Our Guide to Entrepreneurship Development

The question I get asked most often by school administrators, community organizers, and economic development professionals is some version of: "how do I develop entrepreneurship in my community?" The question is too big to answer in one sentence. But after years of running Skypig and helping people build entrepreneurship programs in schools across the country I've worked with, I've come to think about it as a layered problem with three distinct pieces that have to work together.

This is the breakdown I'd offer anyone walking into the question cold.

The Three Layers of Entrepreneurship Development

The first layer is individual capacity. Real entrepreneurship development starts with developing the actual skills and habits of entrepreneurial people. This means programs that teach opportunity recognition, customer discovery, pitching, and resilience under uncertainty. It means giving people repeated chances to invent things, defend ideas, and respond to feedback. Without strong individual capacity, no amount of infrastructure produces founders. This is what most of my writing focuses on — pieces like the entrepreneurship mindset, the top entrepreneurship skills, and learning by doing all live at this layer.

The second layer is local community. Individuals with entrepreneurial capacity become founders much faster when they're part of a community of other founders, would-be founders, mentors, and supporters. Local meetups, pitch nights, coworking spaces, and recurring events create the social fabric that turns individual interest into actual ventures. Organizations like the Kauffman Foundation have documented the importance of this layer extensively — the "ecosystem" effect on entrepreneurship is real and measurable. My piece on how to create a local entrepreneurship group goes deeper into this layer.

The third layer is institutional infrastructure. This includes formal education programs, university entrepreneurship centers, accelerators, incubators, funding networks, and government policy that supports new business formation. Infrastructure alone doesn't produce founders — but without it, even strong individuals and active communities run into ceilings they can't break through. The interesting research from groups like Junior Achievement has shown that institutional support amplifies the effects of the other two layers, but doesn't substitute for them.

The mistake I see communities make most often is investing heavily in one layer while neglecting the others. A town builds a beautiful coworking space (infrastructure) but has no recurring events to fill it (community) and no schools developing entrepreneurial capacity in their students (individual). The space sits empty. Or a school invests in entrepreneurship curriculum (individual capacity) but has no local pitch competitions or founder meetups (community) and no local accelerator to graduate students into (infrastructure). The students leave for cities that have the missing pieces. All three layers have to develop together.

What I'd Tell a Community Starting From Scratch

If I were advising a community trying to develop entrepreneurship from a near-zero starting point, I'd push them to invest in the layers in roughly this order: individual capacity first, community second, infrastructure third. The reason is that individual capacity and community are cheap to develop, while infrastructure tends to be expensive. Communities that try to start with infrastructure usually run out of resources before they've built the demand for it.

The first concrete step is almost always a recurring event — a monthly pitch night, a weekly entrepreneurship meetup, a quarterly Shark Tank–style competition for high schoolers. The event develops both individual capacity (through practice) and community (through repeated interaction) at the same time. It costs almost nothing. And it generates the data you need to figure out where to invest next. My pieces on how to host a pitch competition and six steps to creating a pitch competition in your school are good starting points.

Once a recurring event is established, the next investment is usually education. Bringing entrepreneurship programming into local schools is the single highest-leverage move for long-term community development, because it changes the pipeline of who becomes entrepreneurial in the first place. Products: The Card Game is something I built specifically to give schools and community programs a reliable, ready-to-run format for this kind of educational work. My pieces on how to teach entrepreneurship education and a full curriculum for high school entrepreneurship class cover the educational layer in more depth.

Infrastructure investment — coworking spaces, accelerators, formal funding networks — should follow once the individual and community layers are producing demand for them. This is the order I've seen work in towns and cities that have actually built strong entrepreneurship cultures from a low base. The order matters. Get it backwards and you spend money on things nobody uses.

Entrepreneurship development isn't a single intervention. It's the deliberate, patient cultivation of three layers over years. Communities that understand this and invest accordingly produce founders. Communities that look for the silver-bullet program don't. That's the pattern I keep seeing, and it's the pattern I'd organize any development effort around.