Three Trends, From Vader to Enlightened, & Big Names at a Little Paper
Small Cities Weekly | 10.24.2025
After a hiatus, Small Cities Weekly is back. I’m trying to get back on a weekly cadence and hopefully share some essays I’ve been thinking a lot about. I also have a new project in the works - more on that soon!
Three Trends
Here’s one way that you could imagine leveraging three current trends — the Silver Wave, employee ownership, and AI & automation — to kick start a competitive, authentic entrepreneurial scene in small cities.
Use the Silver Wave as an opportunity to transition the most competitive, longstanding local companies to partial or full employee ownership.
Go all-in on teaching employees “The Great Game of Business”.
Go all-in on teaching employees about the capabilities of AI and automation.
Experiment with implementing AI and automation in ways that improve the business.1
Find the issues that make adopting AI and automation difficult in that industry.
Fund standout employees as founders to solve those problems and sell the solutions to other companies.2
Implement employee ownership in these new firms.
Return to Step #2 & repeat.
Links
You can find links from this and all previous editions here.
From Vader to Evergreen: A CEO’s Journey to Enlightened Ownership, Mark Steele, Evergreen Journal
And so I started this crossing this threshold when I invested in Craftsman. Moving from short-term to long-term. Up to this point I was all about building my track record, and now it was about building a legacy. Rather than ‘me’, it was ‘them’. Rather than the firm, it was about the people. And rather than focusing on execution, it was really about care.
This is a really interesting first-person account by a private equity turnaround specialist on changing his mindset on what it means to build a meaningful company.
They Took Big Pay Cuts to Run a Little Paper, Steven Kurutz, NYTimes
The Villager was formed from the consolidation of four mid-coast newspapers — the Free Press, Courier-Gazette, Camden Herald and The Republican Journal. All were owned by Reade Brower, an eccentric figure The New York Times once called “the media mogul of Maine,” and whom Mr. Britt described as “a genius of postage.”
Mr. Brower, 68, built an empire on a direct-mail company he started in a shed behind his house in Camden. At one point, he owned six of Maine’s seven dailies, and more than a dozen weeklies. By 2023, he was ready to sell those papers, many of which were operating at a loss.
Mr. Brower hired Kathleen Capetta, a native Mainer and the former editor in chief of the local lifestyle magazine Down East, to analyze the newspaper operations and figure out the way forward. They decided the four papers he had retained would become one viable, moneymaking outlet, the Midcoast Villager.
The journalists have yet to figure out exactly how they will make this small paper survive in today’s market, but it’s a cool story of succession plans and the way that smaller cities can intimately invite people into big projects.
AI Will Not Make You Rich, Jerry Neumann, Colossus
The same caveat applies, however: If an app company can build a customer base or an amazing team, it might be acquired. But these companies aren’t really technology companies at all; they are building a market on spec and have to be priced as such. A further caveat is that there will be investors who make a killing arbitraging FOMO-panicked acquirors willing to massively overpay. But this is not really “investing.”
I love this take on business more generally. Building a company to last indefinitely is different than building an asset to get acquired. That goes for both VC and PE. And as the irony seems to always go, the way to build the most valuable thing to sell is to build it to never have to sell.
You can reach me at dustin@invanti.co if you want to chat more about the small city segment!
This is now driven by employees instead of blocked by them, because they own any gains in productivity that result.
This is now possible because your employees understand the game of business - see SRC’s track record on this front.