In any scaling SaaS company, there are inflection-point hires — people who don't just fill a role but fundamentally change the trajectory of the business. Looking back at my journey from startup to exit, three hires stand out above all others. Hire #1: The Operator (VP Operations, Year 3) By year three, we had product-market fit and about 40 customers. I was drowning. Every customer issue came to me. Every process was in my head. I was the single point of failure for everyth

I'm going to say something that might be unpopular: most SaaS companies investing in AI right now are lighting money on fire. Not because AI isn't valuable — it absolutely is. But because they're investing in the wrong things, at the wrong time, for the wrong reasons. The Three Money Pits Money Pit #1: Building custom models when off-the-shelf works. Unless you're sitting on proprietary data that creates a genuine competitive moat, you don't need a custom LLM. You need a sma