Episoder
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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 Mission And Doubts
42:01 Reddit Business Model Fears
47:48 AI Data And Growth Metrics
51:22 Pick One Stock Today
Companies mentioned: ISRG, LULU, MTH, RACE, RDDT, RKLB, TBBB, TMDX, TOST
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 (https://open.spotify.com/show/4SBtOWGEOmD9pmltgIXO8r?si=6213b1574ff04bce)
Apple Podcasts (https://podcasts.apple.com/us/podcast/chit-chat-stocks/id1437766060
YouTube https://www.youtube.com/@ChitChatStocks
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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 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 player QuantumScape still commands a multi-billion dollar market cap.
03:36 Baseball Trash Talk
04:21 Mailbag GLP-1 ETF OZEM
08:04 Active ETF Pros and Cons
15:39 AI Disruption Question
16:37 SaaS and AI Native Future
20:58 AI in Construction and Trades
22:33 AI Productivity vs Disruption
24:07 AI Makes Us Dumber
27:19 Solid Power Overview
29:20 Battery Tech Commoditization
33:43 Windfall Money Plan
39:22 Spending vs Investing Choices
42:07 QuantumScape Market Cap
Companies mentioned: ABNB, BMW, DAVA, F, GOOG, GOOGL, HIMS, KNSL, LEN, LLY, MELI, META, NOW, NVDA, NVO, PFE, PYPL, QS, RKLB, SLDP, 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. Use code Unscripted2026 for 30% off a one-year subscription!
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Manglende episoder?
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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 Principles
22:55 AI Adoption And Growth Math
26:34 Rebalancing In AI Mania
27:23 Trimming Winners Hedging
33:53 Allocation Decisions Retirement
38:08 Have We Just Been Lucky
45:22 Gemini Concentration Fail
Companies mentioned: ADBE, AVGO, CRM, DDOG, KNSL, MELI, NVDA
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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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 Reactions
20:52 Valuation And Competition Risks
26:53 One Year Price Bet Setup
27:32 SpaceX Valuation Debate
28:04 Livestream Banter Fixes
30:04 Portfolio Contest Update
33:40 Lessons From Bad Picks
39:55 Trade Desk Reality Check
47:50 Intuit Versus Adobe
51:15 Oracle AI Risk Talk
54:33 QuantumScape Milestones
58:17 SpaceX IPO Trap Wrap
Companies mentioned: ADBE, GLW, GOOG, INTU, KNSL, LEN, MELI, META, MSFT, NOW, NVDA, ORCL, PYPL, QS, RKLB, TSLA, TSM, 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. Use code Unscripted2026 for 30% off a one-year subscription!
Learn more about your ad choices. Visit megaphone.fm/adchoices -
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 lull. Plus, Jeff pitches point-of-sale platform Toast as it impressively flips into profitability, and the duo speed-runs through a few recent personal portfolio additions, including Procore, Kinsale Capital, and QXO.
01:56 Savvy Trader Pricing Code
03:27 Episode Format Explained
05:47 Jason Picks MercadoLibre
11:07 MELI Risks And Evolution
18:56 Jeff Picks ServiceNow
23:59 AI Disruption Debate
27:00 Key Metrics To Watch
28:56 Meritage Bull Case
30:15 Post-Crisis Housing Shift
33:44 Cycle Risks And Timing
37:27 Long-Term Time Horizon
39:15 Cyclical Trading Approach
40:17 Toast Investment Thesis
43:03 Toast Growth And Margins
46:43 Personal Picks Procore
49:46 Jason Adds Kinsale ISRG QXO
Companies mentioned: BATRA, ISRG, KNSL, MELI, MTH, NOW, PCOR, QXO, TOST
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 PatreonSubscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!
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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 your portfolio is properly allocated, want to understand where you sit in the capital stack during a bankruptcy, or just need to know what Charlie Munger really thought about adjusted EBITDA, this episode serves as the perfect reference guide for new and experienced investors alike.
03:24 GAAP vs Non GAAP Basics
05:26 Adjusted Metrics and Context
09:14 Dividends Distributions and Taxes
14:02 SEC Filings Overview
17:06 10-K 10-Q and Using AI
21:29 Proxy Statements and Incentives
22:48 S-1 IPO Filings Explained
25:29 Asset Allocation and Position Sizing
28:31 Bull Bear and Market Corrections
32:08 Board of Directors Role
33:27 Board Fiduciary Duties
35:03 Capital Basics Explained
37:33 Debt vs Equity Stack
41:33 Bond Market Signals
42:15 Dollar Cost Averaging
44:05 Earnings and EPS
48:31 FFO for REITs
51:08 Market Cap vs EV
54:18 Cash Flow vs Free Cash
57:25 Funds Indexes and ETFs
59:37 Sectors vs Industries
01:00:44 Valuation Metrics Overview
Companies mentioned: AAPL, BN, BRK.B, COST, MA, SAVE, TSLA, TXN, V
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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Learn more about your ad choices. Visit megaphone.fm/adchoices -
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 extreme optimism of David Gardner with the anti-fragility of Nassim Taleb—and the painful valuation lessons learned during the 2022 bear market. They also tackle the burning question: "Will AI kill SaaS?", exploring the protective moats of high switching costs, physical world connections, and mission-critical proprietary data.
