When Jennifer Flynn decided to pivot from her career in senior care to buy a 200+ year-old hotel with five of her friends in Kingsville, ON, she had no way of knowing how successful that gamble would be. Flynn’s entrepreneurial journey with The Grove Hotel has taken a multihyphenate route, with the brand diversifying their revenue streams by adding non-core products, services and experiences to their offerings as they grow. This approach, along with hard work and Flynn’s clear vision, has been instrumental to The Grove’s success.

Here we speak to the co-owner of The Grove Hotel about becoming a multihyphenate operation, providing unique experiences for guests, the “cool kids” who work at The Grove, and what’s next for her expanding business.

On how The Grove went from a pet project to a multihyphenate business

My family’s senior care business was bought out by a public company, and I was ready for a new challenge. The opportunity to buy the hotel came up, and it seemed like a good fit for me. Hospitality is just another way to care for people, so I was confident that my skills would translate into this new venture. My partners and I aimed to inject some life into Kingsville’s downtown core by revitalizing the hotel. When we started out, our main goal was to undertake some serious renovations. The hotel dates back to 1854, and as you can imagine, the place needed a lot of work! We opened as an 18-room hotel in 2016, and things kind of snowballed from there. We subsequently opened The Grove Bike Company (an e-bike and cruiser rental shop), which came about when we were brainstorming how to get back on track regarding tourism in a post-COVID world. We have a huge number of awesome bike trails in Kingsville, so it seemed like a great idea to increase our offerings for our guests in that way, particularly because there are about fifteen wineries on the EPIC Wine route that can be accessed by bike. Then we opened up two coffee shops called Joe Hot+Cold, and The Grove Motel, which we opened in nearby Colchester, ON. It’s been a fabulous journey. It’s a family-run business — both of my kids work for us now. The most rewarding part for me has been seeing the success of what we’ve created and how it’s evolved.

On providing unique experiences for guests

All of our hotel rooms are unique, not one is the same. All of the furniture is different, the wallpaper’s different, and it’s the same at the motel. It’s not like anywhere you’ve ever stayed at before. Our goal is to give our guests a totally memorable experience when they stay with us. We just opened a suite at the motel called The Wink, which started as a honeymoon suite, but of course, I couldn’t just do a standard honeymoon suite! I was able to find a red heart-shaped tub, and that really led me to go full Austin Powers. It has kind of a burlesque feel, with disco balls, and a stripper pole.

Our guests love their stays with us, I can’t tell you how wonderful their feedback is. For five years in a row we’ve been presented with TripAdvisor’s Best of the Best Award, which is an award that’s based entirely on guest feedback. I’ve been told that it’s 1% of hotels in the whole world that get that recognition. So it’s a huge honour to have our commitment to providing unique hospitality acknowledged in that way.

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On staying weird with the cool kids

The tagline for the hotel is Stay Weird. It started with a neon light I found online, and it seemed to speak to the vibe we wanted to create. We have a photo of our team on our website that’s captioned “Stay weird with the cool kids.” That name developed because we were trying to think of a fun way to describe ourselves (that wasn’t “employees” or “team members,” which didn’t seem to reflect our vibe). One person said “Well, we’re the coolest kids around,” and we ran with that. We’re unabashedly eccentric, and even the emails guests receive before their stay are fun and quirky. Our branding is completely based on being fun, edgy and creative, and I think it makes us memorable. The guests really enjoy it, and they even write notes to thank us for their stay and refer to us as “the cool kids.”

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On how Square helps The Grove function as a multifaceted business

Before we got started with Square, we were really struggling as a business in terms of managing our monthly costs. The only way for a business to be successful, in my opinion, is to limit those monthly costs and fees. So we were looking to find a system that was easy to use and would benefit our business financially, while giving us the ability to use the same system across all of the areas of our business, from the cafés to the motel. Square seemed like a better fit than the payment processor we were previously using, which couldn’t give me access to the kind of financial information I wanted to be able to check on the fly. With Square, I get reports emailed to me every day. I can log in at any given time to see what the sales are. Plus, In the hospitality business, aesthetics matter, and Square’s hardware is awesome, super sleek and clean-looking, which is important in the hotel, but especially in the cafés.

Using Square has been a really easy transition. It has allowed us to function as a multifaceted business very easily. With so many businesses and products, it’s important to me that I can have a view into all locations and assess where I’m needed. With Square, even on my cell phone, I can pull up sales for our properties without actually being there. Because we’re a family business, I tend to be wherever it’s needed. Just to know, “Oh, that location’s very busy at the moment, maybe I should check in.” I love that aspect. Seasonally, Square is especially helpful, because we have a downtown property that is business-traveller focused during the week, and we have the motel in a beach community which tends to be busier during the weekend. Square helps us to balance our staffing needs at all of our locations.

On what’s next for The Grove

We are already adding to the offerings at The Grove Motel! We purchased the land beside us, and we are adding a Nordic spa. There will be pools, plunge pools, saunas and steam rooms, that kind of thing. We’re also adding a transportation component to what we offer. We purchased a van, which will transport our guests as a courtesy shuttle, going back and forth between Colchester and Kingsville, making stops along the wine route there. And I’d be remiss if I said I didn’t want to open another hotel. We’re currently looking at properties to complement our portfolio. Otherwise, I would love to have my own Netflix show — just putting that out in the universe! Whatever our next adventure will be, Square will be along for the ride as we continue to grow, because it’s easy, reliable and lets us do what we want to do and expand where we want to.