Investing Unscripted

Jason Hall and Jeff Santoro
  • 4.9 (101)
  • 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. 3D AGO

    202. I (Still) Gotta Think About That One

    In this episode of Investing Unscripted, Jason and Jeff revive a fan-favorite format: letting AI randomly select stocks from their personal portfolios for a rapid-fire review. For each chosen stock, the hosts must explain what the company does, build the best "bear case" against it, and declare whether they would buy it at today's prices. Jeff tackles the tech heavyweights, defending Nvidia against the threat of purpose-built AI chips, exploring how "vibe coding" could eat away at Shopify's margins, and evaluating CrowdStrike's post-outage reality. Meanwhile, Jason embraces his love for "boring" businesses, breaking down the massive cash flows of pipeline operator Enterprise Products Partners, the underwriting discipline of internet-bank Axos Financial, and the cost-of-capital risks for Clearway Energy. 03:13 Spotify Ratings Challenge 04:24 Pick 1 CrowdStrike Bear Case 08:00 Quantum and AI Disruption Talk 14:21 Pick 2 Enterprise Products Explained 20:13 Would You Buy It Valuation Talk 25:09 Pick 3 Nvidia Bear Case Setup 27:47 Nvidia Valuation Debate 30:41 Nvidia Bear Case Shifts 34:40 Axos Financial Overview 36:19 Axos Bank Risks 40:48 Shopify Bear Thesis 43:01 Shopify Platform Risks 51:33 Clearway Energy Yieldco Companies mentioned: AX, CRWD, CWEN, EPD, NVDA, SHOP 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

    57 min

  2. APR 15

    201. SpaceX’s $2 Trillion IPO and the Space Economy with Lou Whiteman

    In this episode, Jason and Jeff bring on Motley Fool analyst Lou Whiteman for a masterclass on investing in the space industry. They break down the hype surrounding SpaceX's potential $2 trillion IPO and debate how much of that valuation is actually justified by its core businesses (Launch, Starlink, Starshield, xAI). Lou outlines his five distinct buckets of the space economy—ranging from launch infrastructure and connectivity to Earth observation and defense tech—and shares why companies like Rocket Lab and Redwire are catching his eye. Plus, Lou reveals the sub-sectors he’s actively avoiding and explains why traditional defense contractors like Lockheed Martin might currently be the most compelling way to play the space boom. 03:08 SpaceX Business Breakdown 05:55 Space Market Tailwinds 08:49 Why Launch Demand Surges 11:20 New Space Use Cases 14:48 SpaceX IPO Valuation Math 19:14 IPO Pricing and Aftermarket 23:11 What Success Looks Like 23:36 Capital Needs Debate 24:40 Starship Risks Ahead 25:46 Space Investing Ad Break 27:13 Mapping Space Sectors 30:59 Where Space Gets Risky 36:20 Top Picks To Research 40:16 Consolidation And Legacy Primes 41:28 Avoiding Hype Traps Companies mentioned: AMZN, ASTS, BKSY, GSAT, KTOS, LDOS, LHX, LMT, LUNR, META, NOC, PL, RDW, RKLB, TMUS, TSLA, V, 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 PatreonSubscribe to our portfolio on Savvy Trader

    45 min

  3. APR 13

    First Fridays 29. April 2026

    In the April 2026 First Friday livestream, Jason and Jeff break down the current "market vibes," debating whether the market's resilience is masking a hair-trigger sensitivity to AI hype and PR spin. They announce the Q1 winner of the listener portfolio contest—congratulations to Discord member Vinny G!—and review the progress of their own 2026 picks. The duo dives deep into the executive turnover at The Trade Desk, the slow-moving turnaround at PayPal, and whether Kinsale Capital is simply a cyclical price taker or a highly efficient operator. Plus, Jason reveals his new Roth 401 (k) strategy, and Jeff vehemently defends his "lazy" personal finance choices. 03:01 Market Vibes Resilience 06:26 AI Hype And Volatility 09:54 Cybersecurity Rumor Debate 12:19 Cringey AI Promo Clip 14:35 Portfolio Contest Rules 16:31 Q1 Winner And Charity 21:09 Patreon Standings And Long Game 24:22 Portfolio Reflections And Trade Desk 28:00 Board Sale Speculation 30:49 Backing Jeff Green 32:19 Position Sizing Rules 32:45 Founder vs Operator Debate 37:11 Kinsale Competition Pressure 38:40 Kinsale Underwriting Edge 42:23 Specialty Insurance Tailwinds 45:30 PayPal Value Trap Risk 52:15 Roth 401k Moves 55:20 Roth Optionality Strategy 57:46 Favorite Dividend Picks Companies mentioned: BIP, BIPC, BORR, CTRE, EPR, GOOG, GOOGL, KNSL, MA, MELI, NOW, PLSDF, PLTR, PYPL, RBRK, RKLB, SECYF, TTD 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

