Why Most Founders Get Finance Wrong, and How to Fix it

Most founders don't fail because of bad finance. They fail because they treat it as reporting instead of decision-making.Before building 82i, Jason Shapiro studied finance and math, taught high school math and coached basketball through Teach for America, and worked in investment banking and private equity before spending years as an early-stage investor speaking with nearly 1,000 founders. That experience led him to a simple but overlooked insight: finance in most startups is treated as reporting, when it should be a decision-making system.In this conversation, he explains why startup finance functions break at scale, how that quietly distorts strategy inside companies, what it takes to turn finance into a true co-pilot for growth, and how his path through teaching, investing, and operating ultimately led him to start 82i.