Investing Unscripted
Investing Unscripted is a podcast where hosts Jason Hall and Jeff Santoro explore investing, the stock market, and personal finance. They ask hard questions and share their own perspectives, acknowledging that they don't have all the answers. The show aims to provide honest, unscripted discussions about financial topics.
Episodes
227. Should You Still Own Bonds?
In this episode, Jason and Jeff tackle the often-misunderstood world of fixed income to answer a critical question: Should you still own bonds? The hosts break down exactly why bond funds were decimated in 2022, the mechanics of the inverse correlation between interest rates and bond prices, and the vital difference between holding bond funds versus holding individual bonds to maturity. Finally, t
226. Investing Unscripted, Unscripted
In this completely unscripted episode, Jason and Jeff tackle the broad economic vibes surrounding the market’s resilience despite mounting geopolitical and macroeconomic uncertainty. The duo debates whether the normalization of sports betting and prediction markets is quietly threatening the culture of long-term stock investing. Plus, they unpack the complicated psychology of adding to massive win
First Fridays 35. October 2026
In the October 2026 First Fridays live stream, Jason and Jeff explore the broader macro vibes surrounding corporate fraud and regulatory boundaries, contrasting today's headlines with the Wild West of 1920s Wall Street. The duo unpacks CareTrust REIT's massive $1.2 billion expansion into the UK, evaluating the enduring power of the "aging baby boomer" demographic tailwind. Later, they debate how q
225. September 2026 Mailbag
In this September 2026 Mailbag, Jason and Jeff tackle listener questions on when it makes sense to "average up" on massive winners, analyzing David Gardner’s contrarian approach to building a Rule Breaker portfolio. The hosts then explore the specific valuation and counter-cyclical margin arguments behind Jason's recent purchase of The TJX Companies, and debate the psychology of co-managing spousa
224. Our Best and Worst Stock Picks
Jason and Jeff pull back the curtain on their Savvy Trader portfolio to examine the core mechanics of long-term portfolio construction. Using real-world examples from their own holdings, the hosts debate the discipline required to let a multi-bagger winner run versus the psychological battle of confronting a 70% drawdown. They tackle the dangerous allure of the sunk-cost fallacy, evaluate whether
223. 5 (More) Stocks for 10 Years
Jason and Jeff revisit their popular 2023 thought experiment to build a brand-new five-stock portfolio designed to hold through 2036. After reviewing how a massive 400% surge in Taiwan Semiconductor carried their original picks past the S&P 500, the hosts lay out their updated high-conviction roster. They break down the rapid store expansion of Mexican discount grocer BBB Foods, the secular land a
222. David Gardner: Rule Breakers, AI, and the Next Great Stocks
In this episode, Jason and Jeff welcome back The Motley Fool co-founder David Gardner to discuss his book, Rule Breaker Investing, and the origins of his market-beating philosophy. The trio unpacks why seemingly overvalued stocks often generate the biggest returns, how AI is impacting established platforms like Booking Holdings, and whether mega-caps like Nvidia and Netflix have graduated from "Ru
First Fridays 34. September 2026
In this September 2026 First Fridays live stream, Jason and Jeff tackle a jam-packed earnings season and a surprisingly resilient market. The hosts dissect The Trade Desk's revenue contraction and strategic missteps against tech walled gardens, debate whether Lemonade's post-earnings drop was justified despite a record-low 60% gross loss ratio, and break down DocuSign's incredibly consistent free
221. Investing Basics: How to Build a Portfolio
In this back-to-basics episode, Jason and Jeff break down the foundational rules of portfolio construction, asset allocation, and true risk diversification. The hosts explore how to blend an index fund baseline with individual stock picking, examine the mechanics of position sizing and rebalancing, and debate different cash-deployment frameworks. To cap it off, both hosts reveal brand-new stock pu
220. August 2026 Mailbag
In this August 2026 Mailbag, Jason and Jeff tackle listener questions on high-conviction stocks gone wrong, unpacking the deceleration and agency friction at The Trade Desk. They explore how co-host overlap can lead to borrowed conviction, discuss what to do when you feel "stuck" in a frothy market, and analyze QuantumScape's shift toward data center power storage and licensing partnerships with H
219. How to Survive a Bull Market
Bull markets can be just as dangerous for your portfolio as market crashes! Jason and Jeff share how to navigate all-time highs, avoid FOMO, and manage your big winners.
