A manager at a successful small business was stunned to receive what looked like a phishing email: a request to Venmo $100 to the company president. The supposed reason? A group gift for the owner. But it wasn’t a scam. It was real. And, apparently, not optional.
The Reddit post, shared under r/smallbusiness, came from an employee who had only been at the 80-person company for less than a year. The business brings in around $50 million in revenue and has no debt. Despite being happy in the role overall, the manager was taken aback by the unexpected demand.
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“Each person’s contribution is $100. Please Venmo me when you have a chance,” the email read. It was sent to 17 managers, totaling a $1,700 contribution to cover a luxury fish subscription for the company owner. The message came from the president, who also happens to be the owner’s nephew and is reportedly being groomed to take over the business.
“My first instinct was to report the email as phishing because I thought there’s no way this guy is asking us all to Venmo him $100,” the original poster wrote. But upon closer inspection, it was legit: “Head of HR and IT were both on the To line.”
The tone of the email didn’t make the contribution sound optional, and the employee questioned the whole premise. “Can’t we just get the guy a tie? Isn’t our gift to him the labor we put in to make him his several million dollar salary?”
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Commenters flooded in, and the consensus was apparent. Most business owners said they’d be horrified if their staff gave them an expensive gift. “This is batsh*t unhinged behavior,” one owner wrote. “Gifts flow down, not up,” another said. Several owners said they prefer to give holiday bonuses and thoughtful gifts to their employees, not the other way around.
One commenter summed it up: “I would be beyond pissed at whoever arranged this and I would pay everyone back.”
There was also concern about power dynamics. “The fact that it’s a family member in a superior position to all of those he is collecting $100 from seems strange,” another wrote. Some even speculated the nephew was setting a precedent for his own leadership style, or worse, trying to pocket the money.

