When Thinking Outside the Box Pays Off

MICHELLE: I had interest in Chicago because I’d never been there before, and it’s on my list. And also I like to go to other cities and see the uniqueness of it through the local’s eyes versus those tourist attractions that you can always just Google. It’s that local experience that makes it unique. And that’s what I was looking for.

EMILY: That’s Michelle. She’s a reviewer living in Orlando, Florida, but she’s telling me about a virtual experience she had with a business in my neck of the woods—Chicago Detours. I met the owner of this business, Amanda, a few years ago when I first relocated back to the Midwest. She attended one of my Yelp for Business events, and I was instantly impressed with her business model and the unique offerings they brought to the world of city tours and experiences. I personally had the pleasure of going on their Fulton Market Meats tour with a dozen local business owners back in 2018. The tour was such an EXPERIENCE! We learned all about the development of Chicago’s meatpacking district and how it’s evolved from a place of warehouses and production to its current state—a destination in the city, housing restaurants, offices, and local businesses. The differentiating factor in the tour was the guide and the history being shared. We weren’t simply stopping in places, grabbing a bite and continuing on. We were learning about local places and hearing tales of rarely shared history.

The pivots they have made since the beginning of the pandemic have been extraordinary. A business built on leading people around a city in person has now shifted entirely online and is somehow still creating the connections and excitement they generated in person, but through Zoom. Let’s hear Michelle’s review.

MICHELLE: As a food tour enthusiast, I was not sure how a virtual tour could compare. From the host to the amazing stories behind the city, I cannot wait to spend some time in Chicago exploring. I am super excited to participate in their other tours because it left me wanting to learn more. Price for admission is definitely worth the amount of knowledge that was shared, and kudos to your team for putting together a great presentation.

EMILY: Being someone who experienced Chicago Detours in person, I read Michelle’s review and knew that their expertise and differentiating factor had translated through to their new virtual offerings. Here’s owner Amanda sharing how Chicago Detours came to be and what her initial goal was in starting the business.

AMANDA: I started Chicago Detours in 2010. I had been working in travel for about a decade and I was in love with the city of Chicago. And most of all, I wanted to offer a way for people to explore the city that was a little bit of an alternative from your standard mass tourism. So I founded the company with a mission to bring specifically curious people to explore stories and places that locals don’t even know. The hidden areas can either be somewhere that a tourist or a local might not normally end up, or it can also be right in the heart of the tourist area. We would share unique angles on stories of famous sites, the kind of forgotten histories behind these famous places. We’ve designed so many different tours. A lot of them would incorporate food and the story of food, some of them might have drinks. We would always make them interactive on some level so that it wasn’t just a person with a giant flag and sign and people kind of following them around like lemmings. It was really a much more personal and authentic kind of experience of Chicago.

EMILY: So much goes into these historical and engaging experiences. Much of what the Chicago Detours guides share is not information you could find online. It’s not the commonly known stories behind a city or business’s history. And the creation of the tours in their explorative way (pre-pandemic) allowed them to give a more engaging experience now that they are on Zoom.

AMANDA: So I think that we really create an exciting connection between the viewers and the locations and the stories behind the locations that we tell through a few different ways. What I would do when telling the stories of historic bars and restaurants and everything, I would contact the owners themselves. And I just ask lots of questions and try to figure out where the story is, what are also the visual aspects of the site that tie in with those stories so that I can be sharing the images and be able to say—here’s this painting at Simon’s Tavern in Andersonville, and you can see Simon himself in the painting. Fun, little details like that. It’s sharing the kind of stories that I think often small business owners don’t realize that people want to hear about and the kind of stories that haven’t necessarily been written about.

You’re not going to find that so easily from a tour guide book or a social media post, the different ways that people search for information now when they travel. We like to look at ourselves as detectives, and we go hunting for good stories. And that could be from an idea that came from an academic article to a history book to a video to talking to the people who have really lived that history.

