Investing Unscripted

By Jason Hall and Jeff SantoroBusiness Investing

Investing Unscripted episodes

June 17 210. Investing Unscripted, Unscripted
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
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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. Use code Unscripted2026 for 30% off a one-year subscription!

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53 min
June 14 First Fridays 31. June 2026
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
1 hr 4 min
June 10 209. Our Best Stock Ideas Right Now
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 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
58 min
June 03 208. The 15 Investing Terms You Need to Know
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
*****************************************
Join our Patreon
Subscribe to our portfolio on Savvy Trader

Learn more about your ad choices. Visit megaphone.fm/adchoices
1 hr 8 min
May 27 207. Missing Fads with Brian Stoffel
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
*****************************************
Join our Patreon
Subscribe to our portfolio on Savvy Trader

Learn more about your ad choices. Visit megaphone.fm/adchoices
1 hr 2 min
May 20 206. May 2026 Mailbag
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 Patreon
Subscribe to our portfolio on Savvy Trader

Learn more about your ad choices. Visit megaphone.fm/adchoices
1 hr 5 min
May 15 205. The 3 Questions Every Investor Should Answer
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
*****************************************
Join our Patreon
Subscribe to our portfolio on Savvy Trader

Learn more about your ad choices. Visit megaphone.fm/adchoices
58 min
May 13 205. The 3 Questions Every Investor Should Answer
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
*****************************************
Join our Patreon
Subscribe to our portfolio on Savvy Trader

Learn more about your ad choices. Visit megaphone.fm/adchoices
57 min
May 06 204. Stocks for the AI Hater
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
*****************************************
Join our Patreon
Subscribe to our portfolio on Savvy Trader

Learn more about your ad choices. Visit megaphone.fm/adchoices
1 hr
May 04 First Fridays 30. May 2026
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 Patreon
Subscribe to our portfolio on Savvy Trader

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