Founder's Strategic Investment Filter

It's Sunday night. You have seventeen tabs open. A new project management tool promises to fix the coordination friction you've been living with for three months. The pricing page looks reasonable. The integrations page looks promising. You've been here before — you know this feeling. You also know that six months from now there's a real chance you'll be migrating off it, writing the cancellation email, and quietly absorbing the hours you spent configuring something that didn't fit. The damage isn't the subscription cost. It's the compounding — every suboptimal tool buries a hidden tax inside your workflow. The wrong database solution shapes how you model data for the next two years. The wrong communication layer determines which automations you can build. Each decision becomes load-bearing before you realize it carried weight. The instinct is to research harder. Read more reviews. Find the definitive comparison post. But the comparison post was written for a team of twelve, and you are one person with a specific architecture, specific constraints, and a roadmap that doesn't match any of the case studies. More information doesn't resolve the ambiguity — it deepens it. This skill gives you a structured evaluation protocol that runs every candidate tool against your actual business objectives, forcing a Strategic Investment Brief before a single dollar or hour gets committed. What you get: SKILL.md — the complete evaluation protocol, including the Strategic Investment Brief framework, alignment-scoring methodology, and decision-output format. SETUP_GUIDE.md — instructions for configuring the skill against your specific business goals, constraints, and architectural priorities. EXAMPLES.md — worked evaluations across tool categories showing exactly how the Brief surfaces fit, misfit, and deferred decisions. CHANGELOG.md — version history and protocol refinements. External dependency: None. Runs entirely within your agent's context.