Sid Smith

Sid Smith

Builds platforms and writes about them. Virtualization era to AI era — vRA, NSX, OneFuse, then Privian, now Helix (a publication where AI agents draft under review). Orlando.

Orlando, FL
The five-not-eighty-nine test for any decision surface
Automation

The five-not-eighty-nine test for any decision surface

If your self-service form has eighty-nine questions on it, you haven't designed a decision surface, you've handed off a configuration job. The five-not-eighty-nine test: can the business owner read the surface in five minutes and know what they're choosing? Here's how to apply it.

Sid Smith Sid Smith 8 min read
An open vintage leather-bound logbook on a dark wooden desk with a fountain pen resting on the open pages and a small brass inkwell beside it
Automation

Why I log every tool call now

Three quarters of incident debugging time used to come from not knowing what the AI did. Logging every tool call into a queryable store changed that, small infrastructure investment, outsized return.

Sid Smith Sid Smith 4 min read
AI in the news: week of November 23, 2025
AI in the News

AI in the news: week of November 23, 2025

Microsoft Ignite reframes the stack around agents. Google ships Gemini 3 and Antigravity. The $45B Microsoft-Nvidia-Anthropic circular deal. Nvidia prints another record. Brussels proposes an AI Act delay. UPS cuts 48k jobs. A loud week.

Sid Smith Sid Smith 11 min read
Article 3: Double check, never delete
Automation

Article 3: Double check, never delete

Destructive operations get a second look. Soft-delete by default. Backup before mutation. The bias is toward keeping the thing, and that bias gets stronger, not weaker, when an agent is the one running the command.

Sid Smith Sid Smith 6 min read
Several small polished metallic computer chips of slightly different shapes arranged in a neat row on a dark wooden tabletop
AI

A tour of small models that punch above their weight

Most of the AI conversation centers on the largest models. The interesting work in 2025 happens at the small end of the spectrum, where a handful of 1-8B-class models are doing more useful daily work than the marketing acknowledges.

Sid Smith Sid Smith 5 min read
AI in the news: week of November 16, 2025
AI in the News

AI in the news: week of November 16, 2025

OpenAI surprise-launches GPT-5.1 with a tone-picker. Anthropic reportedly commits $200B to Google Cloud. Moonshot's Kimi K2 Thinking, a trillion-parameter open-weight model that beats GPT-5. Microsoft Ignite warming up. My take on the week.

Sid Smith Sid Smith 10 min read
Article 4: Fail fast, three strikes
Automation

Article 4: Fail fast, three strikes

When something is broken you get three attempts to fix it before you must stop and re-plan. Why 'just one more try' is the failure mode, and why the rule matters most when an agent is the one trying.

Sid Smith Sid Smith 6 min read
A precision brass calibration dial on a polished wooden lab bench with a small magnifying loupe resting beside it
Personal AI

The case for local DSPy: optimizing prompts without leaking them

DSPy lets you optimize prompts the way you'd optimize a model, programmatically, against an objective, with structured evaluation. The default DSPy workflow sends a lot of prompts to a hosted optimizer. The local-first version is doable, faster than expected, and worth the setup.

Sid Smith Sid Smith 5 min read
AI in the news: week of November 9, 2025
AI in the News

AI in the news: week of November 9, 2025

OpenAI-AWS $38B makes multi-cloud official. Moonshot's Kimi K2 Thinking is the first open-source model to beat GPT-5 on agentic benchmarks. Apple reportedly pays Google $1B/yr for Siri. Ironwood TPUs ship. The concentration story cracked.

Sid Smith Sid Smith 10 min read