Investing Unscripted

Investing Unscripted

By Jason Hall and Jeff SantoroBusinessInvesting
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Investing Unscripted episodes

  • 169. Investing Unscripted, Unscripted Part Deux

    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 opportunities

    18:00 – Adapting investment process: FOMO, bubbles, and Howard Marks’ advice

    22:00 – Market exuberance: Is it 1996 or 1999?

    26:30 – Pivot: Is AI overhyped? Parallels to the Internet bubble

    29:00 – AI’s real impact, business integration, and valuation risks

    33:00 – Energy, infrastructure, and the limits of AI scalability

    35:00 – Personal portfolio management, risk, and long-term goals

    40:00 – Index funds, risk allocation, and retirement planning

    42:00 – Housekeeping, how to support the show, and closing thoughts

    Companies mentioned: AAPL, ASML, BRK.B, CRM, GOOG, META, NVDA, TSM

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

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    Email: [email protected]

    Twitter: @InvestingPod

    Check out our YouTube channel for more content: 

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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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    46 min
  • 168. Why Your Retirement Plan Sucks

    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 Impact of Fees on Long-Term Savings

    24:21 Advocating for Better Retirement Plan Options

    25:48 Empathy for School Districts and Their Challenges

    29:06 The Importance of Offering Low-Cost Retirement Plans

    30:25 Building an Army to Advocate for Better Options

    33:23 The Benefits of a Roth IRA for Educators

    35:38 Navigating Bad 403(b) Plans and Finding Solutions

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    Check out Dan’s work at https://403bwise.org

    Subscribe to the Teach and Retire Rich podcast wherever you get podcasts

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    Join our Patreon

    Subscribe to our portfolio on Savvy Trader 

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

    Email: [email protected]

    Twitter: @InvestingPod

    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

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

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    47 min
  • Misfit Monthly 6. What is Risk?

    Understanding Risk: International Investing Insights with Tyler Crowe

    In 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 that's not always the case. Tyler shares insights from his extensive experience living and investing overseas, emphasizing the importance of evaluating unfamiliar markets and the risks associated with them. The episode aims to equip investors with the tools to better assess risk and make informed decisions that align with their financial goals.


    01:04 Defining Risk in Investing

    21:17 Perceptions of Risk in International Markets

    24:06 The Granny Shot: A Lesson in Unconventional Success

    24:51 Societal Pressure in Decision Making

    26:10 Investment Community and Benchmark Hugging

    27:42 Incentives and Fund Management

    30:56 Stock Buybacks and Market Signals

    33:39 Evaluating Risk in International Markets

    41:09 Final Thoughts on Risk and Investment Strategies

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    Check out Tyler's Misfit Alpha at https://www.misfitalpha.com/unscripted 

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

    Join our Patreon

    Subscribe to our portfolio on Savvy Trader 

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    Email: [email protected]

    Twitter: @InvestingPod

    Check out our YouTube channel for more content: 

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

    To get 15% off any paid plan at finchat.io, 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

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    Learn more about your ad choices. Visit megaphone.fm/adchoices

    51 min
  • 167. The Broken Thesis

    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

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

    Join our Patreon

    Subscribe to our portfolio on Savvy Trader 

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

    Email: [email protected]

    Twitter: @InvestingPod

    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

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    2023 Portfolio Contest

    Learn more about your ad choices. Visit megaphone.fm/adchoices

    52 min
  • First Fridays 22. August 2025

    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

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

    Join our Patreon

    Subscribe to our portfolio on Savvy Trader 

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

    Email: [email protected]

    Twitter: @InvestingPod

    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

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    1 hr 7 min
  • 166. Ruining a Perfectly Good Investment

    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

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

    Join our Patreon

    Subscribe to our portfolio on Savvy Trader 

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

    Email: [email protected]

    Twitter: @InvestingPod

    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

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

    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

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

    Join our Patreon

    Subscribe to our portfolio on Savvy Trader 

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

    Email: [email protected]

    Twitter: @InvestingPod

    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

    Learn more about your ad choices. Visit megaphone.fm/adchoices

    57 min
  • 164. July 2025 Mailbag

    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

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

    Join our Patreon

    Subscribe to our portfolio on Savvy Trader 

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

    Email: [email protected]

    Twitter: @InvestingPod

    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

    Learn more about your ad choices. Visit megaphone.fm/adchoices

    56 min
  • 163. Nick Maggiulli’s The Wealth Ladder

    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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    Buy The Wealth Ladder here: https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039


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

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

    Join our Patreon

    Subscribe to our portfolio on Savvy Trader 

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

    Email: [email protected]

    Twitter: @InvestingPod

    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

    Learn more about your ad choices. Visit megaphone.fm/adchoices

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

    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

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

    Check out Tyler's Misfit Alpha at https://www.misfitalpha.com/unscripted 

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

    Join our Patreon

    Subscribe to our portfolio on Savvy Trader 

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

    Email: [email protected]

    Twitter: @InvestingPod

    Check out our YouTube channel for more content: 

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

    To get 15% off any paid plan at finchat.io, 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


    Learn more about your ad choices. Visit megaphone.fm/adchoices

    49 min

About Investing Unscripted

From the publisher's feed

Welcome to Investing Unscripted, where we ask the hard questions about investing, the stock market, and personal finance.

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