01:06 Markets At New Highs
02:36 Survive A Bull Market
03:48 Recent Crises To Endure
06:30 What Is A Bull Market
08:47 Sidelines And Opportunity Cost
13:44 Fear Vs FOMO
16:37 AI Wave And Market Pockets
20:40 Trade Desk TAM
218. How AI is Changing Everything About Startup Investing with Joe Magyer
In this episode, Jason and Jeff sit down with Joe Magyer of Seaplane Ventures to explore how generative AI has completely rewired the startup investing landscape. The trio discusses how tools like Claude and ChatGPT have drastically lowered the cost of building software, the heavy consolidation of capital into frontier labs like Anthropic and OpenAI, and why genuine domain expertise and network ef
First Fridays 33. August 2026
In this August 2026 First Fridays live stream, Jason and Jeff break down the latest earnings season chaos, exploring why Lemonade dropped despite hitting its lowest gross loss ratio ever. They analyze Twilio’s massive 35% post-earnings pop, debate whether The Trade Desk's open internet thesis is officially broken, and review their 2026 Portfolio Contest standings. Plus, the duo discusses Kinsale C
217. I Still, Still Gotta Think About That One
In this recurring segment, Jason and Jeff let an AI randomly select six stocks from their personal portfolios for a rapid-fire review. The hosts deliver a one-sentence thesis, a bear case, and a final "buy or pass" verdict for Arista Networks, Ferrari, Rocket Lab, Alphabet, Mercado Libre, and Starbucks. They debate the risks of AI slowing down for Arista and Alphabet, weigh Ferrari's massive opera
216. July 2026 Mailbag
In this July 2026 Mailbag, Jason and Jeff tackle listener questions on when logic should yield to emotion in debt payoff decisions, how to accurately benchmark dollar-cost-averaged portfolios, and which modern stocks fit David Gardner's "Rule Breaker" framework. Plus, they explore AI's real-world robotics data bottleneck and evaluate Southern California industrial REIT Rexford Industrial (REXR).
215. Jason Explains Banks
Why do banks count your deposits as liabilities? We're breaking down how banks actually buy and sell money, plus how to evaluate loan books and bank earnings.
00:49 Why Talk Bank Stocks
03:41 Banks Buy And Sell Money
07:24 Bank KPIs That Matter
09:36 Why Banks Look Revenue-Less
13:26 Deposits As Liabilities
18:53 Interest Rates And Margins
22:41 Fixed Rate Loan Squeeze
24:11 Deposit
214. Is it Time to Buy the Mag 7?
Are the mega-caps officially a buy? We're breaking down the valuations, moats, and hidden risks for every Magnificent Seven stock.
00:42 Why Mag Seven Now
05:04 Market Benchmark Setup
05:38 Alphabet AI Optionality
13:40 Apple AI Strategy
21:10 Amazon AI Adjacent Case
35:18 Nvidia Expectations Shift
40:22 Index Fund vs Stock Pick
44:28 Meta Bear Case
51:34 Tesla Hype vs Reality
55:44 Micr
First Fridays 32. July 2026
In this midyear live stream, Jason and Jeff look back at a chaotic first half of 2026, dissecting how the broader market continues to push ahead despite global geopolitical tensions. The hosts dive into a data-backed re-evaluation of their personal portfolios, checking in on massive year-to-date winners like Datadog and Texas Instruments, while reflecting on painful laggards like The Trade Desk. T
213. What the Hell is Going On? With Nick Rossolillo
What the hell is going on with tech valuations? Nick Rossolillo joins us to break down the trillion-dollar AI infrastructure cycle and why "commodity" hardware is running wild.
02:04 Chip Stock Investor Process
05:00 AI Trade Big Picture
06:18 Hyperscaler CapEx Wave
10:24 Who Pays For AI
11:16 AI Beyond Consumers
16:58 Valuations And Risk
22:40 Memory Stocks Spotlight
26:13 Is Memory
212. Stocks We Haven’t Bought…Yet
We're opening up our watchlists! From luxury supercars to social media platforms, we break down why we haven't bought Ferrari, Reddit, or Rocket Lab…yet.
