The Smattering

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This is The Smattering Podcast, where we ask the questions that matter to investors. If you have feedback for the show, you can email thesmatteringshow@gmail.com or follow the show on Twitter: @SmatteringShow

Jason Hall & Jeff Santoro


    • May 20, 2026 LATEST EPISODE
    • weekdays NEW EPISODES
    • 49m AVG DURATION
    • 261 EPISODES

    Ivy Insights

    The Smattering podcast is a gem in the world of investing podcasts. Hosted by Jason Hall and Jeff Santoro, this podcast delivers informative and easy-to-understand content that is perfect for both new and experienced investors. With a focus on mindset, strategy, analysis, and picks, the hosts cover all aspects of investing in a relatable and reasonable way. The show provides valuable insights into the stock market and investing as a whole, making it a must-listen for anyone interested in building their wealth through investing.

    One of the best aspects of The Smattering podcast is the wide range of topics covered. The hosts not only analyze individual stocks but also delve into mindset, news, sector analysis, history, goals, strategy, and more. This diverse coverage ensures that listeners get a well-rounded education on investing and are equipped with knowledge to make informed decisions. Additionally, Jason and Jeff's down-to-earth approach makes complex concepts accessible to non-finance people, making it easier for beginners to grasp the fundamentals of investing.

    Another great aspect of this podcast is the chemistry between Jason and Jeff. Their casual banter creates an enjoyable listening experience that feels like friends having a conversation about investing. They make even dry topics engaging and inject humor into their discussions. This dynamic keeps listeners entertained while still delivering valuable information.

    While there are many positive aspects to The Smattering podcast, one potential downside is that it may not dive deep enough into certain topics for advanced investors. While beginners will find the content informative and comprehensive enough to build a solid foundation in investing, seasoned investors may crave more in-depth analysis or specific strategies tailored to advanced investment approaches.

    In conclusion, The Smattering podcast is a must-listen for those looking to enhance their knowledge and skills in investing. With its wide range of topics covered in an easy-to-understand manner, this podcast offers something for investors at all levels. Jason Hall and Jeff Santoro bring years of experience and a relatable style that makes investing accessible to everyone. Whether you're a beginner or an experienced investor, The Smattering podcast is sure to provide valuable insights and help you develop your investing philosophy and strategy.



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    Latest episodes from The Smattering

    206. May 2026 Mailbag

    Play Episode Listen Later May 20, 2026 64:27


    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

    205. The 3 Questions Every Investor Should Answer

    Play Episode Listen Later May 15, 2026 57:17


    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

    204. Stocks for the AI Hater

    Play Episode Listen Later May 6, 2026 56:54


    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 AI07:27 AI Backlash and Reality Check11:00 Berkshire Weekend Teaser11:53 Picking AI Proof Stocks12:55 Costco as Safe Retailer16:40 Costco Ops and Tech Edge21:37 TJX Treasure Hunt Model25:49 Phinia Gas Engine Parts29:29 Commercial Auto Parts Angle30:10 Delphi Brand Recognition30:33 QXO Rollup Strategy32:56 Synergies And TopBuild Deal38:12 Tech Stack Efficiency Play39:05 CareTrust REIT Overview42:23 EPR Experiential REIT45:42 EPR Dividend Growth Case46:48 Braves Stock BATRA Pitch50:32 Stadium Real Estate Upside51:54 Valuation Versus Padres DealCompanies mentioned: BATRA, COST, CTRE, EPR, PHIN, QXO, TJXFind 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/unscriptedListen 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

    First Fridays 30. May 2026

    Play Episode Listen Later May 4, 2026 47:48


    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 Fails04:11 Portfolio Contest Update09:44 Late Entries Penalty Tab11:38 Ratings Reviews Push13:46 Title Month Mixup17:21 Duolingo Earnings Debate22:43 AI Efficiency Threats24:56 SaaS Risk Positioning26:40 Gemini Video Fail30:18 AI Thumbnail Drama33:14 Starbucks Turnaround Signs37:19 China Strategy Shift40:44 Operational Fixes Ahead42:47 Disruption Beyond Rivals43:49 Earnings Season WinnersCompanies mentioned: AMD, AMZN, BE, DUOL, FIX, GOOG, GOOGL, HOOD, IBM, KNSL, LKNCY, MELI, META, NOW, ROKU, SBUX, SOFI, TTD, TXN, VRTFind 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/unscriptedListen 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

    203. April 2026 Mailbag

    Play Episode Listen Later Apr 29, 2026 49:03


    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 Challenge04:43 Retirement Portfolio Breakdown06:20 Concentration vs Diversification10:54 Options Income Bucket12:49 Trim Small Positions17:58 Enjoy Investing vs Indexing19:57 Taxes and Ezra Klein Plug20:55 Brookfield Infrastructure Update22:52 Modern Infrastructure Shift23:21 Intel Ohio Fab Deal23:47 Energy Pivot Opportunities24:35 Leadership Sam Pollock26:38 Market Sensitivity Brookfield28:35 Dividend Yield Return Math30:45 Private Credit Reality Check37:06 Risk Discounting Framework38:35 AI Prompts Investing Workflow40:41 AI Bias And Transcript Shortcuts46:52 Comment Of The Month WrapCompanies mentioned: ADBE, AXON, BAM, BIP, BIPC, INTC, JPM, NVDA, OWL, QS, ROKU, SOFI, WFC, WRBY, ZMFind 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/unscriptedListen 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

    202. I (Still) Gotta Think About That One

    Play Episode Listen Later Apr 22, 2026 57:17


    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 Challenge04:24 Pick 1 CrowdStrike Bear Case08:00 Quantum and AI Disruption Talk14:21 Pick 2 Enterprise Products Explained20:13 Would You Buy It Valuation Talk25:09 Pick 3 Nvidia Bear Case Setup27:47 Nvidia Valuation Debate30:41 Nvidia Bear Case Shifts34:40 Axos Financial Overview36:19 Axos Bank Risks40:48 Shopify Bear Thesis43:01 Shopify Platform Risks51:33 Clearway Energy YieldcoCompanies mentioned: AX, CRWD, CWEN, EPD, NVDA, SHOPFind 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/unscriptedListen 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

