

Investing Unscripted
Jason Hall and Jeff Santoro
This is The Investing Unscripted Podcast, where we ask the questions that matter to investors.
If you have feedback for the show, you can email investingunscripted@gmail.com or follow the show on Twitter: @InvestingPod
Subscribe to our newsletter: https://investingunscripted.beehiiv.com/subscribe
If you have feedback for the show, you can email investingunscripted@gmail.com or follow the show on Twitter: @InvestingPod
Subscribe to our newsletter: https://investingunscripted.beehiiv.com/subscribe
Episodes
Mentioned books

Oct 1, 2025 • 57min
173. I Gotta Think About That One
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

Sep 24, 2025 • 49min
172. September 2025 Mailbag
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

Sep 17, 2025 • 1h 7min
171. David Gardner’s Rule Breaker Investing
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

Sep 10, 2025 • 50min
170. Stocks Unscripted: What’s Working and What’s Not
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

Sep 7, 2025 • 1h 1min
First Fridays 23. September 2025
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

Sep 3, 2025 • 42min
169. Investing Unscripted, Unscripted Part Deux
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

Aug 27, 2025 • 43min
168. Why Your Retirement Plan Sucks
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

Aug 23, 2025 • 47min
Misfit Monthly 6. What is Risk?
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

Aug 20, 2025 • 48min
167. The Broken Thesis
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

Aug 17, 2025 • 1h 3min
First Fridays 22. August 2025
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