Show Notes
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 Framework 03:45 Define Your Why 04:51 Goals And Time Horizons 08:59 Multiple Goals In Life 11:37 Choose Investor Style 13:30 Target Date Basics 18:20 Fees And Fund Reality 23:31 Avoid Overactivity Trap 25:39 Build A Repeatable Process 27:58 Tracking Performance Wisely 29:19 Detach Stock From Business 30:33 Keep Score With Benchmarks 34:01 Net Worth And Debt Tracking 35:54 Fee-Only Advisor Check In 38:51 Lump Sum Vs Dollar Cost 43:30 Tax Buckets And Accounts 47:40 Roth Limits And Workarounds 49:18 Options Income Tax Placement 50:56 Build A Review Checklist Companies mentioned: AVGO, FTNT, NFLX, NVDA Find 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/unscripted Listen 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
Learn more about your ad choices. Visit megaphone.fm/adchoices
More from Investing Unscripted
In this October 2026 Mailbag, Jason and Jeff tackle listener questions on portfolio management, sector consolidation, and the psychology of holding laggards while the broader market sits near all-time highs. They evaluate whether Zeta Global's business intelligence tools pose a threat to TJX Companies' off-price retail moat, debate how to narrow down starter positions across housing and renewable energy stocks like Meritage Homes, Enphase, and First Solar, and dissect what to do when former long-term winners like MercadoLibre, Netflix, and Axon go through painful drawdowns. Plus, Jeff breaks down how doubling down on Texas Instruments at the bottom of the semiconductor cycle turned a 30% loser into a market-beating position.
In this episode, Jason and Jeff tackle the often-misunderstood world of fixed income to answer a critical question: Should you still own bonds? The hosts break down exactly why bond funds were decimated in 2022, the mechanics of the inverse correlation between interest rates and bond prices, and the vital difference between holding bond funds versus holding individual bonds to maturity. Finally, they explore why the current 5% yield environment makes fixed income a compelling wealth-preservation tool for investors looking to lock in their gains from the AI stock boom.
In this completely unscripted episode, Jason and Jeff tackle the broad economic vibes surrounding the market’s resilience despite mounting geopolitical and macroeconomic uncertainty. The duo debates whether the normalization of sports betting and prediction markets is quietly threatening the culture of long-term stock investing. Plus, they unpack the complicated psychology of adding to massive winners, analyzing why Jason is considering a starter position in Broadcom despite its stretched valuation, and evaluating whether QuantumScape’s latest manufacturing pivots are a sign of commercial maturity or a yellow flag for a cult stock.
In the October 2026 First Fridays live stream, Jason and Jeff explore the broader macro vibes surrounding corporate fraud and regulatory boundaries, contrasting today's headlines with the Wild West of 1920s Wall Street. The duo unpacks CareTrust REIT's massive $1.2 billion expansion into the UK, evaluating the enduring power of the "aging baby boomer" demographic tailwind. Later, they debate how quickly "agentic AI" will disrupt e-commerce habits for companies like Amazon and Airbnb, and dissect why Zoom's shrinking enterprise base makes the stock virtually uninvestable despite its free cash flow.
In this September 2026 Mailbag, Jason and Jeff tackle listener questions on when it makes sense to "average up" on massive winners, analyzing David Gardner’s contrarian approach to building a Rule Breaker portfolio. The hosts then explore the specific valuation and counter-cyclical margin arguments behind Jason's recent purchase of The TJX Companies, and debate the psychology of co-managing spousal IRAs. To close the episode, the duo reviews listener submissions for a "5 Stocks for 10 Years" portfolio, ultimately drafting their own hypothetical decades-long portfolios from the audience's picks.