When is good enough actually good enough? AI is reshaping how I work and live. And a member with a portfolio that's beaten an all-in-one Vanguard LifeStrategy fund for ten years asks whether the complexity is worth it — or whether it's time to simplify. Sponsors Masterworks - Invest in multimillion-dollar artwork offerings Delete Me – Use code David20 to get 20% off Insiders Guide Email Newsletter Get our free Investors' Checklist when you sign up for the free Money for the Rest of Us email newsletter Our Premium Products Asset Camp Money for the Rest of Us Plus Show Notes The Upswing: How We Came Together a Century Ago and How We Can Do It Again by Robert Putnam—Simon &Schuster An update on our model deprecation commitments for Claude Opus 3—Anthropic Claude's Corner—Substack Investments Mentioned Vanguard LifeStrategy Growth Fund Investor (VASGX) Related Episodes 542: Don’t Take Financial Advice from AI 491: The Five Layers of Investing 419: How to Make Portfolio and Asset Allocation Changes Masterworks Disclosures Listeners get priority access to Masterworks at https://www.Masterworks.com/david Art correlation and appreciation data based on repeat-sales index of historical Post-War & Contemporary Art market prices and S&P 500 annualized return (includes dividends reinvested) from 1995 to 2025, developed by Masterworks. There are significant limitations to comparative asset class data. Indices are unmanaged and a Masterworks investor cannot invest directly in an index. Content creator (the “Endorser”) receives cash compensation from Masterworks, LLC (“Masterworks”). Endorser is a client of Masterworks. Masterworks can only make and accept sales after an offering statement has been filed, and “qualified”, by the SEC. Any offers may be revoked before notice of qualification. Indications of interest involve no obligation. Investing involves risk. Past performance not indicative of future returns. For further disclosure on Regulation A Offerings, Risks of Investing, Performance Metrics, Art Market Data, and more visit the offering documents filed with the SEC and Important Disclosures at masterworks.com/cd. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.