How do entrepreneurs turn daily headaches into solutions that benefit an entire industry? In the world of angel investing, even the most tech-savvy find themselves wrangling gruesome spreadsheets and chasing down lost documents—begging the question: why are investors, of all people, stuck managing chaos with outdated tools?

This episode features Zach Holman, one of GitHub’s earliest team members and a prolific angel investor. After years of advising top startups and investing in hundreds of companies, Zach found himself wrestling with the same messy tracking problems plaguing countless others. Drawing on his unique background at the intersection of engineering, advising, and investing, he set out to build Signed—a modern platform purpose-built for angel investors to organize, analyze, and make sense of their portfolios.

Listen here.