Bartender Thinks PayPal VP Is Joking With His Insane Offer—Then She Sees 2 Words on His Bill


We’ve all heard of random acts of kindness. May it be a customer in the drive-thru who starts a chain reaction of 167 people buying each other’s meals, or a woman who meets a homeless man in Burger King and changes his life, there’s no denying that a little bit of kindness can go a long way.

While working her shift at Guyer’s in New York City, Caitlin Cahil never expected her “slow, quiet night” at the bar to turn into one shift she’d never forget.

The bartender chatted on and off with two men who seated themselves at the end of the bar. One of those men was Jack Shelby, former Vice President of PayPal.

He asked Caitlin if she had heard of “Tips for Jesus.”


A movement that aims to do the Lord’s work “one tip at a time,” Tips for Jesus started in 2013 with an Instagram page of the same name. Mystery diners carry out random acts of kindness in the form of extremely generous tips, which are then posted anonymously to the social media page. The last one was posted a year ago.

Jack Shelby revealed himself as the catalyst that started it all.

When Caitlin told the customer she knew what it was, Jack simply responded with, “Well that’s me.”

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Thinking he was joking, Caitlin glanced at his receipt. His bill was just $100, so the bartender was shocked to see that Jack had left her a tip of $5,000!

“I was a little taken aback,” she told CBS New York. “I said ‘are you sure?’ Maybe he had a good time, maybe he was feeling generous.”

Then she noticed two words scrawled across the top of Jack’s bill, signifying his excitement to get the Tips for Jesus movement rolling again after a one-year hiatus: “We back!”

Grateful for the unexpected generosity, Caitlin was excited to share the experience with others.

You don’t have to be a high-rolling former PayPal executive to make someone’s day a little better. Kindness and generosity are contagious. May Jack be an inspiration to us all to do something kind today.

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Bri Lamm
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Bri is an outgoing introvert with a heart that beats for adventure. She lives to serve the Lord, experience the world, and eat macaroni and cheese in between capturing life’s greatest moments on one of her favorite cameras.