Investing Unscripted

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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 In...