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

    Play Episode Listen Later Apr 15, 2026 45:11


    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 Breakdown05:55 Space Market Tailwinds08:49 Why Launch Demand Surges11:20 New Space Use Cases14:48 SpaceX IPO Valuation Math19:14 IPO Pricing and Aftermarket23:11 What Success Looks Like23:36 Capital Needs Debate24:40 Starship Risks Ahead25:46 Space Investing Ad Break27:13 Mapping Space Sectors30:59 Where Space Gets Risky36:20 Top Picks To Research40:16 Consolidation And Legacy Primes41:28 Avoiding Hype TrapsCompanies mentioned: AMZN, ASTS, BKSY, GSAT, KTOS, LDOS, LHX, LMT, LUNR, META, NOC, PL, RDW, RKLB, TMUS, TSLA, V, VZFind 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/unscriptedListen 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

    First Fridays 29. April 2026

    Play Episode Listen Later Apr 13, 2026 60:26


    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 Resilience06:26 AI Hype And Volatility09:54 Cybersecurity Rumor Debate12:19 Cringey AI Promo Clip14:35 Portfolio Contest Rules16:31 Q1 Winner And Charity21:09 Patreon Standings And Long Game24:22 Portfolio Reflections And Trade Desk28:00 Board Sale Speculation30:49 Backing Jeff Green32:19 Position Sizing Rules32:45 Founder vs Operator Debate37:11 Kinsale Competition Pressure38:40 Kinsale Underwriting Edge42:23 Specialty Insurance Tailwinds45:30 PayPal Value Trap Risk52:15 Roth 401k Moves55:20 Roth Optionality Strategy57:46 Favorite Dividend PicksCompanies mentioned: BIP, BIPC, BORR, CTRE, EPR, GOOG, GOOGL, KNSL, MA, MELI, NOW, PLSDF, PLTR, PYPL, RBRK, RKLB, SECYF, TTDFind 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/unscriptedListen 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

    200. 200 Stocks for 200 Episodes

    Play Episode Listen Later Apr 8, 2026 47:08


    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 Challenge05:04 How Many Stocks06:30 Concentration vs Diversification09:06 Is This More Uncertain14:11 Should Uncertainty Change Holdings15:48 Jason Reframes Portfolio Size21:25 Portfolio Size Debate23:55 Conviction Versus Bias26:58 Averaging Up Winners28:42 Kinsale Capital Case32:59 Watchlist FOMO Trap34:48 Concentration And Time40:05 Automate When Anxious43:15 Humility And EvolvingCompanies mentioned: AAPL, AMZN, CDNS, CRWD, DFH, GE, JRVR, KNSL, MSFT, NVDA, S, SNPS, TOST, TTDFind 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/unscriptedListen 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

    199. Knowing When to End a Good Thing

    Play Episode Listen Later Apr 1, 2026 27:33


    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 Ending02:28 Retrospective and Keeping It Light03:28 Favorite Guests and Surprise Connections05:40 Jim Gillies and Early Episodes06:37 First Friday Livestream Memories08:06 Podcast Community and Crossovers09:25 Behind the Scenes Editing and Filler Words10:21 How Podcasting Shaped Investing Views11:14 Podcast Shapes Investing13:40 Investor Identity Distilled16:31 Talking Through Ideas18:02 Favorite Episode Formats20:46 Running Toward Fires26:54 Wrap Up And ThanksCompanies mentioned: BAM, BN, CRWD, MSFT, SFind 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/unscriptedListen 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

    198. March 2026 Mailbag

    Play Episode Listen Later Mar 25, 2026 50:46


    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 Strategy11:54 Nasdaq Index Rule Changes20:27 Dividend Bucket Rethink25:57 Dividend Growth Compounding26:38 Mastercard Low-Yield Lesson27:42 Instagram Mailbag Setup28:50 Consolidating Brokerage Accounts31:47 Schwab Versus Fidelity34:22 Combining Finances After Marriage35:45 Money Talks and Guardrails40:12 Walker and Dunlop Earnings42:43 Investing After Saving Goal45:43 Risk Spectrum and Time HorizonCompanies mentioned: AAPL, BOC, CRM, MA, META, MTH, QQQ, SCHW, WDFind 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/unscriptedListen 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

    197. Investing Through Chaos

    Play Episode Listen Later Mar 18, 2026 51:37


    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 Backdrop03:38 Housekeeping Mailbag Plug04:42 Staying the Course07:18 Markets Recover Before Clarity12:04 Stock Pick PHIN19:01 Renewables Reality Check20:54 Clearway Energy Buy24:50 Energy Security and Oil Flows26:36 Oil And Geopolitics27:29 Krugman On Price Spikes30:33 Toast Stock Breakdown35:44 ServiceNow AI Strategy37:35 Procore Construction Software42:17 Private Credit Risks47:38 Staying Invested In Chaos49:19 Process Over HeadlinesCompanies mentioned: BAM, BEP, BX, CPNG, CWEN, DASH, ENPH, FOUR, KKR, NOW, ORCL, OWL, PCOR, PHIN, PYPL, SHOP, SQ, TOSTFind 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/unscriptedListen 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

    First Fridays 28. March 2026

    Play Episode Listen Later Mar 15, 2026 61:30


    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 Joke04:08 Market Vibes Check06:28 K Shaped Economy Talk12:09 Portfolio Contest Update23:46 QuantumScape Buy Explained27:59 Donut Labs Battery Debate30:57 Battery Value Metrics31:34 Kids Pick Stocks32:58 Market Moves This Week36:56 MercadoLibre Discount Debate44:42 Options Premiums Q&A47:13 Using Claude for Research50:27 Greg Abel Letter Take55:30 Berkshire After BuffettCompanies mentioned: AAPL, AMZN, AXP, BRK.B, ENR, KNSL, KO, MCO, MELI, QS, RKLB, TMFind 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/unscriptedListen 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

    196. Chit Chat Stocks, Unscripted

    Play Episode Listen Later Mar 11, 2026 59:47


    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 Stocks04:30 Origin Story 08:56 Early Podcast Lessons10:26 Valuation Reality Check12:29 Mistakes Shape Process14:09 Bear Market Incentives18:19 Investing In Public21:30 Overthinking Valuation24:07 Match Vs Spotify28:18 Costco One Share Rule29:18 Owning Through Drawdowns29:58 Fund Pressure vs Flexibility32:26 Starter Positions Debate34:07 Psychology Beats Fundamentals38:03 Know Your Investing Style39:57 When Stocks Go Nowhere44:15 Rules to Avoid Selling47:35 Build a Personal Framework51:52 Watchlist Valuation Picks55:40 Where to Find Their Work59:14 Final Wrap and SignoffCompanies mentioned: ADYEY, AMZN, AXP, CAVA, COST, CPNG, CSU, HIMS, IBKR, MELI, MNDY, MRNA, MTCH, PYPL, RKLB, ROKU, SPOT, TSLAFind 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/unscriptedListen 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

