Cities tend to think they’re competing over companies, tourists, residents and investment. They’re also competing over people with ideas. The restaurant someone wants to open can go somewhere else. So can the development. So can the startup. So can the young person who wants to build something. Capital is mobile, but ambition may be even more mobile.

Spend enough time around ambitious people and your definition of normal changes. Spend enough time around people who complain about everything and that changes too. The dog-owner thing (people looking and acting like their dogs) is funny because there’s a serious idea underneath it: we absorb our surroundings. Choose them carefully.

A vacant property registry sounds like incredibly boring municipal policy. Until you think about the information problem. Who owns the building? Where does the owner actually live? How long has it been vacant? Are taxes current? Are there violations? Has anyone spoken with the owner? Is the property getting worse? A city can’t solve a downtown vacancy problem it hasn’t even bothered to inventory. Sometimes innovation starts with knowing what you actually own as a problem.

Went downtown for pizza tonight and some parking was $25. That’s more than the pizza. The place looked empty. We left. The interesting part wasn’t the price. It was what happened next. We drove somewhere parking was free and the restaurant was packed. Cities spend enormous amounts trying to attract people downtown. It might be worth asking how many they successfully attract and then price right back out.

There’s a reason car dealerships occupy so much land, and it isn’t because you need 14 acres to sign paperwork and take a test drive. It’s inventory. 100’s of automobiles sitting outside waiting for somebody to buy them. If cars can eventually move themselves between inexpensive storage facilities and customer-facing dealerships, why would all that inventory continue sitting on some of the most expensive commercial frontage in town?

Maybe the question cities should ask about a vacant building isn’t simply, “Why hasn’t the owner fixed it?” Ask whether doing nothing is currently a rational financial decision. If carrying costs are low, enforcement is minimal and everyone else’s investment keeps increasing the value of the property, waiting might make perfect sense. That’s the problem I’d want to fix.

If I were evaluating a city for economic development, I’d want to know something that probably isn’t in its strategic plan: What happens there when someone tries something unusual? Do people get curious? Do they immediately explain why it won’t work? Do they help improve the idea? Do they resent the person for potentially making money from it? That culture probably tells me more about the city’s economic future than another “business friendly” slogan.

Every city has a list of things everyone agrees should eventually happen. Those are the ones I’d look at first. If everybody agrees, why hasn’t it happened? Sometimes the obstacle isn’t money, politics or public opposition. The project has simply lived on the “future” list so long that waiting became normal.

A downtown isn’t really a collection of independent businesses. It’s closer to one enormous product with hundreds of different owners. One restaurant affects the street. One beautiful building affects the block. One vacant storefront affects the businesses beside it. Which makes downtown revitalization unusually difficult. You’re trying to improve one product without anyone actually owning the whole thing.

Some discussion on prediction markets in politics with @commander_news @Newsweek newsweek.com/vivek-ramaswamy…

Every great local business started with somebody thinking they could do something better than what was already there. Better pizza. Better coffee. Better hotel. Better store. There’s actually a little arrogance required in entrepreneurship. You have to believe people will choose you. Cities that want entrepreneurs probably need cultures that give people permission to think that way.

Here’s a weird economic development thought… Instead of asking what businesses you want to recruit, ask what kind of people you want walking around downtown 5 years from now. Entrepreneurs? Artists? Families? Students? Retirees? Build for the people and eventually the businesses start resembling them.

Restaurants may be one of the most underrated forms of economic development. A really good restaurant can convince someone to drive 20 miles to a neighborhood they otherwise had absolutely no reason to visit. Now they’re there. Maybe they get a drink somewhere else. Maybe they walk around. Maybe they see a store. Maybe they come back next weekend. Enough good restaurants in a small area and eventually people stop saying they’re going to a particular restaurant. They start saying they’re going to the neighborhood. That’s when things get interesting.

I wonder how many downtown turnarounds really began with a comprehensive strategy and how many began because one slightly irrational person looked at a building everyone else ignored and thought, I can make something out of that. Then someone else noticed. There’s probably more economic development happening that way than we give credit for.

Myth: More homes = more traffic chaos. Reality: Dense developments near jobs/shops mean shorter commutes & fewer cars overall. Blocking them forces sprawl, which actually clogs highways. Evidence shows infill eases congestion; let’s embrace it!

I’ve always laughed at couples who start dressing alike and people who somehow resemble their dogs. Then I started thinking about neighborhoods. Live somewhere beautiful and well maintained long enough and you start expecting beauty and maintenance. Live around neglect long enough and eventually some of it becomes invisible. Environment trains expectations.

There might be no better tourism advertisement than seeing people who actually live somewhere enjoying themselves. A crowded neighborhood restaurant does more for me than a restaurant billboard. People walking downtown do more than a downtown slogan. Families using a park do more than a professionally produced video about quality of life. People are remarkably good at recognizing when a place is genuinely working.

Here’s a city planning question I hadn’t considered before: Why does a parking lot have to do only one job? If we’re already spending the money to build it, could the same property provide parking while also storing stormwater underneath, adding shade and taking some pressure off the drainage system during a major storm? Cities of the future are going to have to squeeze more usefulness out of the infrastructure they already have. Parking lots seem like a pretty good place to start experimenting.

The strongest brand statement a city can make isn’t a slogan about innovation. It’s letting people see innovation actually happening. Construction fences. New restaurants. Restored buildings. Experiments. Entrepreneurs trying strange things. Public spaces full of people. You don’t have to tell me your city has momentum if I can see it from the car.

There is something strange about asking a consultant to bring you new ideas while writing 70 pages explaining exactly what you want them to do. I’ve responded to enough RFPs over the years to know what firms eventually learn: answer the question that was asked. Even when you think there may be a better question. That’s completely understandable from the city’s perspective. Government needs specifications, accountability and a fair way to compare proposals. But there has to be some room in the process for a firm to say, “We understand what you asked us to do, but based on our experience, we think you should consider doing this instead.” Otherwise we may be hiring experts and then rewarding them for agreeing with us.