193. Nothing Works All the Time

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

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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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