The Survival Guide to Working with Friends

by . April 29th, 2014

You’re with a group of friends. Everybody is bored and broke. Somebody comes up with this crazy, revolutionary idea, and you guys start a business together with gleaming rays of hope and optimism. Everyone is sure that any problem that comes your way will not stand against the power of friendship.

For a lot of people, this is how the first venture starts. It’s how mine did. And like most people that partner up with friends, I had a lot of issues pop up. Some were about the business. Some were about the friendship. Some were minuscule, and some were so big, they could have ended the friendship had they been taken care of differently.

I’m going to tell you some of the things my friends and I went through. Hopefully, this article will help you see through something you’re going through now or maybe help you avoid the situation completely in the future. It would save you time and energy.

Identity Crisis

The first problem I went through was that nobody had a role. The business was made over a crazy idea and we took care of it like how we did most things. We winged it. Nobody knew what was inside their domain or what was outside, and this led to some major trouble. Everyone was treating it like a school project. Everyone collaborated on everything and somehow made it work.

However, it made things quite inefficient. People were doing the same thing differently, leading to multiple missions and visions. The business did not have a single target market pinned down. Since everyone was doing everyone else’s work but in different ways, pride and ego would kick in. We started working behind each other’s backs. It was as if multiple companies were fighting for the same name. One proposal targeted rich families, and the other targeted students.

We should have met up and settled these problems like the adults we believed ourselves to be. Settle who the authority on what is and don’t cross the line. Sadly, we didn’t get to. The business went broke and we had to separate our ways and move on to new ventures.

When having this talk (and this should be done before the business even starts), know that most startups are too small to have a traditional business structure like you see in the movies (C-level officers, branch managers, large sales teams, etc.) Your position might be fluid, moving from one task to another which is miles different from the first. You will probably take on the description of five or more different jobs that large traditional companies have. This makes it all the more important to set your boundaries, to set your identities.

Connection Lost

For a group that you’d probably have contact on multiple social media platforms, or even their addresses and phone numbers, communication can still be a major issue. Maybe your pride not agreeing with the proposal conflicts with the embarrassment from telling your friends that their ideas suck. Sometimes it’s a friend showing bad work ethic and you’re too afraid to tell them. This fear is not worth it.

In my experience, some things happened within my realm of responsibility that I didn’t know about. Issues and opinions were sugar-coated into maybe-if-we’s and I-kinda-think’s. People slacked off and we let it happen. Phone calls were ignored because the responder was too ashamed to pick up. It still sometimes happens, but we’ve improved a lot.

Talk to your friends. You should be in business with people you trust to not flake off when your perspective butts heads with theirs. If you can’t, I’m going to save you time and money by telling you to get out of the venture now. This point is important and shouldn’t be ignored.

Child Support

Have you ever had that friend who everyone believed this person to be the “baby” of the circle, because there were extremely sheltered, was in a tougher situation than everyone else, and/or you believed you needed them? Such as someone who you gave so much leeway to because of their immediate need, thus everyone else forgetting themselves.

There was a project with another startup that we had to count costs for and evaluate pay for each person affiliated. At first, we didn’t want anyone to feel unimportant, so everyone was to be paid equally no matter how big or how small their role was. When we stopped doing this, the division was still wrong. We were prioritizing those that needed fast money because of emergencies. Eventually we were able to work it out by making our hearts as stone and using wisdom that really should be obvious.

Relationships should not be neglected, but business comes first and should be separate. When working even with friends, everyone should be treated equally and justly. You can pull off favors for friends, but be smart about it and keep it away from work.

Diplomatic Immunity

Possibly the most obvious repercussion due to working with friends is when your authority is made lax because “They’ll understand. They are my friend after all.” From missed deadlines to ignored company policies, your rules as boss are looked past due to over-familiarity. You want to get your point across, but all you’re doing is punching a feather pillow.

Sometimes disciplining them does not work. Because your authority is undermined, your sanctions are seen as you just having a bad day. The problem stays and you are left with no positive change in the work atmosphere.

As an example of the previous three points, a friend of mine who needed income the most prioritized frivolous activities over work. They would run off and form a wall especially for us just so they could spend time with their partner. Communication was such an issue that our only bridge was to call their attention through this companion.

We softened our blows. This was a bad mistake. When we tried pushing harder, nothing happened but the social disappearance of our friend. It was until a mystery miracle (I still have no idea what happened), that we saw progress.

If communication doesn’t work, I’ve learned through experience that donning a secondary persona during work may help. Separate your personal life from your professional one by making your friends feel you are a complete stranger.

Great Divide

When every other plan has backfired, all you’re left with is kicking your friend out of the company. This could also affect other facets of your life unless the two of you handle the situation maturely. You could have been close, maybe dating. Maybe you’re family. Chances are others aren’t going to look at this lightly and one of you is going to look bad. Whatever the case, firing is the smart move even though it might not always be the best one.

Personally, this hasn’t happened to me, but there have been close calls. The planning of how to say it all, the lining up of prospective replacements: the works. Fortunately, we’ve been able to pull back up and are as efficient as ever.


Do take these things into consideration and treat your business and friendships wisely. I’ve seen a best man at a wedding not spoken to anymore due to a failed startup with the groom. There were times that I would think of quitting and making a direct competitor with common friends, just to piss my business partners off.

Despite all that, this post is not meant to stop you from starting a business with your friends. Lots of great things can still come out of it. You more or less trust each other, work becomes comfortable, and you know each other like the palm of your hand. Honestly if you made it work, it would be the best thing.

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