    1 hr

  4. APR 8

    200. 200 Stocks for 200 Episodes

    In this milestone 200th episode of Investing Unscripted (yes, the last episode was an April Fool's joke!), we tackle a question that plagues many investors: how many individual stocks should you actually own? We debate the merits of a heavily concentrated portfolio versus broad diversification, especially during periods of market uncertainty. We also unpack the psychological dangers of blindly adding to your winners and why it's crucial to adapt your investing strategy as your personal financial goals change over time. 03:13 Spotify Ratings Challenge 05:04 How Many Stocks 06:30 Concentration vs Diversification 09:06 Is This More Uncertain 14:11 Should Uncertainty Change Holdings 15:48 Jason Reframes Portfolio Size 21:25 Portfolio Size Debate 23:55 Conviction Versus Bias 26:58 Averaging Up Winners 28:42 Kinsale Capital Case 32:59 Watchlist FOMO Trap 34:48 Concentration And Time 40:05 Automate When Anxious 43:15 Humility And Evolving Companies mentioned: AAPL, AMZN, CDNS, CRWD, DFH, GE, JRVR, KNSL, MSFT, NVDA, S, SNPS, TOST, TTD 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

    47 min

  5. APR 1

    199. Knowing When to End a Good Thing

    In this monumental episode of Investing Unscripted, Jason and Jeff announce that they are bringing the podcast to an end—just one episode shy of their 200th milestone. This short reflection episode looks back on past guests, topics, and what had the biggest impact. 01:00 Why the Show Is Ending 02:28 Retrospective and Keeping It Light 03:28 Favorite Guests and Surprise Connections 05:40 Jim Gillies and Early Episodes 06:37 First Friday Livestream Memories 08:06 Podcast Community and Crossovers 09:25 Behind the Scenes Editing and Filler Words 10:21 How Podcasting Shaped Investing Views 11:14 Podcast Shapes Investing 13:40 Investor Identity Distilled 16:31 Talking Through Ideas 18:02 Favorite Episode Formats 20:46 Running Toward Fires 26:54 Wrap Up And Thanks Companies mentioned: BAM, BN, CRWD, MSFT, S 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

    28 min

  6. MAR 25

    198. March 2026 Mailbag

    In this month's mailbag, Jason and Jeff tackle a wide array of listener questions, ranging from the tax efficiency of holding dividend stocks in taxable accounts to the potential risks of the NASDAQ fast-tracking private giants like SpaceX into its indexes. They also weigh in on newlyweds combining finances and choosing between brokerages like Schwab and Fidelity. Finally, the duo breaks down Walker & Dunlop's recent post-earnings stock drop and debates where to safely park your cash after hitting a major savings goal. 03:14 Taxable Dividend Strategy 11:54 Nasdaq Index Rule Changes 20:27 Dividend Bucket Rethink 25:57 Dividend Growth Compounding 26:38 Mastercard Low-Yield Lesson 27:42 Instagram Mailbag Setup 28:50 Consolidating Brokerage Accounts 31:47 Schwab Versus Fidelity 34:22 Combining Finances After Marriage 35:45 Money Talks and Guardrails 40:12 Walker and Dunlop Earnings 42:43 Investing After Saving Goal 45:43 Risk Spectrum and Time Horizon Companies mentioned: AAPL, BOC, CRM, MA, META, MTH, QQQ, SCHW, WD 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

    51 min

  7. MAR 18

    197. Investing Through Chaos

    Jason and Jeff tackle the current wave of market chaos—from oil price spikes and tariffs to the "AI is killing software" narrative. They dive into how they're personally navigating the noise, sharing recent portfolio additions such as Phinia (PHIN) and Clearway Energy that appear insulated from the macroeconomic volatility. They also unpack the AI software scare with deep dives into Toast, ServiceNow, and Procore, and Jason issues a warning about the hidden risks lurking in the booming private credit market. 01:19 AI Tariffs Oil Backdrop 03:38 Housekeeping Mailbag Plug 04:42 Staying the Course 07:18 Markets Recover Before Clarity 12:04 Stock Pick PHIN 19:01 Renewables Reality Check 20:54 Clearway Energy Buy 24:50 Energy Security and Oil Flows 26:36 Oil And Geopolitics 27:29 Krugman On Price Spikes 30:33 Toast Stock Breakdown 35:44 ServiceNow AI Strategy 37:35 Procore Construction Software 42:17 Private Credit Risks 47:38 Staying Invested In Chaos 49:19 Process Over Headlines Companies mentioned: BAM, BEP, BX, CPNG, CWEN, DASH, ENPH, FOUR, KKR, NOW, ORCL, OWL, PCOR, PHIN, PYPL, SHOP, SQ, TOST 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

    52 min

  8. MAR 15

    First Fridays 28. March 2026

    In this slightly belated "First Fridays" live stream, we dive into the current "vibes" of the stock market, check in on the 2026 Portfolio Contest, debate the long-term viability of MercadoLibre's lending business, and talk about Greg Abel’s first annual letter to Berkshire Hathaway shareholders. 01:53 Index Funds Running Joke 04:08 Market Vibes Check 06:28 K Shaped Economy Talk 12:09 Portfolio Contest Update 23:46 QuantumScape Buy Explained 27:59 Donut Labs Battery Debate 30:57 Battery Value Metrics 31:34 Kids Pick Stocks 32:58 Market Moves This Week 36:56 MercadoLibre Discount Debate 44:42 Options Premiums Q&A 47:13 Using Claude for Research 50:27 Greg Abel Letter Take 55:30 Berkshire After Buffett Companies mentioned: AAPL, AMZN, AXP, BRK.B, ENR, KNSL, KO, MCO, MELI, QS, RKLB, TM 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

    1h 2m
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4.9
out of 5
101 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
    256
  • Rating
    Clean
  • Copyright
    © Jason Hall and Jeff Santoro
  • Show Website
    Investing Unscripted

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