205. The 3 Questions Every Investor Should Answer

EPISODE · May 13, 2026 · 53 MIN

205. The 3 Questions Every Investor Should Answer

from Investing Unscripted · host Jason Hall and Jeff Santoro

Jason and Jeff strip investing down to its core framework. They break down the "Why, What, and How" that every investor needs to answer to build a sustainable and successful portfolio. The duo explores how to align your asset allocation with your time horizon, debates the merits of "set it and forget it" target-date funds versus active stock picking, and highlights the hidden drag of high mutual fund fees. They also tackle the psychological battle of lump-sum investing versus dollar-cost averaging and explain why tracking your overall net worth is far healthier than obsessing over individual stock movements. 01:11 Three Buckets Framework03:45 Define Your Why04:51 Goals And Time Horizons08:59 Multiple Goals In Life11:37 Choose Investor Style13:30 Target Date Basics18:20 Fees And Fund Reality23:31 Avoid Overactivity Trap25:39 Build A Repeatable Process27:58 Tracking Performance Wisely29:19 Detach Stock From Business30:33 Keep Score With Benchmarks34:01 Net Worth And Debt Tracking35:54 Fee-Only Advisor Check In38:51 Lump Sum Vs Dollar Cost43:30 Tax Buckets And Accounts47:40 Roth Limits And Workarounds49:18 Options Income Tax Placement50:56 Build A Review ChecklistCompanies mentioned: AVGO, FTNT, NFLX, NVDAFind where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com*****************************************To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscriptedListen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader

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205. The 3 Questions Every Investor Should Answer

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