The Venmo Challenge surprises two lucky Wayland restaurants


Credit: Screenshot from TikTok's Venmo Challenge

Employees at Wayland’s Dudley Chateau and the Villa were graciously tipped $500 on Friday, Feb. 5 as part of the famous trend, the Venmo Challenge. “It was a fantastic surprise, and it was very much appreciated,” employee Stacey Keating said. “We split it between the waitstaff working, and we were ecstatic to receive the tip.”

Tess Alongi

Since the start of the pandemic, over 204 million videos have been made on TikTok with the hashtag “Venmo Challenge,” a challenge in which someone gifts a substantial tip to their server at a restaurant. When Jillian Kaplan first saw this challenge, she saw people doing it on a national level, but it didn’t seem very personal to her. With the help of Kiat Cormier, the founder of the Facebook group, “Chew on This,” she was able to bring this challenge to a local level.

Like many other local chefs, COVID-19 has greatly affected Cormier. He has made it his mission to donate his time and money to help other local businesses through these tough times. Six years ago, Cormier founded the Facebook group “Chew on This” because he enjoyed food and going out to dine. The group is a place for people to talk about local restaurants and give recommendations. Cormier never expected the group to gain as big of a following as it does today.

“When COVID-19 first started, I only had 900 members and never thought it would grow more than 1,000 members,” Cormier said. “Now, we are at 12,500 members.”

Kaplan, who liked food, wanted to learn more about local restaurants. She enjoyed what the group was doing, so she reached out to Cormier in hopes of lending a helping hand. When she first reached out to Cormier, Kaplan offered to help with making a logo, T-shirts and sweatshirts, so people would recognize his group. Soon, Kaplan’s help prospered into something greater.

“I think a lot of people have offered to help [Cormier] but [don’t] actually follow through,” Kaplan said. “So when he said ‘I could use some more help, are you interested in doing more stuff?’, I was like ‘sure’,” Kaplan said.

Kaplan had the idea to bring the Venmo Challenge to ‘Chew on This.’ The Venmo Challenge has been making its way around TikTok, and it entails someone giving a hefty tip to their server. This challenge started during the pandemic as a way for individuals to help different restaurants by bringing smiles to the faces of people who were working through a tough and unusual time.

“[The] Venmo [Challenge] was something Jillian Kaplan saw on TikTok, and as an admin that helps me, I let her kinda do her own thing,” Cormier said. “[I] never thought it would go past a week or so, but now we are about to be on week seven, and I love how generous everyone has been.”

Jillian Kaplan

Kaplan, like Cormier, did not expect this challenge to continue for weeks, let alone months. When Kaplan first posted about this challenge, she expected it to be a one-time thing and raise only modest funds. Now, the group does the Venmo Challenge weekly and has given away $3,500 cumulatively to numerous restaurants. Currently, the restaurants which have received the tips are located in Natick, Framingham, Holliston, Wellesley, Marlborough and Wayland with Medway, Milford, Ashland, Sudbury, Southborough and Waltham on the list to come next.

“I have no idea [how we raised so much money] to be totally honest,” Kaplan said. “When we started, I said ‘let’s try a week, and see if we can get 100 bucks,’ and then we hit $500 within days. I post the video every week of where we go, and I think that that gets people excited because they are like ‘that is so cool!’”

Each week, Kaplan announces what town the tip will go to but does not disclose the specific restaurant. Instead, she waits until she goes to the restaurant and then posts a video of the staff’s reactions on Facebook. Although there is no exact science to it, there are a couple of things that Kaplan looks for in the restaurants that she gives the tip to.

“I look at restaurants that support and engage with the page so that [I know] that [the restaurants both know] that we exist and [what] we do. [After that], honestly a lot of it is arbitrary,” Kaplan said. “If I see fans are loving the page and certain restaurants or towns, I will choose them.”

On Friday, Feb. 5, the Venmo Challenge visited Wayland. Wayland is the only town to receive the $500 tip at multiple restaurants due to a generous donation made by Cormier, who donated $500 of his own money to the challenge.

“[I] wanted to [donate] my own $500 because, to myself, I thought it was important that restaurants and members see that I love giving back to local communities and that it takes a whole team to make this group what it is,” Cormier said.

The Villa and the Dudley Chateau were the two restaurants in Wayland selected to receive the $500 tip.

“There are a lot of places in Wayland that support us, but I think the [chosen] two have been through a lot and really supported the page,” Kaplan said. “The [Chateau] and the Villa are Wayland staples, they have been there forever. I actually grew up in Wayland, so I had eaten at those places my whole life as well.”

Stacey Keating is an employee at the Chateau and received the $500 tip on Friday. She, like many who received the tip, was aware of the group “Chew on This” and has donated towards the cause herself. The Chateau employees were very happy to receive the tip but were initially doubtful of being selected.

“We honestly didn’t think it was us after we had been waiting on Kiat Friday afternoon,” Keating said. “It was a great feeling because we honestly thought [initially] it wasn’t us because [Kaplan] had mentioned her take out had been placed, and I knew it wasn’t with us. [Also], Kiat told us she was going elsewhere, so it was a fantastic surprise and very much appreciated.”

The Chateau had been closed for a month as a result of positive COVID-19 tests from both employees and patrons. COVID-19 has proved to be challenging for many small businesses, especially restaurants, so benevolent acts like the Venmo Challenge have meant much to these people.

It has been very challenging during the pandemic to work with all the guidelines we have to follow and the restrictions put on us. It makes it very hard to survive.”

— Stacey Keating

“We split it between the waitstaff working and we were ecstatic to receive the tip,” Keating said. “I’m a single mom who has a daughter in college, and after not working for a month, [the money] was definitely put to great use. It has been very challenging during the pandemic to work with all the guidelines we have to follow and the restrictions put on us. It makes it very hard to survive.”

Kaplan and Cormier do not plan on stopping this challenge anytime soon. As long as they continue to raise money, they believe there are many more towns and restaurants that they can continue to help. They have discussed reaching out to restaurants unaware of their group in hopes of helping additional and unexpecting people.

“I was talking to Kiat and I was like ‘I wonder if we can use [our group] to reach out to new places. [We would] show up and say this is what we are and this is what we do’ to get more restaurants engaged,” Kaplan said. “We might change it up a little bit going forward, but we are still going to focus on a new town and city every week.”

“[The] last comments [I have] are how grateful to this community I am for making this all happen,” Cormier said. “[I’m] so happy to be giving back during these times, and I really hope the restaurants see that the community has come together to support them, no matter how big or small.”

For those interested in learning more, additional information can be found on the Facebook group, “Chew on This.” Donations can be made via Venmo to Jillian-Kaplan-3 (Last four digits: 1431).