At my last company, the CEO was genuinely impressive at raising money. And that skill, which sounds like a pure positive, ended up being one of the biggest reasons the tech debt never got paid down.
We had this monolith that was already showing its age when I joined. Interdependent modules, features taking weeks that should have taken days, a number of microservices in the intent to extract functionality but keeping the monolith in sync instead of killing it, the usual. But every time the pain started to build and the team started talking about refactoring, another funding round would close. Apparently there was budget for more hires, more process, even more M&As! But resources to adjust the architecture to the actual demand?
Five years later when I left, they were still struggling. The business side saw the tech department as a black box that kept costing more and delivering less, so they added reporting layers and micromanagement. Those layers made the refactoring even harder. It became a self-reinforcing loop. Easy money removed the urgency to simplify, so complexity kept growing and coordination costs piled up. Those costs triggered more process, which ate into the time engineers had to actually fix anything.
What I couldn't shake was the economics underneath it. The complexity we were maintaining had no demand behind it because obviously no customer was asking for it. But the easier money got, the more of it we tolerated, so the liability kept compounding while the funding just kept the cycle going. I started wondering if every dollar we spent maintaining that mess was effectively subsidizing something the market would never reward.
Have you seen this happen? A company that could afford to stay messy, so it did? I'm wondering if the complexity, and its monetary cost, ever actually caught up to them or if some companies just manage to outrun it forever.