The Money Is Sophisticated. The Process Usually Isn't.
A later-stage investment round moves a remarkable amount of money through a set of remarkably ordinary tools. Opportunities circulate by email. Diligence materials sit in a shared drive, or in several. The paperwork becomes a stack of documents that get sent, signed, countersigned, and chased.
Everyone involved is sophisticated. The process connecting them often isn't. And at Series D and E, where the sums are serious and the timelines are tight, that gap between the money in play and the machinery handling it starts to cost something real.
Every handoff between disconnected systems is a place where a deal slows down, a document goes stale, or an investor quietly loses confidence in how the whole thing is being run. In a market that operates on confidence, that's the expensive failure.