Co-Founding a Startup With Your Best Friend? Read This First

My co-founder, Tim Wikstrom, and I had been friends for several years before we began our startup. We had worked together, formed a very close friendship and, when he was thinking about building a new business and invited me to join, I didn’t have to give it a second thought. We had invested so much time and effort into our relationship and felt so strongly about our connection and our ability to communicate with one another that we felt like we could cross at least one of the hurdles of starting a business off our list.

In a recent Inc. article, executive coach Alisa Cohn writes:

“Productive communication is critical for co-founder success. You have to communicate to stay aligned, to work out normal tensions and conflicts, to create vision and strategy and plans and to regroup when things go off plan. During tough moments, if the co-founders are communicating the company has a better chance of making it through more easily.”

We couldn’t agree more and, reflecting back on the last few years of our partnership, we can easily (and regretfully) point to the times where the breakdown in communication nearly pushed us to the brink.

As much effort as we put into having regular conversations and an overall commitment to feedback and transparency, when the waters become rough, we struggled to maintain focus on our intentions. Far too often over the years, we relied heavily on texts and emails to sort through highly-charged matters rather than pick up the phone to talk. Despite our expertise and deep understanding that written communication can be easily misinterpreted, we fell short on our objectives and allowed the madness of running a startup cloud our judgment. We got caught up in the emotional intensity that comes with building a plane as you fly it.

Business challenges will override your friendship (if you’re not careful)

What was particularly challenging for us was that we were friends first. We hadn’t come together as founders and had a well-established relationship that was nurtured by meaningful and quality time with one another. Outside of our respective partners, we were each other’s “person” and we deeply trusted one another. Assuming this, we expected that we could tackle anything that came our way. However, what we didn’t anticipate was the erosion of our friendship. Both of us made the commitment that we would always put our personal relationship first but, suddenly, when there are investors and employees and we need to feed our families, the business won out. And our friendship took the brunt of it.

Taking a step back to reassess our priorities and mapping out some boundary lines to insulate our business partnership and personal friendship was one of the first steps to ensuring that we could more readily manage the future stressors that would inevitably arise.

Steli Efti, CEO of Close.io offers some great tips to nurture the important relationship between founders. He suggests that “ultimately what you’ll learn is that you’re much better together than you are apart. At the end of the day, that’s what not only makes the relationships work, but also what makes the business work.”

For me and my co-founder, we learned some simple communication lessons (that we had spent a lot of time teaching to others but forgot to apply to ourselves) for co-founding a business with your best friend.

1. Choose your communication channel wisely

Before you hit send on that text message or email, consider the complexity of the topic or the emotional intensity of the message you are sharing. If either of those are high, delete and pick up the phone. Slack is our messaging tool of choice and our rule is when the messages start flying back and forth, it is time to call it quits and find time to connect personally.

2. Establish friend “date nights”

Just like with your significant other, it is important that you set aside time with your co-founder to just hang out as friends and invest in your personal relationship. Even if you were not friends before you started your company, it is important that you devote time to being friends because that will lead to a more trusting and authentic relationship at work.

3. Find a safe word

My husband and I recently recognized that after decades of marriage we had not figured out how to back ourselves out of a fight. And, even when the fight was inane and unnecessary, neither of us backed down. Both of us being too stubborn to relent, we would often exacerbate the argument until we were genuinely angry at one another. So, we decided to institute a safe word to let each other know that it was time to quit the fight. The same tactic works well with your business partner. Sometimes you go off the rails because you’re stressed or anxious and there really is no reason to have a communication fail. Perhaps that is an “antelope” moment.

In the end, remember that no matter how strong the relationship, how well-developed your communication skills might be, things are going to go awry. The sooner you can nip it in the bud and the faster you can remind each other why you started this venture to begin with, the more likely you are to persevere.