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Taking Time How you fight with your potential cofounder(s) matters for a lot of reasons, the simplest of which is that you have time to fight – meaning you’ve worked together long enough to hit disagreements or bumps.

But in order to figure out if you can work together you have to (wait for it…) actually work together.

That could be starting a side-project, heading over to a Startup Weekend or other hackathon, working full-time for a few months or some combination of those options.  However you do it, you need to build something together.  It doesn’t ultimately matter it if ends up being the right product, you will still have areas you disagree on throughout the process. Ask yourself: Have we had disagreements? If you haven’t, maybe you should consider a longer courtship period.

Simulating Real-Life Consider what real startup life is going to be like.  For a long-time (longer than you plan) things are not going to work and you’ll have to figure out what to do – together.  If you do eventually reach a point where the company is making real progress, you’re still going hit crazy challenges on a regular basis that you’ll have to navigate together

let’s agree you’re going to fight. That, in and of itself, doesn’t mean anything. In fact, it’s quite healthy. What matters in real life is what are the fights like? Do they escalate rapidly or become knock down, drag outs? Can you recover quickly and keep moving?

Entrepreneurship and early stage companies are about moving fast; if you’re caught in a disagreement for days at a time it means decisions are not being made and/or people are walking around feeling resentful.  Either one will eventually lead to failure.  Ask yourself: When we fight do we get over it quickly and respectfully?

it matters what the fights are about.

A lot of people approach finding cofounders as just a skill set need and believe once that box is checked, everything will be smooth sailing. Complimentary skill sets are important and if you’re fighting about one functional area  (e.g. design, product) it might be a sign you have too much skill set overlap.

What’s difficult is making sure you’re aligned on the softer side: Why do you want to build a company? What kind of company you want to build? What are your working styles? What are your values?  What are your other priorities (family, etc.)

But you better make sure you’re on the same page as your potential cofounder about those topics. These are the issues that break up relationships, not button colors.