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Making History Personal History Guest is trying to use AI for what it's actually good at: No dry (probably wrong) facts and figures, just a personal story told by some...
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Making History Personal
History Guest is trying to use AI for what it's actually good at: No dry (probably wrong) facts and figures, just a personal story told by some of the most important figures in history, or at least a passing simulacrum of them.
They're a bit soupy in places, but I built a pretty complex system for prompting and custom ablater to strip AI-like repetition/nonsense run-ons, and designed around understanding the emotional reality of our guests. I wanted to know if AI can make literally anything that isn't slop; I think these came out pretty well, and my faves are Machiavelli and Mary Anning. I was impressed how many guests have something genuinely interesting to say about their experience, and occasionally about our modern world too.
show less
History Guest is trying to use AI for what it's actually good at: No dry (probably wrong) facts and figures, just a personal story told by some of the most important figures in history, or at least a passing simulacrum of them.
They're a bit soupy in places, but I built a pretty complex system for prompting and custom ablater to strip AI-like repetition/nonsense run-ons, and designed around understanding the emotional reality of our guests. I wanted to know if AI can make literally anything that isn't slop; I think these came out pretty well, and my faves are Machiavelli and Mary Anning. I was impressed how many guests have something genuinely interesting to say about their experience, and occasionally about our modern world too.
Episodes & Posts
Episodes
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AI-generated content
14 OCT 2026 · He burned his own ships so his men couldn't go home. He wrote five letters to the King of Spain so well-crafted they're still taught in universities — and they're still lying. Hernan Cortes sits down to talk about the gap between what happened and what he put on paper.
He walks us from the causeway into Tenochtitlan — a city that left hardened soldiers speechless — through La Noche Triste, where gold pulled men under and war drums seemed to come from inside the stones. He admits he mistook ritual hospitality for surrender, that smallpox did his killing for him, and that Doña Marina — the Indigenous translator who made every negotiation work — was erased from the record to protect his reputation. He executed his oldest ally's son as a political example and left it out of the dispatch entirely.
Then he draws the line to today: regime change, Iraq, international law as what he calls "the fifth letter." The costumes change. The extraction doesn't. Plus a PR platform ad read that Cortes personally roasts.
Making history personal. One guest at a time. This episode includes AI-generated content.
AI-generated content
7 OCT 2026 · He spent fourteen years as a Florentine civil servant — paid badly, reimbursed never, once literally selling his horse to fund a diplomatic mission. Then the Medici came back, dismissed him, strung him up by the wrists six times, and exiled him to a farm where he couldn't catch a single thrush. So he put on his court clothes every evening, read Livy, and wrote The Prince — the most desperate job application in history. They never answered. Lorenzo de' Medici preferred the hunting dogs.
This conversation covers the antechambers of the French court (where he memorized the wallpaper), Caterina Sforza on the ramparts of Forli, the Borgia massacre at Senigallia, and the citizen militia that took Pisa but broke at Prato. Machiavelli on why "Machiavellian" is an alibi, why virtù isn't gendered, why your republic of commentary is just the Orti Oricellari with Wi-Fi, and why the book he actually believed in — the Discourses — got buried by the scandalous pamphlet. Plus: a ride-share ad he dismantles as a principality.
Making history personal. One guest at a time. This episode includes AI-generated content.
AI-generated content
30 SEP 2026 · The horse story is a lie, and she's been waiting two hundred years for someone to lead with that. Catherine the Great — born Sophie, a German princess who arrived in Russia at fifteen, married a man who couldn't stand her, and waited sixteen years before overthrowing him — sits down to talk about what it actually costs to run an empire when you know you're doing it wrong.
She gets into the gap between writing to Voltaire about the abolition of torture and signing grain requisition orders that starve villages. The Pugachev rebellion — when a man claiming to be her dead husband marched an army up the Volga — and the ten minutes of terror she budgeted herself before going back to her desk to burn villages. Potemkin, the great love who built Sevastopol out of mud and fever. The ice palace she commissioned to prove nothing could shake her. The drawer full of things she never signed: an emancipation draft, a letter to her son, a miniature portrait of Potemkin. And her verdict on modern democracy — you have the vote she never gave, and you're using it to elect people who'd take it away.
What's the line between Catherine the empress and Sophie the woman who read too many books? She's had two centuries to think about it.
Making history personal. One guest at a time. This episode includes AI-generated content.
AI-generated content
23 SEP 2026 · Joan of Arc liked chickens more than wheat. She says so herself. Before the armor, the siege at Orléans, the coronation, and the fire, she was a girl in Domremy who milked cows, spun wool, and laughed at her father's stupid jokes. She talks to Alex and Rae about the four years she heard voices and pretended she didn't — the cows still needed milking — and the morning she left with bread in her pocket and a lie to her crying friend.
