Money For the Rest of Us We Are All Wayfinders
May 13, 2026
A reflection on navigating investing, business, and life using a compass-like approach instead of strict maps. Stories from running live portfolio cohorts and lessons about product fit and experimentation. A look at using AI to analyze twelve years of trades and to build more flexible financial models.
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AI Enables Flexible Custom Financial Simulations
- AI offers flexible, ad-hoc financial modeling beyond traditional planning software constraints.
- Cohort members used AI (Claude, Gemini, ChatGPT) to code Monte Carlo simulations and custom guardrails like Guyton-Clinger spending adjustments.
Wayfinding Beats Roadmaps For Investing And Business
- Investing and building a business require wayfinding rather than a fixed roadmap.
- J. David Stein uses Kevin Lynch's wayfinding idea: landmarks, rules of thumb, and iterations guide decisions without exact step-by-step maps.
Experiment To Find Product Market Fit
- Use experimentation and small iterations to find product-market fit instead of rigid business plans.
- Amy Smilovic's story: make a product, test if it sells, and iterate based on real customer response.
