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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

00:47:38

187. What is Your Investing Echo Chamber?

Investing Unscripted ·

2026/01/07

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

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00:58:11

First Fridays 27. January 2026

Investing Unscripted ·

2026/01/05

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

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00:51:41

186. December 2025 Mailbag

Investing Unscripted ·

2025/12/31

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

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00:45:07

185. The 2026 Portfolio Contest & 2025 Market Review

Investing Unscripted ·

2025/12/24

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

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00:42:58

184. Bill Brewster: From "Junk" to Quality

Investing Unscripted ·

2025/12/17

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

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00:46:30

183. Reckless Predictions 2026

Investing Unscripted ·

2025/12/10

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

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00:40:51

182. Earnings Season Reset

Investing Unscripted ·

2025/12/03

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

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00:47:13

181. November 2025 Mailbag

Investing Unscripted ·

2025/11/26

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

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00:48:23

180. Stocks We Might Be Wrong About

Investing Unscripted ·

2025/11/19

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

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00:56:28

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

Investing Unscripted ·

2025/11/12

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

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01:01:21

First Friday 25. November 2025

Investing Unscripted ·

2025/11/10

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

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00:50:59

178. What If the AI Bubble Never Pops?

Investing Unscripted ·

2025/11/05

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

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00:43:02

177. October 2025 Mailbag

Investing Unscripted ·

2025/10/30

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

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00:46:42

176. Moats Don’t Exist

Investing Unscripted ·

2025/10/22

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

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00:53:18

175. Are You Ready to Retire, Bro?

Investing Unscripted ·

2025/10/15

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

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00:46:31

174. Market Crash 2026 (Ominous Music)

Investing Unscripted ·

2025/10/08

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

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01:00:23

First Fridays 24: October 2025

Investing Unscripted ·

2025/10/05

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

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00:56:34

173. I Gotta Think About That One

Investing Unscripted ·

2025/10/01

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,

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00:49:19

172. September 2025 Mailbag

Investing Unscripted ·

2025/09/24

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

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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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