Investing Unscripted

Jason Hall and Jeff Santoro
  • 4.9 (103)
  • 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. 4D AGO

    206. May 2026 Mailbag

    In the May 2026 Mailbag, Jason and Jeff tackle a series of compelling listener questions, starting with a deep dive into whether "vibe coding" and agentic AI are truly an existential threat to major SaaS companies like Salesforce and Snowflake. The duo also untangles the complicated corporate web of Brookfield Infrastructure (BIPC vs. BIP), exploring why the company might finally be moving to ditch its limited partnership structure. Later, they revisit the ongoing struggles at The Trade Desk, debate the concept of "regret minimization" when dealing with massive winners like Rocket Lab and Nvidia, and discuss how to properly balance single-company risk versus overall portfolio volatility. 00:48 West Coast Game Time Rant 02:46 Mailbag and Discord Shoutout 03:56 Ryan Email and Mascot Story 05:47 Baseball Chaos to Investing Lesson 07:47 AI Versus SaaS Debate 11:15 Pricing Models and Moats 22:11 Brookfield BIP Versus BIPC Explained 26:38 Why BIPC Dropped and Simplification 30:25 Discord Questions Teaser 30:52 Trade Desk Doubts 35:54 Valuation Reality Check 38:55 Execution Not Value 40:10 Rocket Lab Concentration 41:55 Regret Minimization 46:55 Singles vs Home Runs 49:22 Vinnie Risk Trimming 50:06 Three Types of Risk 54:50 Money Unplugged Reflections Companies mentioned: ADBE, ADSK, BAM, BEP, BEPC, BIP, BIPC, CRM, NBIS, NVDA, RKLB, SHOP, SNOW, 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 4m

  2. MAY 15

    205. The 3 Questions Every Investor Should Answer

    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

    57 min
  3. 204. Stocks for the AI Hater

    MAY 6

    204. Stocks for the AI Hater

    In this episode, Jason and Jeff take a much-needed break from the relentless AI hype cycle to focus on "boring" but beautiful businesses. The duo builds an "Anti-AI" portfolio of companies that are positioned to thrive regardless of whether the tech boom goes bust. They break down the pricing power and operational efficiency of retail giants Costco and TJX Companies, unpack the ongoing roll-up strategy of Brad Jacobs' QXO, and explore high-yield opportunities in REITs like CareTrust and EPR Properties. Plus, Jason makes the case for investing with the ultra-wealthy by buying shares of the Atlanta Braves, taking plenty of shots at Jeff's beloved New York Mets along the way.  01:42 Why Look Beyond AI 07:27 AI Backlash and Reality Check 11:00 Berkshire Weekend Teaser 11:53 Picking AI Proof Stocks 12:55 Costco as Safe Retailer 16:40 Costco Ops and Tech Edge 21:37 TJX Treasure Hunt Model 25:49 Phinia Gas Engine Parts 29:29 Commercial Auto Parts Angle 30:10 Delphi Brand Recognition 30:33 QXO Rollup Strategy 32:56 Synergies And TopBuild Deal 38:12 Tech Stack Efficiency Play 39:05 CareTrust REIT Overview 42:23 EPR Experiential REIT 45:42 EPR Dividend Growth Case 46:48 Braves Stock BATRA Pitch 50:32 Stadium Real Estate Upside 51:54 Valuation Versus Padres Deal Companies mentioned: BATRA, COST, CTRE, EPR, PHIN, QXO, TJX 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

    1 hr
  4. First Fridays 30. May 2026

    MAY 4

    First Fridays 30. May 2026

    Join Jason and Jeff for the May First Fridays stream as they review the Portfolio Contest leaderboard, debate Duolingo's AI risks, and unpack the Starbucks turnaround under Brian Niccol. 02:01 Gemini Promo Video Fails 04:11 Portfolio Contest Update 09:44 Late Entries Penalty Tab 11:38 Ratings Reviews Push 13:46 Title Month Mixup 17:21 Duolingo Earnings Debate 22:43 AI Efficiency Threats 24:56 SaaS Risk Positioning 26:40 Gemini Video Fail 30:18 AI Thumbnail Drama 33:14 Starbucks Turnaround Signs 37:19 China Strategy Shift 40:44 Operational Fixes Ahead 42:47 Disruption Beyond Rivals 43:49 Earnings Season Winners Companies mentioned: AMD, AMZN, BE, DUOL, FIX, GOOG, GOOGL, HOOD, IBM, KNSL, LKNCY, MELI, META, NOW, ROKU, SBUX, SOFI, TTD, TXN, VRT 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

    50 min
  5. 203. April 2026 Mailbag

    APR 29

    203. April 2026 Mailbag

    In this April 2026 Mailbag, Jason and Jeff tackle a massive listener question about portfolio concentration in retirement, debating the merits of holding onto tiny "VC-minded" positions like Warby Parker and QuantumScape versus consolidating into bigger winners. They also provide an update on the "boring" but beautiful Brookfield Infrastructure, exploring its pivot toward modern assets like semiconductor fabs and its impressive 17-year streak of dividend increases. Later, they unpack the nuances of the private credit scare—and why major banks might have more exposure than investors realize.  00:35 Spotify Review Challenge 04:43 Retirement Portfolio Breakdown 06:20 Concentration vs Diversification 10:54 Options Income Bucket 12:49 Trim Small Positions 17:58 Enjoy Investing vs Indexing 19:57 Taxes and Ezra Klein Plug 20:55 Brookfield Infrastructure Update 22:52 Modern Infrastructure Shift 23:21 Intel Ohio Fab Deal 23:47 Energy Pivot Opportunities 24:35 Leadership Sam Pollock 26:38 Market Sensitivity Brookfield 28:35 Dividend Yield Return Math 30:45 Private Credit Reality Check 37:06 Risk Discounting Framework 38:35 AI Prompts Investing Workflow 40:41 AI Bias And Transcript Shortcuts 46:52 Comment Of The Month Wrap Companies mentioned: ADBE, AXON, BAM, BIP, BIPC, INTC, JPM, NVDA, OWL, QS, ROKU, SOFI, WFC, WRBY, 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 PatreonSubscribe to our portfolio on Savvy Trader Learn more about your ad choices. Visit megaphone.fm/adchoices

    52 min
  6. 202. I (Still) Gotta Think About That One

    APR 22

    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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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

    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 Learn more about your ad choices. Visit megaphone.fm/adchoices

    48 min
  8. First Fridays 29. April 2026

    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 Learn more about your ad choices. Visit megaphone.fm/adchoices

    1h 3m
See All (209)

4.9
out of 5
103 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
    209
  • Rating
    Clean
  • Copyright
    © Jason Hall and Jeff Santoro
  • Show Website
    Investing Unscripted

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