A Ukrainian 3rd corps ran a multi-brigade offensive and, by its commander's count, lost seven times fewer soldiers than Russia, most of them wounded. 250 prisoners — company commanders among them, most likely a battalion commander. 12,000 captured drones. Hundreds of armoured vehicles left where they stood. Asked when it happened, the man advising that corps answers: "I can't talk about the timeline at all" — because the weaknesses Third Corps exploited are still open. This is Operation Vivaldi, the campaign in the Lyman direction that broke Russia's plan for the year.

Our guest goes by the call sign Jackie. American, a self-described "forever sergeant," he is the senior American military advisor to Ukraine's Third Army Corps. He came to Ukraine in 2022, was wounded almost immediately, and spent his first weeks in a Ukrainian hospital working out who he was fighting for. Rob Lee joins as co-host, so you get the operational picture and the man inside it at the same time.

Along the way: the avalanche assault, ground drones appearing behind Russian lines, a remote-driven BTR-60 packed with ammunition, the mid-strike campaign and the cappuccino line — the last place you can get a barista-made cappuccino before the battle area; Ukraine's sits 23 kilometers back, Russia's is nearing 50. Why every infantryman is now a SIGINT specialist. How a unit that cannot legally punish anyone enforces discipline with trust, honesty and the after-action review. And the story of Grady Kurpasi, the Marine who should have been commanding part of the fight he died in as a rifleman.

Recorded in Kyiv.

Key moments:

0:00 - Maneuver is dead: the verdict Vivaldi broke

13:01 - "I can't talk about the timeline at all"

24:51 - What Vivaldi was for: defeat the northern pincer

40:50 - The avalanche assault, explained

47:40 - Ground drones behind Russian lines

55:04 - The mid-strike campaign: pulling the Russian line back

86:23 - The BTR-60 turned remote-driven bomb

92:26 - Third Corps history: 2014 and the men who knew the enemy

108:16 - The cappuccino line: the most honest metric of this war

113:22 - Culture beats technology: the mind is the weapon

137:37 - The training pipeline: 51, 24, and 14 days

154:43 - The AAR as the only discipline that works

163:11 - Grady Kurpasi: the story to stay for

Produced by the Borderlands Foundation.

Support our work: https://theborderlandsfoundation.org

Why War Matters — Sam's new Washington, DC talk for founders:

https://ukraineforfounders.com/talk/

All episodes: https://ukrainemilitaryhistory.org/

Guests:

Rob Lee: https://x.com/RALee85

Third Army Corps: https://ab3.army

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In the winter of 1855 the most powerful man in Russia put on a summer uniform, walked out into a St Petersburg winter, and inspected parades until it killed him. Nicholas I had started a war he was certain he could not lose: a million and a half men mobilised, the glory of beating Napoleon behind him, God on his side. He lost it in Ukraine. No decisive battle, no enemy at the gates of Moscow, half a million men gone, and an empire that simply ran out of ways to win.

Andriy Zagorodnyuk was Ukraine's Minister of Defence from 2019 to 2020, ran the Ministry's reform office from 2015, and chairs the Centre for Defence Strategies. He has also read the Crimean War for years as a hobby, in Soviet sources and Western ones both, which is why this conversation exists: Yevgeny Tarle writing under Stalin, and Orlando Figes writing in the West, and the same war coming out as two different books.

Along the way: the siege of Sevastopol was never a siege, because the northern road stayed open the whole time. The first war correspondent in history brought down a British government by telegraph while the tsar's own despatches took weeks to reach St Petersburg. By the end, British supplies reached Crimea faster from London than Russian supplies did from Moscow. The Crimean Tatars were the majority population, and 1850s prints of Simferopol show minarets and camels. And Russia, uninvaded, with millions still under arms, signed away its Black Sea fleet, because the coalition refused to leave a grey zone and the alternative was worse than losing.

The argument underneath it is the one to carry around. Analysts say there are two ways to win a war, attrition or annihilation. Zagorodnyuk says Crimea proves there is a third, and it is the one that happens to Russia: the aggressor has to win, it cannot live with uncertainty forever, and when every campaign fails the regime starts lying — not because it is dishonest first, but because it is incapable first. Russia does not lose by being beaten. It loses by running out of ways to win.

Recorded in Kyiv.

