Former DoD Advisor on Iran, China and AI Warfare
A strategic / geopolitical episode on Invest Like the Best — a former DoD advisor on winning open theatres of war, the structural strengths and weaknesses of authoritarian adversaries, and how commercial technology is reshaping warfare. Core frame: **'dictators are enormously strong and enormously weak at the same time'** — strong because they control the state apparatus, weak because they are illegitimate and trust no one. On **Iran**: winning is politically defined (Strait of Hormuz reopening as the minimal goal); the IRGC controls half the economy and all the guns, making regime change hard without an alternative force structure to defect *to*. On **China**: the CCP's illegitimacy is the US edge — *'Xi doesn't know who's on our side in his Standing Committee'* — and the advisor believes China will eventually fall like the USSR did, looking strong right up to the last moment. On **AI / commercial-tech warfare**: the Ukrainian-drone curve (~50 iterations in three years, built in garages through commercial supply chains) shows that **commercial pervasiveness, not Top-Gun hardware, now drives the rate of change in warfare**. Calls for **multi-year procurement authorities** to fix magazine depth and deterrence gaps (one-year money + continuing resolutions block new starts). On **Taiwan**: cites Kevin Rudd's read of Xi as a risk-taker who sees retaking Taiwan as 'the apotheosis of his life's achievement'.
Key points
- **The master frame: legitimacy is the axis of strategic strength.** *'Dictators are enormously strong and enormously weak at the same time. A dictatorship can be enormously weak because they're illegitimate... and at the same time they're strong because they control the apparatus of the state.'* The US advantage is structural legitimacy + separation of powers (*'the genius of the American founding is the guardians guard against each other'*) — a frame that maps directly onto the **AI centralisation-of-power debate in [this week's All-In Pope episode](/issues/2026-05-31)**: who guards the guardians, applied to states rather than AI labs.
- **Iran: winning is politically defined, and regime change needs a force structure to defect TO.** *'The Strait of Hormuz as an economic choke point has to open back up for commerce to work.'* The IRGC controls half the economy and all the guns; even if 85-90% want regime change, *'you need an alternative force structure to do it.'* The martyrdom culture (Shariati's hybridisation of Marxism + martyrdom) means *'you can bring people to the precipice of their own destruction and in that ideology they're winning'* — making decapitation strategies structurally hard.
- **China will fall — eventually — because illegitimacy is terminal.** *'Xi doesn't know who's on our side in his Standing Committee or on his side. Every day he wakes up with the thought of maybe I need to kill someone off. That is our edge.'* The USSR analogy: *'it looked super strong right up until the last moment — there were planning documents at the Pentagon about how strong they were two weeks before they fell.'* The recruitment edge: *'every Chinese person in the Standing Committee has a relative in the United States who owns a small business doing well and is able to live free.'* **A long-horizon contrarian frame, not a tradeable catalyst — but the directional bet (US institutional durability vs CCP fragility) underpins the defense / reshoring thesis.**
- **Commercial tech is now the dominant input into warfare — the Ukraine drone curve is the receipt.** *'The evolution of a Ukrainian drone from three years ago to today — there's like 50 iterations... because you can sit in your garage through commercial supply chains and build the capability.'* *'Things that become permissive and inexpensive in a commercial world have enormously valuable inputs into fighting asymmetric war.'* **Directly investable read: the defense-tech thesis (Anduril, drone supply chains, commercial-to-military dual-use) that [Joe Lonsdale carries in this week's Uncapped](/issues/2026-05-31)** — commercial iteration speed beats primes' procurement cycles.
- **Procurement reform is the bottleneck: one-year money + continuing resolutions block magazine depth.** *'We need multi-year authorities... one-year money or a ten-year contract subject to the availability of funds is scary. We average four or five continuing resolutions a year, and the peccadillo of a CR is no new starts are allowed.'* Names the kinetic stockpile gap explicitly — Tomahawks, 155s, ordnance. **For defense-prime / munitions investors, multi-year-procurement legislation is the watch-trigger that unlocks the magazine-depth capex cycle.**
- **Taiwan: Xi as risk-taker, the apotheosis frame.** Citing Kevin Rudd (ex-Australian PM, Mandarin-fluent China scholar): Xi is a risk-taker who may see retaking Taiwan as *'the apotheosis of his life's achievement... Imperial China is what Taiwan is.'* Pairs with the legitimacy frame — a leader who needs a legacy-defining victory to cement an illegitimate mandate is structurally more dangerous near the end of his tenure. **The single highest-impact tail risk to the entire AI-infra/semis supply chain (TSMC) sits here.**
- **The freedom-degradation dilemma: how do open societies defend against adversaries weaponising their freedoms?** *'Our enemies use our freedoms so successfully against us... the psyop of social media. Are we going to have to degrade a portion of our freedoms in order to protect ourselves? This is going to be the real hard part.'* The disinformation-amplification problem (*'there are no gates on any of this anymore'*) connects to the **Sacks free-speech-vs-trust-and-safety tension running through [this week's All-In](/issues/2026-05-31)** — same dilemma, opposite institutional starting point.
Notable quotes
Dictators are enormously strong and enormously weak at the same time. A dictatorship can be enormously weak because they're illegitimate. And at the same time, they're strong because they control the apparatus of the state.
Xi doesn't know who's on our side in his Standing Committee or on his side. Every day he wakes up with the thought of maybe I need to kill someone off. That is our edge. Our edge is that he is fundamentally illegitimate.
The Soviet Union looked super strong right up until the last moment. There were planning documents circulating at the Pentagon about how strong they were like two weeks before they fell. Because their concept of a constitution is fundamentally corrupt.
The evolution of a Ukrainian drone from three years ago to today, it's like 50 iterations, all these new capabilities. And that's because you can sit in your garage through commercial supply chains and build the capability.
We need multi-year authorities. One year money or a ten year contract subject to the availability of funds is scary. We have on average four or five continuing resolutions a year, and the peccadillo of a CR is no new starts are allowed.
Our enemies use our freedoms so successfully against us. Are we going to have to degrade a portion of our freedoms in order to protect ourselves? This is going to be the real hard part against a very motivated and sociopathic adversary that's illegitimate.
Themes
- US-China strategic competition
- Defense-tech & commercial-to-military dual use
- Procurement reform & munitions capex
- Taiwan tail risk to semis supply chain
- Legitimacy, freedom & information warfare