Investing Unscripted

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

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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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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 PatreonSubscribe to our portfolio on Savvy Trader
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

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

Join our PatreonSubscribe to our portfolio on Savvy Trader
Learn more about your ad choices. Visit megaphone.fm/adchoices

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