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Patrick McKenzie

Patrick McKenzie

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Advisor to Stripe; payments and banking technology

Government Payroll Overhauls Frequently Turn Into Boondoggles
Social•Apr 2, 2026

Government Payroll Overhauls Frequently Turn Into Boondoggles

Complex Systems has been acquired by… darn, a day late for a topical April Fool’s joke. No, this week’s episode is about payroll systems, with an extended riff on why government payroll revamps so often turn into boondoggles.

By Patrick McKenzie
LLMs Still Unreliable for Complex Tax Filings, Penalty Method Matters
Social•Apr 2, 2026

LLMs Still Unreliable for Complex Tax Filings, Penalty Method Matters

Interesting anecdotal report here. FWIW I'd not trust the LLMs with a high complexity tax _filing_ yet but, zooming in on one bit there, there is a tax position one needs to take about which of two calculation methods for an...

By Patrick McKenzie
LLMs Now Threatening Software Security, Experts Confirm
Social•Mar 30, 2026

LLMs Now Threatening Software Security, Experts Confirm

Thomas on LLMs vis software security, or, the thing that has been theorized for years is now, in the judgement of local domain experts, actually happening.

By Patrick McKenzie
AngelList Roll-Ups Spotlight Founders' Key Deals and Dormant Angels
Social•Mar 27, 2026

AngelList Roll-Ups Spotlight Founders' Key Deals and Dormant Angels

One of the many reasons to love AngelList roll-up vehicles is there is an asymmetric amount of attention paid to a) the most important transaction to date in a founder's life and b) an angel who hasn't heard from you...

By Patrick McKenzie
Beyond Potemkin: Real Value of HIPAA and SOC 2
Social•Mar 26, 2026

Beyond Potemkin: Real Value of HIPAA and SOC 2

This week on Complex Systems, we have compliance regimes designed to go viral in and around industries, like HIPAA and the new hotness SOC 2, and we Delve into the difference between Potemkin compliance and the messy-but-real value these regimes...

By Patrick McKenzie
Claude Delivers Elegant Bootstrap Time Estimate for Factorio
Social•Mar 25, 2026

Claude Delivers Elegant Bootstrap Time Estimate for Factorio

How can you not love Claude. (I had asked it approximate time to bootstrap a new loop I had set up in a Factorio mod, and it surprised me with the elegance of its approach.) https://t.co/OsvLfcOFGz

By Patrick McKenzie
SMS Bill Payment Skips Transparency, Risks HIPAA Compliance
Social•Mar 23, 2026

SMS Bill Payment Skips Transparency, Risks HIPAA Compliance

Interesting payment UX: Wife received an SMS saying “This is [medical professional]. You have a bill for $X. Reply 1 to pay the bill with your credit card ending in 1234.” No actual bill or option to see the bill,...

By Patrick McKenzie
Investigative Report Exposes Fraudulent Compliance Startup
Social•Mar 20, 2026

Investigative Report Exposes Fraudulent Compliance Startup

This is a really damning bit of investigative journalism about a Potemkin compliance startup. Hat tip to Byrne. the spectral signature is not a subtle one, and one wonders whether all companies which paid them were actually defrauded. https://t.co/upQRuWAusZ

By Patrick McKenzie
Tether’s Graph Reveals Secured Loan Reduction Progress
Social•Mar 18, 2026

Tether’s Graph Reveals Secured Loan Reduction Progress

I’ve been curious about the shape of this graph for a while, particularly because Tether has long said it intended to reduce secured loans. https://t.co/xjIBxkExHc

By Patrick McKenzie
Crafting Tech Growth Stories with Elite Data & Talent
Social•Mar 17, 2026

Crafting Tech Growth Stories with Elite Data & Talent

Work with very smart people, on top of a dataset that reporters would kill for, to tell stories about economic growth and technology, with very high cultural appreciation for craft.

By Patrick McKenzie
LLMs Turn Server Admin Chores Into Planning Time
Social•Mar 16, 2026

LLMs Turn Server Admin Chores Into Planning Time

As someone who has burned more hours than he wants to think on server administration, a *lot* of the cruft of it gets transformatively easier with LLMs, and in lieu of an hour doing deferred maintenance you can spend an...

By Patrick McKenzie
Slay the Spire 2 Feels Like an Expanded Content Pack
Social•Mar 16, 2026

Slay the Spire 2 Feels Like an Expanded Content Pack

Slay the Spire 2: more slay, more spire. Feels more of a content pack than a separate game, but if your complaint about StS was that the magic eventually wore off, you’ll enjoy it. Some minor observations:

By Patrick McKenzie
AI Adoption Is an Engineering Challenge for Enterprises
Social•Mar 12, 2026

AI Adoption Is an Engineering Challenge for Enterprises

Complex Systems this week is with @philipkiely , who has recently written the book (literally) on Inference Engineering. We discussed what AI adoption looks like as an engineering matter in enterprises.

By Patrick McKenzie
AI Replaces $30k Lobbyist, Speeds Municipal Approvals
Social•Mar 11, 2026

AI Replaces $30k Lobbyist, Speeds Municipal Approvals

Historically this has required a lobbyist, and the lobbyist’s invoice runs about $30k. (“What really?” Modal use is “get the transportation engineer to approve a curb cut which if we don’t have it blocks a 7 figure commercial development.”)

By Patrick McKenzie
DC Council Delays Waymo Safety Report Four Years Late
Social•Mar 11, 2026

DC Council Delays Waymo Safety Report Four Years Late

One of the most important jobs of local journalism, which it historically finds most difficult to do, is saying “There is a quotidian procedural issue which affects this community but will not rate national attention. The government is lying about...

By Patrick McKenzie

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