Investing Unscripted

Jason Hall and Jeff Santoro
  • 0.0 (0)
  • 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. 1 DAY AGO

    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

  2. 1 APR

    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

  3. 25 MAR

    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

  4. 18 MAR

    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

  5. 15 MAR

    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

    1hr 2min

  6. 11 MAR

    196. Chit Chat Stocks, Unscripted

    Ryan Henderson and Brett Schafer from the Chit Chat Stocks podcast join us for a special unscripted episode to track their evolution from college-aged podcasters running a family-and-friends fund to seasoned individual investors. We discuss learning the harsh realities of valuation during the 2022 bear market, the dangers of "analysis paralysis," and whether mastering your own psychology is more important than understanding financial mechanics. We also debate the merits of starter positions, explore Ryan's strict "three-year holding rule," and reveal the current watchlist stocks they are waiting to buy—along with the ones they kick themselves for missing. 02:09 Meet Chit Chat Stocks 04:30 Origin Story  08:56 Early Podcast Lessons 10:26 Valuation Reality Check 12:29 Mistakes Shape Process 14:09 Bear Market Incentives 18:19 Investing In Public 21:30 Overthinking Valuation 24:07 Match Vs Spotify 28:18 Costco One Share Rule 29:18 Owning Through Drawdowns 29:58 Fund Pressure vs Flexibility 32:26 Starter Positions Debate 34:07 Psychology Beats Fundamentals 38:03 Know Your Investing Style 39:57 When Stocks Go Nowhere 44:15 Rules to Avoid Selling 47:35 Build a Personal Framework 51:52 Watchlist Valuation Picks 55:40 Where to Find Their Work 59:14 Final Wrap and Signoff Companies mentioned: ADYEY, AMZN, AXP, CAVA, COST, CPNG, CSU, HIMS, IBKR, MELI, MNDY, MRNA, MTCH, PYPL, RKLB, ROKU, SPOT, TSLA 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

  7. 4 MAR

    195. Stocks Unscripted, March 2026

    Jason and Jeff go completely off-script to discuss what they are actually doing in their portfolios right now. Jeff breaks down why he bought more Datadog on a recent dip and his strategy for adding to Enphase, while Jason explains how he is using options (specifically selling puts) to generate income while waiting for better valuations. Plus, they analyze the risk vs. reward of QuantumScape, debate the new CEO at PayPal, and play a game of "buy or get off the pot" that ends with a live stock purchase. 00:53 Unscripted Earnings Season 04:34 Jeff Did a Thing 06:43 Why Buy Datadog Now 09:14 AI Risks for SaaS 11:34 Selling Puts Strategy 17:06 Market Psychology Chegg 19:41 Market Efficiency Long Term 23:15 Enphase DCA Dilemma 25:46 How to Time Adds 28:08 Quarterly Info Is Noise 28:30 Enphase Through the Cycle 29:49 QuantumScape Solid State Promise 31:50 Timing the Entry Price 33:53 Asymmetric Upside vs Risk 36:24 PayPal CEO Shakeup 38:59 Reframing the PayPal Thesis 44:48 Small Positions to Fix 46:36 Airbnb Growth Proof Points Companies mentioned: ABNB, ADBE, CHGG, DDOG, ENPH, PYPL, QS, 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 PatreonSubscribe to our portfolio on Savvy Trader

    55 min

  8. 25 FEB

    194. February 2026 Mailbag

    We open the February 2026 mailbag to answer your questions on how to handle the psychological toll of the "SaaS apocalypse" and when it actually makes sense to buy the dip. We also discuss how to assess relative risk in a portfolio, dive deep into the differences between SentinelOne and CrowdStrike (including thoughts on stock-based compensation), and reveal the "falling knife" software stocks we are most tempted to buy right now, including ServiceNow and Salesforce. 00:51 First Friday Update 02:03 Mailbag Fear in Downturns 03:56 DCA and SaaS Selloff 06:15 Deploying Cash Rules 08:43 Add to Winners Not Losers 15:49 Risk in Portfolios 20:31 Position Sizing Examples 23:28 SentinelOne Profitability Debate 28:35 SentinelOne vs CrowdStrike 30:44 Cybersecurity Basket Strategy 31:42 M&A and Buyout Odds 33:12 CareTrust REIT Update 35:00 Discord Falling Knife Picks 35:35 ServiceNow Case 37:44 PayPal Options and CEO Risk 38:33 Salesforce AI and Valuation 42:50 How We Add Positions 47:28 Enphase and Gut Conviction 50:19 Secular Trends and EV Lesson 52:05 QuantumScape Battery Bet 52:37 Wrap Up and Where to Ask Companies mentioned: ASML, CRM, CRWD, CTRE, ENPH, NOW, PYPL, QS, S, 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 PatreonSubscribe to our portfolio on Savvy Trader

    54 min
See All (253)

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
    253
  • Rating
    Clean
  • Copyright
    © Jason Hall and Jeff Santoro
  • Show Website
    Investing Unscripted

You Might Also Like