We were lucky enough to talk with a few startup founders, budding entrepreneurs, and heavy-hitting influencers to get their take on what it’s like to be a startup in the Windy City.

The Supportive City

While Chicago isn’t a coastal city, its size has proven that it can hang with the big dogs. And while the coasts provide an incredible sense of accomplishment, the supportive environment in this Illinois city is unparalleled around the country. However, with rising real estate costs and a more competitive market, Chicago is making its case for a competitive powerhouse. Success stories like GrubHub and Groupon have created a surge of ideas and entrepreneurs trying to break into the market. And not everyone can have a piece of the pie. After all, there is only so much room at the top. While it has gotten more competitive, Chicago’s supportive roots have provided founders and employees alike with a community that wants to see them succeed.

Deep-Dish Funding

Sure, the pizza in Chicago is plentiful. But when it comes to funding, not being a major city has proven to make getting that essential capital a little difficult. Fortunately, investors in Chicago have realized that not living in a big city can be an advantage in certain rights. They’ve opened their wallets and found that a little Midwest charm can go a long way in facilitating growth outside of San Francisco and New York. In a city that values hard work and determination, funding is never too far away. You just have to be able to look in the right spot.

Culture in Chicago

As the little brother to large cities like Los Angeles, San Francisco, and New York, Chicago has always been viewed as “less-than” by coastal cities. This has cultivated a culture of tenacity and determination that shows them that Chicago means business. There is nothing that can hold Chicago down. This city knows what it wants, fights for what it believes in, and never takes success for granted. Because the people are what makes this city so great. Photo: Flickr / Roman Boed