"The first time is handmade" refers to an entrepreneurial principle coined by 📝John Zdanowski implying that the initial iteration of a capability should be executed manually before systematization or scaling. The principle was echoed by Collin Stewart, co-founder of 📝Predictable Revenue, who argues “You can't scale what you haven't done yourself,” citing his 2018 attempt to pivot from a cold email agency to a full 📝SDR outsourcing model. Stewart reports that what seemed like adding channels actually required building a new business, revealing gaps across four levels of work—📝Individual Contributor (IC), management, leadership, and executive.
Shortly after we met, John shared this principle with me and the story of how he had hand built over 150 financial models before codifying those insights into what would become 📝Assembled Brands—the $100M venture debt firm he co-founded with 📝Adam Pritzker, highlighting the value of founder-led discovery prior to hiring specialists or formalizing processes.
It stuck with me and keeps me from automating prematurely and pushes me to validate workflows hands-on before I commit to tooling or hires. Because of it, I now assume the IC role first, then climb one level at a time.