Did Akron Get Lucky Twice? (And Did It Run Out of Luck?)
I was walking with Rocky the other morning, talking about Akron.
We own two houses here. I’ve spent the better part of a decade fighting for homeless people in this city, and I like having homes somewhere affordable enough that I can help a few people find their footing.
But I’m not very optimistic about Akron’s future.
I look at Cleveland, Pittsburgh and Detroit and I see cities with more money, more institutions and more momentum to reinvent themselves. I’m not convinced Akron has any of that.
So I said to Rocky, “Maybe Akron becomes Calcutta.”
I was thinking about Mother Teresa. A place where hardship is so permanent that caring for people becomes the city’s identity. (That’s an unfair picture of Kolkata, which was a great industrial city and still is a huge one. But it’s the picture that came to mind.)
What if Akron just doesn’t come back?
And then I started thinking about how Akron got here in the first place. What if Akron got lucky twice, built a whole city around those two breaks, and has been living off them ever since?
Before Akron there was Middlebury, settled in 1807. It had mills and businesses before Akron existed.
Then the Ohio and Erie Canal came. Simon Perkins saw what it could mean. He and Paul Williams founded Akron in 1825 on the canal route, and by 1827 boats were running to Cleveland. Middlebury lost out, and Akron swallowed it in 1872. Today it’s one of the poorest neighborhoods in the city.
That sounds like luck. But Perkins didn’t sit around waiting for it. He saw what a new technology could do and he put a town right in its path.
Forty-five years later it happened again.
In 1870 B. F. Goodrich moved his rubber business from New York to Akron, because local businessmen talked him into it. Then came Goodyear, Firestone, General Tire and everything that grew up around them. Akron became the Rubber Capital of the World.
Between 1910 and 1920 the city went from about 69,000 people to more than 208,000. It tripled in ten years. By 1960 it was almost 290,000.
Today it’s under 190,000.
A whole city grew up around one enormous jobs machine. Then the machine moved away.
People are still trying. We have polymer research, the university, manufacturers, economic development offices. I just don’t know if any of it is big enough for what’s coming.
And then it hit me. I might be part of what’s coming.
I used to want 40 employees. Now I don’t want any.
By 2008 SageRock had about 20 employees and I was picturing 30 or 40.
Then the crash. Clients ran. I laid off everybody, some of them family. It hurt me, and it hurt them a lot more. I never wanted to do that to people again.
And honestly, managing people was hard even in the good years. Some of my employees were wonderful. Some weren’t. I once found out a talented guy hadn’t done any real work for one of our clients in six months. Six months. How did I miss that?
A couple of years later, in 2010, I bought an old hospital building at 15 Broad Street for what was left of the company. It was a lot more building than a small company needed. That turned out to matter, but I’ll get to that.
I’ve kept SageRock small ever since. And now AI has made small mean something completely different.
I sit on my couch with my MacBook and talk into Wispr Flow. I describe an idea, usually messily, and AI turns it into code, research, marketing, websites. A computer at home runs agents while I’m somewhere else. Work that used to take a room full of people gets done while I’m at law school.
For me, it’s thrilling.
For Akron, what does it mean?
I don’t need an office full of people driving downtown every morning. No desks, no parking spaces, no lunches at the place around the corner. My company can get a lot more productive and the city will barely notice.
When I talked this through with GPT-6, it pushed back. A company with five people instead of fifty hasn’t failed its city, it said. It might offer better services at lower prices. And Akron leaning on a few giant employers is exactly what made it so fragile.
Fair enough. But it also asked the question I can’t shake: when productivity goes up and local paychecks don’t, who gets the money? Business owners, customers and the AI companies will be fine. The people who used to have those jobs, and the city that used to tax them, maybe not.
So why do I even live here?
My customers can be anywhere. My agents don’t sleep when I sleep. I could work from Italy or the desert Southwest and nobody would know the difference.
I’m building out a camper van. With Starlink, a campground is an office. I’ve got friends in other parts of the country who’d love me to move closer. I honestly don’t know where I’ll end up.
But Akron gave me something huge: cheap housing.
I bought my house for about $103,000. It’s a duplex and I live in both units. My housing costs less than a lot of people’s rent. That’s what let me take risks with the business, go to law school, and help a few homeless friends get stable.
Funny thing. Zillow says it’s worth $284,800 today.
So even the one big thing Akron has going for it is slipping away. Good for me on paper. Not so good for the people I know living on $900 a month.
Akron has other good stuff too. The national park, the Metro Parks, the trails and the trees. Friends.
I like all of that. But I don’t have a ton of civic pride, and I’m not going to pretend I do.
Akron and I have some history. I’ll get to that too.
In 1912 F. A. Seiberling started Goodyear Heights because the factories had grown faster than the housing. He built it carefully, with real homes and real public spaces.
I once heard a story that a worker could drop a broken lawnmower at a shed in the morning and pick it up fixed after work. There were parks and places to gather. Was it paternalistic? Sure. When your boss owns your house, your job and your lawnmower shed, that’s a lot of power over your life.
