5 Questions You Should Ask Before Choosing a Startup Co-Founder

5 Questions You Should Ask Before Choosing a Startup Co-Founder

Choosing the wrong co-founder can kill your business before it starts. Make sure you think through it first.

I don't know how solo founders do it.

I could not imagine starting or growing either of our two bootstrapped SaaS businesses without founding partners. Even when you split the business in half, the sense of responsibility and stress seems to be too much to handle.

Playing sports growing up taught me that having talented teammates makes life easier. You still have to practice hard everyday individually to prepare but you know that when the game gets tight, someone will have your back. Having great co-founders sometimes feels like playing 5 vs 3 against the competition.

Building any sustainable and growing business is hard AF. I probably don't need to explain to you why having a great co-founder is a good idea. The problem is that having the wrong co-founder(s) can kill even the best product or business before it gets going.

We have been blessed over the last 4 years to have 6 partners across 3 bootstrapped software companies and haven't had a serious issue with a founding partner. However, I could only imagine how draining and demoralizing it would be to do so.

Maybe we have been lucky. But in the event that we might know something valuable, here are a few questions to ask yourself before partnering up:

Will they deliver value where I can't?

The biggest advantage to having great co-founder(s) is when they bring skills, experience, and approaches that don't come natural to you. As a solo founder, you are left to figuring out these areas yourself or outsourcing them. The latter coming with a whole host of new problems.

When skill sets compliment one another instead of overlap, efficiency occurs as a natural by-product. It's clearer and easy to communicate who is going to own what.

The most obvious fit for SaaS style businesses is the combination of an engineering and sales/marketing co-founder. Those two skill sets cover most of the necessary functions to get a bootstrapped SaaS business off the ground.  

Would you share your personal bank account with them?

Because one day when your business is making loads of money, you basically will be.

This question is a good summary on the serious risks that come with partnering. The basic assumption you want to arrive to is "I can trust my co-founder with trade secrets, millions of dollars, and the business itself".

PRO TIP: Obviously, many founders don't know their potential co-founder well enough to truly answer this question. If that is the case, push back the start of the company and spend a good amount of time working together and getting to know one another before making it official.

Are our incentives aligned?

This one is tricky because it requires a level of trust to have very personal conversations about what you want out of life & your future. It's also possible that one party doesn't quite know yet what they want out of life.

If one partner's dream is to own a yacht in the Mediterranean and the other partner wants to work a few hours a week with minimal stress, there are going to be issues down the road.

Make sure that your potential co-founder has similar dreams & aspirations as you do. This ensures you are using the same lenses when making business decisions.

Are they hungry?

It takes an incredible amount of effort over a long period of time to build a great company. Especially for us bootstrappers that start with limited resources. You want to be sure that your future cofounder is as hungry as you are and ready to work.

Anyone can say they are hungry and ready. But the best way to confirm this is to look at their history of projects. Ideally, they have created and put things (blog, company, product, etc.,) out into the world in the past and at a regular pace.

Can they keep their cool and be flexible?

I think the most important thing you can do to vet a potential co-founder is to understand how they make decisions.

Decision making is the most important recurring act in business. As the business gets larger, your direct work contribution goes down and the number of decisions you make go up. Plus, the decisions become higher stakes as revenues increase.

It's inevitable. One day, you and your co-founder are going to disagree on a big decision that needs to be made. How will you two handle it? Are they going to break down, blow up, or will they be able to work through it and come to a compromise.

When in doubt, take it slow.

The worst thing you can do is get into business with a bad co-founder. And choosing a co-founder is a decision that is filled with uncertainty. If you are uncertain about whether or not to jump in business with someone, the best course of action is to take it slow.

My business partner and I spent months meeting at Starbucks to just chat over ideas. That's how I learned how he approached problems, what he wanted to work on, and what his life goals were. Looking back, I'm glad we did.

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