Sid Sijbrandij, founder of GitLab, faced a life-altering diagnosis when he was told he had cancer in November 2022. Known for building one of the largest fully remote companies with over 2,500 employees and a $6.4 billion market cap, Sid's approach to his health mirrored his business philosophy of intensive information management. After enduring a brutal treatment regimen, including surgery and aggressive chemotherapy, his cancer returned in 2024. Faced with a lack of viable options from conventional medicine, he decided to take control of his care, assembling a team to navigate and customize his treatment. Sid created a comprehensive documentation system titled “Sid Health Notes,” which has grown to over 1,000 pages in just one year. This document details every medical interaction and diagnostic result, reflecting his commitment to maximal diagnostics. He built a “therapeutic ladder” of potential treatments, repurposing existing medications and exploring personalized therapies developed in collaboration with researchers. His efforts have led to remarkable outcomes; his cancer is currently in remission, allowing him to start a new software company while still managing his venture capital fund and a charitable foundation. Despite his success, Sid's journey highlights significant barriers in cancer care, even for someone with extensive resources. He faced challenges accessing his own medical records and ordering diagnostics. The healthcare system often defaults to a conservative approach, equating caution with inaction, which can hinder aggressive treatment options. Moreover, broader issues in drug development and regulatory standards complicate the landscape for personalized therapies. Sid notes the growing disparity between the cost of developing a new drug and the expense of personalized treatments, emphasizing the need for a shift in how medicines are designed and approved.