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.
Managers Were Expected To Chip In
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.
Don't Miss:
- The AI Marketing Platform Backed by Insiders from Google, Meta, and Amazon — Invest at $0.85/Share
- Deloitte's #1 Fastest-Growing Software Company Lets Users Earn Money Just by Scrolling — Accredited Investors Can Still Get In at $0.50/Share.
“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?”
Trending: 7 Million Gamers Already Trust Gameflip With Their Digital Assets — Now You Can Own a Stake in the Platform
Most Business Owners Called It Insane
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.
See Also: Missed Tesla? EnergyX Is Tackling the Next $200 Billion Opportunity — Lithium
So What’s The Right Move?
While some advised simply paying to avoid future awkwardness, others suggested quietly checking in with coworkers to gauge whether everyone else was truly on board. “You don’t want to skip it and be the only guy not participating without understanding the consequences,” one person said.
Others said if it’s a good-paying job, just treat it like a parking ticket and pay the fine.
The original poster later added that they like the owner and believe he’s generous with bonuses and parties. Still, they felt the ask was inappropriate: “Because he holds a position of power over me, I don’t think it’s appropriate for me to be required to give him a gift.”
Whether it’s a cultural norm at the company or not, the internet was firm in its stance: contributing $100 to a lavish gift for the boss, especially at the direction of his nephew, crosses a line.
Read Next: From Moxy Hotels to $12B in Real Estate — The Firm Behind NYC's Trendiest Properties Is Letting Individual Investors In.
Image: Shutterstock
© 2025 Benzinga.com. Benzinga does not provide investment advice. All rights reserved.

