View from the Office. 

I met up with Casey Woo for breakfast at Angelina Paris, a cafe near Bryant Park which is Instagram famous for its rich and creamy hot chocolate. We both had the omelets. 

Casey was visiting from San Francisco where he is the CEO and founder of Operators Guild, a community of professionals who serve as the behind-the-scenes talent that helps founders scale Silicon Valley startups. 

Operators Guild was founded a decade ago with the idea of creating a networking opportunity for the people who served in roles such as CFO, COO, business operations and strategy, many of whom were joining startups from previous careers in more traditional firms. 

Casey was one of those people. He began his career at Morgan Stanley in New York and then did stints at Maverick Capital and a couple other hedge funds before moving to San Francisco in 2014 to work for a series of start ups. 

He compares the “scalers,” as he calls them, to the special forces in the military because they solve broad problems. Peter Thiel has been saying something similar recently. In an interview, Thiel said AI would be “much worse for math people than word people.” 

Casey posts actively on social media, often with provocative takes. This week he wrote about how the VC fundraising cycle is shortening from every 18 months to “micro-raises” every six months or so. 

AI is not only changing how startups raise money but will likely transform the “survival rate,” Casey said. He expects more companies to fail, but for the survivors to have even bigger gains. 

Nevertheless, he expects the migration to startups from traditional jobs at consultants like McKinsey or Wall Street firms to continue. There is a bevy of reasons ranging from greater job satisfaction to lower risk due to generally higher salaries driving the change. 

The Operating Guild has more than 1,000 members and operates in over 20 chapters. The organization’s three main functions are: knowledge sharing, networking and job leads. The group has also started to participate in early-stage investments. 

You can connect with Casey on LinkedIn or DM for a warm intro.