01:47 Dave Ramsey Story
04:00 From Teacher to Fool
07:25 Buffett Book and Costa Rica
11:56 Berkshire Meeting Takeaways
18:33 Evolving Investing Style
25:30 AI and SaaS Moats
29:15 SaaS Winners in Selloff
29:47 Shopify and Toast Moats
31:56 Physical World Edge
32:54 Proprietary vs Synthetic Data
34:23 Leadership and SaaS Evolution
36:17 Margins TAM and Volume
37:23 Compute Costs and Jevons
43:16 AI Everywhere Anecdotes
45:58 Investor Mindset Rules
47:32 Fads Position Sizing
52:33 Luck Skill and Plugs
56:51 Closing Thanks Disclaimer
Check out Brian’s work: https://www.stockinvestingmentor.com
Companies mentioned: AMZN, AXON, CRM, CRWD, DDD, GOOG, GOOGL, NET, NFLX, NVDA, SHOP, SSYS, 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
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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 ditch its limited partnership structure. Later, they revisit the ongoing struggles at The Trade Desk, debate the concept of "regret minimization" when dealing with massive winners like Rocket Lab and Nvidia, and discuss how to properly balance single-company risk versus overall portfolio volatility.
00:48 West Coast Game Time Rant
02:46 Mailbag and Discord Shoutout
03:56 Ryan Email and Mascot Story
05:47 Baseball Chaos to Investing Lesson
07:47 AI Versus SaaS Debate
11:15 Pricing Models and Moats
22:11 Brookfield BIP Versus BIPC Explained
26:38 Why BIPC Dropped and Simplification
30:25 Discord Questions Teaser
30:52 Trade Desk Doubts
35:54 Valuation Reality Check
38:55 Execution Not Value
40:10 Rocket Lab Concentration
41:55 Regret Minimization
46:55 Singles vs Home Runs
49:22 Vinnie Risk Trimming
50:06 Three Types of Risk
54:50 Money Unplugged Reflections
Companies mentioned: ADBE, ADSK, BAM, BEP, BEPC, BIP, BIPC, CRM, NBIS, NVDA, RKLB, SHOP, SNOW, 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 PatreonSubscribe to our portfolio on Savvy Trader
Learn more about your ad choices. Visit megaphone.fm/adchoices -
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 fund fees. They also tackle the psychological battle of lump-sum investing versus dollar-cost averaging and explain why tracking your overall net worth is far healthier than obsessing over individual stock movements.
01:11 Three Buckets Framework
03:45 Define Your Why
04:51 Goals And Time Horizons
08:59 Multiple Goals In Life
11:37 Choose Investor Style
13:30 Target Date Basics
18:20 Fees And Fund Reality
23:31 Avoid Overactivity Trap
25:39 Build A Repeatable Process
27:58 Tracking Performance Wisely
29:19 Detach Stock From Business
30:33 Keep Score With Benchmarks
34:01 Net Worth And Debt Tracking
35:54 Fee-Only Advisor Check In
38:51 Lump Sum Vs Dollar Cost
43:30 Tax Buckets And Accounts
47:40 Roth Limits And Workarounds
49:18 Options Income Tax Placement
50:56 Build A Review Checklist
Companies mentioned: AVGO, FTNT, NFLX, NVDA
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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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 strategy of Brad Jacobs' QXO, and explore high-yield opportunities in REITs like CareTrust and EPR Properties. Plus, Jason makes the case for investing with the ultra-wealthy by buying shares of the Atlanta Braves, taking plenty of shots at Jeff's beloved New York Mets along the way.
01:42 Why Look Beyond AI
07:27 AI Backlash and Reality Check
11:00 Berkshire Weekend Teaser
11:53 Picking AI Proof Stocks
12:55 Costco as Safe Retailer
16:40 Costco Ops and Tech Edge
21:37 TJX Treasure Hunt Model
25:49 Phinia Gas Engine Parts
29:29 Commercial Auto Parts Angle
30:10 Delphi Brand Recognition
30:33 QXO Rollup Strategy
32:56 Synergies And TopBuild Deal
38:12 Tech Stack Efficiency Play
39:05 CareTrust REIT Overview
42:23 EPR Experiential REIT
45:42 EPR Dividend Growth Case
46:48 Braves Stock BATRA Pitch
50:32 Stadium Real Estate Upside
51:54 Valuation Versus Padres Deal
Companies mentioned: BATRA, COST, CTRE, EPR, PHIN, QXO, TJX
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 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 Risk Positioning
26:40 Gemini Video Fail
30:18 AI Thumbnail Drama
33:14 Starbucks Turnaround Signs
37:19 China Strategy Shift
40:44 Operational Fixes Ahead
42:47 Disruption Beyond Rivals
43:49 Earnings Season Winners
Companies mentioned: AMD, AMZN, BE, DUOL, FIX, GOOG, GOOGL, HOOD, IBM, KNSL, LKNCY, MELI, META, NOW, ROKU, SBUX, SOFI, TTD, TXN, VRT
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 PatreonSubscribe to our portfolio on Savvy Trader
Learn more about your ad choices. Visit megaphone.fm/adchoices -
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
*****************************************
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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Learn more about your ad choices. Visit megaphone.fm/adchoices -
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
*****************************************
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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Learn more about your ad choices. Visit megaphone.fm/adchoices -
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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Learn more about your ad choices. Visit megaphone.fm/adchoices -
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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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
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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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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 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
*****************************************
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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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
*****************************************
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 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
*****************************************
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 PatreonSubscribe to our portfolio on Savvy Trader
Learn more about your ad choices. Visit megaphone.fm/adchoices - Vis mere