    195. Stocks Unscripted, March 2026

    Play Episode Listen Later Mar 4, 2026 55:02


    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 Season04:34 Jeff Did a Thing06:43 Why Buy Datadog Now09:14 AI Risks for SaaS11:34 Selling Puts Strategy17:06 Market Psychology Chegg19:41 Market Efficiency Long Term23:15 Enphase DCA Dilemma25:46 How to Time Adds28:08 Quarterly Info Is Noise28:30 Enphase Through the Cycle29:49 QuantumScape Solid State Promise31:50 Timing the Entry Price33:53 Asymmetric Upside vs Risk36:24 PayPal CEO Shakeup38:59 Reframing the PayPal Thesis44:48 Small Positions to Fix46:36 Airbnb Growth Proof PointsCompanies mentioned: ABNB, ADBE, CHGG, DDOG, ENPH, PYPL, QS, UPSTFind 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/unscriptedListen 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

    194. February 2026 Mailbag

    Play Episode Listen Later Feb 25, 2026 53:55


    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 Update02:03 Mailbag Fear in Downturns03:56 DCA and SaaS Selloff06:15 Deploying Cash Rules08:43 Add to Winners Not Losers15:49 Risk in Portfolios20:31 Position Sizing Examples23:28 SentinelOne Profitability Debate28:35 SentinelOne vs CrowdStrike30:44 Cybersecurity Basket Strategy31:42 M&A and Buyout Odds33:12 CareTrust REIT Update35:00 Discord Falling Knife Picks35:35 ServiceNow Case37:44 PayPal Options and CEO Risk38:33 Salesforce AI and Valuation42:50 How We Add Positions47:28 Enphase and Gut Conviction50:19 Secular Trends and EV Lesson52:05 QuantumScape Battery Bet52:37 Wrap Up and Where to AskCompanies mentioned: ASML, CRM, CRWD, CTRE, ENPH, NOW, PYPL, QS, S, TSLA, TSMFind 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/unscriptedListen 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

    193. Nothing Works All the Time

    Play Episode Listen Later Feb 18, 2026 43:56


    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 Housekeeping03:53 Episode Setup06:37 Three AI Threats to SaaS: 09:23 Is AI Really Different? 12:59 Stock Spotlight: Adobe18:35 The Real Issue: Moats, Stickiness, Switching Costs, and Resetting SaaS Multiples23:18 LLMs Aren't Free23:49 Why SaaS Stocks Are Selling Off25:11 Shopify vs. Toast27:06 Disruption Timelines & Valuation Reratings29:19 Earnings Season as the Reality Check31:53 Tactical Moves: Selling Puts for Margin of Safety33:02 Barbell Portfolio Strategy: Growth on One Side, Dividends on the OtherCompanies mentioned: ABNB, ADBE, ASAN, CRM, CRWD, ENPH, EPR, MNDY, MSFT, NOW, O, PYPL, SHOP, SQ, TEAM, TOST, TTDFind 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/unscriptedListen 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

    192. Emily Flippen, Investing Survivor

    Play Episode Listen Later Feb 11, 2026 58:36


    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 Flippant01:55 Emily's Journey to The Motley Fool02:48 The Contrarian Path: Studying Business in China03:13 The Ethical Dilemma and Finding The Motley Fool06:11 The Art of Investing: Embracing Mistakes08:07 The Weight of Public Stock Recommendations12:29 Evolution as an Investor: From Value to Growth19:35 Consumer Goods: The Fun Side of Investing23:31 The 'Too Hard' Pile: Avoiding Complex Sectors29:16 AI: The Double-Edged Sword30:20 Is It a Bubble?30:45 The Reality of AI Investments31:08 Personal Investment Strategies31:36 The Hype and Risks of AI34:15 The Importance of Financial Goals38:30 AI's Impact on Consumer Goods43:18 The Future of AI and Society48:07 Exciting Market TrendsCompanies mentioned: CROX, ONON, PYPLFind 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/unscriptedListen 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

    191. Stocks We're Excited About

    Play Episode Listen Later Feb 4, 2026 52:26


    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 Season01:48 Analyzing Financial Statements and Risks02:56 The Importance of Full-Year Results04:16 Exciting Stocks and Future Prospects05:57 Deep Dive into Canadian Solar12:17 Exploring the Renewable Energy Market17:55 Lemonade: A Stock with Potential27:21 Lemonade Stock's Volatility and Future Outlook28:11 Deep Dive into QuantumScape32:15 Rocket Lab's Progress and Challenges36:50 SentinelOne's Potential in Cybersecurity40:42 PayPal's Strategic Focus and Future Prospects46:58 Lightning Round: Stock Picks and PredictionsCompanies mentioned: CRWD, CSIQ, LMND, PYPL, QS, RKLB, SFind 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/unscriptedListen 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

    190. January 2026 Mailbag

    Play Episode Listen Later Jan 28, 2026 48:53


    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 Support02:53 Diving into Listener Questions03:04 Explaining Life Insurance Retirement Plans09:03 Super Bowl Commercials: Worth the Investment?16:47 Exploring ETF Diversification23:10 Introduction and Wayne's Email23:17 Colin's Energy Market Inquiry24:04 Oil and Gas Market Dynamics27:38 Investment Strategies in Energy Sector29:48 Wayne's Question on ADRs32:17 John's Query on Stock Buybacks37:41 Ramey's AI and Investment Question43:27 Future Investment Picks47:23 Spam Comment of the MonthCompanies mentioned: ADBE, AZO, CRWD, GDDY, KNSL, KR, ORLY, PSX, PYPL, RKLB, TBBB, TTE, TXNFind 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/unscriptedListen 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

    189. The 3 Financial Docs You Need to Know

    Play Episode Listen Later Jan 21, 2026 61:29


    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 Statements04:59 Understanding the Income Statement11:07 Revenue and Cost of Goods Sold16:02 Operating Expenses and Income18:39 Interest, Taxes, and Net Income23:06 Depreciation, Amortization, and Goodwill28:33 Introduction to the Balance Sheet31:42 Understanding Current Assets and Liabilities33:18 Accounts Receivable and Revenue Recognition34:49 Inventory Management Insights39:59 Exploring Goodwill and Intangible Assets44:21 Diving into Liabilities and Working Capital47:04 Cash Flow Statement Breakdown58:32 Using Tools to Analyze Financial StatementsCompanies mentioned: AAPL, BRK.B, INTC, MKL, NVDA, TGT, TJX, TREXFind 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/unscriptedListen 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

