Honestly, I remember this one time a few years back, I was deep in due diligence for a Series B round, crunching numbers for a fintech darling. We were debating a $5M valuation cap for their option pool, and I was adamantly against it, convinced it was too dilutive. The real answer is, I dug my heels in so hard, pushing back against the founders and even some of my own partners, that we nearly wal