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 against the threat of purpose-built AI chips, exploring how "vibe coding" could eat away at Shopify's margins, and evaluating CrowdStrike's post-outage reality. Meanwhile, Jason embraces his love for "boring" businesses, breaking down the massive cash flows of pipeline operator Enterprise Products Partners, the underwriting discipline of internet-bank Axos Financial, and the cost-of-capital risks for Clearway Energy.

03:13 Spotify Ratings Challenge

04:24 Pick 1 CrowdStrike Bear Case

08:00 Quantum and AI Disruption Talk

14:21 Pick 2 Enterprise Products Explained

20:13 Would You Buy It Valuation Talk

25:09 Pick 3 Nvidia Bear Case Setup

27:47 Nvidia Valuation Debate

30:41 Nvidia Bear Case Shifts

34:40 Axos Financial Overview

36:19 Axos Bank Risks

40:48 Shopify Bear Thesis

43:01 Shopify Platform Risks

51:33 Clearway Energy Yieldco

Companies mentioned: AX, CRWD, CWEN, EPD, NVDA, SHOP

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

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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 infrastructure and connectivity to Earth observation and defense tech—and shares why companies like Rocket Lab and Redwire are catching his eye. Plus, Lou reveals the sub-sectors he’s actively avoiding and explains why traditional defense contractors like Lockheed Martin might currently be the most compelling way to play the space boom.

03:08 SpaceX Business Breakdown

05:55 Space Market Tailwinds

08:49 Why Launch Demand Surges

11:20 New Space Use Cases

14:48 SpaceX IPO Valuation Math

19:14 IPO Pricing and Aftermarket

23:11 What Success Looks Like

23:36 Capital Needs Debate

24:40 Starship Risks Ahead

25:46 Space Investing Ad Break

27:13 Mapping Space Sectors

30:59 Where Space Gets Risky

36:20 Top Picks To Research

40:16 Consolidation And Legacy Primes

41:28 Avoiding Hype Traps

Companies mentioned: AMZN, ASTS, BKSY, GSAT, KTOS, LDOS, LHX, LMT, LUNR, META, NOC, PL, RDW, RKLB, TMUS, TSLA, V, VZ

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 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 at The Trade Desk, the slow-moving turnaround at PayPal, and whether Kinsale Capital is simply a cyclical price taker or a highly efficient operator. Plus, Jason reveals his new Roth 401 (k) strategy, and Jeff vehemently defends his "lazy" personal finance choices.

03:01 Market Vibes Resilience

06:26 AI Hype And Volatility

09:54 Cybersecurity Rumor Debate

12:19 Cringey AI Promo Clip

14:35 Portfolio Contest Rules

16:31 Q1 Winner And Charity

21:09 Patreon Standings And Long Game

24:22 Portfolio Reflections And Trade Desk

28:00 Board Sale Speculation

30:49 Backing Jeff Green

32:19 Position Sizing Rules

32:45 Founder vs Operator Debate

37:11 Kinsale Competition Pressure

38:40 Kinsale Underwriting Edge

42:23 Specialty Insurance Tailwinds

45:30 PayPal Value Trap Risk

52:15 Roth 401k Moves

55:20 Roth Optionality Strategy

57:46 Favorite Dividend Picks

Companies mentioned: BIP, BIPC, BORR, CTRE, EPR, GOOG, GOOGL, KNSL, MA, MELI, NOW, PLSDF, PLTR, PYPL, RBRK, RKLB, SECYF, TTD

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 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 adding to your winners and why it's crucial to adapt your investing strategy as your personal financial goals change over time.

03:13 Spotify Ratings Challenge

05:04 How Many Stocks

06:30 Concentration vs Diversification

09:06 Is This More Uncertain

14:11 Should Uncertainty Change Holdings

15:48 Jason Reframes Portfolio Size

21:25 Portfolio Size Debate

23:55 Conviction Versus Bias

26:58 Averaging Up Winners

28:42 Kinsale Capital Case

32:59 Watchlist FOMO Trap

34:48 Concentration And Time

40:05 Automate When Anxious

43:15 Humility And Evolving

Companies mentioned: AAPL, AMZN, CDNS, CRWD, DFH, GE, JRVR, KNSL, MSFT, NVDA, S, SNPS, TOST, TTD

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 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 and Early Episodes

06:37 First Friday Livestream Memories

08:06 Podcast Community and Crossovers

09:25 Behind the Scenes Editing and Filler Words

10:21 How Podcasting Shaped Investing Views

11:14 Podcast Shapes Investing

13:40 Investor Identity Distilled

16:31 Talking Through Ideas

18:02 Favorite Episode Formats

20:46 Running Toward Fires

26:54 Wrap Up And Thanks

Companies mentioned: BAM, BN, CRWD, MSFT, S

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 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 Walker & Dunlop's recent post-earnings stock drop and debates where to safely park your cash after hitting a major savings goal.

