I come from a family of doctors. I left my Ph.D. program to join a friend's startup when it had a budding team of just 20. I took the lead in establishing the APAC headquarters from the ground up and built strong ties with several major university hospitals. With a lean team, we developed, sold, and implemented a cloud-based product. We also achieved PMDA approval for another product within two months during the Tokyo lockdown of 2020. Recognizing the limitations of Medical AI, I branched out to launch my own company, I.W.G. Our solution, drawing from the best of JIRA, Dropbox, and WhatsApp but tailored specifically for doctors, has been deployed in 8 hospitals and is patent-pending. I share my journey, both successes and mistakes, hoping others can learn from it, especially those navigating similar paths.