Investing Unscripted

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 trap, and give their unfiltered take on whether recent political news finally makes Cannabis stocks investable.

00:23 Listener Mailbag and Community Engagement

03:09 First Listener Question: Balancing Financial Results and Industry Knowledge

06:50 Using AI Tools for Investment Research

08:27 Real-World Examples and Industry Research

11:04 Brookfield Corporation: Legal Issues and Investment Risks

14:50 MTY Foods: Cash Flow and Investment Potential

22:28 Rebalancing Portfolios: Strategies and Considerations

26:10 Risk Management in Asset Allocation

26:54 Personal Investment Stories and Lessons

28:21 Strategies for 401k, Roth, and Brokerage Accounts

37:29 Handling Inheritance and Tax Implications

45:26 Investing in Cannabis Stocks

50:54 Conclusion and Viewer Engagement

Companies mentioned: AEO, AMZN, BN, CAVA, CMG, CRWD, CTRE, DRI, EAT, EPR, GOOGL, LOB, MCD, MELI, MO, MTY, NFLX, NUE, STLD, TAP, TSM, YUM

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The Smattering Six

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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. Finally, they share their "YOLO" picks and confess what they got wrong in 2025.

01:25 Upcoming Contest Announcement

02:00 2025 Year in Review

05:47 AI Dominance and Market Trends

13:08 Stock Picks for 2026

18:19 Sector Predictions for 2026

23:25 AI and Renewable Energy: The China Factor

24:53 Reflecting on 2025: Biggest Misjudgments

27:39 Lemonade's Unexpected Success

30:48 Top Performing Stocks of 2025: Predictions for 2026

34:47 Robinhood's Race Against Time

37:30 2026 Stock Contest: Rules and Guidelines

44:29 Wrapping Up: Final Thoughts and Holiday Wishes

Companies mentioned: GOOGL, ENPH, LMND, MU, NEM, NVDA, PLTR, HOOD, STX, SNPS, WBD, WDC

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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

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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 room."

00:24 Introducing the Guest: Bill Brewster

00:50 Bill's Investment Philosophy

04:05 Frameworks vs. Rules in Investing

06:59 Evolving as an Investor

11:01 David Gardner's Influence

18:18 Goals vs. Incentives in Investing

24:03 Building a Robust Investing Framework

24:27 Traits of Quality Enterprises

26:18 Economic Moats and Management Insights

27:45 Disney's Leadership and Strategic Shifts

32:58 Berkshire Hathaway's Future Leadership

Companies mentioned: BN, BRK.B, CLPT, COST, DIS, FAST, GIS, JPM, MCD, MELI, NFLX, OLN, OXY, PM, SHOP, WBD, WMT

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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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

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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 Accountability

00:34 Catching Up After the Holidays

01:42 Reviewing Last Year's Predictions

06:03 Stock Picks for 2025

11:10 Stocks to Avoid in 2025

20:46 Reflecting on Housing Market Predictions

24:30 S&P 500 Prediction Review

25:16 New Predictions for 2026

26:35 Oracle's Market Potential

27:29 Alphabet's AI Advantage

28:43 ASML and GE Aerospace Predictions

31:55 Kinsale Capital and Stock Picks

34:29 Stocks to Avoid in 2026

40:31 Reckless Predictions for 2026

Companies mentioned: AAPL, ASML, BRK.B, DFH, ENPH, GE, GOOGL, GRBK, INTC, KNSL, LLY, LEN, MELI, META, MSFT, MSTR, MTH, NVDA, ORCL, PHM, PLTR, TREX, TSLA, WMT

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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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

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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 "Quiet Time" Research 

29:00 Timing Buys Around Earnings Dates

35:00 Improvements: Investing Journal? (Airbnb)

Companies mentioned: ABNB, CRWD, CSIQ, REXR, TTD

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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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

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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 Mailbag: Answering Your Questions

03:01 First Question: Lemonade's Book Value Bear Thesis

16:25 Second Question: Adding to a Losing Position

23:40 Pandemic Impact on Digital Growth

23:48 PayPal's Strategic Shift

24:22 Dividend Announcement and Future Outlook

25:15 Investment Decisions and Opportunity Cost

25:59 PayPal's IPO Journey and Current Challenges

26:46 Investor Caution and Decision-Making

28:23 Market Confusion and Analytical Challenges

31:58 Chipotle vs. Kava: Investment Insights

32:13 Fast Casual Dining Industry Analysis

41:16 Brookfield Renewable vs. Brookfield Corporation

Companies mentioned: BAM, BEP, BN, CAVA, CMG, DRI, ETSY, LMND, PINS, PYPL, SBUX, SOFI

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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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

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The Smattering Six

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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: Texas Instruments

23:22 The Importance of Analog Semiconductors

24:34 Texas Instruments' Business Strategy

25:59 Challenges and Opportunities in the Analog Chip Market

27:40 Evaluating Texas Instruments' Stock Performance

32:53 Home Builders: A Sector Analysis

33:48 Dream Finders Homes: A Deep Dive

35:14 Investment Strategies and Portfolio Management

Companies mentioned: AMD, DFH, GRBK, HLT, MAR, MTH, NVDA, NVR, O, RHP, TXN

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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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

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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 Economic Impact

30:36 Legacy Companies in AI Infrastructure

32:15 Cyclical Nature of Markets and Inflation

33:29 Interest Rates and Economic Policies

36:07 Pricing Power and Consumer Behavior

43:56 AI Adoption and Market Potential

48:36 Investment Strategies and Market History

54:54 Conclusion and Final Thoughts

Companies mentioned: APH, BIP, BN, CMG, INTC, NVDA

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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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

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The Smattering Six

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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 the Cybersecurity Landscape

34:58 The Impact of Cybersecurity Outages

37:42 SanDisk and the AI Boom

41:43 Investing Unscripted Portfolio Contest

45:58 Reflections on Stock Picks and Market Trends

56:17 Political Implications on the Stock Market

59:44 Closing Remarks and Future Plans

Companies mentioned: AAPL, AMZN, BAM, BN, CRWD, GOOGL, META, S, SNDK, TSLA

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******************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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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

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2025 Portfolio Contest

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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 does this mean for nuclear power?) 

How we're thinking about investing and building a resilient portfolio right now.

00:23 Exploring the AI Bubble

00:56 Pitching the Premium Plan

03:38 Market Crash Expectations

06:33 AI's Impact on the Market

15:55 Energy and AI: A Symbiotic Relationship

22:41 The Future of Jobs in an AI-Driven World

26:16 AI's Impact on Employment and Economy

27:08 Amazon's AI Evolution with Alexa

28:05 AI's Role in Business and Education

33:34 AI's Influence on Market and Investments

37:10 Future of Top Companies and AI

42:06 Investment Strategies Amid AI Uncertainty

Companies mentioned: ADBE, AMD, AMZN, ASML, LMND, NOK, NOW, NVDA, TSM

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******************************************

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

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The Smattering Six

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