    188. How to Use AI to Research Stocks (w/ Brian Feroldi)

    Play Episode Listen Later Jan 14, 2026 47:22


    Brian Feroldi, founder of Long-Term Mindset, joins us to explain how he uses AI tools like Gemini and NotebookLM to supercharge his stock research. We discuss the difference between a "price bubble" and an "earnings bubble" (and which one Nvidia might be in), share specific prompting strategies to stop AI from hallucinating, and run a live demo analyzing Green Brick Partners from scratch.00:55 Introducing the Guest: Brian Feroldi01:43 AI in Investing: A Game Changer03:40 Understanding AI Bubbles07:08 Using AI for Stock Research10:57 Optimizing AI Prompts for Investing16:59 The Role of AI in Investment Decisions19:42 AI Tools and Techniques26:25 Understanding AI's Learning Process26:49 Effective Prompting Techniques26:54 Role Assignment and Citations27:45 Step-by-Step Instructions for AI28:08 Resources for AI Prompting28:26 Using Notebook LM for Data Sources29:55 Practical AI Prompt Demonstration30:53 Analyzing Green Brick Partners32:45 Evaluating AI's Financial Analysis39:35 Customizing AI Prompts for Investment45:12 Challenges and Future of AI in FinanceCompanies mentioned: AAPL, CRWD, GILD, GOOGL, GRBK, LEN, LGIH, META, NVDACheck out Brian's work at https://www.longtermmindset.co/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/unscriptedListen 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

    187. What is Your Investing Echo Chamber?

    Play Episode Listen Later Jan 7, 2026 47:38


    We kick off 2026 by auditing our own 2025 portfolio performance, where Jeff confesses to trailing the market by 3% and Jason explains why his 401(k) only returned 9% (and why he is perfectly okay with that). We also discuss why Jason's "boring" dividend portfolio outperformed the AI-driven market, and explore the dangers of "investing echo chambers".01:32 Reflecting on 2025: Portfolio Performance04:30 Jeff's Personal Investment Breakdown14:22 Jason's Investment Strategy and Performance23:25 Transitioning Investments to Bonds and Cash24:21 Building a High-Yield Dividend Portfolio26:13 Reflecting on Investment Performance28:41 The Importance of Long-Term Investment Perspective31:13 Analyzing Stock Picking Strategies34:44 Echo Chambers in Stock PickingCompanies mentioned: BEP, BIP, BRK.B, CTRE, GOOGL, KNSL, MELI, NOW, NTB, PSX, PYPL, RKLB, S, SPG, TFSL, TSM, TTDFind 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/unscriptedListen 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

    First Fridays 27. January 2026

    Play Episode Listen Later Jan 5, 2026 58:11


    In our first live stream of 2026, we do a deep dive into QuantumScape's latest partnerships and what the "solid-state" future looks like for EVs. We also break down the winners (and massive losers) of our 2025 portfolio contest, reveal why a 4th grader is betting on Kontoor Brands, and share our own high-conviction picks for the year ahead, including Alphabet, Rocket Lab, and The Trade Desk.00:50 Nostalgia: 90s vs 80s Debate02:39 Engagement with Listeners04:13 Deep Dive into QuantumScape18:00 Small Caps and Market Trends25:58 Annual Stock Picking Contest29:32 Charity Contributions and Podcast Updates30:13 Full Year Winner Announcement31:05 Saad's Winning Portfolio Breakdown31:57 Contest Performance and Long-Term Investing36:25 2026 Contest Launch and Rules38:36 Listener Engagement and Community Building48:02 Final Thoughts and Portfolio StrategiesCompanies mentioned: DAVA, F, GOOGL, KNSL, KTB, MELI, NOW, PLTR, PYPL, QS, RKLB, TBBB, TSLA, TTDFind 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/unscriptedListen 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

    186. December 2025 Mailbag

    Play Episode Listen Later Dec 31, 2025 51:41


    In the final episode of 2025, Jason and Jeff empty the mailbag to answer listener questions about managing sudden wealth, tax strategies, and portfolio management. They debate the pros and cons of rebalancing versus letting your winners run (featuring a look at Jason's highly concentrated Roth IRA) and discuss how to handle a financial windfall like an inheritance. The hosts also break down the risks of complex conglomerates like Brookfield, analyze whether MTY Food Group is a value play or a value trap, and give their unfiltered take on whether recent political news finally makes Cannabis stocks investable.00:23 Listener Mailbag and Community Engagement03:09 First Listener Question: Balancing Financial Results and Industry Knowledge06:50 Using AI Tools for Investment Research08:27 Real-World Examples and Industry Research11:04 Brookfield Corporation: Legal Issues and Investment Risks14:50 MTY Foods: Cash Flow and Investment Potential22:28 Rebalancing Portfolios: Strategies and Considerations26:10 Risk Management in Asset Allocation26:54 Personal Investment Stories and Lessons28:21 Strategies for 401k, Roth, and Brokerage Accounts37:29 Handling Inheritance and Tax Implications45:26 Investing in Cannabis Stocks50:54 Conclusion and Viewer EngagementCompanies mentioned: AEO, AMZN, BN, CAVA, CMG, CRWD, CTRE, DRI, EAT, EPR, GOOGL, LOB, MCD, MELI, MO, MTY, NFLX, NUE, STLD, TAP, TSM, YUM*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    185. The 2026 Portfolio Contest & 2025 Market Review

    Play Episode Listen Later Dec 24, 2025 45:07


    In this holiday special, Jason and Jeff wrap up 2025 by reviewing the year's biggest stories—from the AI boom to inflation and trade wars. They discuss whether the AI narrative is showing any cracks and debate which sectors might dominate in 2026, with Jason making a case for homebuilders and Jeff eyeing the energy sector. The hosts also reveal the simplified rules for the 2026 Investing Unscripted Portfolio Contest, inviting listeners to submit their "buy and hold" picks for charity. Finally, they share their "YOLO" picks and confess what they got wrong in 2025.01:25 Upcoming Contest Announcement02:00 2025 Year in Review05:47 AI Dominance and Market Trends13:08 Stock Picks for 202618:19 Sector Predictions for 202623:25 AI and Renewable Energy: The China Factor24:53 Reflecting on 2025: Biggest Misjudgments27:39 Lemonade's Unexpected Success30:48 Top Performing Stocks of 2025: Predictions for 202634:47 Robinhood's Race Against Time37:30 2026 Stock Contest: Rules and Guidelines44:29 Wrapping Up: Final Thoughts and Holiday WishesCompanies mentioned: GOOGL, ENPH, LMND, MU, NEM, NVDA, PLTR, HOOD, STX, SNPS, WBD, WDC*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    184. Bill Brewster: From "Junk" to Quality

