This book describes the technology-enabled business models of five companies from inception through the present. Webvan pioneered grocery delivery at scale and failed. Why did it fail? What are the lessons for today's delivery businesses? At the other extreme, Schwab started as a small discount brokerage and became the industry's leader. How has it done that and what was the role of technology? Dropbox made file sharing easy and is extending its reach into the enterprise. Fundbox is using AI to underwrite small business loans quickly and efficiently. How does it do that? What are the lessons for deploying AI-based solutions? Rent The Runway rents out dresses and other items to women, starting from the very high end and moving to the mass market. Can Rent The Runway be successful?