William “Trey” Gates III’s journey from Lakeside School to the mogul life in Medina entailed far more than zipping across the 520 floating bridge. Gates, alongside classmate and eventual Microsoft cofounder Paul Allen, had rare access to a computer terminal at their storied private school, setting them up with the skills and social capital to grow a scrappy microcomputing software outfit into a multinational conglomerate. Since stepping down from his full-time role as CEO of Microsoft, Gates has become better known for channeling his jaw-dropping wealth into public health–oriented philanthropic efforts through the Gates Foundation, which he cofounded in 2000 with then-wife Melinda. 

Allen stepped away from Microsoft leadership in 1983 following a diagnosis of Hodgkin’s lymphoma. In his memoir, he accused Gates and Steve Ballmer of successfully scheming to take shares away from him after his cancer diagnosis. “It was mercenary opportunism, plain and simple,” Allen wrote. Gates’s and Allen’s paths diverged thereafter in other ways. Allen channeled his wealth into sports (as majority owner of the Seattle Seahawks and Portland Trail Blazers) as well as real estate, playing a decisive role in the bluechipification of South Lake Union through his company Vulcan, and building the colorful landmark Museum of Pop Culture (initially called the Experience Music Project). Gates and Allen reportedly mended fences before Allen passed in 2018. The Paul G. Allen Family Foundation maintains a powerful PNW-focused philanthropic presence.

Joining Microsoft as its 30th employee, Ballmer functioned as Gates’s thought partner, a role known to result in fraught debates and shouting matches. Ballmer climbed the ranks to CEO by January 2000, after Gates grew burned out by the demands of running a tech company with a market cap dwarfing most GDPs. “Thank God he’s willing to do this for me,” Gates said at the time. Where Ballmer and Gates seemingly once had a blood bond, Ballmer said their relationship soured following his push for Microsoft to lean into the smartphone market. A resident of Hunts Point, Ballmer is the 10th-richest person on the planet—flying under the public’s radar, compared to Musk, Zuck, Bezos, et al. One of Ballmer’s signature acquisitions at Microsoft was Skype, which the company recently shuttered.

Nadella replaced Ballmer as CEO in 2014. Rhyming with Amazon CEO Andy Jassy’s climb to the C-suite through his leadership of Amazon Web Services, Nadella previously led Microsoft’s cloud and enterprise group, which no doubt influenced Microsoft’s investments in Azure cloud computing and other data-focused services during his reign. Nadella’s tenure as CEO has featured major acquisitions, including professional social-media platform LinkedIn and gaming giant Activision Blizzard. That last acquisition compelled the Federal Trade Commission to sue Microsoft for antitrust violations, claiming the purchase would unfairly suppress competition in the gaming industry. The FTC’s efforts were unsuccessful in court. Nadella is also a minority owner of the Seattle Sounders. More recently, he has navigated an uneasy relationship with artificial-intelligence giant OpenAI, as well as internal worker dissent against Microsoft’s strengthening ties with the Pentagon and militaristic applications of its technologies. (Hey, “Don’t be evil” was Google’s motto.)

Microsoft president since 2015, Smith is now the most veteran leader in Microsoft’s executive ranks. Smith joined the company in 1993 and was in charge of defending it in landmark antitrust cases. His ascent has largely been tied to his olive-branch approach, which involves conciliatory settlements with plaintiffs and similar interfacing with regulators. Smith was less forthcoming with President Donald Trump during his first administration, stating that federal authorities would have to “go through us” to deport employees if their Deferred Action for Childhood Arrivals (DACA) status had been revoked. More recently—and tracking with the tech industry’s growing coziness with Trump during his second administration—Smith has shared a “vision for technology success during the next four years” that conveniently hinges upon increased use of AI tools. Using “AI to make the government itself more effective and efficient…will put the country on a promising path,” he wrote. Sounds DOGE-y.

There’s another Sounders minority owner on this list: Microsoft’s chief financial officer. A graduate of Duke and Harvard Business School, Hood has helped guide the company through a litany of acquisitions, including GitHub for $7.5 billion in 2018. (Hood was the second-highest-paid Microsoft exec the following year, earning $20.3 million.) She plays a Ballmer-esque role to Nadella through Microsoft’s AI-invested next stage of life. Internal memos and other communications suggest Hood is often called upon to keep Microsoft employees in line: The same week a new AI model from Chinese company DeepSeek launched publicly and outperformed more infrastructure-intensive competitors, Hood instructed employees to “focus” on Microsoft’s own AI infrastructure and services despite “a lot of AI-related news.” Hood has also previously had to respond to regulatory ire on behalf of the company, such as when the IRS delivered a whopping $29B tax bill in 2023 following an audit of Microsoft’s tax practices.