    Play Episode Listen Later Dec 17, 2025 42:58


    Bill Brewster, host of The Business Brew, joins us for a candid conversation about the mental toll of stock picking and his evolution from "cigar butt" value investing to quality compounders. We dive deep into his sharp criticism of Disney CEO Bob Iger, debate whether Berkshire Hathaway is facing a "conglomerate discount" after its recent management shakeup, and discuss why sometimes the best investing strategy is simply admitting you might be the "dumbest person in the room."00:24 Introducing the Guest: Bill Brewster00:50 Bill's Investment Philosophy04:05 Frameworks vs. Rules in Investing06:59 Evolving as an Investor11:01 David Gardner's Influence18:18 Goals vs. Incentives in Investing24:03 Building a Robust Investing Framework24:27 Traits of Quality Enterprises26:18 Economic Moats and Management Insights27:45 Disney's Leadership and Strategic Shifts32:58 Berkshire Hathaway's Future LeadershipCompanies mentioned: BN, BRK.B, CLPT, COST, DIS, FAST, GIS, JPM, MCD, MELI, NFLX, OLN, OXY, PM, SHOP, WBD, WMT*****************************************Check out The Business Brew: https://www.thebusinessbrew.com/*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    183. Reckless Predictions 2026

    Play Episode Listen Later Dec 10, 2025 46:30


    It's time to grade our 2025 predictions (spoiler: we were mostly wrong) and make some reckless new calls for 2026. We debate whether Oracle or Alphabet will be the next mega-cap winner, if Tesla's full self-driving ambitions will crash the stock, and why Strategy might be the single most dangerous stock to own next year. Plus, we ask the big question: Will the market finally crash in 2026, or is the AI bubble just getting started?00:16 Reckless Predictions and Accountability00:34 Catching Up After the Holidays01:42 Reviewing Last Year's Predictions06:03 Stock Picks for 202511:10 Stocks to Avoid in 202520:46 Reflecting on Housing Market Predictions24:30 S&P 500 Prediction Review25:16 New Predictions for 202626:35 Oracle's Market Potential27:29 Alphabet's AI Advantage28:43 ASML and GE Aerospace Predictions31:55 Kinsale Capital and Stock Picks34:29 Stocks to Avoid in 202640:31 Reckless Predictions for 2026Companies mentioned: AAPL, ASML, BRK.B, DFH, ENPH, GE, GOOGL, GRBK, INTC, KNSL, LLY, LEN, MELI, META, MSFT, MSTR, MTH, NVDA, ORCL, PHM, PLTR, TREX, TSLA, WMT*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    182. Earnings Season Reset

    Play Episode Listen Later Dec 3, 2025 40:51


    Jason and Jeff discuss why the best time to analyze a company might be weeks after they report, and share their personal strategies for this quieter period. 03:00 Why You Should Wait a Month Before Analyzing Earnings 06:00 Early Investing Mistakes 12:00 Panic-Buying and the CrowdStrike Example 15:00 How Incentives (and "Being First") Skew Financial Media 20:00 Annual Reports & The Rexford Industrial Deep Dive 24:00 The Value of Community: Canadian Solar 26:00 Spreadsheets and "Quiet Time" Research 29:00 Timing Buys Around Earnings Dates35:00 Improvements: Investing Journal? (Airbnb)Companies mentioned: ABNB, CRWD, CSIQ, REXR, TTD*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    181. November 2025 Mailbag

    Play Episode Listen Later Nov 26, 2025 47:13


    In this month's mailbag, Jason and Jeff tackle the "Book Value" bear thesis for Lemonade and discuss when the company might finally reach profitability. They also address a listener's dilemma about what to do with a losing position in PayPal, debating the sunk cost fallacy and the company's turnaround prospects. Finally, the hosts weigh in on whether Cava or Chipotle is the better buy right now and explain how to choose between Brookfield Corporation and Brookfield Renewable.01:13 Mailbag: Answering Your Questions03:01 First Question: Lemonade's Book Value Bear Thesis16:25 Second Question: Adding to a Losing Position23:40 Pandemic Impact on Digital Growth23:48 PayPal's Strategic Shift24:22 Dividend Announcement and Future Outlook25:15 Investment Decisions and Opportunity Cost25:59 PayPal's IPO Journey and Current Challenges26:46 Investor Caution and Decision-Making28:23 Market Confusion and Analytical Challenges31:58 Chipotle vs. Kava: Investment Insights32:13 Fast Casual Dining Industry Analysis41:16 Brookfield Renewable vs. Brookfield CorporationCompanies mentioned: BAM, BEP, BN, CAVA, CMG, DRI, ETSY, LMND, PINS, PYPL, SBUX, SOFI*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    180. Stocks We Might Be Wrong About

    Play Episode Listen Later Nov 19, 2025 48:23


    Jason and Jeff challenge their own investing biases and debate whether they're wrong about holding three specific stocks: Ryman Hospitality Properties (RHP), Texas Instruments (TXN), and Dream Finders Homes (DFH).00:42 Today's Topic: Questioning Your Investment Thesis02:26 Listener Engagement and Support04:21 Stock Spotlight: Ryman Hospitality Properties09:36 Analyzing Ryman's Performance and Strategy22:29 Stock Spotlight: Texas Instruments23:22 The Importance of Analog Semiconductors24:34 Texas Instruments' Business Strategy25:59 Challenges and Opportunities in the Analog Chip Market27:40 Evaluating Texas Instruments' Stock Performance32:53 Home Builders: A Sector Analysis33:48 Dream Finders Homes: A Deep Dive35:14 Investment Strategies and Portfolio ManagementCompanies mentioned: AMD, DFH, GRBK, HLT, MAR, MTH, NVDA, NVR, O, RHP, TXN*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    179. The AI Bubble & the State of the Market with John Rotonti

    Play Episode Listen Later Nov 12, 2025 56:28


    Jason and Jeff are joined by John Rotonti for a conversation on the current state of the market and the AI bubble. John explains his "iron fist" investing philosophy and why the worst thing you can do is let go of a true compounding machine too early.01:38 John's Career Update04:21 Investment Philosophy and Challenges11:55 Market Insights and AI Discussion16:57 Infrastructure and Technological Shifts28:59 Tariffs and Economic Impact30:36 Legacy Companies in AI Infrastructure32:15 Cyclical Nature of Markets and Inflation33:29 Interest Rates and Economic Policies36:07 Pricing Power and Consumer Behavior43:56 AI Adoption and Market Potential48:36 Investment Strategies and Market History54:54 Conclusion and Final ThoughtsCompanies mentioned: APH, BIP, BN, CMG, INTC, NVDA*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    First Friday 25. November 2025

