Investing Unscripted

In this episode, Jason and Jeff welcome semiconductor analyst Jose Najarro to unpack the current state of the AI and chip cycle. Jose explains why he views AI as an ongoing storm made of distinct waves—from consumer chatbots and coding tools to autonomous agents—and introduces "token economics" as the ultimate gauge for whether we are in an AI bubble. The trio explores why severe supply bottleneck...

In this October 2026 Mailbag, Jason and Jeff tackle listener questions on portfolio management, sector consolidation, and the psychology of holding laggards while the broader market sits near all-time highs. They evaluate whether Zeta Global's business intelligence tools pose a threat to TJX Companies' off-price retail moat, debate how to narrow down starter positions across housing and renewable...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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 Reality...

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...

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...

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...

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). 0...

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 Rates La...

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 Microsoft Copi...

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...

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 A Commo...

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 TransMedics Missi...

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...

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 Princi...

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 IPO Reac...