As an exercise, I put together a few risk patterns that I’ve observed over the years. These are low precision proxies, weak on their own. However, the stronger the signal, the likelier the problem. Trust your gut.

When we invest in a new company, I spend the first few weeks getting to know the team to understand their current challenges to help where I can. A common topic is that of the product lifecycle, everything from defining a north star, to developing a written roadmap, to executing and delivering a successful product. Last month, I wrote down some of the key points that emerged during those discussions. In particular, I wanted to highlight some of the most salient points of tension that emerged during these discussions.

Big refactorings often end up becoming a creative endeavor or a quest to add cool new technology, as opposed to a set of well defined, independently valuable, and progressively executed milestones, with concrete and measurable results.