    Play Episode Listen Later Nov 10, 2025 61:21


    In the November livestream, we started with a market "vibe check" on the recent AI stock sell-off, debated the "AI bubble", floated a hot take on Apple's "wait and license" strategy, and answered live questions from viewers. We also announced the Q3 portfolio contest winner.01:58 Market Vibes and Stock Performance10:29 AI Revolution and Market Speculations25:41 Brookfield Asset Management and Sentinel One Insights34:13 Exploring the Cybersecurity Landscape34:58 The Impact of Cybersecurity Outages37:42 SanDisk and the AI Boom41:43 Investing Unscripted Portfolio Contest45:58 Reflections on Stock Picks and Market Trends56:17 Political Implications on the Stock Market59:44 Closing Remarks and Future PlansCompanies mentioned: AAPL, AMZN, BAM, BN, CRWD, GOOGL, META, S, SNDK, TSLA*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    178. What If the AI Bubble Never Pops?

    Play Episode Listen Later Nov 5, 2025 50:59


    Jason and Jeff chat about the "circular" AI deals, whether AI stocks are just hype, and what it would actually take for this bubble to keep inflating. In this episode, we ask:Are AI stocks dangerously overvalued? What are these "circular deals" between companies like Nvidia, AMD, and OpenAI? Is this AI rally just like the dot-com bubble? Will AI lead to massive job losses, or will it just change what our jobs look like? Where will all the energy come from to power AI? (And what does this mean for nuclear power?) How we're thinking about investing and building a resilient portfolio right now.00:23 Exploring the AI Bubble00:56 Pitching the Premium Plan03:38 Market Crash Expectations06:33 AI's Impact on the Market15:55 Energy and AI: A Symbiotic Relationship22:41 The Future of Jobs in an AI-Driven World26:16 AI's Impact on Employment and Economy27:08 Amazon's AI Evolution with Alexa28:05 AI's Role in Business and Education33:34 AI's Influence on Market and Investments37:10 Future of Top Companies and AI42:06 Investment Strategies Amid AI UncertaintyCompanies mentioned: ADBE, AMD, AMZN, ASML, LMND, NOK, NOW, NVDA, TSM*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    177. October 2025 Mailbag

    Play Episode Listen Later Oct 30, 2025 43:02


    Jason and Jeff answer listener questions about Pinterest stock, the nature of individual stock-picking, their financial goals, favorite podcasts, and Halloween candies on this episode of Investing Unscripted.01:14 Analyzing Pinterest as an Investment03:24 The Challenges of Monetizing Pinterest10:10 Listener Question: Are Stock Pickers Narcissists?23:09 Determining Financial Goals24:33 Understanding Retirement Income Needs25:16 The 4% Rule Explained26:56 Building Healthy Financial Habits27:51 Personal Investment Strategies29:50 Reflecting on Long-Term Investment Returns30:40 Fun Questions: Podcasts and Halloween Candy34:24 Investing in Candy CompaniesCompanies mentioned: HSY, MDLZ, NSRGY, PINS*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    176. Moats Don't Exist

    Play Episode Listen Later Oct 22, 2025 46:42


    Jason and Jeff discuss the concept of moats in investing, exploring their validity, limitations, and real-life applicability across various industries, including technology, retail, and pharmaceuticals.01:25 Debating the Existence of Moats04:01 Intangible Asset Moats: Apple and Nike15:12 Pharmaceutical Moats and Patent Protection16:42 Cost Advantages and Efficient Scale24:13 Amazon's Distribution Network Moat24:44 The Amazon Shopping Experience26:05 Amazon's Cost Advantage and Business Model28:18 Switching Costs and Market Stickiness29:12 Shopify's Role in E-commerce31:15 The Risk of Complacency in Companies with High Switching Costs36:59 Network Effects in Business43:55 The Importance of Competitive AdvantagesCompanies mentioned: AAPL, ADBE, AMZN, KO, MA, NKE, ON, SHOP, TSM, UA, V*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    175. Are You Ready to Retire, Bro?

    Play Episode Listen Later Oct 15, 2025 53:18


    Jason and Jeff are joined by financial planning expert Robert Brokamp to discuss key concepts in retirement planning for individuals at every stage of their career, covering topics such as 401(k)s, Roth IRAs, pensions, and the importance of cash and bonds in both accumulation and retirement phases.00:48 Introducing the Guest: Robert Brokamp01:31 Previous Episodes and Listener Feedback02:32 Retirement Planning for New Adults04:51 Maximizing Employer Match Contributions09:25 Roth vs. Traditional 401(k)13:21 Pensions and Retirement Income21:46 Retirement Lifestyle and Planning25:56 Emergency Funds and Cash Management27:14 Living in Uncertainty: The Need for a Backup Plan27:47 Retirement Savings: Stocks vs. Cash28:02 The Importance of Cash in Volatile Markets29:46 Approaching Retirement: Adjusting Your Portfolio30:55 Building a Cash Cushion and Transitioning to Bonds33:02 Understanding Bonds: Funds vs. Individual Bonds36:01 The Impact of Interest Rates on Bonds44:51 Holding Stocks in Retirement49:21 Required Minimum Distributions and Tax Strategies50:51 Finding Joy in Work and Retirement*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    174. Market Crash 2026 (Ominous Music)

    Play Episode Listen Later Oct 8, 2025 46:31


    Jason and Jeff discuss the potential for an upcoming market crash in 2026, reflecting on last year's predictions, and explore the impacts of AI investment, interest rates, inflation, and tariffs on the market, providing insights on how to adjust investment strategies in uncertain times.01:55 Reflecting on Last Year's Market Crash Predictions06:09 The AI Boom and Market Speculation14:37 Interest Rates and Economic Concerns24:06 Economic Stability and Employment24:23 Impact of AI on Entry-Level Jobs24:55 Government Shutdown and Unemployment25:43 Inflation and Tariffs30:27 Investment Strategies and Market Predictions30:52 Savvy Trader Portfolio Insights32:28 Long-Term vs Short-Term Investment Goals37:37 Practical Uses of AI in Investing40:06 Preparing for Market CrashesCompanies mentioned: CRWV, MSFT NVDA *****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    First Fridays 24: October 2025

