Investing Unscripted

Jason Hall and Jeff Santoro
  • 4.9 (96)
  • 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

    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

  2. MAR 4

    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

  3. FEB 25

    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

  4. FEB 18

    193. Nothing Works All the Time

    We discuss the recent market dislocation where SaaS stocks are crashing while the broader market hits all-time highs. We break down the three main fears driving the sell-off and debate which companies—like Adobe and Salesforce—are actually at risk. Finally, we share how we are handling the volatility, with Jeff buying more Shopify and Jason using a "barbell strategy" to stay sane. 02:27 Housekeeping 03:53 Episode Setup 06:37 Three AI Threats to SaaS:  09:23 Is AI Really Different?  12:59 Stock Spotlight: Adobe 18:35 The Real Issue: Moats, Stickiness, Switching Costs, and Resetting SaaS Multiples 23:18 LLMs Aren’t Free 23:49 Why SaaS Stocks Are Selling Off 25:11 Shopify vs. Toast 27:06 Disruption Timelines & Valuation Reratings 29:19 Earnings Season as the Reality Check 31:53 Tactical Moves: Selling Puts for Margin of Safety 33:02 Barbell Portfolio Strategy: Growth on One Side, Dividends on the Other Companies mentioned: ABNB, ADBE, ASAN, CRM, CRWD, ENPH, EPR, MNDY, MSFT, NOW, O, PYPL, SHOP, SQ, TEAM, 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

    44 min

  5. FEB 11

    192. Emily Flippen, Investing Survivor

    We are joined by The Motley Fool's Emily Flippen to discuss her "Survivor" origins and why she believes empathy is the most underrated skill for investors. We also debate the difference between a "fad" and a "trend" in consumer goods (using Crocs vs. On Holding as the prime example), and Emily gives her honest take on "AI burnout." 00:32 Introducing Special Guest Emily Flippant 01:55 Emily's Journey to The Motley Fool 02:48 The Contrarian Path: Studying Business in China 03:13 The Ethical Dilemma and Finding The Motley Fool 06:11 The Art of Investing: Embracing Mistakes 08:07 The Weight of Public Stock Recommendations 12:29 Evolution as an Investor: From Value to Growth 19:35 Consumer Goods: The Fun Side of Investing 23:31 The 'Too Hard' Pile: Avoiding Complex Sectors 29:16 AI: The Double-Edged Sword 30:20 Is It a Bubble? 30:45 The Reality of AI Investments 31:08 Personal Investment Strategies 31:36 The Hype and Risks of AI 34:15 The Importance of Financial Goals 38:30 AI's Impact on Consumer Goods 43:18 The Future of AI and Society 48:07 Exciting Market Trends Companies mentioned: CROX, ONON, PYPL 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

    59 min

  6. FEB 4

    191. Stocks We’re Excited About

    We break down the six stocks we are most excited to watch this earnings season (and why "excited" doesn't necessarily mean we're buying). Jeff discusses Lemonade's path to 2026 profitability and why Rocket Lab is entering a critical "prove it" phase with its Neutron rocket, while Jason makes the case for Canadian Solar trading at half its book value and explains why SentinelOne offers a better risk/reward profile than CrowdStrike. 00:32 Discussing Stocks and Earnings Season 01:48 Analyzing Financial Statements and Risks 02:56 The Importance of Full-Year Results 04:16 Exciting Stocks and Future Prospects 05:57 Deep Dive into Canadian Solar 12:17 Exploring the Renewable Energy Market 17:55 Lemonade: A Stock with Potential 27:21 Lemonade Stock's Volatility and Future Outlook 28:11 Deep Dive into QuantumScape 32:15 Rocket Lab's Progress and Challenges 36:50 SentinelOne's Potential in Cybersecurity 40:42 PayPal's Strategic Focus and Future Prospects 46:58 Lightning Round: Stock Picks and Predictions Companies mentioned: CRWD, CSIQ, LMND, PYPL, QS, RKLB, 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

    52 min

  7. JAN 28

    190. January 2026 Mailbag

    We open the mailbag to answer your questions on whether Life Insurance Retirement Plans (LIRPs) are a scam, if spending millions on a Super Bowl commercial is ever a good idea (looking at you, CrowdStrike), and if equal-weight S&P 500 ETFs are the best way to hedge against a tech crash. Plus, we debate the future of the energy sector, discuss the power of "stock cannibals" like Adobe and PayPal, and reveal the two stocks we think could generate life-changing returns over the next 15 years. 01:44 Housekeeping and Listener Support 02:53 Diving into Listener Questions 03:04 Explaining Life Insurance Retirement Plans 09:03 Super Bowl Commercials: Worth the Investment? 16:47 Exploring ETF Diversification 23:10 Introduction and Wayne's Email 23:17 Colin's Energy Market Inquiry 24:04 Oil and Gas Market Dynamics 27:38 Investment Strategies in Energy Sector 29:48 Wayne's Question on ADRs 32:17 John's Query on Stock Buybacks 37:41 Ramey's AI and Investment Question 43:27 Future Investment Picks 47:23 Spam Comment of the Month Companies mentioned: ADBE, AZO, CRWD, GDDY, KNSL, KR, ORLY, PSX, PYPL, RKLB, TBBB, TTE, TXN 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

    49 min

  8. JAN 21

    189. The 3 Financial Docs You Need to Know

    In this special "toolbox" episode, Jason and Jeff strip away the jargon to teach you how to actually read the three most important documents in investing: the Income Statement, the Balance Sheet, and the Statement of Cash Flows. Using Nvidia’s recent Q3 earnings report as a real-world case study, the hosts walk through these important financial statements line by line. 01:33 The Importance of Financial Statements 04:59 Understanding the Income Statement 11:07 Revenue and Cost of Goods Sold 16:02 Operating Expenses and Income 18:39 Interest, Taxes, and Net Income 23:06 Depreciation, Amortization, and Goodwill 28:33 Introduction to the Balance Sheet 31:42 Understanding Current Assets and Liabilities 33:18 Accounts Receivable and Revenue Recognition 34:49 Inventory Management Insights 39:59 Exploring Goodwill and Intangible Assets 44:21 Diving into Liabilities and Working Capital 47:04 Cash Flow Statement Breakdown 58:32 Using Tools to Analyze Financial Statements Companies mentioned: AAPL, BRK.B, INTC, MKL, NVDA, TGT, TJX, TREX 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 1m
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4.9
out of 5
96 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
    248
  • Rating
    Clean
  • Copyright
    © Jason Hall and Jeff Santoro
  • Show Website
    Investing Unscripted

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