Some thoughts on Vibe Coding, SaaS vs AI (10 Moats) and Guidewire Software
Executive Summary:
This post does not contain any actionable investment advice but rather some personal ramblings on Vibe coding and the attempt to analyze a specific Software company (Guidewire) according to a Template of 10 Moats for Software companies and their vulnerability to the AI threat.
Introduction:
My track record as a Software investor is to put it mildly, very poor. My best Software Investment so far is Chapters Group which I bought as a net-net before it even became a VMS Serial Acquirer. My blog and portfolio archive also tell me that I sold Microsoft in 2011 at ~25$ per share with a 4% gain because I thought that the Office products had no future. So please take everything I say about Software with a grain of salt or even better, just ignore it.
I do have a background in Software development. Although I would not call it Software development but “Code butchering”. It started as a teenager on a C64 with Basic and Assembler and ended in the late 1990s with Cobol/PLSQL working for a large US Consulting Company (yes, I was young and needed the money). Knowing the speed of financial institutions, I would not be surprised if some of my Spaghetti code would still be running somewhere….
Why am I saying this ? Because of course, Software stocks have been doing quite poorly over the past weeks/months. In addition, I also had the opportunity to play around with Claude Code first hand.