03:48 Watchlist Episode Setup
06:14 Ferrari Luxury Thesis
11:27 Lululemon Value Debate
19:15 Options Lessons Puts Calls
23:44 BBB Foods Watchlist Pick
29:29 Rocket Lab Valuation Debate
34:16 Options Strategy For Volatility
35:32 TransMedi
211. June 2026 Mailbag
In this June 2026 Mailbag, Jason and Jeff dive into OZEM, the world’s first actively managed GLP-1 weight-loss drug ETF, debating whether its steep fees are worth outsourcing your portfolio research. They also explore how generative AI is shifting white-collar labor, detail exactly how they would allocate a surprise $250,000 windfall, and answer a critical valuation question on why pre-revenue pla
210. Investing Unscripted, Unscripted
What if AI plateaus and remains structurally mediocre? Jason and Jeff challenge Wall Street's unstoppable narrative, talk portfolio rebalancing, and dissect the line between investing skill and pure luck.
00:29 Mailbag Callout
01:57 Episode Setup AI Doubts
04:25 Will AI Stay Mid
08:43 LLMs Limits Learning
12:36 AI In Investing Workflow
16:08 Spending Hype Reality
19:17 Deck Building First
First Fridays 31. June 2026
Did the SpaceX IPO live up to the hype? We’re breaking down why Elon Musk's space venture might be a trap for retail investors, plus deep dives into The Trade Desk's struggles, QuantumScape's data center pivot, and the AI threat to Intuit.
00:41 Show Intro And Agenda
04:20 Market Vibes Check In
05:35 Dividend Portfolio Surprise
10:09 Chat Soccer Detour
12:37 Extra Time Debate
18:34 SpaceX IP
209. Our Best Stock Ideas Right Now
In this episode, Jason and Jeff open up their "Savvy Trader" portfolio to reveal their four most recent stock purchases. They break down the evolving credit risks and e-commerce dominance of MercadoLibre, explain why ServiceNow's early AI integration makes it largely insulated from software disruption, and debate the merits of buying entry-level homebuilders like Meritage Homes during a cyclical l
208. The 15 Investing Terms You Need to Know
Jason and Jeff break down 15 essential investing terms that are constantly thrown around in the financial world. The duo translates Wall Street jargon into plain English, explaining the difference between GAAP and non-GAAP metrics, why enterprise value is often more important than market cap, and how to efficiently navigate SEC filings such as 10-Ks and S-1s. Whether you're trying to figure out if
207. Missing Fads with Brian Stoffel
In this episode of Investing Unscripted, Jason and Jeff are joined by longtime friend and investing educator Brian Stoffel. Brian shares his fascinating journey from a middle school writing teacher in Washington, D.C., to discovering Warren Buffett in Costa Rica, and eventually becoming a prominent writer for The Motley Fool. The trio dives deep into Brian's investing evolution—blending the extrem
206. May 2026 Mailbag
In the May 2026 Mailbag, Jason and Jeff tackle a series of compelling listener questions, starting with a deep dive into whether "vibe coding" and agentic AI are truly an existential threat to major SaaS companies like Salesforce and Snowflake. The duo also untangles the complicated corporate web of Brookfield Infrastructure (BIPC vs. BIP), exploring why the company might finally be moving to ditc
205. The 3 Questions Every Investor Should Answer
Jason and Jeff strip investing down to its core framework. They break down the "Why, What, and How" that every investor needs to answer to build a sustainable and successful portfolio. The duo explores how to align your asset allocation with your time horizon, debates the merits of "set it and forget it" target-date funds versus active stock picking, and highlights the hidden drag of high mutual f
204. Stocks for the AI Hater
In this episode, Jason and Jeff take a much-needed break from the relentless AI hype cycle to focus on "boring" but beautiful businesses. The duo builds an "Anti-AI" portfolio of companies that are positioned to thrive regardless of whether the tech boom goes bust. They break down the pricing power and operational efficiency of retail giants Costco and TJX Companies, unpack the ongoing roll-up str
First Fridays 30. May 2026
Join Jason and Jeff for the May First Fridays stream as they review the Portfolio Contest leaderboard, debate Duolingo's AI risks, and unpack the Starbucks turnaround under Brian Niccol.
