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Thinking
Essays and notes on enterprise AI, production systems, investing, work, and the strange business of staying useful while the world rewires itself.
8 Jun 2026
Survive to be right
The best venture bet of the decade was sitting on FTX's balance sheet, and it still went to zero. The reason is the most under-rated force in investing: timing. Being early and bankrupt looks exactly like being wrong.
capital allocationAIrisktiming
5 min
18 May 2026
1926 meets 2026
Anthropic launched Claude for Legal last Tuesday. The same week I posted a paper property information form to my solicitor in a stamped envelope. Both are the real 2026, and the gap between them is structural — not a complaint about pace.
AIlegalregulationcapital allocation
7 min
27 Apr 2026
The honest number
OpenAI is reportedly guaranteeing private equity partners 17.5% a year to anchor its new enterprise AI venture. That number is a confession — and it tells PE exactly where the operating margin has moved.
AIcapital allocationprivate equityoperating model
6 min
18 Mar 2026
The solo billionaire thesis
Why the first one-person billion-dollar company is no longer a fantasy — and what the existence of that category does to every PE operating model built after it.
AIcapital allocationoperating model
2 min
24 Feb 2026
The hybrid CEO
Half executive, half engineer, all accountable. Why the next generation of operating leaders will code every day — and why the resistance to this is entirely generational.
leadershipAIoperating model
2 min
28 Jan 2026
Frontier over open-weight: a capital allocator's read
The open-weight story is seductive and mostly wrong for enterprise. Here is how I think about the trade — expressed in the language allocators actually use.
AIcapital allocationenterprise
2 min