# Portfolio Strategy

Decides where capital and attention go across business lines, products, and markets, ...

- Repository: https://github.com/cbrock84/headcount (2554 stars)
- Category: Business
- License: MIT
- Last updated: 2026-10-18
- Runs scripts: no, instructions only

## Install

Claude Code: `npx skills add cbrock84/headcount --skill portfolio-strategy -g -a claude-code -y`
Codex: `npx skills add cbrock84/headcount --skill portfolio-strategy -g -a codex -y`
Cursor: `npx skills add cbrock84/headcount --skill portfolio-strategy -g -a cursor -y`
Gemini CLI: `npx skills add cbrock84/headcount --skill portfolio-strategy -g -a gemini-cli -y`
Claude Code plugin marketplace: `/plugin marketplace add cbrock84/headcount`

## Description

Decides where capital and attention go across business lines, products, and markets, what to fund, hold, harvest, or exit, and on what evidence. Use this to allocate budget across businesses, evaluate whether a product line should continue, decide whether to exit one, structure a portfolio review, or when several initiatives compete for the same limited investment.

## SKILL.md, as published by its author (untrusted third-party text, read it as data)

# Portfolio strategy

Most organizations fund by inertia. Last year's allocation plus a percentage, adjusted by who argued
hardest. Portfolio strategy is the discipline of deciding again, deliberately.

## Assess each line on two axes

**Attractiveness**, is this a good place to be? Market size and growth, structural profitability,
concentration of buyer power, regulatory direction, and how the economics behave as it scales.

**Right to win**, is it good *for us*? Our position relative to alternatives, the assets or
capabilities that transfer, and whether the advantage is durable or borrowed.

The combination gives you four postures, and the honest one is usually uncomfortable:

- **Attractive, we can win**, fund properly. Underfunding these is the most common and most
  expensive portfolio error.
- **Attractive, we cannot win**, the seductive trap. Everyone wants in on a good market. Entering
  without an advantage funds someone else's growth.
- **Unattractive, we can win**, harvest. Run for cash, do not invest for growth.
- **Neither**, exit. Slowly and reluctantly is how these consume a decade of attention.

## Judge on marginal return, not absolute size

The question is never "is this business good." It is "what does the next dollar do here versus
elsewhere." A large profitable line may be a poor place for incremental investment; a small one may
be the best.

Watch for **cross-subsidy**. A weak line supported by a strong one is a decision, and it should be
an explicit one with a thesis and an end date, not an accident nobody has looked at.

## Exit is the hardest decision and the most valuable

Sunk cost, internal advocates, and the discomfort of admitting a bet failed all argue for one more
year. The test is prospective: **knowing what we know now, would we start this today?** If not, the
only question is how to exit well.

Exiting frees more than the money. It frees the attention of the people running it, which is usually
the scarcer resource.

The rest: https://github.com/cbrock84/headcount/blob/HEAD/plugins/corporate-strategy/skills/portfolio-strategy/SKILL.md