Investing Unscripted
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.
Episodes
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 ...
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 s...
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 Th...
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 choo...
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 Thesis
02:26 Listener Engagement and Support
04:21 Stock Spotlight: Ryman Hospitality Properties
09:36 Analyzing Ryman's Performance and Strategy
22:29 Stock Spotlight: ...
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 Update
04:21 Investment Philosophy and Challenges
11:55 Market Insights and AI Discussion
16:57 Infrastructure and Technological Shifts
28:59 Tariffs and ...
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 Performance
10:29 AI Revolution and Market Speculations
25:41 Brookfield Asset Management and Sentinel One Insights
34:13 Exploring th...
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 lo...
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 Investment
03:24 The Challenges of Monetizing Pinterest
10:10 Listener Question: Are Stock Pickers Narcissists?
23:09 Determining Financial Goals
24:33 Understanding Retirement Income Needs
25:16 The ...
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 Moats
04:01 Intangible Asset Moats: Apple and Nike
15:12 Pharmaceutical Moats and Patent Protection
16:42 Cost Advantages and Efficient Scale
24:13 Amazon's Distribution Network Moat
24:44 The Amazon Sh...
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 Brokamp
01:31 Previous Episodes and Listener Feedback
02:32 Retirement Planning for New Adults
04:51 Ma...
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 Predictions
06:09 The AI Boom and Market Speculation
14:37 Interest Rates and Economic Concerns
24...
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 Uncertainty
08:40 Stock Talk: QuantumScape and Investment Strategies
29:13 Ducati's Quantum Leap
29:36 Corning Partnership Boosts Stock
30:26 Investor Concerns and Mark...
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 Challenge
04:08 First Stock Analysis: LGI Homes
11:59 Second Stock Analysis: Roku
18:21 Third Stock Analysis: QXO
25:27 Fourth Stock Analysis: Airbnb
35:48 Simon Property Group: Malls Aren't Dead Yet
42:28 Procore: Modernizing the Construction Industr...
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 Engagement
02:58 Quarterly Earnings Debate
17:32 YouTube Comments and Trade Desk Discussion
23:27 Market Sentiment and Trade Desk Analysis
23:48 Ad Tech Industry Dynamics
...
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 Gardner
01:27 David's Early Investing Journey
03:24 The Rule Breaker Philosophy
08:52 The Importance of Holding
19:30 Valuation and Intangibles
33:16 Misunderstandings of Rule Breaker Investing
37:23 Reflecting on ...
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 Engagement
04:09 Starting the Stock Discussion: Mercado Libre
05:54 Deep Dive into Mercado Libre's Performance
18:31 Exploring Lemonade and Upstart
27:03 Navigating Investm...
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 Technologies
03:07 AI and Investment Predictions
06:46 Market Vibes and S&P 500 Discussion
15:13 Investment Strategies and Options Trading
20:43 Economic Outlook and Rate Cuts
32:21 Crypto and AI Speculation
32:57 Potential AI...
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 year
04:45 – Interest rates, tariffs, and recurring macro themes
07:20 – The Fed, rate cuts, and market reactions
13:00 – How macro noise impacts personal investing decisions
15:20 – Homebuilders, housing affordability, and investment o...
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 Story
05:35 The Problem with 403(b) Plans
15:26 The Importance of Fiduciary Standards
21:41 Understanding Expense Ratios in Index Funds
22:07 Hiring a Fee-Only Financial Advisor
22:53 The ...
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