But Goodyear needed people, and the people needed a neighborhood. The company and the community were tied together.
My AI agents don’t need houses. They don’t need parks or lawnmower repair. They don’t spend their paychecks at Acme.
So what happens to a community when the businesses that are succeeding don’t need people living nearby anymore?
Years ago I spent a week at Community First! Village in Austin, a permanent community for people who’d been chronically homeless.
I’m a camper, and it was the best campground I’d ever seen. Outdoor kitchens, gathering spaces, little homes that architects had obviously cared about. And the people living there were proud of it. That hit me as hard as the price.
I remember the founder, Alan Graham, saying the billionaires who fund the village and the homeless people who live there have one thing in common: everybody hates them. I’m going from memory, but I’ve never forgotten it.
Everybody there pays rent. You’re a neighbor, not a charity case.
I came home wanting to build that in Akron.
And I did, sort of. Just not the way I planned.
In January 2017 the city swept a homeless camp on the Freedom Trail, and people asked if they could stay at my place. That’s how Second Chance Village started, in the back of 15 Broad Street. That building that was too big for my little company? The basement became a day center run by homeless people. Out back we had up to 70 tents. The residents elected their own council. Everybody worked an hour a day.
It was the most beautiful organization I’ve ever been part of.
And the city shut it down.
City Council voted 8 to 4 against the zoning exception in 2018. The New York Times wrote about us. The Institute for Justice took our case, and we lost. We tried again, three or four different ways, and I ended up under a permanent injunction. One more tent and I go to jail.
I’ve said it before: every solution I’ve ever come up with to shelter homeless people ends up being illegal.
Then came 2023.
In May I ran for City Council in Ward 8. I knocked on thousands of doors on an e-bike. I lost 30 to 70. I lost precisely because they knew me.
In August my friend Hermaine Powell was shot to death in our yard, right where the tents used to be. Shot in the face. A little memorial grew up on the spot, like the ones you see tied to telephone poles.
After that the police finally came and looked at all the rumors they’d been passing around about me for a year. There was nothing to find. But they wanted the housing inspector in, and the house where our friends lived got closed. Another person with nowhere to go. Even the donut dumpster I raided every Sunday for church got locked.
That was the lowest I’ve ever been. I spent about a month fantasizing about drinking again, and about the different ways I could kill myself. What kept me here was Camus, the one goal I still had (a place, any place, for people with nowhere to go), and honestly Taco Bell. (Chances are there’s no Taco Bell where I’d be going.)
I sold 15 Broad Street in December 2024 to Robert Keith. He runs a music studio there now. I’m glad something good is happening in that building.
So when I say I don’t have a lot of civic pride, that’s where it comes from. I tried to give back to Akron in the most direct way I knew how, and Akron said no.
I still think about it though.
I know people living on $900 or $1,000 a month. Picture a beautiful little home for about a third of that, utilities included, with shared kitchens and neighbors who actually know each other.
That rent alone wouldn’t pay for it. Land, construction, insurance, upkeep and support staff all cost money. It would need donated capital and ongoing help. And not everybody wants to live in a village. Some people just want an apartment and a door that locks, and that’s fine.
But this is the part that ties it together for me. Goodyear built Goodyear Heights because it needed workers. Businesses like mine don’t need workers the same way anymore. So what if the people who are getting more productive than ever, with fewer employees than ever, put some of that back into a place like that? Not because they need the people. Because they live here too.
I don’t think that replaces real housing policy. A city shouldn’t depend on a few generous business owners to keep people housed. But it could be one more good option.
And it would have to be legal this time.
No, I’m not building a village right now. I’m growing SageRock, I’m in law school, and I’m helping a few people get stable. That’s where my energy is.
But this whole line of thinking changed the question I’m asking about Akron.
Simon Perkins saw a transportation revolution and acted. Local businessmen saw rubber coming and went and got Goodrich. Both of those technologies pulled people into Akron.
AI might do the opposite. It might let more and more people make a living without being anywhere in particular.
Maybe cities won’t just compete for companies anymore. Maybe they’ll compete for people who can live anywhere. Akron’s parks and trees and the people we love here could matter a lot. But cheap houses alone won’t make anybody stay, and our houses aren’t even that cheap anymore. People stay where they belong.
I don’t think it’s an entrepreneur’s job to hire people he doesn’t need. I don’t think one guy’s charity fixes a broken economy either. I don’t know what the answer is. I just know this technology is going to force us to figure out how a business and the town around it share in the wins.
I don’t have to love Akron to love the people who live here.
Maybe Akron didn’t just get lucky twice. Maybe it worked because people saw the world changing and imagined what their town could be.
The next opportunity won’t look like a canal or a tire factory.
Akron gives me the freedom to leave. I don’t know if it can give people enough reasons to stay.
I love you,
Sage
I wrote this with help from GPT-6 and Claude. The stories and opinions are mine.