Dave Duffield was 64 years old and three months into retirement when he decided that rocking chairs and model airplanes were not sufficient purpose for a man who had built and lost one of the world's most successful enterprise software companies. The loss was not financial — Duffield had sold PeopleSoft to Oracle for $10.3 billion in January 2005 after an 18-month hostile takeover battle that began with a $5.1 billion initial offer in June 2003 — but personal and professional. PeopleSoft, which Duffield had founded in 1987 and grown into the second-largest application software company in the world, employed 11,000 people when Oracle's bid launched. Within a week of the acquisition closing, Oracle laid off approximately 5,000 of them. Duffield wrote personal $10,000 checks to every laid-off employee, a gesture that cost him millions but established a loyalty bond that would prove decisive. In March 2005, sixty days after Oracle closed the PeopleSoft deal, Duffield called Aneel Bhusri, a 38-year-old former PeopleSoft executive who had become a partner at Greylock Partners, one of Silicon Valley's most storied venture capital firms. They met at a diner in Truckee, near Duffield's Lake Tahoe compound, and over breakfast built the thesis that would become Workday. The cloud was no longer theoretical. Salesforce.com had proven that enterprise software could live on servers you didn't own. The opportunity was to apply that architecture to the most critical software in every large organization: HR and financial management. But the deeper insight was structural. Oracle and SAP had built their entire business models on perpetual licenses and maintenance fees. Moving to the cloud would cannibalize their installed bases. They were structurally paralyzed. Workday would have no such paralysis. It would build everything cloud-native from day one. No on-premise version. No legacy code. No upgrade cycles. Just a single, continuously updated platform that every customer ran on simultaneously. Greylock Partners led the first institutional funding round alongside Duffield's personal investment. The founding team was assembled from former PeopleSoft engineers, product managers, and salespeople who had been laid off by Oracle or quit in disgust. Duffield and Bhusri personally interviewed the first 500 employees, not to interrogate credentials but to find people who shared the belief that enterprise software could be better — that the people who maintained payroll data and financial records deserved software as thoughtful as their consumer apps. Workday launched publicly in November 2006, with the HR suite first and financial management to follow. The decision to go cloud-only was not universally applauded. Enterprise CIOs were deeply skeptical about putting sensitive HR data — salaries, social security numbers, performance reviews, terminations — on servers accessible over the public internet. Workday's counter-argument was architectural: a multi-tenant cloud model allowed for security investments at a scale no individual company's IT department could match, and updates rolled out continuously to all customers simultaneously. The early years were slow, grinding, skeptic-by-skeptic work. By the spring of 2012, Workday had 310 corporate customers — a mix of mid-sized companies and Fortune 500 names that had placed extraordinary trust in a seven-year-old startup. The company had attracted investors including Michael Dell and Jeff Bezos. On October 12, 2012, Workday went public on the New York Stock Exchange. The shares, initially priced at $28, surged 74% on opening day. The IPO raised $591.5 million — the largest cloud computing IPO in U.S. history at that point — valuing the company at over $9.5 billion. Duffield's 85 million shares were worth approximately $3.9 billion. At 72 years old, he had built his second multi-billion-dollar company. Larry Ellison, Oracle's CEO, had dismissed Workday as a 'frail toy' at the AllThingsD conference. The frail toy now generates $9.55 billion in annual revenue.