Investing Unscripted

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 semiconductor fabs and its impressive 17-year streak of dividend increases. Later, they unpack the nuances of the private credit scare—and why major banks might have more exposure than investors realize. 
00:35 Spotify Review Challenge
04:43 Retirement Portfolio Breakdown
06:20 Concentration vs Diversification
10:54 Options Income Bucket
12:49 Trim Small Positions
17:58 Enjoy Investing vs Indexing
19:57 Taxes and Ezra Klein Plug
20:55 Brookfield Infrastructure Update
22:52 Modern Infrastructure Shift
23:21 Intel Ohio Fab Deal
23:47 Energy Pivot Opportunities
24:35 Leadership Sam Pollock
26:38 Market Sensitivity Brookfield
28:35 Dividend Yield Return Math
30:45 Private Credit Reality Check
37:06 Risk Discounting Framework
38:35 AI Prompts Investing Workflow
40:41 AI Bias And Transcript Shortcuts
46:52 Comment Of The Month Wrap
Companies mentioned: ADBE, AXON, BAM, BIP, BIPC, INTC, JPM, NVDA, OWL, QS, ROKU, SOFI, WFC, WRBY, ZM
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
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 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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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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Subscribe to our portfolio on Savvy Trader

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
*****************************************
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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Subscribe to our portfolio on Savvy Trader

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

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