KEY MOMENTS 0:00 - Cold open: Nicholas I in a summer uniform 4:39 - Zagorodnyuk, unmanned systems, and the Centre for Defence Strategies 9:42 - Why the Crimean War is the war to study now 11:34 - The same regime 170 years apart, and its three priorities 12:38 - He wanted Istanbul and said he was protecting Christians 17:46 - Two libraries: Tarle under Stalin, Figes in the West 19:35 - Putin's rehabilitation of Nicholas I 27:32 - The siege of Sevastopol was never a siege 29:17 - The first war correspondent, the telegraph, and Florence Nightingale 34:15 - Supplies faster from London than from Moscow 37:09 - Losing without a single decisive battle 39:45 - Not attrition, not annihilation: running out of options 41:37 - Incapable first, lying second 46:34 - Precise affordable mass, and people spent like munitions 51:25 - The Crimean Tatars, blamed and punished 57:24 - The Paris Treaty, and the fleet Russia had to give up 62:56 - What would end this war the same way

Produced by the Borderlands Foundation. Support our work: https://theborderlandsfoundation.org

Why War Matters — Sam's San Francisco talk. Part I is free: https://ukraineforfounders.com/talk/

All episodes: https://ukrainemilitaryhistory.org/

Guest: Andriy Zagorodnyuk / Centre for Defence Strategies: https://defence.org.ua

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They did not win the hackathon. They did not even place. Twenty-four hours in a room in Los Angeles, two hours of sleep, a 3D printer that would not cooperate, and somebody putting dubstep on at four in the morning to keep everyone upright. The judges said "cool, sounds good" and moved on. Ian Laffey posted what they had built, slept eighteen hours, and woke up to millions of views and a phone full of messages. Today that technology flies on the front line in Ukraine.

Ian Laffey is co-founder and CEO of Theseus. They build navigation that lets a drone fly with no GPS at all, which is the single hardest constraint on a battlefield where satellite navigation is jammed across every inch of ground that matters. He had never touched a drone before February 2024, and he met his third co-founder in the hackathon room.

Sam Cook sat down with him in Kyiv for the clearest account yet of how a defense product actually gets proven. Ukraine, Ian argues, is the closest thing to a free market that exists anywhere in defense: units buy what works, at brigade level and below, often with donated money, and there is nowhere to hide. Ship a hundred million dollars of kit here and if it is not good enough it sits in a warehouse and everybody knows. His line: you can prove you can sell a hundred million dollars of something somewhere else, but you cannot prove it works anywhere but here.

He is unusually hard on himself about getting it wrong. On the first visit in November 2024 the drone was launched off a catapult his team had never seen, and the product failed outright. There are three ways to do this, he says, and two of them fail. Fly in for two days and take photographs, which is worse than not coming at all. Come for a fortnight at a time and watch every relationship go cold the moment you leave, because nobody here is sitting by a laptop waiting for your Zoom invite. Or move here. He moved here.

Then it turns to Washington. The three most critical technologies in this war, two of them American and neither of them military: the Chinese commercial electronics supply chain, Starlink, and AI. Why he thinks building interceptors in the United States makes little sense when there is nowhere to get the repetitions. And why SBIR dollars spent on slide decks made in America could instead fund American companies to develop and validate the same technology in the one place it is actually employed.

And the reason he is here at all: a best friend adopted from Ukraine just after independence, a father who told him never to hit first but to hit back as hard as he possibly can, and his own conclusion that it is a terrible circumstance, but in a lot of ways a privilege to get to work on things that matter.

Recorded in Kyiv, October 2026.

KEY MOMENTS 4:58 - "Completely by accident": what Theseus builds 17:49 - His best friend is Ukrainian, and "I'm not a sniper" 19:17 - Jack's adoption, and his father's rule about hitting back 22:49 - 24 hours, two hours of sleep, and dubstep at 4 a.m. 26:44 - "You can't delay your stupid moment" 27:09 - Getting your ass handed to you by the real world 36:40 - Every combat drone in the world is in one place 38:29 - The closest thing to a free market in defense 42:53 - Three ways to come to Ukraine, and two of them fail 45:44 - "I just need to move here" 56:43 - The three technologies deciding this war 61:12 - SBIR dollars for slide decks, and what they could buy here 71:41 - "I'm not putting you in a Signal group chat from California" 76:21 - Price it so Ukraine can field it, and the money follows

Produced by the Borderlands Foundation. Support our work: https://theborderlandsfoundation.org

Why War Matters — Sam's San Francisco talk. Part I is free: https://ukraineforfounders.com/talk/

All episodes: https://ukrainemilitaryhistory.org/

Guest: Ian Laffey / Theseus: https://www.theseus.us

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