Co-founded or confounded, that is the question...
I spent five (great) years at Google as the CIO and Vice President of Engineering, working for two strong, visionary co-founders: Larry Page and Sergey Brin. While business analysts tend to disagree about this model of dual leadership, I've found that this dynamic works beautifully for building great companies -- both at large companies like Google and in start-ups like my own.
Personally, I could not have founded my company without a strong co-founder, who is quite different from me. If not properly considered and maintained, however, a co-founding relationship could also result in endless bickering and divided teams.
There are a few key questions co-founders need to take into consideration about partnerships before they make the leap. Think of this as your premarital checklist to co-founding a company:
1) Be Realistic About Diversity
There is a lot of evidence that diverse teams come up with better answers to the problems they're interested in fixing. They get better answers, in large part, because their teams plan and assess the business using different implicit measures. For aspiring entrepreneurs, your odds of succeeding increase with a partner who pushes you in different directions.
That said, there is a real cost to having diverse teams (even if it's just you and your partner): You will disagree a lot. That's the point. You have different perspectives, and those different perspectives create conflict, resulting in productive discussions from different points of view and, ultimately, a more thoughtful solution to the problem.
While this conflict can be constructive, it can also destroy value. The first question you need to ask yourself is: Will this co-founder help me, or confound me?
**Side note: I am using confound in the "old-fashioned" way, which refers to preventing someone from being successful.**
2) Ensure You Share Deep-seated Values
Personal values seem unimportant to business, but, surprisingly, we don't stop being people when we become employees or entrepreneurs. When you watch the news, what gets your blood boiling? When you walk past a homeless person, are you saddened or annoyed? Do you believe that religion has a role in modern life? Do you object to tattoos?
I could generate a countable infinity of such questions, but the questions that matter to me may not matter to you. I promise, however, that you have a set of values, and if your co-founder radically disagrees on any of those "core values," your relationship is doomed.
It's doomed because there is no way to resolve these deep values -- you may believe that you are far enough up Maslow's hierarchy of needs that you can rationally agree to disagree, but you aren't. You will trip over one of these issues, and, although you will both smile and say, "it's fine," it won't be. It will grate on you during those dark hours at night when you are afraid that your company is going to die.
Trust me, if you're starting a company, you don't have enough extra emotional bandwidth to deal with things like this.
Don't found a company with someone you aren't deeply connected to.
3) Find a Happy Medium on Work Issues
People come pre-wired with expectations of how businesses should be run. Do people show up for work at 9:00 a.m.? Is it OK to show up for work in a hoodie and unshaved? How about remote employees -- is that OK or too much trouble? Do you want to have offices and reserved parking spaces, or a big open loft with a loud game of ping-pong happening in the middle of the workday?
You will likely disagree on this stuff, which is OK as long as you identify and work through the key issues, i.e., we need to work enough shared hours to maintain shared context, we need to ensure people get feedback weekly, etc. Once you've identified these issues, go to a local bar and work through them. Give yourself 30 minutes for each, and at the end of the session, you'll have a loose set of corporate rules.
4) Be Explicit With Others About Your Working Relationships
Every day, you are sending messages to your employees, your investors, and your clients. Many of these messages aren't explicit, but they are there anyway. Is your head up when you walk into the office, or are you looking down and muttering to yourself? As a founder, you're always sending lots of messages whether you're aware of it or not.
Some of those messages relate to the differences between you and your co-founder. Once, an employee commented on an argument between two co-founders who I know as saying, "It's like watching Mom and Dad argue." The co-founders, by the way, thought it was just a normal discussion.
That "argument" caused a lot of churn in the organization, simply because the co-founders didn't tell everyone "this is fine and how we like to work with each other." Label your conflicts for your team so they understand whether things are OK or not.
5) Find a "Third"
No matter how great of a relationship you have with your co-founder, there are going to be times when you cannot come to an agreement or a lot of small arguments have piled up and people are starting to feel badly. All good relationships benefit from helpful and timely intervention -- ask any married couple.
Finding a wise and trusted adviser you both respect will go a long way in helping smooth out the bumps along the way.
Larry and Sergey had Eric, who we often lovingly referred to as the "adult supervision," because he was the tie breaker when one was needed, the guy who could say, "hold up guys, lets back it up for a minute." In my organization, my co-founder and I have an objective, unflappable CFO, who plays a mean referee when we need one.
Overall, I've found having a co-founder key to my ability to creating a great company. Joint decision-making isn't easy, but if done well, can result in much better outcomes. As with any strategic business decision, your mileage may vary. Consult your attorney first, and do not mark below the dotted line.