02:01 Gemini Promo Video Fails
04:11 Portfolio Contest Update
09:44 Late Entries Penalty Tab
11:38 Ratings Reviews Push
13:46 Title Month Mixup
17:21 Duolingo Earnings Debate
22:43 AI Efficiency Threats
24:56 SaaS
203. April 2026 Mailbag
In this April 2026 Mailbag, Jason and Jeff tackle a massive listener question about portfolio concentration in retirement, debating the merits of holding onto tiny "VC-minded" positions like Warby Parker and QuantumScape versus consolidating into bigger winners. They also provide an update on the "boring" but beautiful Brookfield Infrastructure, exploring its pivot toward modern assets like semico
202. I (Still) Gotta Think About That One
In this episode of Investing Unscripted, Jason and Jeff revive a fan-favorite format: letting AI randomly select stocks from their personal portfolios for a rapid-fire review. For each chosen stock, the hosts must explain what the company does, build the best "bear case" against it, and declare whether they would buy it at today's prices. Jeff tackles the tech heavyweights, defending Nvidia agains
201. SpaceX’s $2 Trillion IPO and the Space Economy with Lou Whiteman
In this episode, Jason and Jeff bring on Motley Fool analyst Lou Whiteman for a masterclass on investing in the space industry. They break down the hype surrounding SpaceX's potential $2 trillion IPO and debate how much of that valuation is actually justified by its core businesses (Launch, Starlink, Starshield, xAI). Lou outlines his five distinct buckets of the space economy—ranging from launch
First Fridays 29. April 2026
In the April 2026 First Friday livestream, Jason and Jeff break down the current "market vibes," debating whether the market's resilience is masking a hair-trigger sensitivity to AI hype and PR spin. They announce the Q1 winner of the listener portfolio contest—congratulations to Discord member Vinny G!—and review the progress of their own 2026 picks. The duo dives deep into the executive turnover
200. 200 Stocks for 200 Episodes
In this milestone 200th episode of Investing Unscripted (yes, the last episode was an April Fool's joke!), we tackle a question that plagues many investors: how many individual stocks should you actually own? We debate the merits of a heavily concentrated portfolio versus broad diversification, especially during periods of market uncertainty. We also unpack the psychological dangers of blindly add
199. Knowing When to End a Good Thing
In this monumental episode of Investing Unscripted, Jason and Jeff announce that they are bringing the podcast to an end—just one episode shy of their 200th milestone. This short reflection episode looks back on past guests, topics, and what had the biggest impact.
01:00 Why the Show Is Ending
02:28 Retrospective and Keeping It Light
03:28 Favorite Guests and Surprise Connections
05:40 Jim Gillies
198. March 2026 Mailbag
In this month's mailbag, Jason and Jeff tackle a wide array of listener questions, ranging from the tax efficiency of holding dividend stocks in taxable accounts to the potential risks of the NASDAQ fast-tracking private giants like SpaceX into its indexes. They also weigh in on newlyweds combining finances and choosing between brokerages like Schwab and Fidelity. Finally, the duo breaks down Walk
197. Investing Through Chaos
Jason and Jeff tackle the current wave of market chaos—from oil price spikes and tariffs to the "AI is killing software" narrative. They dive into how they're personally navigating the noise, sharing recent portfolio additions such as Phinia (PHIN) and Clearway Energy that appear insulated from the macroeconomic volatility. They also unpack the AI software scare with deep dives into Toast, Service
First Fridays 28. March 2026
In this slightly belated "First Fridays" live stream, we dive into the current "vibes" of the stock market, check in on the 2026 Portfolio Contest, debate the long-term viability of MercadoLibre's lending business, and talk about Greg Abel’s first annual letter to Berkshire Hathaway shareholders.
01:53 Index Funds Running Joke
04:08 Market Vibes Check
06:28 K Shaped Economy Talk
12:09 Portfolio Co
196. Chit Chat Stocks, Unscripted
Ryan Henderson and Brett Schafer from the Chit Chat Stocks podcast join us for a special unscripted episode to track their evolution from college-aged podcasters running a family-and-friends fund to seasoned individual investors. We discuss learning the harsh realities of valuation during the 2022 bear market, the dangers of "analysis paralysis," and whether mastering your own psychology is more i
195. Stocks Unscripted, March 2026
Jason and Jeff go completely off-script to discuss what they are actually doing in their portfolios right now. Jeff breaks down why he bought more Datadog on a recent dip and his strategy for adding to Enphase, while Jason explains how he is using options (specifically selling puts) to generate income while waiting for better valuations. Plus, they analyze the risk vs. reward of QuantumScape, deba
194. February 2026 Mailbag
We open the February 2026 mailbag to answer your questions on how to handle the psychological toll of the "SaaS apocalypse" and when it actually makes sense to buy the dip. We also discuss how to assess relative risk in a portfolio, dive deep into the differences between SentinelOne and CrowdStrike (including thoughts on stock-based compensation), and reveal the "falling knife" software stocks we
193. Nothing Works All the Time
We discuss the recent market dislocation where SaaS stocks are crashing while the broader market hits all-time highs. We break down the three main fears driving the sell-off and debate which companies—like Adobe and Salesforce—are actually at risk. Finally, we share how we are handling the volatility, with Jeff buying more Shopify and Jason using a "barbell strategy" to stay sane.
