

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

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

Aug 13, 2025 • 51min
166. Ruining a Perfectly Good Investment
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

Aug 6, 2025 • 53min
165. Are You Putting Too Much in Your 401(k)?
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

Jul 30, 2025 • 52min
164. July 2025 Mailbag
Jason and Jeff dive into diverse investing questions from listeners and their Patreon members, offering insights on holding stocks in a bear market, the benefits of dividend stocks, the impact of macroeconomic factors like inflation on investment philosophy, and more, while also sharing personal anecdotes and practical advice.00:19 Mailbag Episode Introduction00:57 Question 1: Holding Stocks in a Bear Market11:47 Question 2: Dividend Investing Strategies20:15 Question 3: Stable Coins and Payment Networks26:21 Comprehensive Stock Research and Podcast Overview26:52 Stable Coins and Streaming Services Analogy28:01 The Future of Stablecoins and Blockchain30:06 Impact of Inflation on Investment Philosophy32:15 Interest Rate Environment and Investment Decisions36:41 Dealing with Disinterest in Active Investing43:38 Strategies for Drawing Down Investments in Retirement48:50 Spam Comment of the Month and Closing RemarksCompanies mentioned: MA, 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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest

Jul 23, 2025 • 42min
163. Nick Maggiulli’s The Wealth Ladder
Jason and Jeff interview Nick Maggiulli, author of 'The Wealth Ladder,' discussing different levels of wealth, personal finance strategies, and the role of income and investments in building wealth over time.00:25 Introducing the Guest: Nick Majuli02:29 Nick Maggiulli’s Background and Journey05:44 The Importance of Income in Wealth Creation09:38 The Wealth Ladder: Levels and Strategies16:03 Frameworks and Financial Decision Making21:16 Reflections on Wealth and Time23:34 Analyzing Wealth Mobility24:35 The Impact of Age on Wealth Accumulation26:54 Challenges Faced by Younger Generations28:54 Adapting to Market Changes34:13 The Role of Writing in Financial Understanding37:26 Personal Investment Strategies*****************************************Buy The Wealth Ladder here: https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039Of Dollars and Data Newsletter: https://ofdollarsanddata.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******************************************2025 Portfolio Contest2024 Portfolio Contest2023 Portfolio Contest