She describes arriving at Chinon, being stared at in a cell by courtiers testing whether she'd contradict herself, and walking past the decoy on the throne straight to the Dauphin. Then comes army life: the noise, the smell, sleeping in armor sitting up against a cart, saddle sores in the wrong place for a woman, a fever she rode through because lying down meant dying. At Orléans she found commanders who'd been sitting behind walls waiting to starve and told them wood burns and men bleed. She crossed the river at night, took the fort, and learned that most people follow not from belief but because they're afraid of missing the victory. After it fell, a woman handed her warm bread. La Hire held loaves to his ears and said they were still singing. She laughed for the first time since leaving home.
The conversation turns to what happens when a girl who hears voices becomes a tool for captains who never believed in them — useful until Paris failed, then a problem. She talks about conviction and being misread, about how a girl today with the same experience would get therapy, a talent agent, and a priest all arguing over whose costume is most legitimate. It ends on a field of wheat and a girl walking through it. That's what she misses.
Making history personal. One guest at a time. This episode includes AI-generated content.
AI-generated content
16 SEP 2026 · The carpet story is wrong. Cleopatra walks Alex and Rae through what actually happened — a linen sack, not a carpet, and she was dressed, composed, and carrying a plan. She was a monarch pitching an alliance, not a seductress performing a scene. She talks about growing up in a family that made the Borgias look like a debating society, learning that loyalty is a performance until it's tested, and that trust is a resource you spend like grain.
The conversation gets into the real work: moving harvests down the Nile, calibrating fear and honesty among officials, negotiating with priests who own land and command loyalty. She explains the coinage as propaganda that travels through every merchant's pocket, the temple appearances as governance rather than theatre, and the barge at Tarsus — not as a pleasure cruise but as a budget presentation aimed at Antony and, through him, every eastern client kingdom deciding whose side to take. She made him wait. She stole his audience before she arrived. It cost less than a month's revenue and bought a decade on the throne.
Then it turns to the propaganda war. Octavian didn't defeat her militarily — he defeated her narratively, turning a fiscal partnership into a sexual surrender, a war between empires into a cautionary tale about a good Roman undone by a foreign woman. She and Alex trace the same mechanism through Merkel's diamond, through modern women in power praised for softness and blamed for hard reality. The asp, she says, might be entirely an invention. Let them have the asp. She had the grain.
Making history personal. One guest at a time. This episode includes AI-generated content.
AI-generated content
Transcribed
9 SEP 2026 · Before the hair, the equation, and the magazine covers, Einstein was a patent clerk in Bern grading gravel sorters and tobacco humidifiers - and quietly dismantling absolute time between applications. He talks to Alex and Rae about the supervisor who taught him to find the core of an idea, the stubborn notebook he wrote relativity in (the one that wouldn't lie flat, that bled ink, that he couldn't throw away), and the friend Besso who told him the problem wasn't the answer but the question itself.
Then 1919 happens. An eclipse. Suddenly he's famous, and the symbol eats the person. He describes developing a "thinking face" to survive bakeries, the hair becoming a trap he couldn't cut without causing a fuss, and the violin as the one place the symbol couldn't follow. The conversation turns to the crisis of celebrity science - influencers chosen for being watchable, not for being right - and then to 1933: watching from Belgium as Germany burned his books, the survivor's guilt, signing affidavits he knew wouldn't be enough. It builds to the Roosevelt letter - the one Szilard brought to his sailboat - and the regret he carried for the rest of his life, caught between two regrets with no way to tell which is worse. It ends on Mercer Street, on cracks in the pavement, on the small rituals that hold a day together when the big picture is chaos.
Making history personal. One guest at a time. This episode includes AI-generated content.
Making History Personal History Guest is trying to use AI for what it's actually good at: No dry (probably wrong) facts and figures, just a personal story told by some...
show more
Making History Personal
History Guest is trying to use AI for what it's actually good at: No dry (probably wrong) facts and figures, just a personal story told by some of the most important figures in history, or at least a passing simulacrum of them.
They're a bit soupy in places, but I built a pretty complex system for prompting and custom ablater to strip AI-like repetition/nonsense run-ons, and designed around understanding the emotional reality of our guests. I wanted to know if AI can make literally anything that isn't slop; I think these came out pretty well, and my faves are Machiavelli and Mary Anning. I was impressed how many guests have something genuinely interesting to say about their experience, and occasionally about our modern world too.
show less
History Guest is trying to use AI for what it's actually good at: No dry (probably wrong) facts and figures, just a personal story told by some of the most important figures in history, or at least a passing simulacrum of them.
They're a bit soupy in places, but I built a pretty complex system for prompting and custom ablater to strip AI-like repetition/nonsense run-ons, and designed around understanding the emotional reality of our guests. I wanted to know if AI can make literally anything that isn't slop; I think these came out pretty well, and my faves are Machiavelli and Mary Anning. I was impressed how many guests have something genuinely interesting to say about their experience, and occasionally about our modern world too.
Information
| Author | Bob |
| Organization | Bob |
| Categories | History , Personal Journals , Society & Culture |
| Website | - |
| podcasts@bobbigmac.com |
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