PODCAST · business
Investing Unscripted
by Jason Hall and Jeff Santoro
Welcome to Investing Unscripted, where we ask the hard questions about investing, the stock market, and personal finance. We don't have THE answers, we only have OUR answers.
Episodes
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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...
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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...
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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,...
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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…
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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...
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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...
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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...
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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...
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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…
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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...
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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…
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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…
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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...
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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...
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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...
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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...
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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…
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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...
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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...
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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…
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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...
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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...
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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...
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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...
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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...
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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…
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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...
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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...
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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…
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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...
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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...
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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...
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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,...
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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...
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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,...
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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...
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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…
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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…
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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....
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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…
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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...
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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…
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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...
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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...
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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...
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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...
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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,...
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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…
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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…
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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...
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Frequently Asked Questions
How many episodes does Investing Unscripted have?
Investing Unscripted currently has 259 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Investing Unscripted about?
Welcome to Investing Unscripted, where we ask the hard questions about investing, the stock market, and personal finance. We don't have THE answers, we only have OUR answers.
How often does Investing Unscripted release new episodes?
Investing Unscripted publishes regularly with 259 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Investing Unscripted?
You can listen to Investing Unscripted on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Investing Unscripted?
Investing Unscripted is created and hosted by Jason Hall and Jeff Santoro.
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