Winter Garden resident Matt Sutton always has loved baking. 

He grew up making cookies, cakes and pies with his mom, and they would ramp up their production during the holidays.

That tradition has continued throughout Sutton’s life and now serves as a way to promote his job and immerse himself into the community. 

Sutton dresses up in a Cookie Monster outfit and takes his “cookie-distribution assistant” Barb Stewart, around Winter Garden one Friday per month to deliver fresh cookies and introduce themselves to businesses. 

Recipe for success

It all started last October, when Sutton was thinking about his business as a Realtor and Stewart’s job as a lender. 

They met through mutual friends when Stewart was doing local events at restaurants in Winter Garden. The business connection is what sparked their friendship.

“We had the idea to hand out cookies down here, a great way to kind of get our name out there, get in front of people and people are a little bit more welcoming when you’re dressed like a goofball versus someone in a suit,” Sutton said. “We tried it out to see how it would even take off and everyone’s been surprisingly receptive to it.” 

Stewart said when they were discussing the idea, she randomly asked Sutton, “Any chance you have a Cookie Monster costume?” 

And he did. 

Sutton had the costume from a previous Halloween when he dressed up as the Cookie Monster and Elmo with his daughter. So he dug through his closet to find the outfit, and Stewart grabbed a Cookie Monster hat to play the assistant role. 

Their goal was two-fold: meet business owners and promote their business. Stewart has an office in Winter Garden and spends much of her time downtown. 

“It’s a great way to meet people in the community to see if there’s anything that they need that we can help them with, without being overly sales pushy but also giving people a reason to smile,” Sutton said. “You get handed a cookie from one of us and it’s hard not to smile. It’s bringing smiles, making people laugh on a random Friday with no strings attached.”

They began preparing with places to go, and Sutton got to baking. 

Sweet venture

The mornings of their outings, Sutton wakes up early to bake chocolate chip cookies. 

“It’s one thing to hand them cookies, but I’m also very proud of my recipe, and I’m proud of what I do, so I don’t want to hand them bad products for the sake of saving time,” Sutton said. “I’d bake anywhere between 100 to 120 — just so we have enough to make sure we get all the different stores and people walking around.” 

All of his cookies are a different take on a chocolate chip cookie. He’ll bake them according to the season. For July, he made red, white and blue cookies. For Christmas, he makes a peppermint cookie.

After bagging up the baked goods, they head out to the town. 

When they walk into a business, they start by “kicking down the door,” Sutton joked. They open the door and enter if it’s not flooded with customers, instantly attracting the eyes and smiles of customers and employees. 

“It’s a hard miss,” Sutton said about his fuzzy blue costume with lopsided eyes that block his peripheral vision and his matching bright blue shoes. 

He holds a white tub with a cookie handle, stuffed to the brim with his fresh goodies, while Stewart holds the phone and wears her Cookie Monster baseball hat. 

Stewart works on introducing themselves and Sutton focuses on handing out cookies. It brings him joy to be able to share his passion for baking with the community and give people a reason to laugh during their work day.

“(Stewart) really helps when we go into different businesses, and she’s really great at that first initial conversation, talking to the owners, talking to people in the store and kind of, like, grabbing attention,” Sutton said.

After the ice is broken and cookies are delivered, they stay to talk about real estate and lending if the business has any questions, and they thank the owners for being a part of the community.

For the most part, they’ve had a positive reaction from businesses in their 10 months of doing this. They’ve picked up on the businesses that don’t really want the foot traffic and cookies, while others are waiting eagerly for their arrival. 

“We’re kind of like Santa Claus,” Stewart said with a smile.

When they visit a business for the first time, they’re met with curiosity. But when they walk into a place they’ve been to before, employees now greet the Cookie Monster with cheers and excitement. 

“My favorite part is watching some of the store’s employees come running up to him,” Stewart said. “The bike store the other day, they’re like, ‘We saw you walking down the road, and we were hoping you would come over and see us.’ It’s gotten to the point where they expect us, they just don’t know when we’re going to pop in.”

Stewart said it’s a team effort. She’s there to help film the social media videos and get the media out there. She’s learned how to edit for her job and has easily translated the skills for this venture. 

“We kind of have a sense of humor. We like to use it, and we’d like to show it through video and social media,” Stewart said.

They incorporate humor — such as Sutton throwing a shoebox at Stewart or driving around town in a side-by-side while wearing a Cookie Monster helmet. She’s enjoyed being able to catch employees’ joyful reactions to their arrival on camera, too.  

“We started as a business to get it promoted, but then it became more like now we’re doing it for fun, and we know eventually business will come from it,” Sutton said. 

They prioritize visiting the same businesses to build up repetition while also branching out to new ones. 

“It’s a lot easier to remember two people in a blue suit handing out cookies, against all the entire city of Realtors in the area,” Sutton said. “So it’s just something to help differentiate ourselves a little bit but also making people smile, it works out well.”

Cookies cause connections

Since starting this, Sutton has felt a lot more integrated into the Winter Garden community. He’s started to get invited to events like Polka Dogz Pet Rescue’s Reading with Kids Day, to which he’s brought his daughter. 

“I’ll walk into stores out of character and they still know exactly who I am,” Sutton said. “There’s a lot in the community that goes on that I feel more a part of now because I can actually wave to the different business owners and talk as opposed to just being a customer.” 

It’s also increased their engagement with residents in the area. 

As they’re walking along Plant Street, people often come up to them and ask what they’re doing and how it started.

“People will walk by and you can hear them say, ‘Cookie Monster,’” Sutton said. “They say it kind of low, and then I’ll turn around and ask if they want a cookie, and they’re shocked 100% of the time. 

“One place we went in, they were like, ‘I told my boss I saw a guy in a Cookie Monster outfit walking around downtown and he didn’t believe me,’” he said. When the boss saw Sutton’s outfit he said, “You do exist?” 

They said people never expect to actually be given cookies so those random encounters make their day. After they visit all of the businesses, Sutton will head over to Oakland and give utility workers any extra cookies to brighten their days, too.

 

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