High Line Advisors
Insights

Insights

Shorter than a paper and quicker to write: a reading of something that just happened, or an argument not yet worth twelve pages.

Subject
AI Code is the new tech debt

Forget COBOL, mainframes, and IDMS. Your tech debt is about to get worse.

Sep 2026
AI regulation for financial services is already here.

"Failure to supervise" the agent or the operator is well-established ground and already accounts for a high percentage of enforcement actions.

Sep 2026
The "killer app" for enterprise AI

Project management of humans working with AI in a sovereign, aligned, and cryptographically-secure environment. Let's get into it.

Sep 2026
The supervisory letter nobody circulated

A short observation on who actually reads the second paragraph.

Jul 2026 3 min
Two questions before you buy the model

Both are about your own data, not the vendor.

Jun 2026 4 min
On collateral upgrades

The trade is fine. The habit of not re-reading the documents is not.

Apr 2026 2 min
What the calendar knows

Why funding stress is usually a scheduling problem wearing a solvency costume.

Feb 2026 5 min

Notes are not revised after publication. Where one is overtaken by events, a later note says so rather than the earlier one changing.