Investing Unscripted

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

They run through market chaos from oil spikes and tariffs to the AI scare in software. They explain recent buys in industrials and renewables that aim to weather macro volatility. They debate AI strategies at major software names and flag hidden risks in the booming private credit market. The conversation keeps circling back to process over headlines when investing through uncertainty.

They check the current market vibes and compare today’s mood to past downturns. A lively debate on solid-state batteries, QuantumScape, and Donut Labs explores first-to-market risks. Discussion covers MercadoLibre’s lending business and whether Latin America risk keeps it perpetually discounted. They also recap the 2026 portfolio contest and react to Greg Abel’s first Berkshire Hathaway shareholder letter.

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

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

They answer mail about the psychology of buying into big tech sell-offs and whether dollar-cost averaging or waiting makes sense. They compare SentinelOne and CrowdStrike, including stock-based compensation and profitability concerns. They debate tempting “falling knife” software names like ServiceNow, PayPal, and Salesforce and discuss position sizing, portfolio risk, and bets on secular trends such as EVs and batteries.

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

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

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

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