On Wednesday night, Seth Collins of Lexington, Ky., did just that, leaving a $500 tip for a Friendly's waitress in Springfield, Vt. It's part of a nationwide tour that Collins is carrying out in the name of his brother, who died in July 2012 at the age of 30.
In a story provided by the Eagle Times of Claremont, the Friendly's waitress, Julie Bombria, said she thought she was going to faint after getting the generous tip.
"This is the nicest thing anyone has done," she said.
In his will, Aaron Collins asked his family to give his money to people in need. His cause of death is still unknown, according to the newspaper. Through his family, he's given away 81 tips throughout the Midwest, Pacific and Mountain West regions and is now in New England.
Initially, Seth Collins took family and friends to dinner at a Lexington restaurant, gave their server $500 and recorded it. Aaron's wish was fulfilled but far from over. Seth Collins put a video of his first tipping spree on Facebook and started getting donations from around the world. The total's up to $50,000.
"(Aaron) thought it would be a one-shot deal," Collins said. "I was going to do this like three or four times, but people were so compelled that they kept giving money. I'm going to give it back on behalf of my brother."
He is on his way to Maine, then he will work his way down through New Hampshire, Massachusetts, Rhode Island and the Mid-Atlantic.
"Being on the other side of the table and giving away $500 tips is very rewarding," Collins said.
In July, Vanessa Goldschmidt, a server at Pequod's Pizza in Lincoln Park, was on cloud nine after receiving the same tip from Seth Collins.
"That's amazing. Thank you so much," said Goldschmidt. "Still a shock for sure that someone would just do that."
Seth Collins had just finished a meal with friends at Pequod's, and after paying the $45 tab, it was time to present the tip.
"This is for you. It's $500," said Collins.
"I'm like shaking right now. Are you serious?" said Goldschmidt. "My knees literally just got weak. And I started shaking. And I was just trying to fight back tears."
For Collins, this act of gratitude is born from grief. A year earlier, Aaron died suddenly and mysteriously.
"We don't really know how he passed. His friend found him, and at that point his heart had stopped," said Collins.
Aaron once worked in a restaurant, his brother says, and in his will was a request.
"The last thing in it, he asked that we go out to dinner and leave an awesome tip. And he said, 'I'm not talking about 25 percent. I mean $500 on a pizza,'" said Collins. "He would have been really blown away that so many people were touched and connected with this idea that he had."
Collins has set up a website to post his videos and accept donations at http://aaroncollins.org/.
The Associated Press contributed to this report.