Investing Unscripted 194. February 2026 Mailbag
Feb 25, 2026
They answer mail about the psychology of buying into big tech sell-offs and whether dollar-cost averaging or waiting makes sense. They compare SentinelOne and CrowdStrike, including stock-based compensation and profitability concerns. They debate tempting “falling knife” software names like ServiceNow, PayPal, and Salesforce and discuss position sizing, portfolio risk, and bets on secular trends such as EVs and batteries.
AI Snips
Chapters
Transcript
Episode notes
Limit Position Size Based On Survival Impact
- Size positions so no single stock threatens your retirement; smaller stakes for higher-risk names.
- Jeff keeps most wealth in index funds and limits any single risky stock's weight so a zero won't derail plans.
Semiconductors Remain Core Even If AI Hype Fades
- Even concentrated AI-related positions (ASML, TSM) can make sense because semiconductors remain fundamental across industries.
- Jason added ASML and TSM after ChatGPT and argues chips are needed regardless of AI outcomes.
Measure SBC Impact By Share Count Growth And Valuation
- Stock-based compensation inflates dilution but is endemic to tech; compare share-count growth rates across competitors.
- Jason notes SentinelOne's shares up ~30% since IPO vs CrowdStrike ~15%, and uses valuation (S) 4x revenue vs CRWD 19x as deciding factor.