02:27 Housekeepi
192. Emily Flippen, Investing Survivor
We are joined by The Motley Fool's Emily Flippen to discuss her "Survivor" origins and why she believes empathy is the most underrated skill for investors. We also debate the difference between a "fad" and a "trend" in consumer goods (using Crocs vs. On Holding as the prime example), and Emily gives her honest take on "AI burnout."
00:32 Introducing Special Guest Emily Flippant
01:55 Emily's Journ
191. Stocks We’re Excited About
We break down the six stocks we are most excited to watch this earnings season (and why "excited" doesn't necessarily mean we're buying). Jeff discusses Lemonade's path to 2026 profitability and why Rocket Lab is entering a critical "prove it" phase with its Neutron rocket, while Jason makes the case for Canadian Solar trading at half its book value and explains why SentinelOne offers a better ris
190. January 2026 Mailbag
We open the mailbag to answer your questions on whether Life Insurance Retirement Plans (LIRPs) are a scam, if spending millions on a Super Bowl commercial is ever a good idea (looking at you, CrowdStrike), and if equal-weight S&P 500 ETFs are the best way to hedge against a tech crash. Plus, we debate the future of the energy sector, discuss the power of "stock cannibals" like Adobe and PayPal, a
189. The 3 Financial Docs You Need to Know
In this special "toolbox" episode, Jason and Jeff strip away the jargon to teach you how to actually read the three most important documents in investing: the Income Statement, the Balance Sheet, and the Statement of Cash Flows. Using Nvidia’s recent Q3 earnings report as a real-world case study, the hosts walk through these important financial statements line by line.
01:33 The Importance of Fina
188. How to Use AI to Research Stocks (w/ Brian Feroldi)
Brian Feroldi, founder of Long-Term Mindset, joins us to explain how he uses AI tools like Gemini and NotebookLM to supercharge his stock research. We discuss the difference between a "price bubble" and an "earnings bubble" (and which one Nvidia might be in), share specific prompting strategies to stop AI from hallucinating, and run a live demo analyzing Green Brick Partners from scratch.
00:55 I
187. What is Your Investing Echo Chamber?
We kick off 2026 by auditing our own 2025 portfolio performance, where Jeff confesses to trailing the market by 3% and Jason explains why his 401(k) only returned 9% (and why he is perfectly okay with that). We also discuss why Jason's "boring" dividend portfolio outperformed the AI-driven market, and explore the dangers of "investing echo chambers".
01:32 Reflecting on 2025: Portfolio Performance
First Fridays 27. January 2026
In our first live stream of 2026, we do a deep dive into QuantumScape's latest partnerships and what the "solid-state" future looks like for EVs. We also break down the winners (and massive losers) of our 2025 portfolio contest, reveal why a 4th grader is betting on Kontoor Brands, and share our own high-conviction picks for the year ahead, including Alphabet, Rocket Lab, and The Trade Desk.
00:50
186. December 2025 Mailbag
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 ri
185. The 2026 Portfolio Contest & 2025 Market Review
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 Unscripte
184. Bill Brewster: From "Junk" to Quality
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 inve
183. Reckless Predictions 2026
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 t
182. Earnings Season Reset
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 Ind
181. November 2025 Mailbag
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 an
180. Stocks We Might Be Wrong About
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
179. The AI Bubble & the State of the Market with John Rotonti
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
First Fridays 25. November 2025
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 S
178. What If the AI Bubble Never Pops?
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 cha
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 Underst
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 Distribu
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 Reti
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
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
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: Mo
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
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 Inv
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
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
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,
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 Hirin
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 t
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 Bankr
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 Unit
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
2
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 Financ
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
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 F
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
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