EMILY: Creating a memorable and engaging tour experience has so many more components than I thought. Amanda didn’t start this business by researching famous landmarks online and putting together packets of factoids for her employees to memorize. She connects with local business owners and hears their personal stories. Going a layer deeper and putting together various resources to give texture and color to the stories that they’re sharing. It’s not a presentation of wikipedia facts. It’s an expression of a city’s history through small business stories and hidden walking paths.

Since so much of Amanda’s success comes from telling great stories of local businesses, I asked for her advice when it comes to how business owners can best tell their own stories.

AMANDA: I love this question. Every business has a story to tell, and you need to start out with the basics. A story has to have characters, a setting, and there has to be some sort of a conflict to really make it into a good story.

And I think that people love hearing the behind the scenes—the real story that goes on. I think historically it would be like, no, we’re a professional business, and here are pictures of our perfect restaurant and everything. But people want to see the mess that’s left over afterward. They want to know about your struggles as a business owner. They want to know about your failures and your successes and what you’ve learned and how you’re evolving as a business owner. In sharing those stories, the more transparent people can be, the more that they’re going to gain loyalty from their customer base because they’re hitting people on a personal level.

And I think anyone from a dry cleaner to a restaurant to a DIY store to a nail salon, there are stories to tell.

EMILY: Every business has a story to tell. I know that to be true from my personal experience as well. Amanda and her team have a craft for sharing stories in an engaging and entertaining way. Serving those specifically curious people as Amanda called them. Those who maybe want to see more than “The Bean” when they’re in town. People like Michelle.

MICHELLE: My husband and I are young empty-nesters—or at least I’d like to think that I’m a young empty-nester. And so we try to plan something every couple of months. An adventure. Where are we going to go? Just to keep things interesting in our lives. And with this COVID, it’s been a little hard to do that, but doing the virtual tours has kind of fulfilled that a little bit.

We can still stay safe but still gain the knowledge, and then think about places where we want to go and make that plan. Because as soon as travel restrictions are up, my list is ready to go. I’m ready to go to Chicago, and I’m going to hit every single one of those places that were recommended.

EMILY: I’ll be honest with you, I don’t know that the concept of a virtual tour is something that would pique my interest pre-2020. But here we are.

AMANDA: So March of 2020, of course, a surprise for us all. Our first inclination was, we’re all going to be online, and we’re all going to be looking for diversions from the extreme situation that we were in. And what we had to offer as tour guides are stories about Chicago. People were cooped up in their homes and not aware if they really could leave and what you could do. And so we just started. We’ve got a team of people who have, collectively, probably about 50 years of experience of being tour guides. So we have all this knowledge of Chicago history and neighborhoods and architecture and food and historic bars and you name it. So we just set out to share that with people, and we just threw together images and media and video and just dived right into Zoom.

It was a little crazy. We just did it and learned by doing, and it was awesome actually because since we adopted it so early, people were incredibly grateful that we were doing it, and they were also incredibly supportive and patient with mistakes that we made along the way.

EMILY: In the midst of chaos, Amanda leaned into what she knew her business did best: tell great stories about a place people love. As Amanda suspected, people like Michelle were looking for diversions and distractions in those early days and weeks of COVID, but her business has sustained beyond those early days because of the high quality product they’re presenting. They’ve been able to reach a global audience and have opened up a revenue stream that they will maintain even after the pandemic eases. Being forced to upend everything they knew about in-person tours created a virtual option that increased their customer base to remote corporate groups, universities, and even just family or friends who can’t be together physically.

Chicago Detours isn’t just Amanda. Like she mentioned, her team combined has probably over 50 years of experience in the industry. I asked her about that process and how she’s been able to find tour guides that meet her standards for the types of experiences she researches and creates for clients.

AMANDA: It’s absolutely been a challenge to find people who balance both the knowledge that they have of Chicago history and architecture with a passion and a love for sharing it with others. And so we’ve always hired people who have a background as educators and not necessarily entertainment or comedians. Historically, a lot of tour guides would come from that path. We’re just fun people. We really looked for people who had a background as educators who can explain, make high level concepts, be something simple and accessible for people—who can make learning interesting and fun and who really know their stuff. So I created an entire training program. I believe it’s the most rigorous tour guide training in the city in that it had more to do with really being a good tour guide, which is a blend of knowledge, presentations skills, interpersonal skills, customer service, attention to detail, and more than just learning facts about architecture. So we have managed to really be able to bring on who I think has been the most awesome team of tour guides in the city.