    Play Episode Listen Later Oct 5, 2025 60:23


    In the October livestream, Jeff and Jason discuss the challenges of trimming stocks amid rapid gains, the temptation of big winners, QuantumScape's potential, and managing personal investment decisions to maximize long-term gains.04:32 Market Trends and Economic Uncertainty08:40 Stock Talk: QuantumScape and Investment Strategies29:13 Ducati's Quantum Leap29:36 Corning Partnership Boosts Stock30:26 Investor Concerns and Market Reactions31:53 Speculative Investments and Market Sentiment35:06 Strategies for Managing High-Performing Stocks38:07 Balancing Portfolio and Trimming PositionsCompanies mentioned: MELI, NVDA, QS, SHOP, SOFI, WINA*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    173. I Gotta Think About That One

    Play Episode Listen Later Oct 1, 2025 56:34


    Jason and Jeff randomly analyze each other's stock portfolios, presenting spontaneous bear cases and discussing whether they would buy shares today.00:35 Explaining the Random Stock Challenge04:08 First Stock Analysis: LGI Homes11:59 Second Stock Analysis: Roku18:21 Third Stock Analysis: QXO25:27 Fourth Stock Analysis: Airbnb35:48 Simon Property Group: Malls Aren't Dead Yet42:28 Procore: Modernizing the Construction Industry52:26 Reflecting on Investment StrategiesCompanies mentioned: ABNB, LGIH, ROKU, SPG, QXO*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    172. September 2025 Mailbag

    Play Episode Listen Later Sep 24, 2025 49:19


    Jason and Jeff respond to listener questions on stock-based compensation, restaurant industry investments, and recent market dynamics related to the Trade Desk, while sharing their insights on various investing strategies and market trends.00:37 Listener Questions and Engagement02:58 Quarterly Earnings Debate17:32 YouTube Comments and Trade Desk Discussion23:27 Market Sentiment and Trade Desk Analysis23:48 Ad Tech Industry Dynamics26:08 Stock Valuation and Future Prospects30:25 Stock-Based Compensation Discussion38:44 Investing in Restaurant Stocks47:45 Spam Comment of the MonthCompanies mentioned: AMZN, ASAN, CAVA, CFLT, CMG, CPNG, CRWD, MCD, MELI, MSFT, SBUX, SE, TTD, XYZ*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    171. David Gardner's Rule Breaker Investing

    Play Episode Listen Later Sep 17, 2025 66:31


    Jason and Jeff interview David Gardner, co-founder of The Motley Fool, to talk about his new book 'Rule Breaker Investing,' investing philosophies, and a friendly stock-picking competition.00:48 Welcoming David Gardner01:27 David's Early Investing Journey03:24 The Rule Breaker Philosophy08:52 The Importance of Holding19:30 Valuation and Intangibles33:16 Misunderstandings of Rule Breaker Investing37:23 Reflecting on Stock Picks and Surprises37:48 The Humility in Investing38:27 Lessons from Stock Picking41:42 The Value of Direct Stock Buying43:11 Fun with Stock Picking Games43:55 Introducing the Smattering Six46:06 Stock Picking Contest01:04:06 The Importance of Long-Term InvestingCompanies mentioned: AMZN, AX, CPNG, MELI, NVDA, PCOR, TBBB, TMDX, WRBYCheck out David's new book: https://www.rulebreakerinvesting.com/*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************The Smattering Six2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    170. Stocks Unscripted: What's Working and What's Not

    Play Episode Listen Later Sep 10, 2025 50:22


    Jason and Jeff discuss stocks that are performing well and those struggling in their portfolios, evaluate the companies' performances, and share their thoughts on portfolio management and future investment strategies.02:33 Discussing the Mailbag and Listener Engagement04:09 Starting the Stock Discussion: Mercado Libre05:54 Deep Dive into Mercado Libre's Performance18:31 Exploring Lemonade and Upstart27:03 Navigating Investment Conviction and Price Anchoring29:07 Evaluating Lemonade's Growth Strategy32:05 Understanding Upstart's Market Position35:55 Moderna: A Long-Term Bet on mRNA Technology42:38 Live Oak Bank: A Small Business Lender's Journey49:27 Wrapping Up and Final ThoughtsCompanies mentioned: AX, LMND, MELI, LOB, MRNA, SHOP, UPST*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    First Fridays 23. September 2025

    Play Episode Listen Later Sep 7, 2025 61:27


    Jason and Jeff discuss cryptocurrencies, delve into financial strategies like options trading, and take questions from the audience about market trends, the housing market, and more.00:32 3D Printing and Future Technologies03:07 AI and Investment Predictions06:46 Market Vibes and S&P 500 Discussion15:13 Investment Strategies and Options Trading20:43 Economic Outlook and Rate Cuts32:21 Crypto and AI Speculation32:57 Potential AI Market Risks33:57 Electricity Generation Concerns34:16 Gradual Slowdown in AI Spending34:57 Crypto Bubble Indicators36:23 Housing Market Stability36:43 Sopranos and New Jersey38:10 Housing Market Fundamentals46:14 QuantumScape Investment Discussion51:09 Office Real Estate and Labor Market53:05 Pandemic Stocks and Market Perception53:39 Zoom's Future and Investor SentimentCompanies mentioned: LMND, QS, ROKU, TBBB, TFSL, UPS, ZM*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    169. Investing Unscripted, Unscripted Part Deux

    Play Episode Listen Later Sep 3, 2025 41:59


    Jason and Jeff go completely unscripted, diving into interest rates, market uncertainty, AI hype, and personal investing strategies in a candid, wide-ranging conversation.02:40 – Reflections on the past year04:45 – Interest rates, tariffs, and recurring macro themes07:20 – The Fed, rate cuts, and market reactions13:00 – How macro noise impacts personal investing decisions15:20 – Homebuilders, housing affordability, and investment opportunities18:00 – Adapting investment process: FOMO, bubbles, and Howard Marks' advice22:00 – Market exuberance: Is it 1996 or 1999?26:30 – Pivot: Is AI overhyped? Parallels to the Internet bubble29:00 – AI's real impact, business integration, and valuation risks33:00 – Energy, infrastructure, and the limits of AI scalability35:00 – Personal portfolio management, risk, and long-term goals40:00 – Index funds, risk allocation, and retirement planning42:00 – Housekeeping, how to support the show, and closing thoughtsCompanies mentioned: AAPL, ASML, BRK.B, CRM, GOOG, META, NVDA, TSM*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    168. Why Your Retirement Plan Sucks

