There’s no denying that Middle America is a large place—heartlanders have been known to take multi-day car trips without blinking an eye. However, there are several cities that are much closer together than your standard five-hours-to-anywhere drive. Indianapolis, Indiana, Louisville, Kentucky, and Cincinnati, Ohio are three regional metropolises within just two hours’ drive of one another.

In addition to their proximity, these three cities have something else in common: thriving entrepreneurship ecosystems. Individually, these cities each have impactful entrepreneur success stories. The sale of ExactTarget in Indianapolis helped jumpstart the city’s technology sector, Louisville entrepreneurs grew Humana into a Fortune 75 company, and Cincinnati boasts one of the nation’s fastest-growing startup scenes.

Despite these successes, it is no secret that mid-American cities are facing daunting challenges: most cities throughout the region are dealing with fraying infrastructure, workforce misalignments, and a lack of resources. Given this, it has become imperative for entrepreneurship ecosystems to collaborate, support, and learn from each other. Below, read up on why entrepreneurs and entrepreneur ecosystems in Indianapolis, Louisville, and Cincinnati should join forces and work together as much as possible.


This may seem obvious, but it tends to be overlooked. Given that each city is in a different state, the perception is that they are further apart than in reality. The three cities form a triangle—with only two hours between them—meaning entrepreneurs can easily capitalize on all three metropolitan markets. The Cincinnati metropolitan area is the largest, with a population of just under 2.2 million, while Indianapolis edges slightly over 2 million and Louisville checks in at 1.3 million, for a combined total of over 5.5 million people.

Indianapolis, Ohio, Louisville map

Not only do these cities present accessible markets for entrepreneurs, they are also resources for companies in search of commercial partners, producers, or talent. Each city has different strengths that can be leveraged, and for entrepreneurs, it can be useful to know who is in your neighborhood before reaching out further. Business relies on strong relationships, and being able to easily meet in-person is a combined strength for Indianapolis, Louisville, and Cincinnati.

Entrepreneurship Best Practices

As the saying goes, knowledge is power—and when it comes to entrepreneurship, this certainly holds true. In Indianapolis, TechPoint promotes and develops the local tech sector, with programs such as Sales Bootcamp and the Mira Awards. Cintrifuse connects startups with venture capital and “BigCo” partnerships in Cincinnati. In Louisville, Endeavor has been operating since 2015—we’ve already selected 11 companies from Kentucky, Indiana, and Ohio to join the highly-selective global network of entrepreneurs. All of these organizations support entrepreneurs, create programs, and help business owners discover insights and best practices in their home cities.

As each city discovers new ways to support entrepreneurs and foster startups, sharing these insights is invaluable. Not only can these ecosystems learn from each other, entrepreneurs in the three cities have the opportunity to share their experiences and learn from peers facing similar challenges. Each ecosystem has generated successes and failures, and sharing these experiences is vital to the collective growth of the region.

“We are seeing more and more ‘middle-of-the-country’ corporations investing in the discovery and support of people developing new ideas, products, and thought…[This support is] now coming from localized talent and leadership capital that exists in our own backyard,” said Jonathon Erwin, the founder and CEO of Red e App. “And frankly, it’s wildly gratifying.”

Shared Industries

Middle America is known for several large industries, particularly agriculture and manufacturing. This certainly holds true for Indiana, Kentucky, and Ohio. However, in addition to these well-known industries, technology, healthcare, life sciences, and more are becoming increasingly more important to the region. Technology in particular is an industry that is continuing to disrupt and permeate many other industries and sectors—all three cities have seen growth in technology companies and investment. Given the similarities in key industries, the three cities are simultaneously impacted by advances in technology, industry shifts, and other external factors.

As entrepreneurs in these three cities continue to build and grow businesses, there is a strong case for why they should work together. Collaboration between Indianapolis, Louisville, and Cincinnati can help attract top talent to the region, create more jobs, and foster the growth of entrepreneurs in key industries. Proximity, shared best practices, and mutual industries are just a few of the many reasons why the region can benefit from collaboration. Indianapolis, Louisville, and Cincinnati all gain from strong entrepreneurs—and working together will only multiply this success. 

If you’re a high-impact entrepreneur and want to learn more about the Endeavor network, reach out to us via our application page. We’d love to hear from you!