Some people who build significant wealth prefer to keep their money to themselves, and that’s okay. When you work hard and become successful, you deserve to enjoy what you’ve earned. And you shouldn’t feel obligated to share that money with friends.
But in one Reddit post, we meet someone whose business has taken off. The OP now has built a net worth of around $15 million. They want to enjoy their success and spend more time traveling with friends. The only issue is that they want their friends to join them.
Not surprisingly, though, their friends can’t necessarily afford to take extended trips, either because they need to keep working their regular jobs or because the travel itself would be too expensive.
To help their friends gain the funds necessary for extended travel, the poster is considering creating jobs for their buddies so they can all travel together. The OP mentions assigning titles like photographer, social media manager, and security guard/trainer (even though the roles may not reflect real job responsibilities). They’re now wondering whether this is actually a good idea.
I have some immediate thoughts. And spoiler alert: I think the poster may be taking on unnecessary risk.
This post was updated on April 8, 2026.
There are so many issues with this plan
I’m not an employment lawyer, so I can’t speak definitively to the legal implications of a plan like this. But legalities aside, I do think the poster may be making a risky move.
Mixing money and friendship can create complications, so it’s something that should be handled carefully.
Even if the jobs were completely legitimate, things could still get complicated when you employ a friend. It changes the dynamic and shifts the balance of power in the relationship. So even if the poster genuinely needed someone to fill a real 40-hour-a-week office role, I’d still be cautious about hiring a friend.
Whether this arrangement is legal depends on how the roles are structured, including whether the work is legitimate, how the workers are classified, and whether labor and tax laws are being followed.
Potential issues could include worker misclassification, payroll tax problems, fraud concerns (if the jobs aren’t legitimate), and insurance or liability issues while traveling.
A business owner can absolutely hire people for legitimate roles, but those positions generally need to involve real work and comply with employment and tax laws. If the poster wanted to hire someone to help with errands or administrative tasks, that would likely be permissible. Business owners can legally hire assistants or contractors for support work like personal or logistical help.
But rather than dealing with all the ins and outs of employment to hire friends for questionable roles, a better option may be to simply cover part or all of group trips. They don’t have to be months-long adventures if the friends can’t afford to step away from work for that long.
The poster could book a nice villa for a week or pay for a stay at a resort with plenty of amenities. And if they want company for more extensive travel, they could also look into meeting fellow travelers through online communities or travel groups.
It’s best to consult a professional
This is a potentially tricky situation, and I don’t want to see the poster create legal or financial problems while trying to be generous.
If they are still considering moving forward with their plan, I’d recommend that they talk to an employment lawyer. They should also consult a financial advisor to make sure they’re not being too reckless with their money, even though they clearly have a lot of it.
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