    Play Episode Listen Later Aug 27, 2025 43:19


    Jason and Jeff welcome Dan Otter from 403bwise.org to discuss the difficulties educators face with 403(b) retirement plans, how to advocate for better options, and strategies for navigating and improving these retirement plans.02:27 Dan Otter's Origin Story05:35 The Problem with 403(b) Plans15:26 The Importance of Fiduciary Standards21:41 Understanding Expense Ratios in Index Funds22:07 Hiring a Fee-Only Financial Advisor22:53 The Impact of Fees on Long-Term Savings24:21 Advocating for Better Retirement Plan Options25:48 Empathy for School Districts and Their Challenges29:06 The Importance of Offering Low-Cost Retirement Plans30:25 Building an Army to Advocate for Better Options33:23 The Benefits of a Roth IRA for Educators35:38 Navigating Bad 403(b) Plans and Finding Solutions*****************************************Check out Dan's work at https://403bwise.orgSubscribe to the Teach and Retire Rich podcast wherever you get podcasts*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    Misfit Monthly 6. What is Risk?

    Play Episode Listen Later Aug 23, 2025 46:54


    Understanding Risk: International Investing Insights with Tyler CroweIn this month's Misfit Monthly Episode, Jason Hall and Tyler Crowe delve into the concept of risk in investing. They discuss the broad definitions and perceptions of risk, focusing particularly on the differences between volatility and the probability of permanent loss of capital. The conversation also explores the common view that international markets are considered risky, using examples like Poland and Mexico to show that's not always the case. Tyler shares insights from his extensive experience living and investing overseas, emphasizing the importance of evaluating unfamiliar markets and the risks associated with them. The episode aims to equip investors with the tools to better assess risk and make informed decisions that align with their financial goals.01:04 Defining Risk in Investing21:17 Perceptions of Risk in International Markets24:06 The Granny Shot: A Lesson in Unconventional Success24:51 Societal Pressure in Decision Making26:10 Investment Community and Benchmark Hugging27:42 Incentives and Fund Management30:56 Stock Buybacks and Market Signals33:39 Evaluating Risk in International Markets41:09 Final Thoughts on Risk and Investment Strategies*****************************************Check out Tyler's Misfit Alpha at https://www.misfitalpha.com/unscripted Follow Tyler on BlueSky: https://bsky.app/profile/misfit-alpha.bsky.socialJoin our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************To get 15% off any paid plan at finchat.io, 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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    167. The Broken Thesis

    Play Episode Listen Later Aug 20, 2025 48:20


    Jason and Jeff discuss how to identify and handle situations where the thesis for owning a particular stock might be broken or changed, using various companies as examples.01:02 Understanding the Broken Thesis03:07 Evaluating Investment Theses09:03 Case Study: The Trade Desk19:46 Case Study: Boston Omaha24:26 The Broken Thesis: A Personal Experience25:11 TPI Composites: A Case Study in Bankruptcy29:36 Brunswick Corporation: A Journey Through Time33:31 Nvidia: From Video Cards to AI Powerhouse40:24 Evaluating Investment Theses: Lessons LearnedCompanies mentioned: AMZN, BC, BOC, CTRE, NFLX, NVDA, OM, RDFN, ROKU, CLNETPIC, TTD*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    First Fridays 22. August 2025

    Play Episode Listen Later Aug 17, 2025 63:00


    In the August livestream, Jason and Jeff answer questions live, discuss notable earnings reports from the last month, and provide an update on the Investing Unscripted portfolio contest.01:21 Viewer Interaction and Comments02:50 Market Vibes and Economic Outlook15:50 Earnings Season Insights25:31 Confluent and Outset Medical Discussion33:07 Investment Strategies and Position Sizing35:34 UnitedHealth and Berkshire's Investment Moves40:29 Portfolio Contest Update46:00 Tobacco Stocks and Meme Stocks Discussion48:51 QuantumScape's Progress and Potential51:36 Airbnb's Growth and Challenges57:19 Enphase Energy and Solar Market InsightsCompanies mentioned: ABNB, CFLT, ENPH, OM, TTD, UNH, QS*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    166. Ruining a Perfectly Good Investment

    Play Episode Listen Later Aug 13, 2025 50:42


    Jason and Jeff discuss the impacts of strategic business shifts in companies like Airbnb, Amazon, Netflix, and Tesla, examining which moves added value, which ones did not, and where the jury is still out.01:27 Airbnb Investment Discussion02:38 Airbnb's Future and CEO Analysis05:15 Challenges and Opportunities for Airbnb13:52 Successful Business Transformations14:31 Amazon's Strategic Moves21:12 Microsoft's Resurgence26:38 The Impact of the iPhone on Apple's Future26:56 Microsoft's Struggles with Innovation27:19 Steve Ballmer's Infamous Moment28:01 Berkshire Hathaway: A Unique Conglomerate30:42 Under Armour's Rise and Fall33:27 Shopify's Strategic Decisions36:24 Companies with Uncertain Futures45:10 Tesla: The Ultimate Story StockCompanies mentioned: ABNB, AMZN, BRK.B, CPNG, MELI, MSFT, NFLX, SBUX, SHOP, SOFI, TSLA, UA*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

    165. Are You Putting Too Much in Your 401(k)?

    Play Episode Listen Later Aug 6, 2025 52:35


    Jason and Jeff discuss optimizing investment strategies, evaluating contributions to 403(b) and 401(k) plans versus Roth IRAs and brokerage accounts, and tackle personal finance essentials such as building an emergency fund, managing taxes, and saving for college.00:54 Understanding 403(b) and Investment Strategies02:49 Balancing Tax-Deferred and Taxable Accounts11:45 Emergency Funds and Financial Safety Nets16:24 Maximizing Employer 401(k) Matches19:23 Tracking Expenses and Adjusting Contributions25:14 Alternative Investment Strategies27:19 Tax Implications of Roth and 401k Withdrawals27:54 Strategizing Contributions: Roth vs. 401k28:58 Employer Contributions and Taxable Brokerage Accounts29:26 Advice for Younger Investors30:47 Issues with 401k and 403b Plans34:18 Alternative Investment Strategies35:01 Saving for College: Different Perspectives41:19 Balancing Investments for Flexibility43:21 Tax Considerations in Investment StrategiesCompanies mentioned: NVDA, QS*****************************************Join our PatreonSubscribe to our portfolio on Savvy Trader *****************************************Email: investingunscripted@gmail.comTwitter: @InvestingPodCheck out our YouTube channel for more content: ******************************************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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

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