Investing Unscripted

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.

02:03 Patreon Shoutout

03:07 Rapid Fire Housekeeping

04:15 Mailbag Begins

04:58 Double Down Winners

16:50 TJX Valuation Debate

24:42 ResMed Growth Outlook

28:20 When to Take Profits

29:56 When Valuation Matters

31:50 Couples Managing IRAs

34:49 Risk Across Net Worth

38:18 Spreadsheets And Aggregation

43:06 Five Stocks For 10 Years

44:19 Discord Picks Breakdown

48:23 Picking Five From The List

Companies mentioned: AER, AMZN, ASML, AXON, BAM, BN, BRK.B, COST, CVX, ISRG, LLY, LMND, MA, MEDP, META, RBRK, RMD, SBUX, TBBB, TJX, TSM

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

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Jason and Jeff pull back the curtain on their Savvy Trader portfolio to examine the core mechanics of long-term portfolio construction. Using real-world examples from their own holdings, the hosts debate the discipline required to let a multi-bagger winner run versus the psychological battle of confronting a 70% drawdown. They tackle the dangerous allure of the sunk-cost fallacy, evaluate whether high-growth portfolios actually benefit from defensive "ballast" stocks, and break down how position sizing can keep single-stock blowups from derailing your long-term compounding.

00:27 Football and Fandom

02:04 College Football Detour

02:44 Back to Investing Talk

03:15 Savvy Trader Concept

06:39 How the Portfolio Works

10:06 Biggest Winner CrowdStrike

14:24 Why Hold CrowdStrike

20:02 Risks and Disruption Fears

23:56 Pivot to Biggest Loser

24:54 Position Size Breakdown

25:39 Lessons From Conviction

29:51 Why Keep Holding

32:29 Sunk Cost And Catalysts

37:24 Guidance Trend Reality Check

38:57 New Stock Ideas Debate

40:04 Ballast Stocks Or Index

45:58 AI Picks And Shovels

50:30 Final Picks And Wrap Up

Companies mentioned: AAPL, AMZN, BRK.B, CRWD, FPS, FTNT, GOOG, GOOGL, MELI, MRNA, MRVL, PANW, TJX, TTD, TXN, VOO, ZS

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

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Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!
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Jason and Jeff revisit their popular 2023 thought experiment to build a brand-new five-stock portfolio designed to hold through 2036. After reviewing how a massive 400% surge in Taiwan Semiconductor carried their original picks past the S&P 500, the hosts lay out their updated high-conviction roster. They break down the rapid store expansion of Mexican discount grocer BBB Foods, the secular land and housing tailwinds powering Green Brick Partners, the skilled nursing consolidation runway at CareTrust REIT, and debate whether to round out the portfolio with steady cash-flow giant ASML or speculative battery play QuantumScape.

00:46 Redux Setup Five Stocks

03:09 Housekeeping Speed Run

04:37 Old Picks Performance Review

07:54 Swaps and Digital Realty

10:03 MercadoLibre Surprise Factor

15:02 New 10 Year Framework

19:12 MercadoLibre Still Core

20:32 BBB Foods Growth Thesis

25:01 Store Growth Debate

27:12 Housing Market Weirdness

29:55 Green Brick Pick

31:55 Why Not Earlier

34:20 CareTrust REIT Thesis

39:14 Valuation And Run Up

42:07 ASML Or QuantumScape

47:46 Portfolio Rules Fight

49:42 Listener Picks Wrap Up

Companies mentioned: ASML, BN, BOC, COST, CTRE, DLR, FTNT, GOOG, GOOGL, GRBK, HD, MELI, NVDA, O, ORLY, QS, RHP, RKLB, TBBB, TSM

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!
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In this episode, Jason and Jeff welcome back The Motley Fool co-founder David Gardner to discuss his book, Rule Breaker Investing, and the origins of his market-beating philosophy. The trio unpacks why seemingly overvalued stocks often generate the biggest returns, how AI is impacting established platforms like Booking Holdings, and whether mega-caps like Nvidia and Netflix have graduated from "Rule Breakers" to "Rule Makers". Plus, Jason and Jeff expand their ongoing stock-picking contest by pitching new additions to their portfolios.

00:43 Final Stock Market Book

02:53 How Rule Breaker Began

05:32 Yahoo Lesson on Valuation

08:36 Rule Breakers vs Goliaths

09:59 Values and Stock Picking

15:16 Overvalued Can Be a Signal

21:24 Market Outlook and Optimism

27:51 Sponsor Break and Tools

29:39 AI Selloff and Long View

34:24 Bubbles and Staying Invested

39:18 Rule Breakers Framework

39:43 Nvidia Still Breaking Rules

44:34 AI To Robotics Next

44:43 Netflix Rule Maker Era

47:44 Giving Appreciated Stock

49:45 Booking Versus AI Threat

51:09 Platforms Network Effects

56:36 Smattering Six Results

01:01:56 Power Law And Snap Test

01:07:48 Conscious Capitalism Closing

Companies mentioned: ABNB, AMZN, AX, BKNG, CPNG, NFLX, NVDA, PCOR, PTON, QXO, RKLB, SBUX, SHOP, TBBB, TJX, TMDX, TSLA, WRBY

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

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Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!
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In this September 2026 First Fridays live stream, Jason and Jeff tackle a jam-packed earnings season and a surprisingly resilient market. The hosts dissect The Trade Desk's revenue contraction and strategic missteps against tech walled gardens, debate whether Lemonade's post-earnings drop was justified despite a record-low 60% gross loss ratio, and break down DocuSign's incredibly consistent free cash flow generation. The duo also checks in on the portfolio contest, explores the nuances of trimming big winners like ASML and Datadog to rebalance, and evaluates QuantumScape's pivot to manufacturing partnerships with its new Honda deal.

00:32 First Friday Roll Call

02:57 How We Promote Stuff

05:41 Market Vibes Check

09:58 AI Supercycle Debate

13:13 DocuSign Breakdown

20:41 SavvyTrader and Community

23:05 Why TJX Is a Buy

28:25 New Stock Ideas PRCT

29:20 Medical Devices Watchlist

31:24 ResMed and GLP-1 Impact

32:35 Surgical Robots Competition

36:07 Baseball Cards and Value

41:06 Smattering Contest Update

43:18 New Picks Rocket Lab

47:54 Listener Portfolio Standings

51:53 Selling Stock Regrets

57:03 Wrap Up and Disclosures

Companies mentioned: AAPL, AFG, APH, ASML, AVGO, BOC, CLF, COST, CPNG, DAVA, DDOG, DOCU, IONQ, ISRG, KNSL, LEN, LMND, MDT, MELI, MRNA, MTH, NNI, NOW, NVDA, PCOR, PRCT, PYPL, QS, QXO, RHP, RKLB, RMD, SOUN, TJX, TTD, TWLO, WINA

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

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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

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Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!
Learn more about your ad choices. Visit megaphone.fm/adchoices