Picking a co-founder. It’s as personal as picking a spouse and as financially binding as picking an investor. Co-founders are the pillar of your company and a relationship most entrepreneurs don’t spend enough time thinking about. If you get it wrong, ending the relationship is incredibly difficult.

A rare few will marry someone within weeks of meeting, while most people spend months getting to know someone before they ever pop the question. Yet when starting a company you often don’t have years to spend dating before you can decide if you want to take the leap.

My being back in the founder dating world is an awkward transition. No different than when I left a long term relationship, I’m out meeting people. Thankfully this time around I know myself a whole lot better.

Looking back at Contour, like anyone in their 20’s, I spent most of the last decade discovering myself. Subconsciously I was figuring out what kind of entrepreneur I wanted to be, what kind of companies I wanted to build, and what type of people I wanted to work with.  My quest to better understand what makes me happy is helping me think through who I want to work with next.

As I go through this process I have put together a simple guide of how you can pick your next co-founders.

It Starts With You
Before you can date someone you have to know yourself. While being honest with yourself can be hard, it’s necessary if you want to be a great entrepreneur. If you can’t understand what makes you happy, you will start and run the wrong company.

To discover this I like to ask myself a few questions:

1. “What am I passionate about?” – This can start with big subjects like “music” and as you think about each thing you are passionate about in life try to define it further, so for example what exactly about music are you passionate about and why.

2. “What am I passionate about in a company?” – This comes back to what traits or values will be the anchor of the company you start. It doesn’t need to be a long list, but a few items that are so important that if they do not exist you will not start the company.

3. “What am I strong/weak at?” – knowing what things you like to do in a company, what things you hate, and what things you aren’t good at is important. You are looking for people with complimentary skills and ideally people who are strong where you are weak.

4. “Does size matter?” – (insert joke here). Often times you don’t know how big of a company your idea can turn into, but having an understanding if you want to change an industry (build a massive category leading company) or if you want to keep it small and build more intimate products is important. These are completely differently lifestyle choices.

Chemistry
The same chemistry you looked for in finding a significant other is the same chemistry you need in finding a co-founder. The attraction aside, you either click with the person or you don’t. It’s okay if you don’t, but you are looking for the basic signs that you like someone. Remember you are building a very long term relationship, which means you are looking to build inseparable trust.

A good way to figure this out is spend time with them. And not just a coffee meeting. Spend time with them for breakfast, lunch, dinner, and the bar. Figure out if you like the person in the morning as much as the evenings. Spend time talking about ideas, business philosophy, family, food, interests, life, etc. Just like when you date you want to find out if you have similar interests. You can only do this if you spend time with that person.

People often get confused that you need to be best friends with the person, I don’t think you do. But you have to really like the person and want be around them. You will be spending a lot of time together.

Sharing Similar Beliefs 
Give your potential co-founders the same questions you answered and see what they say. It will tell you instantly if you believe in the same things. If you don’t, end the dating. You CAN NOT compromise on what you believe in or you’ll end up the cliche spouse in the relationship admitting you gave up on your dreams when you got married.

You need to be able to talk about your answers. It’s one thing to write them down but you have to be able to talk about them openly. Talking about your feelings can be hard, but you have to. You have to ask questions that make both of you vulnerable. If you can’t do this, you will never be able to have the type of communication you need down the road.  A co-founder is like a spouse, you have to be able to talk about everything.

Knowing They Won’t Give Up
Building a company will test you in ways you can never imagine. It will push you emotionally, drain you physically, and challenge your soul. Coming to work everyday is a choice and you want to make sure the person next to you will do it no matter how massive the challenges are in front of you.

An easy solution is picking a fellow co-founder who has also started a company. Joining one early is nice, but finding someone who has been through hell and back as a founder is an invaluable experience. It doesn’t mean their company needed to have been a success, but you want to know they didn’t give up.

If they haven’t started a company you want to go back to their roots and understand what tragedies they have faced, what set-backs have they had to overcome, or what challenges have they beat. This can include a variety of life experiences from a rough childhood to losing someone to excelling at sports. You are looking for experiences they can talk about that took incredible personal commitment to overcome.

Conclusion
When you are in the dating phase with your potential new co-founder, BE OBSERVANT. Looking at small things can tell you a lot, such as how do they talk about other people, are they positive or negative, do they follow through, and/or are they on time? Small clues tell you a lot about the person, signs you want to pick up as early as possible.

Getting to this point in the relationship is the most important part. If you have the same beliefs, a strong chemistry, totally open communication, and you know the person won’t give up, you can figure out the rest. Determining roles, ownership structure, which idea to pursue, etc can be worked out. In fact, working these out together will better confirm your choice to take the co-founder plunge.

Good Luck!

 

Photo Rights: Costin Thampikutty (http://www.flickr.com/photos/costinthampikutty/8043415014/) via Creative Commons