Investing Unscripted

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
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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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Ryan Henderson and Brett Schafer from the Chit Chat Stocks podcast join us for a special unscripted episode to track their evolution from college-aged podcasters running a family-and-friends fund to seasoned individual investors. We discuss learning the harsh realities of valuation during the 2022 bear market, the dangers of "analysis paralysis," and whether mastering your own psychology is more important than understanding financial mechanics. We also debate the merits of starter positions, explore Ryan's strict "three-year holding rule," and reveal the current watchlist stocks they are waiting to buy—along with the ones they kick themselves for missing.
02:09 Meet Chit Chat Stocks
04:30 Origin Story 
08:56 Early Podcast Lessons
10:26 Valuation Reality Check
12:29 Mistakes Shape Process
14:09 Bear Market Incentives
18:19 Investing In Public
21:30 Overthinking Valuation
24:07 Match Vs Spotify
28:18 Costco One Share Rule
29:18 Owning Through Drawdowns
29:58 Fund Pressure vs Flexibility
32:26 Starter Positions Debate
34:07 Psychology Beats Fundamentals
38:03 Know Your Investing Style
39:57 When Stocks Go Nowhere
44:15 Rules to Avoid Selling
47:35 Build a Personal Framework
51:52 Watchlist Valuation Picks
55:40 Where to Find Their Work
59:14 Final Wrap and Signoff
Companies mentioned: ADYEY, AMZN, AXP, CAVA, COST, CPNG, CSU, HIMS, IBKR, MELI, MNDY, MRNA, MTCH, PYPL, RKLB, ROKU, SPOT, TSLA
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

Jason and Jeff go completely off-script to discuss what they are actually doing in their portfolios right now. Jeff breaks down why he bought more Datadog on a recent dip and his strategy for adding to Enphase, while Jason explains how he is using options (specifically selling puts) to generate income while waiting for better valuations. Plus, they analyze the risk vs. reward of QuantumScape, debate the new CEO at PayPal, and play a game of "buy or get off the pot" that ends with a live stock purchase.
00:53 Unscripted Earnings Season
04:34 Jeff Did a Thing
06:43 Why Buy Datadog Now
09:14 AI Risks for SaaS
11:34 Selling Puts Strategy
17:06 Market Psychology Chegg
19:41 Market Efficiency Long Term
23:15 Enphase DCA Dilemma
25:46 How to Time Adds
28:08 Quarterly Info Is Noise
28:30 Enphase Through the Cycle
29:49 QuantumScape Solid State Promise
31:50 Timing the Entry Price
33:53 Asymmetric Upside vs Risk
36:24 PayPal CEO Shakeup
38:59 Reframing the PayPal Thesis
44:48 Small Positions to Fix
46:36 Airbnb Growth Proof Points
Companies mentioned: ABNB, ADBE, CHGG, DDOG, ENPH, PYPL, QS, UPST
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

We open the February 2026 mailbag to answer your questions on how to handle the psychological toll of the "SaaS apocalypse" and when it actually makes sense to buy the dip. We also discuss how to assess relative risk in a portfolio, dive deep into the differences between SentinelOne and CrowdStrike (including thoughts on stock-based compensation), and reveal the "falling knife" software stocks we are most tempted to buy right now, including ServiceNow and Salesforce.
00:51 First Friday Update
02:03 Mailbag Fear in Downturns
03:56 DCA and SaaS Selloff
06:15 Deploying Cash Rules
08:43 Add to Winners Not Losers
15:49 Risk in Portfolios
20:31 Position Sizing Examples
23:28 SentinelOne Profitability Debate
28:35 SentinelOne vs CrowdStrike
30:44 Cybersecurity Basket Strategy
31:42 M&A and Buyout Odds
33:12 CareTrust REIT Update
35:00 Discord Falling Knife Picks
35:35 ServiceNow Case
37:44 PayPal Options and CEO Risk
38:33 Salesforce AI and Valuation
42:50 How We Add Positions
47:28 Enphase and Gut Conviction
50:19 Secular Trends and EV Lesson
52:05 QuantumScape Battery Bet
52:37 Wrap Up and Where to Ask
Companies mentioned: ASML, CRM, CRWD, CTRE, ENPH, NOW, PYPL, QS, S, TSLA, TSM
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

We discuss the recent market dislocation where SaaS stocks are crashing while the broader market hits all-time highs. We break down the three main fears driving the sell-off and debate which companies—like Adobe and Salesforce—are actually at risk. Finally, we share how we are handling the volatility, with Jeff buying more Shopify and Jason using a "barbell strategy" to stay sane.
02:27 Housekeeping
03:53 Episode Setup
06:37 Three AI Threats to SaaS: 
09:23 Is AI Really Different? 
12:59 Stock Spotlight: Adobe
18:35 The Real Issue: Moats, Stickiness, Switching Costs, and Resetting SaaS Multiples
23:18 LLMs Aren’t Free
23:49 Why SaaS Stocks Are Selling Off
25:11 Shopify vs. Toast
27:06 Disruption Timelines & Valuation Reratings
29:19 Earnings Season as the Reality Check
31:53 Tactical Moves: Selling Puts for Margin of Safety
33:02 Barbell Portfolio Strategy: Growth on One Side, Dividends on the Other
Companies mentioned: ABNB, ADBE, ASAN, CRM, CRWD, ENPH, EPR, MNDY, MSFT, NOW, O, PYPL, SHOP, SQ, TEAM, 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