Investing Unscripted

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

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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 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

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

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

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 PatreonSubscribe to our portfolio on Savvy Trader

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