As part of the work we are doing on the Small City Segment, we send out a brief weekly post of thoughts, links, and research in progress that reflect the week’s work. I’d love to hear from you if you have any thoughts, questions, disagreements, or things to add. Please forward this on to people you think might enjoy reading it.

Problem Discovery
It may come as no surprise that the most important asset I think small cities have to encourage more entrepreneurship is not co-working spaces, programming, funding, hip coffee shops, or frequent networking events. The most powerful thing we have is our own problems.
I’m not the first to say that entrepreneurship starts with finding a pressing problem to solve. It is a cliché in the startup world. Problems are the foundations of entrepreneurship - everything else is important, but none of it matters if a problem is not being solved.
Every place, industry, team has its own problems. If there are humans around, there are issues to be solved. Some entrepreneurs have a natural knack for spotting what these are and an intuition for how and why it can be a business. Others are more methodical, investigating something deeply and its context, and then choosing to act. Both paths work, just in different ways.
One hypothesis that Maria and I have is that if you’re short on the former profile, there might be ways to activate more of the latter. Our attempt to do this has been through what we as engineers know best - process.
The original purpose of this Substack (at the time called Frameworks, Inc.) was to share what we had learned about navigating this often underexplored part of the entrepreneurial process. Most startup advice will tell you that finding a problem is important and the first step, but not elaborate on what a “good” problem for a new company looks like and how to go about finding and evaluating them.
Over the course of a few years, we set out to find a way to do this. We are self-aware enough to know that this isn’t the only way to start a business and there is no reason to think it is the best either. It is a way that works for a certain profile of latent entrepreneur in search of a particular brand of problem.
Most of the subscribers that are here now were not around when we originally published our take on this, so I thought it might be a good time to re-share the posts and the downloadable frameworks for those interested in seeing if it is for them (you can also find all of this on our website under the “Our Process” section).
The outline of the process is:
Reflect on your skills, experiences, and curiosities
Look for contradictions - things that just don’t make sense, given what you know about the world
Define the opportunity - why is a better way possible?
Define the economic value that is unlocked by doing it in a new way
Define the scale and trends of the problem
Revisit #1 and gut check to make sure what you’ve defined is aligned with you
The hardest part of this process is that it’s more discovery than definition. You don’t always get to the other end of the process with a business opportunity that makes sense. That’s part of the game. Our goal with the process is to help founders (1) get started and (2) take more calculated risks by doing some upfront work before they’ve fully taken the leap into starting a company.
The best part of the process is that you need very little to get started. As you’ll read in the first post below:
This is probably the most exciting part of stumbling on the contradiction framework when it comes to encouraging entrepreneurship. Starting only requires two things: experiences and curiosity.
Below are a list of essays that correspond to each of the steps above. They are best read in order and together before trying to circle back and give any one of them a try. (The only deviation from above order is that I’ve put the founder reflection essay last below - you’ll see why as you read through them).
We’ve also created digital frameworks with activities, video and written explainers, and outputs for each of the above steps. You can find links to those below. Once you submit the form, you’ll get email instructions on how to make your own copy (all free, no spam).
My favorite feature of entrepreneurship is its aspiration to be permissionless.
This is an asymptotic goal - always more to do, never truly finished. At any given time, it is more and less permissionless for different people and the way one wants to build a company is not always the route available.
But unlike many other professions, there is no credentialing needed (even if it is sometimes helpful), no test to start, and no hiring process to navigate.
Our aspiration with these frameworks is to contribute in our own small way toward a world in which nothing stops you from noticing a problem, finding a better way to solve it, and offering that solution to those who need it.
Links
You can find links from this and all previous editions here.
Tornadoes Are Coming in Bunches. Scientists Are Trying to Figure Out Why., Delger Erdenesanaa, NYTimes
In the 1950s through the 1970s, on average about 69 percent of tornadoes in the United States happened on days with fewer than 10 tornadoes, and about 11 percent happened on days with 20 or more tornadoes. These percentages have shifted significantly in recent decades, according to a 2019 study. The researchers found that since 2000, on average only about 49 percent of tornadoes have happened on less busy days and about 29 percent have happened on days with 20 or more tornadoes.
Tornadoes are scary and destructive and usually wreak their havoc on smaller towns and cities. The fact that they may not be changing in number but in distribution is a pretty wild phenomenon.
Is Hunterbrook Media a News Outlet or a Hedge Fund?, Clare Malone, The New Yorker
For now, Hunterbrook’s biggest challenge is one familiar to most newsrooms: finding enough stories to sustain its business model. But in its case there is arguably an even higher degree of difficulty. To be profitable, Hunterbrook needs stories that are both open-source and powerful enough to move markets. “My biggest concern is that we do really exceptional work, we open-source a lot of valuable information, but that we’re not able to do that sustainably for years,” Horwitz said. In a few recent investigations—including stories about companies doing business with Myanmar’s junta—Hunterbrook did not trade on their information, presumably because the reporting either contained non-public disclosures or couldn’t be leveraged for a return on the market. “I’m not asking people to trust this new model,” Horwitz told me. “It needs to prove itself.”
Here is another iteration of new business models for journalism - in this case specifically investigative journalism. I don’t know how this could or would impact journalism on a more local level, but it is interesting to see the issues that arise when tying new financial models to it.
Cities and Ambition, Paul Graham
Great cities attract ambitious people. You can sense it when you walk around one. In a hundred subtle ways, the city sends you a message: you could do more; you should try harder.
The surprising thing is how different these messages can be. New York tells you, above all: you should make more money. There are other messages too, of course. You should be hipper. You should be better looking. But the clearest message is that you should be richer.
What I like about Boston (or rather Cambridge) is that the message there is: you should be smarter. You really should get around to reading all those books you've been meaning to.
When you ask what message a city sends, you sometimes get surprising answers. As much as they respect brains in Silicon Valley, the message the Valley sends is: you should be more powerful.…
How much does it matter what message a city sends? Empirically, the answer seems to be: a lot. You might think that if you had enough strength of mind to do great things, you'd be able to transcend your environment. Where you live should make at most a couple percent difference. But if you look at the historical evidence, it seems to matter more than that. Most people who did great things were clumped together in a few places where that sort of thing was done at the time.
…
So far the complete list of messages I've picked up from cities is: wealth, style, hipness, physical attractiveness, fame, political power, economic power, intelligence, social class, and quality of life.
My immediate reaction to this list is that it makes me slightly queasy. I'd always considered ambition a good thing, but I realize now that was because I'd always implicitly understood it to mean ambition in the areas I cared about. When you list everything ambitious people are ambitious about, it's not so pretty.I found this an interesting prompt - what message of ambition does your city send? What do you want it to send?
If you…
are interested in building for the small city segment…
are already building for the small city segment…
know someone who might be/should be building for the small city segment…
want to contribute expertise to problem profiles…
or want to help us expand our network in small cities…
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