Insights · Tommy’s notes

From the seat

You’re reading too much
and learning too little.

Founders inhale newsletters. Most are recycled frameworks dressed as insight. These are the notes Tommy actually writes from the seat — the patterns that show up across engagements, the mistakes that get repeated, and the moves that don’t.

Cornerstones

Four pieces, in production.

Each one is a long-form read drawn from live engagements. Subscribe to receive them as they ship — all four land in the next six weeks.

01

Strategy

Why boards confuse strategy decks with strategic decisions.

Most board packs are slide ware, not decisions. The pattern, the cost, and the structure that fixes it.

9 min readForthcoming

02

Marketing

Why founders confuse hiring a CMO with running marketing.

The seat is operational. The hire is symbolic. Why the wrong order costs you twelve months and three campaigns.

7 min readForthcoming

03

Pitching

The four founder maturity registers — and why they break pitches.

Engineer, Operator, Marketer, Hybrid. Mismatch the register and the room nods politely while the deal dies. The decoder ring.

11 min readForthcoming

04

Risk governance

The audit cycle is 90 days. The risk moves in real time.

Enterprise advisory firms now describe agentic continuous monitoring as the only viable architecture for AI risk governance. Here is what that means for mid-market boards carrying enterprise-grade AI exposure without enterprise-grade risk teams.

8 min readForthcoming

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What lands in your inbox

  • ICP and positioning sharpening
  • Pipeline and channel allocation
  • Board reporting and measurement spine
  • Founder voice and narrative architecture
  • When to hire — and when not to

Roughly 800 words. Read in five minutes. Skim in two.

Past reading. Now what.

If a piece lands and you want the work done — not just read about — there’s a door for that too.