Investing Unscripted

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 quickly "agentic AI" will disrupt e-commerce habits for companies like Amazon and Airbnb, and dissect why Zoom's shrinking enterprise base makes the stock virtually uninvestable despite its free cash flow.

01:56 Wrigley Field Promo Clip

02:52 Chat Greetings and Baseball Talk

06:30 Market Vibes Everything Is Fraud

08:04 Incentives and Man City Case

12:39 Old Wall Street Fraud History

17:29 CareTrust REIT UK Expansion

18:13 Why CareTrust Has Won

23:31 UK Healthcare and Capital Allocation

24:27 Selling CTRE and REIT Rate Sensitivity

26:25 Rates Hit REIT Valuations

27:14 Realty Income vs Diversifying

29:30 Why O Acts Like Bonds

31:31 CareTrust Growth Angle

32:45 REITs vs Bonds and T Bills

34:06 Cost of Capital Explained

37:30 Dividend Growth Comparison

38:39 Agentic AI Shopping Threat

45:58 Ads Trust and New Models

49:31 Zoom Stock Long Term View

54:52 Portfolio Contest and UNICEF

Companies mentioned: ABNB, AMZN, BKNG, CTRE, O, RMD, TJX, ZM 

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

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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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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 spousal IRAs. To close the episode, the duo reviews listener submissions for a "5 Stocks for 10 Years" portfolio, ultimately drafting their own hypothetical decades-long portfolios from the audience's picks.

02:03 Patreon Shoutout

03:07 Rapid Fire Housekeeping

04:15 Mailbag Begins

04:58 Double Down Winners

16:50 TJX Valuation Debate

24:42 ResMed Growth Outlook

28:20 When to Take Profits

29:56 When Valuation Matters

31:50 Couples Managing IRAs

34:49 Risk Across Net Worth

38:18 Spreadsheets And Aggregation

43:06 Five Stocks For 10 Years

44:19 Discord Picks Breakdown

48:23 Picking Five From The List

Companies mentioned: AER, AMZN, ASML, AXON, BAM, BN, BRK.B, COST, CVX, ISRG, LLY, LMND, MA, MEDP, META, RBRK, RMD, SBUX, TBBB, TJX, TSM

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!

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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 high-growth portfolios actually benefit from defensive "ballast" stocks, and break down how position sizing can keep single-stock blowups from derailing your long-term compounding.  

00:27 Football and Fandom

02:04 College Football Detour

02:44 Back to Investing Talk

03:15 Savvy Trader Concept

06:39 How the Portfolio Works

10:06 Biggest Winner CrowdStrike

14:24 Why Hold CrowdStrike

20:02 Risks and Disruption Fears

23:56 Pivot to Biggest Loser

24:54 Position Size Breakdown

25:39 Lessons From Conviction

29:51 Why Keep Holding

32:29 Sunk Cost And Catalysts

37:24 Guidance Trend Reality Check

38:57 New Stock Ideas Debate

40:04 Ballast Stocks Or Index

45:58 AI Picks And Shovels

50:30 Final Picks And Wrap Up

Companies mentioned: AAPL, AMZN, BRK.B, CRWD, FPS, FTNT, GOOG, GOOGL, MELI, MRNA, MRVL, PANW, TJX, TTD, TXN, VOO, ZS  

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!

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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 and housing tailwinds powering Green Brick Partners, the skilled nursing consolidation runway at CareTrust REIT, and debate whether to round out the portfolio with steady cash-flow giant ASML or speculative battery play QuantumScape. 

00:46 Redux Setup Five Stocks

03:09 Housekeeping Speed Run

04:37 Old Picks Performance Review

07:54 Swaps and Digital Realty

10:03 MercadoLibre Surprise Factor

15:02 New 10 Year Framework

19:12 MercadoLibre Still Core

20:32 BBB Foods Growth Thesis

25:01 Store Growth Debate

27:12 Housing Market Weirdness

29:55 Green Brick Pick

31:55 Why Not Earlier

34:20 CareTrust REIT Thesis

39:14 Valuation And Run Up

42:07 ASML Or QuantumScape

47:46 Portfolio Rules Fight

49:42 Listener Picks Wrap Up

Companies mentioned: ASML, BN, BOC, COST, CTRE, DLR, FTNT, GOOG, GOOGL, GRBK, HD, MELI, NVDA, O, ORLY, QS, RHP, RKLB, TBBB, TSM 

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!

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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 "Rule Breakers" to "Rule Makers". Plus, Jason and Jeff expand their ongoing stock-picking contest by pitching new additions to their portfolios. 

00:43 Final Stock Market Book

02:53 How Rule Breaker Began

05:32 Yahoo Lesson on Valuation

08:36 Rule Breakers vs Goliaths

09:59 Values and Stock Picking

15:16 Overvalued Can Be a Signal

21:24 Market Outlook and Optimism

27:51 Sponsor Break and Tools

29:39 AI Selloff and Long View

34:24 Bubbles and Staying Invested

39:18 Rule Breakers Framework

39:43 Nvidia Still Breaking Rules

44:34 AI To Robotics Next

44:43 Netflix Rule Maker Era

47:44 Giving Appreciated Stock

49:45 Booking Versus AI Threat

51:09 Platforms Network Effects

56:36 Smattering Six Results

01:01:56 Power Law And Snap Test

01:07:48 Conscious Capitalism Closing

Companies mentioned: ABNB, AMZN, AX, BKNG, CPNG, NFLX, NVDA, PCOR, PTON, QXO, RKLB, SBUX, SHOP, TBBB, TJX, TMDX, TSLA, WRBY

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!

