‘They’re out to eat our lunch’: Tech investor Charles Fitzgerald says Seattle is drifting while Cleveland hustles for its future
Aug 13, 2026, 4:00 PM
Seattle tech veteran and angel investor Charles Fitzgerald went to Cleveland and came back with a warning: a city that was once the joke of the country is now more focused on its future than Seattle is.
Fitzgerald told “The John Curley Show” on KIRO Newsradio that he and GeekWire publisher John Cook spent several days in Cleveland meeting with startups, big companies, university leaders, and politicians, including Cleveland Mayor Justin Bibb, the county commissioner, and Ohio Gov. Mike DeWine. The trip grew out of a GeekWire column Fitzgerald wrote earlier this year comparing 1950s Cleveland to present-day Seattle, both cities that enjoyed 30 years of economic growth and were home to the dominant tech companies of their era.
“The thing that happened with Cleveland is 20 years later they were completely in the ditch,” Fitzgerald said. “The Rust Belt starts to rust, and the politicians did everything they could to make it worse. And they’ve spent the last 50-plus years really digging out of that hole.”
The column got an unexpected response. Cleveland’s mayor replied the next morning, and within a day, Fitzgerald was on the phone with him.
“The mayor of Cleveland is way more plugged into the Seattle tech scene than anybody in Seattle on the political side,” Fitzgerald said.
Bibb then invited Fitzgerald and Cook to visit. What they found was a city pulling in one direction.
“You could take some of those guys are Democrats, some of those guys are Republicans,” Fitzgerald said. “You could take a quote from any of them, and you wouldn’t know who it came from. They’re focused on jobs. They’re focused on prosperity. They’re focused on economic development in a way that, it’s just, it’s stunning.”
He said they sat down with the mayor with no handlers and no staff rushing to end the conversation.
“We’re two randos from out of town,” Fitzgerald said. “We can have a substantive conversation with the mayor. He can more than hold his own. There’s no staff there waiting to, ‘Ooh, he was asked a question. We better get him out of here.'”
What Seattle’s mayor could learn from Cleveland’s
Fitzgerald said Bibb offered a simple framework for being a mayor.
“He said, look, half of it is just fixing the potholes,” Fitzgerald said. “Literally, he said that. Making sure the police get paid on time, making sure that you deliver government services effectively and efficiently. And then the other half is charting a path for where the city is going to go.”
KIRO host John Curley then laid out the contrast in spending priorities. Cleveland’s $920 million general fund goes to police, fire, roads, sewer, garbage, parks, building inspection, courts, and basic administration. Seattle’s $2 billion general fund, he said, is weighted toward homeless housing affordability, behavioral health, food security, violence prevention, racial equity, community empowerment, social services, and alternative public safety responses.
“The basic nuts and bolts of running a city are not important because the luxury of success allows the city to get to a certain point,” Curley said. “So now the money is redirected towards that, while the car runs into the pothole and the tire breaks, or the person calls the cop and the cop doesn’t show up because it’s 14 or 15 minutes to a call. So the basic function of the city is left to deteriorate while spending the money on the rest of the stuff seems to only increase the number of people that want these services.”
Take out Boeing, Gates, and Bezos
Fitzgerald said Seattle’s entire modern identity rests on three people.
“Let’s take three people out of the last 100 years of Seattle history,” he said. “So if we take Bill Boeing out, Bill Gates out, and Jeff Bezos out, what does the city look like over the last century? It’s really hard to know what that is.”
All three, Fitzgerald noted, chose to build their businesses in Seattle. Boeing came from the East Coast. Gates founded Microsoft in Albuquerque before deciding to come home. Bezos drove his Chevy Blazer across the country and picked Seattle.
“It’s not clear to me that we have that kind of appeal,” he said. “We’re obviously seeing some prominent people leave. Bezos is gone. Schultz is gone. Rich Barton’s gone. Gabe Newell’s gone.”
He pointed to a recent headline about former Amazon executive Dave Clark moving his startup to Texas, noting that Clark said the move wasn’t a diss on Seattle “and then he proceeds to diss Seattle for the rest of the interview.”
Highest unemployment, steepest housing decline
Fitzgerald said the warning signs are stacking up.
“We now have the highest unemployment in the country,” he said. “You guys just read a headline about we’ve got the steepest decline in the residential housing market. We’ve seen Starbucks and other companies. There’s just kind of a slow exodus.”
He said Seattle still has enormous advantages but that no city’s success is guaranteed.
“John Cook at GeekWire, his summary of the trip to Cleveland is they’re out to eat our lunch, and Seattle still has a ton of advantages, but everybody else is out to eat our lunch too,” Fitzgerald said. “Our success is not guaranteed.”
Fitzgerald said he’d like to hear from the mayor about plans to reduce the vacancy rate downtown, and from the governor, who he noted has acknowledged there is no economic plan for the state.
“Maybe we should get somebody else who could actually focus on those issues,” he said.
Seattle’s mayor and governor declined to visit Cleveland
Fitzgerald said he and Cook invited both Mayor Katie Wilson and Gov. Bob Ferguson to join them on the trip. Neither responded.
“We did not hear from either of them,” Fitzgerald said. “I assume they had other things that were a higher priority. But we’d love to talk to the mayor about what the plan is.”
He said the conversation he wants to have is simple.
“I would love to hear from the mayor, the governor, about why Seattle is not going to be the next Cleveland, and we’re going to spend 50 years in the ditch,” Fitzgerald said. “And it’ll be on them.”
Watch the full discussion in the video above.
Listen to John Curley weekday afternoons from 3 – 7 p.m. on KIRO Newsradio, 97.3 FM. Subscribe to the podcast here.



