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Chicago Nightlife Could Sparkle with New York’s Pitch Show Twist

Chicago Nightlife Could Sparkle with New York's Pitch Show Twist

By: John Glover (MBA)

As a young journalist in Chicago always on the hunt for the city’s next big thing, I recently stumbled upon a concept that caught my eye and could very well redefine our local nightlife: The Pitch Show. Born in the bustling streets of New York City, this unique blend of entertainment and entrepreneurship is quickly gaining momentum and seems tailor-made for Chicago’s vibrant and eclectic scene.

At its core, The Pitch Show is not just another night out. It’s a lively mashup of innovation and fun, turning the traditional business pitch on its head by placing it in a setting you’d least expect—a bar, complete with live music, food, drinks, and an audience ready to be both entertained and engaged. “It came from a few places” explains Alan Siege, the brain behind the concept. “I started attending business pitch contests back in 2015, and even though these events were beneficial, they were quite boring and exclusionary. That got me thinking—what if these pitches were judged not by a panel of experts but by a crowd of everyday people, in a fun and engaging environment?”

What sets The Pitch Show apart is its commitment to making entrepreneurship accessible and enjoyable for everyone—not just business aficionados. The audience plays a significant role, actively participating from the moment they walk in. Alan describes the experience, “The Pitch Show is an immersive experience. Right from the start, the audience is all in. From delivering The Pitch Show Cheer to winning drink tickets to knowing business terms, it’s a whole new world of interaction.”

Imagine sitting in a bar where the usual trivia night is replaced by energetic entrepreneurs pitching their hearts out, with the audience not just watching but actively deciding who wins the prize. “Couples, friends, or even solo attendees aren’t just spectators; they engage with the pitches, ask tough questions, and ultimately decide who gets the funding to propel their ideas forward,” Siege adds. This element of audience participation enhances the date night experience by adding layers of conversation, teamwork, and a dash of competition.

One memorable pitch that really highlights the diversity and impact of The Pitch Show was by Jermaine Smith, a NYC-based writer, director, and producer who used the platform to further his project that began as a stage play and evolved into a book and an indie film. “Jermaine’s story is a testament to what The Pitch Show is all about. His pitch wasn’t just a business proposal; it was his life’s work, aimed at making a difference through art” says Siege. Awarded first place, Jermaine plans to invest his winnings back into his project, showcasing the direct impact The Pitch Show can have on local entrepreneurs.

Looking to the future, Siege has big plans to expand The Pitch Show’s reach. “My first goal is to live stream every show so it can be viewed anywhere on the planet. We’re looking to bring The Pitch Show to new cities, engaging local communities and featuring local entrepreneurs” he explains. This expansion includes adapting the format to different locales, each bringing its unique flavor to the pitches and the entertainment, making each event distinct.

As someone who loves exploring Chicago’s nightlife and cultural scene, I know The Pitch Show would be a fresh and exciting addition to our city if it were to come here. Since it assures not only a great night out but would also provide an opportunity to participate in the thriving, creative economy of Chicago. The combination of entrepreneurial spirit, community involvement, and sheer entertainment value could make The Pitch Show a new staple for those looking to experience something different from their evening escapades.

If The Pitch Show sounds like your kind of evening, stay tuned. Because if you’re reading this from The Big Apple, the next show is right around the corner. On June 5th, the Pitch Show will be hosting their, “The Heat Wave Edition of The Pitch Show.” Tickets are available now on eventbrite. So grab your significant other, grab your friends and head on down to Sour Mouse for an evening you sure won’t forget. 

Published by: Holy Minoza

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