 years is what they built together: a system for staying wrong gracefully. Amendments, elections, a free press… the whole machinery of revision, installed by men who assumed in advance that they’d made mistakes. That’s the exact mindset AI demands right now, because nobody (including the people building it, and I’ve asked them) knows how this plays out. The winners will be the ones who ask good questions, act on the best current answer, and keep one hand on the edit button.

Happy 250th, America. You were founded by people asking much better questions than “will this scale?” (Though to be fair… it did.)

So who gets the laptop? I’ve made my case for Franklin, but I genuinely go back and forth on it, and this is exactly the kind of argument I miss having in person. Write me (Edward@Roske.AI) and make yours. I read every single one, and the best answer gets quoted in a future post… with credit, cause I’m not a monster.

Asking good questions, Edward