Seattle tech veteran and angel investor Charles Fitzgerald issued a stark warning to the Emerald City in a provocative guest column on GeekWire, drawing parallels between modern-day Seattle and Cleveland, Ohio in the 1950s—a once-prosperous metropolis that declined dramatically after failing to adapt to economic change. The headline "Don't become the next Cleveland" has sparked significant dialogue about Seattle's future in the AI era.
Fitzgerald's historical comparison is sobering. In the 1950s, Cleveland was a thriving hub—America's seventh-largest city with median household incomes rivaling New York's. It was home to industrial giants like Standard Oil, Republic Steel, and Sherwin-Williams, with companies like General Motors and Westinghouse maintaining strong local presences. Within two decades, however, Cleveland’s fortunes reversed catastrophically. The infamous 1969 Cuyahoga River fire cemented its reputation as "the mistake on the lake." The city's population plummeted 60 percent, dropping from 7th to 56th largest in the nation, and today median incomes are less than half the national average.
Fitzgerald sees troubling warning signs in Seattle's current trajectory. While the region hosts two of the world's five largest companies—Amazon and Microsoft—both appear past peak employment as they pivot toward AI-driven productivity and capital-intensive operations. Recent layoffs across Amazon (2,200 in Washington), Microsoft (6,000 globally), Expedia, Zillow, Meta, and T-Mobile, combined with plummeting tech job listings, signal that Seattle isn't punching above its weight in the AI era the way it did in the software boom.
Equally concerning is an apparent exodus of entrepreneurs, executives, and technologists leaving Seattle for more competitive markets like San Francisco, citing difficulties competing in the white-hot AI market and deteriorating business conditions.
While the tech sector grapples with existential questions, Fitzgerald argues that Seattle and Washington state political leadership appears oblivious. Rather than focusing on job creation or nurturing future industries, government appears fixated on revenue generation, treating tech companies as a "bottomless source of revenue" rather than partners in economic development. The traditional civic partnership between business and government has frayed, with little learning from Boeing's gradual migration out of Washington—which now hosts just one-third of the company's workforce.
The consequences of civic complacency are visible throughout Seattle. Downtown office vacancy rates hit record highs. Persistent challenges with public safety, housing, and homelessness yield to "progressive panaceas" with limited success. Most alarmingly, education has seemingly fallen off the policy radar entirely, despite the majority of Seattle's fourth and eighth graders failing to achieve proficiency in reading or math—a "mandatory prerequisite for an advanced civilization" that has been abandoned.
Fitzgerald contrasts Cleveland's confrontational government approach during its decline with Pittsburgh's collaborative management of industrial transition, which defined the post-industrial urban playbook. Cleveland politicians made their situation worse; Seattle risks following that path.
Seattle has historically been a "lucky city," Fitzgerald notes, with prosperity arriving unexpectedly through the Alaska gold rush, Boeing (Bill #1), Microsoft (Bill #2), and Amazon (Jeff). The next wave could emerge from space, energy, robotics, biotech, or something unimaginable. "But hope," Fitzgerald concludes, "is not a strategy."
The article generated significant response, including from Cleveland Mayor Justin Bibb, who invited Fitzgerald to witness his city's ongoing revival firsthand. While Bibb bristled at the comparison to his city's troubled past, he acknowledged Cleveland's experience as instructive: "We didn't pivot fast enough, and the world left us behind."
Charles Fitzgerald is a Seattle area angel investor and long-time CAPEX obsessive. He is @charlesfitz on Twitter and blogs at www.platformonomics.com.