03:14 Taxable Dividend Strategy

11:54 Nasdaq Index Rule Changes

20:27 Dividend Bucket Rethink

25:57 Dividend Growth Compounding

26:38 Mastercard Low-Yield Lesson

27:42 Instagram Mailbag Setup

28:50 Consolidating Brokerage Accounts

31:47 Schwab Versus Fidelity

34:22 Combining Finances After Marriage

35:45 Money Talks and Guardrails

40:12 Walker and Dunlop Earnings

42:43 Investing After Saving Goal

45:43 Risk Spectrum and Time Horizon

Companies mentioned: AAPL, BOC, CRM, MA, META, MTH, QQQ, SCHW, WD

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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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, ServiceNow, and Procore, and Jason issues a warning about the hidden risks lurking in the booming private credit market.

01:19 AI Tariffs Oil Backdrop

03:38 Housekeeping Mailbag Plug

04:42 Staying the Course

07:18 Markets Recover Before Clarity

12:04 Stock Pick PHIN

19:01 Renewables Reality Check

20:54 Clearway Energy Buy

24:50 Energy Security and Oil Flows

26:36 Oil And Geopolitics

27:29 Krugman On Price Spikes

30:33 Toast Stock Breakdown

35:44 ServiceNow AI Strategy

37:35 Procore Construction Software

42:17 Private Credit Risks

47:38 Staying Invested In Chaos

49:19 Process Over Headlines

Companies mentioned: BAM, BEP, BX, CPNG, CWEN, DASH, ENPH, FOUR, KKR, NOW, ORCL, OWL, PCOR, PHIN, PYPL, SHOP, SQ, TOST

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 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 Contest Update

23:46 QuantumScape Buy Explained

27:59 Donut Labs Battery Debate

30:57 Battery Value Metrics

31:34 Kids Pick Stocks

32:58 Market Moves This Week

36:56 MercadoLibre Discount Debate

44:42 Options Premiums Q&A

47:13 Using Claude for Research

50:27 Greg Abel Letter Take

55:30 Berkshire After Buffett

Companies mentioned: AAPL, AMZN, AXP, BRK.B, ENR, KNSL, KO, MCO, MELI, QS, RKLB, TM

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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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 important than understanding financial mechanics. We also debate the merits of starter positions, explore Ryan's strict "three-year holding rule," and reveal the current watchlist stocks they are waiting to buy—along with the ones they kick themselves for missing.

02:09 Meet Chit Chat Stocks

04:30 Origin Story 

08:56 Early Podcast Lessons

10:26 Valuation Reality Check

12:29 Mistakes Shape Process

14:09 Bear Market Incentives

18:19 Investing In Public

21:30 Overthinking Valuation

24:07 Match Vs Spotify

28:18 Costco One Share Rule

29:18 Owning Through Drawdowns

29:58 Fund Pressure vs Flexibility

32:26 Starter Positions Debate

34:07 Psychology Beats Fundamentals

38:03 Know Your Investing Style

39:57 When Stocks Go Nowhere

44:15 Rules to Avoid Selling

47:35 Build a Personal Framework

51:52 Watchlist Valuation Picks

55:40 Where to Find Their Work

59:14 Final Wrap and Signoff

Companies mentioned: ADYEY, AMZN, AXP, CAVA, COST, CPNG, CSU, HIMS, IBKR, MELI, MNDY, MRNA, MTCH, PYPL, RKLB, ROKU, SPOT, TSLA

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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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, debate the new CEO at PayPal, and play a game of "buy or get off the pot" that ends with a live stock purchase.

00:53 Unscripted Earnings Season

04:34 Jeff Did a Thing

06:43 Why Buy Datadog Now

09:14 AI Risks for SaaS

11:34 Selling Puts Strategy

17:06 Market Psychology Chegg

19:41 Market Efficiency Long Term

23:15 Enphase DCA Dilemma

25:46 How to Time Adds

28:08 Quarterly Info Is Noise

28:30 Enphase Through the Cycle

29:49 QuantumScape Solid State Promise

31:50 Timing the Entry Price

33:53 Asymmetric Upside vs Risk

36:24 PayPal CEO Shakeup

38:59 Reframing the PayPal Thesis

44:48 Small Positions to Fix

46:36 Airbnb Growth Proof Points

Companies mentioned: ABNB, ADBE, CHGG, DDOG, ENPH, PYPL, QS, UPST

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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