Executive Relations: How to Keep the Relationship with Your Co-Founder Healthy

When you start a company with someone, you are entering into a relationship that’s statistically more likely to fail than the average marriage. It’s a journey full of obstacles and challenges—tight finances, massive uncertainty, hiring and firing people, legal matters… the list goes on. This is especially true if you bootstrap your business, which my co-founder and I did for eight years.

Mike and I started Wyzant our first year out of college, in 2005. I get asked a lot how we still get along so well after all these years. Like any startup, it’s been a rollercoaster, but our partnership has never wavered. Upon reflection, I’ve realized that although we didn’t take any formal co-founder vows (and actually never even had a written agreement between us), there are a few key tenets that have led to this durability.

Trust

Trust is built through honesty over time. For us, there has never been anything but brutal honesty. That’s the standard. It’s not good enough to simply avoid lies and deception. You have to call each other out, as well as admit your own errors. To do this, you must be open and forgiving about mistakes—because they’re going to happen. It’s a team sport, and you share the wins and the losses together. Neither of us has ever said, “I told you so,” or “That was my idea.”

The trust we’ve built manifests itself in many constructive ways. For instance, we communicate bluntly and directly, cutting right to the chase to avoid confusion or wasted time. We have a comfort level and latitude to say things that may otherwise be considered insensitive or offensive. It’s definitely not always a lovefest. We get mad, but then we get over it very quickly because we know it’s not personal. On the flipside, we also don’t waste time worrying about hidden agendas. We constantly challenge each other, but we never question the underlying motives. 

Trust is also based on competence. It’s hard to trust someone that you don’t think is highly capable of executing the task at hand. As first-time founders and executives, it’s not uncommon to question yourself from time to time. But we believe in each other. We’ve seen up close what the other is capable of doing, and no matter how much gets thrown at us from various directions, we continue to support and motivate one another.

Commitment

To have any chance of succeeding, both founders have to be fanatically committed to not just the company, but also to one another. On the business side, you have to have conviction that the problem you are setting out to solve with your startup is big and important, and you have to truly believe that you can solve that problem better than anyone else—current or future competitors. On the personal side, you have to genuinely care about and believe in one another. If you’re wavering on either of these points, I suggest you cut your losses and look for the next opportunity.

There have been many times when it would have been easier to walk away than to battle against the odds. I remember a particularly low point in 2007, when we had maxed out our credit cards, and were so desperate, we even contemplated moving into my parents’ basement for awhile. (No offense, Mom and Dad.) And then in 2009, we hired too quickly and then had to layoff a handful of employees, including some good friends. That same year, we also needed an emergency loan of $200,000, which we somehow managed to get from an investor at the last second. But in these moments, we always knew deep down that there was unfinished business to attend to, and we certainly weren’t going to leave each other to fight it alone.

Grabbing Beers

Every few weeks, either Mike or I will say, “Hey man, let’s grab beers sometime soon.” We use this time to check in on one another, vent, share feedback and talk about our lives outside of work. Regardless of what is discussed, we leave these sessions feeling more aligned, recharged and usually with some great business ideas. (Note: drinking beers isn’t necessary, although it doesn’t hurt to loosen things up. Any relaxing activity outside of the office can serve this same purpose.)

Most importantly, grabbing beers helps us decompress and have a few laughs about the craziness of it all. In this way, it’s like a perspective calibration. Startups have a tendency to feel like life or death sometimes, and taking a step back over a beer is a crucial way for us to help each other keep our sense of humor and gratitude. We try to give ourselves a pat on the back for what we’ve accomplished so far, and then get fired up about the massive opportunity that’s still out there.

We spent our third year at Wyzant working out of a dumpy apartment in Summit, New Jersey. There was a bar in Summit appropriately named, “The Office,” where we did a lot of our evening work. It was at The Office where our thinking and goals grew from what was originally a lifestyle business, to trying to build a company that impacts education on a global level. From there, we began to make more aggressive and scalable decisions, including building out a team and raising growth capital to help us take the business to the next level. I’m certain that getting out of our apartment and relaxing over a beer was, and continues to be, an important part of developing our vision.

Understand Your Strengths and Weaknesses

I have heard many stories of founders who are constantly at odds over decisions that need to be made. The same is true for non-founder executives. This is because either the lines of ownership are blurry, or people have too much overlap in their skillsets or areas of interest.

Mike is incredibly technical and analytical. I am much more inclined to think strategically and spend time being outward-facing. As a result, I’ve always been the CEO, and Mike has always been in charge of engineering and performance marketing. It’s never been a question because we’re aware of each other’s strengths and weaknesses.

If you aren’t self-aware and humble enough to recognize your strengths weaknesses, you’re not going to be able to grow and evolve, and neither will your business. Similarly, if you can’t identify, recruit and manage people who are more capable than yourself in key areas of the business, you’ll never be able to build a high-performing team. Most people understand these principles implicitly, but for some reason, founders and cofounders often exempt themselves from the same scrutiny they apply to the rest of their organization. This is why we do annual performance reviews for ourselves as well as our employees. Everyone has to know their strengths, weaknesses and opportunities for development—especially co-founders.    

As a first-time CEO, I know I have a lot to learn. But one thing Mike and I have definitely done right is created a partnership that’s highly effective and enduring. Now that we have more than 100 employees, the dynamic has evolved, but the tenets haven’t changed. And these same principles have translated to strong relationships across the company, especially within our executive team.