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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 cash flow generation. The duo also checks in on the portfolio contest, explores the nuances of trimming big winners like ASML and Datadog to rebalance, and evaluates QuantumScape's pivot to manufacturing partnerships with its new Honda deal. 

00:32 First Friday Roll Call

02:57 How We Promote Stuff

05:41 Market Vibes Check

09:58 AI Supercycle Debate

13:13 DocuSign Breakdown

20:41 SavvyTrader and Community

23:05 Why TJX Is a Buy

28:25 New Stock Ideas PRCT

29:20 Medical Devices Watchlist

31:24 ResMed and GLP-1 Impact

32:35 Surgical Robots Competition

36:07 Baseball Cards and Value

41:06 Smattering Contest Update

43:18 New Picks Rocket Lab

47:54 Listener Portfolio Standings

51:53 Selling Stock Regrets

57:03 Wrap Up and Disclosures

Companies mentioned: AAPL, AFG, APH, ASML, AVGO, BOC, CLF, COST, CPNG, DAVA, DDOG, DOCU, IONQ, ISRG, KNSL, LEN, LMND, MDT, MELI, MRNA, MTH, NNI, NOW, NVDA, PCOR, PRCT, PYPL, QS, QXO, RHP, RKLB, RMD, SOUN, TJX, TTD, TWLO, WINA

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

*****************************************

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

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Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!

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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 purchases made during the recording: Jeff's starter position in Brad Jacobs' roll-up vehicle QXO and Jason's opportunistic buy of The TJX Companies. 

00:59 Welcome to Investing Unscripted

03:25 Portfolio Basics Setup

04:47 Why Portfolios Matter

08:32 Diversification and Allocation

10:16 Risk Factors Explained

15:29 Beginner Diversification Tips

17:15 Cash and Time Horizon

22:24 Big Picture Diversification

24:27 Mindset and Risk Tolerance

27:55 Simple Starter Portfolio

28:19 Building a Stock Base

29:17 Know Your Investor Style

31:07 Buy Market or Companies

33:22 Index Funds First

35:17 Automating Early Investing

37:57 DCA vs Loose Cadence

39:35 Avoid Cash Timing Traps

41:58 Rollover Deployment System

45:35 Opportunistic Buys and Trims

46:52 New Positions TJX and QXO

49:24 QXO Strategy and Competition

Companies mentioned: ASML, DDOG, ENPH, FSLR, HD, LOW, NVDA, QS, QXO, SBUX, TJX, TSLA, TSM

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

*****************************************

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

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Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!

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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 Honda and Volkswagen. 

04:24 Trade Desk Conviction Lessons

14:01 Valuation Regret And CEO Signals

18:52 Portfolio Overlap And Bias

22:57 Public Disagreements And Recent Buys

23:57 Valuation Debate Winmark

25:03 Rocket Lab Regret

26:02 Building Positions Slowly

27:51 Selling Rocket Lab Puts

30:02 Feeling Stuck Investing

32:56 Do Nothing Discipline

35:31 QuantumScape Honda Red Flag

36:18 QuantumScape Licensing Model

39:55 Verticals Mission Creep

44:50 Position Sizing Fun Bets

Companies mentioned: AMZN, APH, GLW, GOOG, GOOGL, HMC, KNSL, META, MRNA, NFLX, NNI, NU, QS, RKLB, SE, SOUN, TTD, VWAGY, WINA

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

*****************************************

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

*****************************************

Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!

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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 Check

22:12 Datadog Vs SoFi Trimming

25:47 Portfolio Concentration Mindset

27:33 Trimming Winners Wisely

28:32 Position Size vs Age

30:28 Rebalancing Asset Allocation

32:59 Framework Over Emotion

33:26 Lessons From 2022

36:01 Dry Powder Strategy

38:55 Cash Psychology Differences

44:07 Bull Market Mistakes

47:44 Regret Minimization Framework

49:38 When Everyone Asks

Companies mentioned: CRWD, CSCO, DDOG, MSFT, NVDA, SOFI, TTD, ZM

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

*****************************************

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

*****************************************

Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!

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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 effects are more valuable than ever for venture capitalists navigating an AI-native world.

01:36 Why AI Changes VC

03:55 VC Concentration Shift

06:05 Cheaper Startup Building

08:42 More Pitches to Sift

11:24 Using AI for Diligence

14:28 Human Edge and Alpha

20:41 Culture and Expertise Future

27:38 Apprenticeships and Jobs

32:06 AI Jobs History

34:19 Venture Hit Rates

37:52 Defensibility Network Effects

40:07 VC Consolidation Debate

43:14 Founder Leverage Value Add

46:20 Portfolio Support Metrics

49:36 AI Costs Falling Fast

54:47 Next Trillion Giants

57:24 Where To Find Joe

Companies mentioned: AAPL, EBAY, GOOG, GOOGL, META, UBER

Find Joe at https://www.seaplaneventures.com/

Find where to listen & subscribe,  portfolio contests, and contact information at https://investingunscripted.com

*****************************************

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

*****************************************

Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!

Learn more about your ad choices. Visit megaphone.fm/adchoices