Investing Unscripted

Jason Hall and Jeff Santoro
  • 4.9 (108)
  • Investing
  • Updated Weekly

Welcome to Investing Unscripted, where we ask the hard questions about investing, the stock market, and personal finance. We don't have THE answers, we only have OUR answers.

  1. 3h ago

    First Fridays 35. October 2026

    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. 01:56 Wrigley Field Promo Clip 02:52 Chat Greetings and Baseball Talk 06:30 Market Vibes Everything Is Fraud 08:04 Incentives and Man City Case 12:39 Old Wall Street Fraud History 17:29 CareTrust REIT UK Expansion 18:13 Why CareTrust Has Won 23:31 UK Healthcare and Capital Allocation 24:27 Selling CTRE and REIT Rate Sensitivity 26:25 Rates Hit REIT Valuations 27:14 Realty Income vs Diversifying 29:30 Why O Acts Like Bonds 31:31 CareTrust Growth Angle 32:45 REITs vs Bonds and T Bills 34:06 Cost of Capital Explained 37:30 Dividend Growth Comparison 38:39 Agentic AI Shopping Threat 45:58 Ads Trust and New Models 49:31 Zoom Stock Long Term View 54:52 Portfolio Contest and UNICEF Companies mentioned: ABNB, AMZN, BKNG, CTRE, O, RMD, TJX, ZM  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 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

  2. 5d ago

    225. September 2026 Mailbag

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

  3. Sep 23

    224. Our Best and Worst Stock Picks

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

  4. Sep 16

    223. 5 (More) Stocks for 10 Years

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

  5. Sep 9

    222. David Gardner: Rule Breakers, AI, and the Next Great Stocks

    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 ***************************************** 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

  6. Sep 6

    First Fridays 34. September 2026

    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 ***************************************** 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 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

  7. Sep 2

    221. Investing Basics: How to Build a Portfolio

    In this back-to-basics episode, Jason and Jeff break down the foundational rules of portfolio construction, asset allocation, and true risk diversification. The hosts explore how to blend an index fund baseline with individual stock picking, examine the mechanics of position sizing and rebalancing, and debate different cash-deployment frameworks. To cap it off, both hosts reveal brand-new stock purchases made during the recording: Jeff's starter position in Brad Jacobs' roll-up vehicle QXO and Jason's opportunistic buy of The TJX Companies.  00:59 Welcome to Investing Unscripted 03:25 Portfolio Basics Setup 04:47 Why Portfolios Matter 08:32 Diversification and Allocation 10:16 Risk Factors Explained 15:29 Beginner Diversification Tips 17:15 Cash and Time Horizon 22:24 Big Picture Diversification 24:27 Mindset and Risk Tolerance 27:55 Simple Starter Portfolio 28:19 Building a Stock Base 29:17 Know Your Investor Style 31:07 Buy Market or Companies 33:22 Index Funds First 35:17 Automating Early Investing 37:57 DCA vs Loose Cadence 39:35 Avoid Cash Timing Traps 41:58 Rollover Deployment System 45:35 Opportunistic Buys and Trims 46:52 New Positions TJX and QXO 49:24 QXO Strategy and Competition Companies mentioned: ASML, DDOG, ENPH, FSLR, HD, LOW, NVDA, QS, QXO, SBUX, TJX, TSLA, TSM 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 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

  8. Aug 26

    220. August 2026 Mailbag

    In this August 2026 Mailbag, Jason and Jeff tackle listener questions on high-conviction stocks gone wrong, unpacking the deceleration and agency friction at The Trade Desk. They explore how co-host overlap can lead to borrowed conviction, discuss what to do when you feel "stuck" in a frothy market, and analyze QuantumScape's shift toward data center power storage and licensing partnerships with Honda and Volkswagen.  04:24 Trade Desk Conviction Lessons 14:01 Valuation Regret And CEO Signals 18:52 Portfolio Overlap And Bias 22:57 Public Disagreements And Recent Buys 23:57 Valuation Debate Winmark 25:03 Rocket Lab Regret 26:02 Building Positions Slowly 27:51 Selling Rocket Lab Puts 30:02 Feeling Stuck Investing 32:56 Do Nothing Discipline 35:31 QuantumScape Honda Red Flag 36:18 QuantumScape Licensing Model 39:55 Verticals Mission Creep 44:50 Position Sizing Fun Bets Companies mentioned: AMZN, APH, GLW, GOOG, GOOGL, HMC, KNSL, META, MRNA, NFLX, NNI, NU, QS, RKLB, SE, SOUN, TTD, VWAGY, WINA 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 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

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4.9
out of 5
108 Ratings

About

Welcome to Investing Unscripted, where we ask the hard questions about investing, the stock market, and personal finance. We don't have THE answers, we only have OUR answers.

Information

  • Creator
    Jason Hall and Jeff Santoro
  • Years Active
    2022 - 2026
  • Episodes
    285
  • Rating
    Clean
  • Copyright
    © Jason Hall and Jeff Santoro
  • Show Website
    Investing Unscripted

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