Back in 2017, Casey Woo decided it was time to graduate from early-stage companies. “What I like to tell people is that as an operator you will be characterized and judged by the age of your businesses,” remarks Woo, who from 2011 to 2017 had served in a succession of finance leadership roles at a number of early-stage “A-B-C series”–funded companies. “At that point, I had three A-B-Cs under my belt, and for me, the concern was that if I took a fourth, I’d be labeled a ‘Van Wilder,’” recalls Woo, naming the Ryan Reynolds character whose seventh year of college served as the backdrop for a National Lampoon movie. “I understood what hypergrowth and product market fit were, but I was not able to say that I had seen ‘scale,’” Woo reports, as he explains what led him to nab the position that he now credits with having opened his next CFO chapter—and enabled him to add “scale” to the list of descriptors in his professional portfolio. The role to which Woo refers was noteworthy as much for its transformative effect on Woo’s future as it was for the company itself: WeWork. “They needed a regional CFO, but this was a huge step up for me, as the size of my P&L on Day 1 was 10 times greater than that of any other business I had ever been a part of,” reports Woo, who from 2017 to 2019 oversaw finance and operations for the flexible workspace company’s U.S. western region and Canada. At the same time, Woo’s timing placed him inside the headline-grabbing WeWork saga that would ultimately lead to the ouster of the firm’s founder and CEO, Adam Neumann, and withdrawal of the company’s IPO. “We were asked by some of the biggest investors in the company to go fast, so in a weird way we were doing what we were told … and following orders,” comments Woo, whose tour of duty at WeWork gave his real estate credentials the boost needed to allow him to soon thereafter step into the CFO office at Landing, a company specializing in flexible-lease apartments. Asked what lessons he may have gleaned from his days at WeWork, Woo observes: “After Adam left, everything changed—the culture went from ‘Go, go, go!’ and ‘We’re top of the world!’ to the reverse and layoffs.” It sounds like Van Wilder may have finally graduated. –Jack Sweeney