One of the advantages of owning your own business is you can hire whomever you want.  Often, that lets you cut through normal bureaucracy and irrational behavior to find the right people and build a really good team. But having that kind of autonomy also means it's easy to talk yourself into things and make mistakes.

Over the years, I've hired a number of friends to come work with us at Tusk Holdings (and our subsidiary companies). Some of those hires have worked out really, really well. Others have been a disaster. I've learned a few lessons along the way.

1. Don't hire someone just to help them out.

Being a good friend is a mitzvah and that means helping friends in need. You can give them advice and emotional support. You can make connections and introduce them to people. You can even give them money. But you can't give someone a job just because you want to help them. At the end of the day, if there's not a clear need and a clear fit, you're not helping anyone. They end up taking a job they're not equipped for. Your employees are suspicious when the friend you just hired can't perform or produce (because you put them in the wrong role in the first place).

At first, you encourage them to hang in there but eventually, you grow frustrated that you're keeping someone around who'd otherwise never last. And they grow frustrated quickly too--they want to produce, they want to help, and when they can't, it's just as upsetting for them (probably more so).

Over time, you resent them, they resent you and they end up leaving. And even worse, there's no rescuing the friendship. I've now made this mistake three different times. I really liked and respected each of the people before hiring them. And my relationships with each of them are irreparably broken (we pretend otherwise but we know we're just pretending).

2. Hire friends if they have the exact skill set you need.

I've also hired friends who have gone on to be some of our best employees, highest performers and wonderful colleagues. The reason it has worked each time is because they did already what we do. They had the skill set, interest, and background to hit the ground running on day one. They're able to add value immediately and win credibility with the rest of the team immediately. But the clear lesson is that they were each people I would have hired whether I already knew them or not. If you can't answer yes to that question, don't make the hire in the first place.

3. Even when you're hiring friends who are completely qualified, there's still risk.

Sometimes things don't work out. It may because your business goes south. It may be because they lost interest over time or just messed something up that's unfixable. Who knows? Luckily, the friends I've hired who were already qualified for the job  have all worked out really well. But I know I'm taking the risk of seeing something go wrong and seeing our friendship suffer as a result.

4. Sometimes the relationship is equal, sometimes it isn't.

Even when a friend becomes an employee, outside of work, they're still your friend and any good friendship is based on a relationship of equals. But when you're at work, even in the most collegial, flat structure imaginable, you're still the boss. Remembering which is which at the right time can be tricky (especially since the lines between working hours and non-working hours are so blurry)--but it's also essential.

5. Becoming friends with employees is fun, but be careful.

When you work closely with people you like and respect, you often become friends with them. Many of my friends outside of work were colleagues or employees in jobs I used to have. There's nothing wrong at all with becoming friends with your employees but especially in the critical moment we're living in right now, you have to always remember that you have more power in the relationship than they do and that they may feel compelled to agree with you.

This is obvious when it comes to romantic relationships (we don't permit anyone to date someone who reports to them or they report to) but anyone who supervises anyone else should always be mindful of this (if that wasn't obvious before Harvey Weinstein, it should be extremely clear now).

6. Even after getting the "hiring friends" thing both right and wrong over the years, I'd still do it again.

It's helped me build my company and enjoy the people I work with every single day. But I also regret the occasions where I hired people for the wrong reasons (well-intentioned but still stupid) and destroyed those friendships in the process.

It can be a tough path to navigate but for better and worse, it comes down to one simple rule: if you'd hire them regardless of whether you already knew them or not, go for it. If the only reason you're hiring them is because you know them and want to help, don't do it.

Ultimately, you're not helping them or yourself.