Investing Unscripted

Jason Hall and Jeff Santoro
  • 4.9 (107)
  • 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. 1d ago

    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

  2. 5d ago

    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

  3. 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

  4. Aug 19

    219. How to Survive a Bull Market

    Bull markets can be just as dangerous for your portfolio as market crashes! Jason and Jeff share how to navigate all-time highs, avoid FOMO, and manage your big winners. 01:06 Markets At New Highs 02:36 Survive A Bull Market 03:48 Recent Crises To Endure 06:30 What Is A Bull Market 08:47 Sidelines And Opportunity Cost 13:44 Fear Vs FOMO 16:37 AI Wave And Market Pockets 20:40 Trade Desk TAM Reality Check 22:12 Datadog Vs SoFi Trimming 25:47 Portfolio Concentration Mindset 27:33 Trimming Winners Wisely 28:32 Position Size vs Age 30:28 Rebalancing Asset Allocation 32:59 Framework Over Emotion 33:26 Lessons From 2022 36:01 Dry Powder Strategy 38:55 Cash Psychology Differences 44:07 Bull Market Mistakes 47:44 Regret Minimization Framework 49:38 When Everyone Asks Companies mentioned: CRWD, CSCO, DDOG, MSFT, NVDA, SOFI, TTD, 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

  5. Aug 12

    218. How AI is Changing Everything About Startup Investing with Joe Magyer

    In this episode, Jason and Jeff sit down with Joe Magyer of Seaplane Ventures to explore how generative AI has completely rewired the startup investing landscape. The trio discusses how tools like Claude and ChatGPT have drastically lowered the cost of building software, the heavy consolidation of capital into frontier labs like Anthropic and OpenAI, and why genuine domain expertise and network effects are more valuable than ever for venture capitalists navigating an AI-native world. 01:36 Why AI Changes VC 03:55 VC Concentration Shift 06:05 Cheaper Startup Building 08:42 More Pitches to Sift 11:24 Using AI for Diligence 14:28 Human Edge and Alpha 20:41 Culture and Expertise Future 27:38 Apprenticeships and Jobs 32:06 AI Jobs History 34:19 Venture Hit Rates 37:52 Defensibility Network Effects 40:07 VC Consolidation Debate 43:14 Founder Leverage Value Add 46:20 Portfolio Support Metrics 49:36 AI Costs Falling Fast 54:47 Next Trillion Giants 57:24 Where To Find Joe Companies mentioned: AAPL, EBAY, GOOG, GOOGL, META, UBER Find Joe at https://www.seaplaneventures.com/ 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

  6. Aug 9

    First Fridays 33. August 2026

    In this August 2026 First Fridays live stream, Jason and Jeff break down the latest earnings season chaos, exploring why Lemonade dropped despite hitting its lowest gross loss ratio ever. They analyze Twilio’s massive 35% post-earnings pop, debate whether The Trade Desk's open internet thesis is officially broken, and review their 2026 Portfolio Contest standings. Plus, the duo discusses Kinsale Capital’s underwriting discipline, speculative quantum computing plays, and potential market black swans.  00:31 Splitting Wood Talk 02:30 Podcast Intro Bits 03:28 Jeff Has Girl Hands 05:02 Show Agenda Setup 05:49 Market Vibes Check 09:36 Hydration Hat Jokes 10:25 Lemonade Earnings Breakdown 16:31 Twilio Pops Off 20:40 Juiced Earnings Debate 25:13 Short Interest Downturn Risks 26:47 Leverage Crash Scenarios 27:40 Rate Hikes and Inflation 29:33 Hair Dye Poll Break 32:34 Portfolio Contest Update 37:52 Trade Desk Postmortem 44:45 Surprising Contest Winners 47:19 Kinsale Insurance Debate 51:04 Quantum Computing Bets 54:44 Options Put Selling Rules 55:52 Poll Results and Sign Off Companies mentioned: AFG, ALL, AMZN, APH, BRK.B, CRWD, DAVA, DDOG, GOOGL, IBM, IONQ, KNSL, LEN, LMND, MELI, MRNA, NOW, NVDA, PGR, PYPL, SOUN, TREX, TTD, TWLO, UPST 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. Aug 5

    217. I Still, Still Gotta Think About That One

    In this recurring segment, Jason and Jeff let an AI randomly select six stocks from their personal portfolios for a rapid-fire review. The hosts deliver a one-sentence thesis, a bear case, and a final "buy or pass" verdict for Arista Networks, Ferrari, Rocket Lab, Alphabet, Mercado Libre, and Starbucks. They debate the risks of AI slowing down for Arista and Alphabet, weigh Ferrari's massive operating margins against its valuation, explore Rocket Lab's upcoming Neutron launch, and discuss whether Starbucks can reclaim its former glory. 01:25 Rules and Stock Randomizer Setup 03:20 Who Goes First AI Coin Flip 04:49 Arista Networks 05:37 Arista Risks Valuation and Space Bet 12:49 Jason Weighs In on Arista 15:00 Ferrari Thesis and Bear Case 22:30 Rocket Lab Thesis and Risks 03:24 Rocket Lab Bull Bear 32:30 Alphabet Thesis Risks 36:38 Alphabet Valuation Debate 38:51 MercadoLibre Credit Risk 45:03 Starbucks Thesis Turnaround 54:49 Wrap Up Listener Call Companies mentioned: AAPL, ANET, CMG, COST, CSCO, F, GM, GOOG, GOOGL, HOG, KO, MELI, NKE, NU, NVDA, RACE, RKLB, SBUX, SE, UAA, VZ 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. Jul 29

    216. July 2026 Mailbag

    In this July 2026 Mailbag, Jason and Jeff tackle listener questions on when logic should yield to emotion in debt payoff decisions, how to accurately benchmark dollar-cost-averaged portfolios, and which modern stocks fit David Gardner's "Rule Breaker" framework. Plus, they explore AI's real-world robotics data bottleneck and evaluate Southern California industrial REIT Rexford Industrial (REXR). 01:05 Ratings And Mailbag 02:17 Soccer Clip Goes Viral 05:34 Incentives And Ragebait 07:09 AI Disruption Debate 17:46 Rule Breakers Picks 22:53 Whose Picks Are Winning 23:27 Feelings Versus Logic 25:09 Regret Minimization Framework 28:17 HELOC Tradeoffs And Two-Way Doors 31:20 Money Talks With Partners 33:13 Build The Investor Muscle 35:08 Eyes Wide Open Decisions 36:15 Consider A Fiduciary Advisor 38:59 Benchmarking Weekly Deposits 44:34 How To Track Performance 46:30 Rexford Industrial Outlook Companies mentioned: AAPL, CRWD, DDOG, F, GM, GOOG, GOOGL, MELI, META, NVDA, PLD, QXO, REXR 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
107 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
    280
  • Rating
    Clean
  • Copyright
    © Jason Hall and Jeff Santoro
  • Show Website
    Investing Unscripted

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