Picture this: You're a manager at a successful company, and you get an email asking you to Venmo $100 to the company president. Your first thought? Classic phishing scam. Your second thought, after realizing it's actually real? Considerably worse.

That's exactly what happened to one manager at an 80-person company pulling in around $50 million in revenue. The business is doing well, carries no debt, and the manager had been generally happy in the role. Then came the email.

The Email That Wasn't Phishing (Unfortunately)

The message was straightforward and blunt: "Each person's contribution is $100. Please Venmo me when you have a chance." It went out to 17 managers, collecting a total of $1,700 for a luxury fish subscription for the company owner. The sender? The company president, who also happens to be the owner's nephew and is reportedly being groomed to eventually take over.

The manager, who shared the story on Reddit's r/smallbusiness forum, admitted their immediate reaction was suspicion. "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," they wrote. But a closer look confirmed it was legitimate — the head of HR and the IT director were both copied on the email.

The tone didn't exactly make participation sound voluntary, either. The manager questioned the entire 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?"

Business Owners Were Not Having It

The response from other small business owners was swift and decisive. Most were appalled. "This is batsh*t unhinged behavior," one owner commented. The phrase "gifts flow down, not up" appeared repeatedly. Multiple business owners said they'd be mortified if their employees felt pressured to buy them expensive gifts, with several noting they prefer giving holiday bonuses and thoughtful gifts to their staff instead.

One owner put it plainly: "I would be beyond pissed at whoever arranged this and I would pay everyone back."

Beyond the general inappropriateness, commenters zeroed in on the power dynamics at play. "The fact that it's a family member in a superior position to all of those he is collecting $100 from seems strange," another person wrote. Some speculated the nephew might be establishing his own leadership style before taking over, while others questioned whether he might even be pocketing the money.

Pay Up Or Stand Out?

When it came to practical advice, opinions split. Some suggested just paying the $100 to avoid awkwardness or potential career consequences. One commenter recommended quietly checking with coworkers first to see if everyone else was truly on board: "You don't want to skip it and be the only guy not participating without understanding the consequences."

Others took a more pragmatic view — if it's a good-paying job, treat it like a parking ticket and pay the fine to move on.

The original poster later clarified that they actually like the owner and believe he's generous with bonuses and company events. Still, the fundamental issue remained: "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."

That sentiment captures the heart of the problem. Whether or not this is standard practice at the company, the internet was nearly unanimous: asking employees to contribute $100 to a lavish gift for their wealthy boss — especially when the request comes from his nephew — crosses a line that shouldn't be crossed.

In a healthy workplace culture, appreciation and gifts flow from the top down, not the other way around. When that dynamic gets flipped, it stops being generosity and starts looking like something else entirely.