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PODCAST

Investing Unscripted

Jason Hall and Jeff Santoro

Welcome to Investing Unscripted, where we ask the hard questions about investing, the stock market, and personal finance. We don"t have THE answers, we only have OUR answers.

business investing

All Episodes

01:06:31

171. David Gardner’s Rule Breaker Investing

Investing Unscripted ·

2025/09/17

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

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00:50:22

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

Investing Unscripted ·

2025/09/10

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

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01:01:27

First Fridays 23. September 2025

Investing Unscripted ·

2025/09/07

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

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00:41:59

169. Investing Unscripted, Unscripted Part Deux

Investing Unscripted ·

2025/09/03

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

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00:43:19

168. Why Your Retirement Plan Sucks

Investing Unscripted ·

2025/08/27

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

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00:46:54

Misfit Monthly 6. What is Risk?

Investing Unscripted ·

2025/08/23

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

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00:48:20

167. The Broken Thesis

Investing Unscripted ·

2025/08/20

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

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01:03:00

First Fridays 22. August 2025

Investing Unscripted ·

2025/08/17

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

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00:50:42

166. Ruining a Perfectly Good Investment

Investing Unscripted ·

2025/08/13

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

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00:52:35

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

Investing Unscripted ·

2025/08/06

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

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00:51:33

164. July 2025 Mailbag

Investing Unscripted ·

2025/07/30

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

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00:42:11

163. Nick Maggiulli’s The Wealth Ladder

Investing Unscripted ·

2025/07/23

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

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00:44:35

Misfit Monthly 5. AI Isn’t a Dot-Com Bubble

Investing Unscripted ·

2025/07/19

In this episode of Misfit Monthly, Jason and Tyler discuss the possibility of an AI bubble, exploring historical market bubbles, investor behavior, and how to stay disciplined in the current investment landscape.01:28 The Concept of Investing Therapy03:49 Understanding Market Bubbles07:03 The Dot-Com Bubble and Its Lessons09:12 Comparing AI to Past Bubbles15:33 The Role of Investor Psyche in Market Bubbles17:27 Promotional Segment: Fiscal.ai and Chitchat Stocks Podcast18:56 Reflecting on the Dot-Com

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00:56:02

162. Starting from Scratch

Investing Unscripted ·

2025/07/16

Jason and Jeff discuss the lessons they've learned from years of investing, recount their early financial missteps, and explore what they would do differently if they had to start their investment journeys from scratch today.00:36 Starting from Scratch: A New Investor's Journey01:33 Reflecting on Past Mistakes and Learning02:37 Investing in Your Early Twenties vs. Now03:19 Adapting Investment Strategies Over Time16:04 The Importance of Automating Savings23:30 Earnings Growth and Financial

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01:02:30

First Fridays 21. July 2025

Investing Unscripted ·

2025/07/13

In this month’s livestream, Jason and Jeff discuss the Q2 portfolio contest winner, the recent performance of SoFi and QuantumScape, and share their economic predictions amidst ongoing tariff talks.00:32 First Friday Live Stream Tradition01:16 Engaging with the Audience01:27 Investing Unscripted 2025 Portfolio Contest02:44 Discussing Rocketing Stocks: SoFi and QuantumScape04:13 SoFi: A Deep Dive16:22 QuantumScape: The Future of Solid-State Batteries30:41 Balancing Index Funds and Individual

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00:45:12

161. Concentration vs. Diversification

Investing Unscripted ·

2025/07/09

Jason and Jeff discuss concentration vs. diversification in investing, examine personal factors like risk tolerance and time. The conversation includes their own investment journeys and how portfolios can become more concentrated over time. 01:36 Main Topic: Concentration vs Diversification01:43 Warren Buffett vs Peter Lynch03:38 Berkshire Hathaway's Portfolio04:48 Personal Investment Strategies07:23 Temperament and Risk Tolerance10:42 Portfolio Management Examples19:52 Learning Through

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00:59:34

160. Finding Long-Term Value With Short-Term Tools

Investing Unscripted ·

2025/07/02

Jason and Jeff discuss how to manage long-term investment strategies with short-term information. Inspired by a Patreon member's question, they delve into the challenges investors face when trying to balance immediate news and quarterly reports with the vision of holding stocks for decades. 00:15 The Origin of Today's Topic00:53 Balancing Short-Term Information with Long-Term Goals02:17 John's Suggestion and Our Approach04:44 Identifying Long-Term Value Drivers05:03 Secular Tailwinds and Industry

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00:47:28

159. Alex Morris: Buffett and Munger Unscripted

Investing Unscripted ·

2025/06/25

Jason and Jeff welcome Alex Morris, a second-time guest and author of 'Buffett and Munger Unscripted.' The trio discusses the significance of Berkshire Hathaway meetings and the making of Alex's book. They delve into Warren Buffett's and Charlie Munger's investment philosophies, the evolution of their strategies, and how individual investors might apply these lessons. 01:03 Introducing the Guest: Alex Morris02:05 Discussing Alex's Book: Buffett and Munger Unscripted06:07

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00:36:28

Misfit Monthly 4: Jeff Was Right

Investing Unscripted ·

2025/06/21

Jason and Tyler discuss market efficiency, referencing Cliff Assnes's paper on the 'Less Efficient Market Hypothesis.' They explore value investing, the influence of social media on market behavior, and strategies for individual investors. The hosts emphasize the importance of exploring under-the-radar stocks and maintaining a mix of index funds and individual picks, advocating for thoughtful, long-term investment strategies.01:03 Discussing the Previous Episode: Finding an Edge01:29 The

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00:51:46

158. Flyover Stocks Unscripted

Investing Unscripted ·

2025/06/18

Jason and Jeff chat with Todd Wenning, founder of KNA Capital and creator of the Flyover Stocks newsletter. They discuss Todd's origin story in investing, the importance of management and company culture in evaluating investments, and how durable competitive advantages play a role. The conversation also explores the current economic landscape, strategies for navigating market volatility, and offers advice for retail investors. 00:51 Introducing the Guest: Todd Wenning02:21 Todd's Origin

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240 results

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