When Thinking Outside the Box Pays Off

This week we talk with Amanda Scotese, owner and founder of Chicago Detours - a touring company that is always pushing the limits of what is expected to create an unforgettable - and more importantly, irreplicable - experience for their customers.

learn more about Emily Washcovick

By Emily Washcovick

Chicago Detours

Opinions expressed by Entrepreneur contributors are their own.

Behind the Review host and Yelp's Small Business Expert, Emily Washcovick, shares a look at this week's episode of the podcast.

Sometimes being an expert isn't enough. You have to find that something extra—the "X factor." On this week's episode, we speak with Amanda Scotese, owner and founder of Chicago Detours, a touring company that is always pushing the limits of what is expected to create an unforgettable—and more importantly, irreplicable—experience for its customers. That mindset enabled them to thrive during a pandemic when in-person tours had been out of the question. Because of that, our Yelp reviewer Michelle R. was able to experience the Chicago tour from her living room in Orlando, an offering Amanda wouldn't have ever imagined just one year ago.

Amanda started her business because she "wanted to offer a way for people to explore the city that was a little bit of an alternative from your standard mass tourism. [She] founded the company with a mission to bring specifically curious people to explore stories and places that locals don't even know."

It's her ability to uncover stories that are unknown to even Chicago natives that has led to her company's success. She puts in the work—asking questions and listening to the answers, all with the goal of curating tours full of information that can't be easily found through an online search, a tour guide, or a social media post.

As with many businesses, the pandemic threw a wrench in her plans—and a wrench puts it lightly. Her entire business was no longer possible. But instead of closing down, Amanda took her tours online, creating virtual experiences for the first time ever. Michelle R., came across Amanda's business because of her interest in Chicago, a place she'd never visited in person. An Orlando native, Michelle was able to "explore" the city virtually and is now even more enthused about the "Windy City."

Amanda took what was an exclusively in-person experience and transformed it into something entirely new that was just as engaging and successful. Chicago Detours now reaches people all over the world, creating an entirely new revenue stream and one that they'll continue to offer long after the pandemic eases.

Here are a few things you'll learn from this episode:

  • Find the most engaging way to tell your story. The deep-down appeal of Chicago Detours is that it tells exciting stories of the city and its people. This can also be applied to the way you tell your own story. Engage your customers by sharing more about your business—whether it's how you started or the purpose that drives you every day. Once you've figured that out, how can you elevate that message?
  • Think outside the box. It takes courage and determination to take a business that was reliant on in-person and flip it on its head to create an entirely new business model. Of course this same flip doesn't work for all business owners, but think about how you can use Amanda's pivot as inspiration when thinking differently about your business. Explore all angles.
  • Deliver something unique. There is nothing necessarily revolutionary about a touring company, but what sets Chicago Detours apart is its ability to give something unique to consumers—something that they can't get elsewhere. This applies to all business types. Think about how you can make your business offering unique. And even if you can't drastically alter the offering, think about how you can uplevel the customer service or better engage consumers. Maybe it's a carwash with a thoughtful card store and gift shop connected or a hair salon that offers virtual coloring services while clients wait to be back in person.

Listen to the episode below to hear directly from Amanda and Michelle, and subscribe to Behind the Review for more from new business owners and reviewers every Thursday.

To hear from more female entrepreneurs this Women's History Month, check out Yelp's Women in Business Summit taking place March 24-25.

Emily Washcovick

Small Business Expert at Yelp

As Yelp’s Small Business Expert, Emily is meticulously focused on helping local business owners succeed and grow. Her expertise lies in customer engagement, reputation management, and all things digital marketing. Through speaking engagements and thought leadership, Emily shares industry insights that entrepreneurs in any business category can leverage for the growth and well-being of their businesses. She is also the host of Behind the Review, a podcast from Yelp and Entrepreneur Media, where each episode features conversations with a business owner and a reviewer about the story and lessons behind their interactions.

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