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Portfolio Strategy

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cbrock84
portfolio-strategy

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.

Overview

Publishercbrock84
Repositoryheadcount
Skill nameportfolio-strategy
Stars
1.6K
Forks
237
Bundled files
1
LicenseMIT
Links
  • Markdown instructions

    A SKILL.md file the model loads on demand, so it only costs tokens when a request actually matches.

  • Works with any LLM

    AI skills are plain Markdown, not provider-specific code, so this works with GPT, Claude, Gemini, Grok, or a local model.

  • 1 bundled files

    Scripts, templates, and references the model can read while it works. Files are read-only and never executed.

  • Open source

    Published by cbrock84 on GitHub. Read the source before you install it.

Installation

Install the Portfolio Strategy AI skill in TypingMind to use it with any LLM, or drop it into another agent that reads SKILL.md.

1

Install in TypingMind

TypingMind installs a skill straight from its GitHub folder — it reads SKILL.md, bundles the resource files, and stores the result locally.

  1. Open the app and go to Plugins → Skills.
  2. Choose "Install from GitHub".
  3. Paste the skill folder URL below and confirm.
  4. Enable the skill in any chat where you want it available.
Plugins → Skills → Add skill → From GitHub URL, then paste the folder URL and press Continue.
2

Install in another agent

Any agent that reads the Agent Skills format can use this skill — copy the folder into that agent's skills directory.

Claude Code — .claude/skills
git clone --depth 1 https://github.com/cbrock84/headcount.git /tmp/headcount
mkdir -p .claude/skills
cp -r /tmp/headcount/plugins/corporate-strategy/skills/portfolio-strategy .claude/skills/portfolio-strategy
Restart Claude Code after copying so it picks up the new skill.

Use it in TypingMind

Enable Portfolio Strategy in any TypingMind chat and the model takes it from there. Its name and description sit in the system prompt, and the moment a request matches, the model loads the full instructions itself — you never invoke it by hand, and it costs no tokens until it is actually used.

The model loads Portfolio Strategy on its own as soon as a request matches it.

Works with any AI model

AI skills are plain Markdown instructions rather than provider-specific code, so Portfolio Strategy is not tied to the model it was written for. Install it once in TypingMind and use it with GPT-5, Claude, Gemini, Grok, DeepSeek, Mistral, Llama, or a local model you run yourself — all on your own API keys.

  • Loaded only when it is needed

    The system prompt carries just the name and description. The instructions are fetched on the first matching request, so an idle skill costs nothing.

  • Switch models mid-chat

    Because the skill is instructions rather than code, changing model does not break it — the next model reads the same SKILL.md.

Skill instructions

This is the SKILL.md content the model loads. Read it before installing — a skill is instructions your model will follow.

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.

Plan exits properly: customer commitments, employee treatment, and contractual obligations. A badly run exit costs more than the business was losing.

Running a review

Same evidence for every line, prepared by a neutral party rather than by each line's advocate. Set the criteria and weights before seeing the numbers — weighting afterward reproduces the allocation you already had.

Force a ranking. Tiers are how everything stays funded.

Sources

references/sources.md in this skill lists the outside authorities that settle the questions here — what each one is authoritative for, and what you may do with it. Check them before answering on anything they cover, and cite what you used. Most are free to read and not free to reproduce; the use note on each is binding.

Never

  • Fund a line because it is large. Fund it on marginal return.
  • Keep a line alive on sunk cost.
  • Starve a line without deciding to exit it. Slow starvation costs more than a clean exit.
  • Review the portfolio only when a line is already in trouble.

Return contract

Each line with its posture and evidence, the recommended allocation and what changed from last period, what you are stopping, and the indicator that would reverse each call.

Bundled files

The model reads these on demand while the skill is loaded. They are exposed as readable files and are never executed.

Frequently asked questions

What does the Portfolio Strategy AI skill do?

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.

Why use Portfolio Strategy on TypingMind?

Because you install it once and use it with any model. Portfolio Strategy is plain Markdown rather than provider-specific code, so the same skill runs on GPT-5, Claude, Gemini, Grok, or a local model — and you can switch model mid-chat without it breaking. TypingMind runs on your own API keys, so you pay providers directly instead of a per-seat subscription, and your skills and chats stay in your own storage.

How do I install Portfolio Strategy in TypingMind?

Open Plugins → Skills → Install from GitHub in TypingMind and paste https://github.com/cbrock84/headcount/tree/main/plugins/corporate-strategy/skills/portfolio-strategy. TypingMind reads its SKILL.md and bundles its files and installs it as a skill you can enable per chat.

Which AI models can use Portfolio Strategy?

Any model you connect in TypingMind. AI skills are plain Markdown instructions rather than provider-specific code, so GPT, Claude, Gemini, Grok, and local models can all load this skill when a request matches it.

How many AI models can I use with Portfolio Strategy?

As many as you like. As long as a model supports skills, you can use Portfolio Strategy with it — GPT, Claude, Gemini, Grok, DeepSeek, Mistral, Llama and more — all on TypingMind with your own API keys.

Is the Portfolio Strategy AI skill free?

Yes. It is published on GitHub by cbrock84 under the MIT license. You only pay your own AI provider for the tokens you use.

What are AI skills?

An AI skill is a reusable instruction bundle that teaches an AI model how to do one specific task. It follows the open Agent Skills format: a SKILL.md file with a name and description, plus any scripts, templates or reference files the model may need. The model reads the instructions only when your request matches the skill, so an installed skill costs nothing until it is used.

How are AI skills different from plugins or MCP servers?

A plugin or MCP server gives a model new tools to call — code that runs somewhere and returns a result. An AI skill gives the model knowledge and process instead: how to approach a task, which steps to follow, what good output looks like. Skills are plain Markdown, so they need no server, no API key and no runtime, and they work with any model.

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