Investing Unscripted

By Jason Hall and Jeff SantoroBusiness Investing

Investing Unscripted episodes

October 30, 2025 177. October 2025 Mailbag
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 4% Rule Explained
26:56 Building Healthy Financial Habits
27:51 Personal Investment Strategies
29:50 Reflecting on Long-Term Investment Returns
30:40 Fun Questions: Podcasts and Halloween Candy
34:24 Investing in Candy Companies
Companies mentioned: HSY, MDLZ, NSRGY, PINS
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Twitter: @InvestingPod
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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
2025 Portfolio Contest
2024 Portfolio Contest
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48 min
October 22, 2025 176. Moats Don’t Exist
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 Shopping Experience
26:05 Amazon's Cost Advantage and Business Model
28:18 Switching Costs and Market Stickiness
29:12 Shopify's Role in E-commerce
31:15 The Risk of Complacency in Companies with High Switching Costs
36:59 Network Effects in Business
43:55 The Importance of Competitive Advantages
Companies mentioned: AAPL, ADBE, AMZN, KO, MA, NKE, ON, SHOP, TSM, UA, V
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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
******************************************
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
******************************************
The Smattering Six
2025 Portfolio Contest
2024 Portfolio Contest
2023 Portfolio Contest

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51 min
October 15, 2025 175. Are You Ready to Retire, Bro?
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 Maximizing Employer Match Contributions
09:25 Roth vs. Traditional 401(k)
13:21 Pensions and Retirement Income
21:46 Retirement Lifestyle and Planning
25:56 Emergency Funds and Cash Management
27:14 Living in Uncertainty: The Need for a Backup Plan
27:47 Retirement Savings: Stocks vs. Cash
28:02 The Importance of Cash in Volatile Markets
29:46 Approaching Retirement: Adjusting Your Portfolio
30:55 Building a Cash Cushion and Transitioning to Bonds
33:02 Understanding Bonds: Funds vs. Individual Bonds
36:01 The Impact of Interest Rates on Bonds
44:51 Holding Stocks in Retirement
49:21 Required Minimum Distributions and Tax Strategies
50:51 Finding Joy in Work and Retirement
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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
******************************************
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
******************************************
The Smattering Six
2025 Portfolio Contest
2024 Portfolio Contest
2023 Portfolio Contest

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57 min
October 08, 2025 174. Market Crash 2026 (Ominous Music)
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
24:06 Economic Stability and Employment
24:23 Impact of AI on Entry-Level Jobs
24:55 Government Shutdown and Unemployment
25:43 Inflation and Tariffs
30:27 Investment Strategies and Market Predictions
30:52 Savvy Trader Portfolio Insights
32:28 Long-Term vs Short-Term Investment Goals
37:37 Practical Uses of AI in Investing
40:06 Preparing for Market Crashes
Companies mentioned: CRWV, MSFT NVDA
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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 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
******************************************
The Smattering Six
2025 Portfolio Contest
2024 Portfolio Contest
2023 Portfolio Contest

Learn more about your ad choices. Visit megaphone.fm/adchoices
51 min
October 05, 2025 First Fridays 24: October 2025
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 Market Reactions
31:53 Speculative Investments and Market Sentiment
35:06 Strategies for Managing High-Performing Stocks
38:07 Balancing Portfolio and Trimming Positions
Companies mentioned: MELI, NVDA, QS, SHOP, SOFI, WINA
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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 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
1 hr 5 min
October 01, 2025 173. I Gotta Think About That One
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 Industry
52:26 Reflecting on Investment Strategies
Companies mentioned: ABNB, LGIH, ROKU, SPG, QXO
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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
******************************************
The Smattering Six
2025 Portfolio Contest
2024 Portfolio Contest
2023 Portfolio Contest

Learn more about your ad choices. Visit megaphone.fm/adchoices
1 hr 1 min
September 24, 2025 172. September 2025 Mailbag
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
26:08 Stock Valuation and Future Prospects
30:25 Stock-Based Compensation Discussion
38:44 Investing in Restaurant Stocks
47:45 Spam Comment of the Month
Companies mentioned: AMZN, ASAN, CAVA, CFLT, CMG, CPNG, CRWD, MCD, MELI, MSFT, SBUX, SE, TTD, XYZ
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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
******************************************
The Smattering Six
2025 Portfolio Contest
2024 Portfolio Contest
2023 Portfolio Contest

Learn more about your ad choices. Visit megaphone.fm/adchoices
53 min
September 17, 2025 171. David Gardner’s Rule Breaker Investing
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 Stock Picks and Surprises
37:48 The Humility in Investing
38:27 Lessons from Stock Picking
41:42 The Value of Direct Stock Buying
43:11 Fun with Stock Picking Games
43:55 Introducing the Smattering Six
46:06 Stock Picking Contest
01:04:06 The Importance of Long-Term Investing
Companies mentioned: AMZN, AX, CPNG, MELI, NVDA, PCOR, TBBB, TMDX, WRBY
Check out David’s new book: https://www.rulebreakerinvesting.com/
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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
******************************************
The Smattering Six
2025 Portfolio Contest
2024 Portfolio Contest
2023 Portfolio Contest

Learn more about your ad choices. Visit megaphone.fm/adchoices
1 hr 11 min
September 10, 2025 170. Stocks Unscripted: What’s Working and What’s Not
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 Investment Conviction and Price Anchoring
29:07 Evaluating Lemonade's Growth Strategy
32:05 Understanding Upstart's Market Position
35:55 Moderna: A Long-Term Bet on mRNA Technology
42:38 Live Oak Bank: A Small Business Lender's Journey
49:27 Wrapping Up and Final Thoughts
Companies mentioned: AX, LMND, MELI, LOB, MRNA, SHOP, UPST
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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
******************************************
2025 Portfolio Contest
2024 Portfolio Contest
2023 Portfolio Contest

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54 min
September 07, 2025 First Fridays 23. September 2025
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 Market Risks
33:57 Electricity Generation Concerns
34:16 Gradual Slowdown in AI Spending
34:57 Crypto Bubble Indicators
36:23 Housing Market Stability
36:43 Sopranos and New Jersey
38:10 Housing Market Fundamentals
46:14 QuantumScape Investment Discussion
51:09 Office Real Estate and Labor Market
53:05 Pandemic Stocks and Market Perception
53:39 Zoom's Future and Investor Sentiment
Companies mentioned: LMND, QS, ROKU, TBBB, TFSL, UPS, ZM
*****************************************
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
1 hr 6 min