The allure of the cofounder is easy to understand. Why go the hard road of entrepreneurship alone when you can have a partner-in-crime? But for every Ben and Jerry out there, there are dozens of partnerships that have broken up (Jobs and Wozniack, Allen and Gates). Notice I didn’t say failed. Many partnerships — including my own with my former business partner, Neil — can be incredibly productive and fruitful while they last, and their ending just represents a natural evolution of the company, not a tragedy. But just like marriages, cofounder relationships can have devastating fall-out when they come undone. All the more reason to proceed with caution at the outset.

In those first heady days of a new business venture, it’s easy to imagine that you and your cofounder will always see each other in a rosy light. After all, if you weren’t an optimist, you wouldn’t be an entrepreneur. But asking some deeper questions before the wild ride of starting a company begins will help you navigate this potentially rewarding, but extremely complicated relationship.

· How well-suited are you for the cofounder relationship? For instance, how do you feel about sharing control? Or even ceding it? What brings out your best self and ideas? Is it collaboration or solitude?

· Do you have expertise in the industry in which you want to start a company? If not, it may be crucial to look for a cofounder, someone who will be as invested as you are but can make up for the gaps in your knowledge.

· How well do you know your potential cofounder? Just as with marriage, committing to someone too early can be a death knell for a business partnership. It’s easy to get excited about smart, cool potential collaborators, especially if they are charismatic. But it’s worth taking the time to get to know someone you’re considering going all in with on a deeper level. What are their views of how to manage life in a start-up? Do they think you need to be all-in, or do they believe it’s possible to have life outside of work? What gets on their nerves? Who are their favorite people to spend time with? Ask them questions as simple as how they like to spend their weekends. You’re dating, in a sense — these are all things you need to know.

· Do you share a vision and values? Discuss what you both want out of your work, what you want to contribute to your industry and the world around you. Do you agree on the core leadership philosophies? Are you aligned on a mission? How much do you each want to work? How will you handle a situation wherein you feel one person is pulling more weight than the other? Hypotheticals often reveal values, so take the time to come up with scenarios and think them through together.

· Would another kind of support system be better for you? No one truly goes it alone in business — but perhaps what you need is a team of advisors, a mentor, or investors who can offer direction as well as capital. The question of having a cofounder isn’t an all or nothing choice. Consider all of your options before going forward.

Originally published at on October 13, 2016.

Originally published at