The pitfalls of going into business with a friend

Hi friends,

One of the first things people ask Sam and I when they meet us is if we’re actually best friends. And the truth is no. I really can’t stand her. Having to talk to her all day, every day is excruciating, and I hate it. I kid, I kid, but only because we proofread each other’s blogs and I figured she’d get a kick out of that.

But seriously, we get the same questions and comments all the time. People inevitably question the wisdom of working with friends or warn us of the pitfalls of going into business with people you know. And in most cases, they’re right. If you asked me which of my other friends I could/would work with this closely, day in and day out, I’m not sure I could name one. Not because I don’t love them, I do. That’s actually why I wouldn’t, because I know that specific friendship wouldn’t be able to handle working together and I don’t want to jeopardize it. Liking to hang out with someone and being able to effectively collaborate in a professional setting are two very different things.

So how do Sam and I make it work, while still maintaining our friendship?

First, we weren’t starting from scratch. As interns, we spent countless hours together as roommates and teamed up (along with our friend Ken) to enter the intern pitch competition, committing to even more time with one another during that project. That fall, we traveled with College Game Day, working together every weekend. Call it a pilot study. In other words, we had a baseline. We knew that we had successfully worked together before. While we both have very different working styles, our skillsets complement one another well and we had proven to ourselves that we could work together (at least on a smaller scale).

Next, we aligned on what was important to us. Priority number one was (and still is) our friendship. As we alluded to in our first-year anniversary post, we set boundaries early on…and I mean reaaaaallly early on, like empowHERed-was-still-a-concept-and-we-were-just-throwing-ideas-in-a-Google-doc early. First, we established open lines of communication. We planned a daily meeting, just the two of us, every morning at 8 am, that allows us to touch base on our ongoing to-do list, divide duties, and plan for any other meetings or upcoming events. One of the biggest benefits of running a business with a friend is that you’re in touch constantly. There are days that I talk to Sam more than my husband. However, that can be a double-edged sword, as it can also lend itself to a work-centric relationship. To combat that, we also created ground rules, such as a daily cutoff time for work communications. To maintain work-life balance and our close relationship, we decided that after 6 pm Monday through Friday, we would only text/call one another about friend-related topics. While we bend the rules on occasion, such as when we’re together in person, hosting a webinar, or something major and time sensitive is going on, we largely stick to this. Additionally, we don’t talk about work on weekends when we’re not traveling for conferences, panels, and other events. It’s a nice break and allows us a chance to catch up on each other’s personal lives and genuinely enjoy one another’s company.

Lastly, we developed a safe word to be used in case of emergency - think code red, break-glass-if-necessary type of situations. If either of us gets too overwhelmed or stressed or irritated with the other, we text the word “penguin”. That signifies that the person who said it needs a break, and the other person is to give them space for as long as they need to cool down or regroup. More than a year and a half into this business, we still haven’t had to use it. Don’t get me wrong, that’s not to say that every day is perfect. Running a business is hard and it’s easy to let stress build or affect your mood. We get on each other’s nerves, doubt ourselves, and question our own sanity often (no seriously, ALL the time). Still, we also recognize that we couldn’t do this without one another. More importantly, I wouldn’t want to do this with anyone else.

So to answer any lingering questions, yes, we are best friends. Yes, we’ve heard all the cliches about going into business with a pal. No, we don’t care, because it works for us. If you find yourself in a similar situation or even just working on the same team or in the same department as a friend, we highly recommend setting your own boundaries to ensure that you find a way to effectively navigate the colleague/friend dynamic. Jobs come and go, but good friends are hard to find, especially in this business.