EMILY: Amanda has grown her team over the years through a set of desired qualities she’s looking for when she’s hiring as well as a training program that helps develop and educate her employees once they’re on board. The personality to not only have knowledge about the city of Chicago but an interest in sharing that knowledge with others. Because her team was built with these values in mind, the company’s transition to virtual experiences was well received by customers digitally as well.

MICHELLE: I feel like they’re very knowledgeable. The history that they provided. It was stuff that I had never heard before. And it wasn’t something that you could just go online and find out. You had to physically live there. Physically have to be involved in that community to know that knowledge. And that’s what I think is kind of cool. They make it interactive. You’re allowed to ask questions. The question asking is really, what’s kind of fun about it. And then you get involved with them, and then you ask questions, and they’re like, “Oh, I know the answer to that, but I didn’t think that that would be important to anyone.” But it is! So that’s kind of fun.

So if they offered something else or if they have other tours, I would like to see what they can bestow upon me. So I look like I had that kind of knowledge too. When I get there, I’ve never been there, but hey, if you’re going with me, I’ve been on that tour. So let me show you around, so that’s what I like.

EMILY: If you go look at the reviews for Chicago Detours, you’ll notice these same themes mentioned throughout. From pre-pandemic to the current day, people are connected to the unique and local experiences shared through small business stories. Amanda looks at reviews to ensure these patterns are being felt consistently by customers. She also shared with me some insights she’s found in her years of engaging with her online reviews.

AMANDA: Reviews have been everything for us in supporting our business. I highly doubt that anybody buys anything online anymore without looking at a review and especially when it comes to experiences. I think that—and I know that—people will check on all the review sites to look for legitimacy and consistency. Because you can find five stars on one site and then you go to the other and it’s two, and a big red flag goes up. So reviews have been enormously helpful for us.

One surprising thing about reviews that’s helpful is that sometimes people make us realize things about our products that we didn’t even know. Sometimes they help us with our marketing terminology. You know, they give us feedback either on the accuracy of it or they end up wording something in a way where we’re like, oh, that is a great nugget. We’re gonna use that.

That feedback is a crucial part of running a small business. And I think sometimes small business owners get fixated on keeping up the 5-star review and the quantification of it. But actually reading those reviews is so valuable, making that feedback as part of your whole loop and how you create your products and how you offer your service and how you really strive to be the best in what you do.

EMILY: To pause and ask yourself if there is any insight you can possibly take from a review – good or bad! To especially look at critical reviews or reviews with feedback as a chance to understand your business from the consumer’s perspective.

Contrary to popular belief, reviewers are sharing their positive experiences far more than their negative ones on Yelp. Here’s Michelle sharing why she specifically has written an overwhelming amount of positive reviews.

MICHELLE: I feel like there’s enough negativity in the world that I try to be positive. So if there’s a local business or there’s something that I really enjoy, that I feel like other people would enjoy, I review it. It’s one of those things, if you don’t have anything nice to say, don’t say anything at all. So I try not to do any negative reviews because who does that serve? My taste may not be the same as somebody else’s tastes, but if it is, it’s worth putting it out there, hoping that someone else will have the same experience that I’ve had.

EMILY: To close out, I wanted to let Amanda share some of her experiences as a female entrepreneur.

AMANDA: I got into being an entrepreneur because I couldn’t imagine doing anything else really. I mean, it was just what I had to do, and I never really thought a ton initially about being a female entrepreneur. It’s kind of been over time that I’ve started to understand better what it means to be a female entrepreneur. And I think that there is an element of collaboration that is very innate for women, that is a part of being a business owner, that I think has helped in my success.

But the exciting thing for me is that, as there are more female entrepreneurs, it builds on itself, and those women connect with other women and support one another. And I think it’s a very exciting future for female entrepreneurs.