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 Thesis

03:07 Evaluating Investment Theses

09:03 Case Study: The Trade Desk

19:46 Case Study: Boston Omaha

24:26 The Broken Thesis: A Personal Experience

25:11 TPI Composites: A Case Study in Bankruptcy

29:36 Brunswick Corporation: A Journey Through Time

33:31 Nvidia: From Video Cards to AI Powerhouse

40:24 Evaluating Investment Theses: Lessons Learned

Companies mentioned: AMZN, BC, BOC, CTRE, NFLX, NVDA, OM, RDFN, ROKU, CLNE

TPIC, TTD

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2025 Portfolio Contest

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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 Comments

02:50 Market Vibes and Economic Outlook

15:50 Earnings Season Insights

25:31 Confluent and Outset Medical Discussion

33:07 Investment Strategies and Position Sizing

35:34 UnitedHealth and Berkshire's Investment Moves

40:29 Portfolio Contest Update

46:00 Tobacco Stocks and Meme Stocks Discussion

48:51 QuantumScape's Progress and Potential

51:36 Airbnb's Growth and Challenges

57:19 Enphase Energy and Solar Market Insights

Companies mentioned: ABNB, CFLT, ENPH, OM, TTD, UNH, QS

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2025 Portfolio Contest

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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 Discussion

02:38 Airbnb's Future and CEO Analysis

05:15 Challenges and Opportunities for Airbnb

13:52 Successful Business Transformations

14:31 Amazon's Strategic Moves

21:12 Microsoft's Resurgence

26:38 The Impact of the iPhone on Apple's Future

26:56 Microsoft's Struggles with Innovation

27:19 Steve Ballmer's Infamous Moment

28:01 Berkshire Hathaway: A Unique Conglomerate

30:42 Under Armour's Rise and Fall

33:27 Shopify's Strategic Decisions

36:24 Companies with Uncertain Futures

45:10 Tesla: The Ultimate Story Stock

Companies mentioned: ABNB, AMZN, BRK.B, CPNG, MELI, MSFT, NFLX, SBUX, SHOP, SOFI, TSLA, UA

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2025 Portfolio Contest

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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 Strategies

02:49 Balancing Tax-Deferred and Taxable Accounts

11:45 Emergency Funds and Financial Safety Nets

16:24 Maximizing Employer 401(k) Matches

19:23 Tracking Expenses and Adjusting Contributions

25:14 Alternative Investment Strategies

27:19 Tax Implications of Roth and 401k Withdrawals

27:54 Strategizing Contributions: Roth vs. 401k

28:58 Employer Contributions and Taxable Brokerage Accounts

29:26 Advice for Younger Investors

30:47 Issues with 401k and 403b Plans

34:18 Alternative Investment Strategies

35:01 Saving for College: Different Perspectives

41:19 Balancing Investments for Flexibility

43:21 Tax Considerations in Investment Strategies

Companies mentioned: NVDA, QS

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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 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 Introduction

00:57 Question 1: Holding Stocks in a Bear Market

11:47 Question 2: Dividend Investing Strategies

20:15 Question 3: Stable Coins and Payment Networks

26:21 Comprehensive Stock Research and Podcast Overview

26:52 Stable Coins and Streaming Services Analogy

28:01 The Future of Stablecoins and Blockchain

30:06 Impact of Inflation on Investment Philosophy

32:15 Interest Rate Environment and Investment Decisions

36:41 Dealing with Disinterest in Active Investing

43:38 Strategies for Drawing Down Investments in Retirement

48:50 Spam Comment of the Month and Closing Remarks

Companies mentioned: MA, V

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2025 Portfolio Contest

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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 Majuli

02:29 Nick Maggiulli’s Background and Journey

05:44 The Importance of Income in Wealth Creation

09:38 The Wealth Ladder: Levels and Strategies

16:03 Frameworks and Financial Decision Making

21:16 Reflections on Wealth and Time

23:34 Analyzing Wealth Mobility

24:35 The Impact of Age on Wealth Accumulation

26:54 Challenges Faced by Younger Generations

28:54 Adapting to Market Changes

34:13 The Role of Writing in Financial Understanding

37:26 Personal Investment Strategies

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Of Dollars and Data Newsletter: https://ofdollarsanddata.com/

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2025 Portfolio Contest

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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 Therapy

03:49 Understanding Market Bubbles

07:03 The Dot-Com Bubble and Its Lessons

09:12 Comparing AI to Past Bubbles

15:33 The Role of Investor Psyche in Market Bubbles

17:27 Promotional Segment: Fiscal.ai and Chitchat Stocks Podcast

18:56 Reflecting on the Dot-Com Bubble and SPACs

21:47 Market Highs and AI Speculation

22:53 The AI Bubble Debate

25:22 Nvidia's Role in AI

28:15 Historical Comparisons and Market Dynamics

30:55 Investor Strategies and Market Outlook

35:44 Valuation Perspectives and Final Thoughts

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Follow Tyler on BlueSky: https://bsky.app/profile/misfit-alpha.bsky.social

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2025 Portfolio Contest

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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 Journey

01:33 Reflecting on Past Mistakes and Learning

02:37 Investing in Your Early Twenties vs. Now

03:19 Adapting Investment Strategies Over Time

16:04 The Importance of Automating Savings

23:30 Earnings Growth and Financial Success

30:50 Understanding Compounding and Inflation

32:58 Teaching Financial Literacy to Kids

34:09 Reflecting on Investment Strategies

35:07 The Role of Humility in Investing

38:58 Starting Over: Portfolio Strategies

42:10 Rolling Over Retirement Accounts

49:25 Aligning Finances with Values

52:53 Frameworks vs. Rules in Financial Planning

Companies mentioned: AAPL, CRWD, KNSL

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

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Check 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 Contest

2024 Portfolio Contest

2023 Portfolio Contest