How to choose the right cofounder

As a founder, there are few more important decisions you’ll make in the early days of running your startup than choosing whom to trust and collaborate with.

‍

Why to consider finding a cofounder.

Starting a company requires a tremendous amount of work, and as the expression goes, two brains are better than one.

That’s why it’s helpful to collaborate with one or more cofounders early on. Together you can pool your resources, connections, skill sets and talent to give your company a better chance of success. It’s also helpful to divide up the amount of work, bounce ideas off one another and lean on one another for emotional support (working at a startup is hard!)

But while working with one or more cofounders can help improve ideas and ease the financial burden, it’s also important to consider the social, financial and professional implications of working with the wrong cofounder(s).

Why choosing a cofounder matters.

Choosing a cofounder is just as important as choosing a spouse or life partner.

Why? You’ll be spending a lot of time together. You’ll be going through a lot of stress while navigating high-pressure situations. You’ll be co-creating solutions, dealing with unforeseen challenges and navigating all kinds of decisions. It’s also your opportunity to impress possible investors with your ability to attract and recruit smart, savvy business partners.

So it’s important to pick someone you trust, who adds value, who looks good on paper, and who you actually enjoy spending time with. You also need to work with someone who understands your key users and what you want to build (both short-term and long-term).

Someone who shares your values, while bringing a fresh perspective to the table. Who can push you and your assumptions without making everything dramatic and awkward. You need a cofounder who is not afraid of hard work and won’t bail at the first sign of struggle or trouble.

When you’re a small team, there’s simply no room for dead weight, unnecessary conflict or power struggles.

Questions to ask cofounder candidates.

Most of the time cofounders have a relationship before sitting down to create a company. Maybe you’re friends, siblings, spouses, peers or colleagues. Regardless of your personal relationship to one another, it’s important not to assume you know the answers to these questions, so make sure you ask them outright:

• Do you have any previous experience working at a startup?
• Why do you want to help build and grow this company?
• Why do you care about this problem and/or this community of users?
• What is your goal for this company? What does success look like?
• What type of role and accountabilities do you want to lead? (e.g. Marketings/Sales, Operations, Technology, Finance, Customer Service)
• How do you deal with conflict?
• How will we resolve disagreements?
• Are you in a financial position to take this risk?
• Are you willing to commit to this company full/part/whatever-time? How many hours and how much money can you invest in the business?

Questions to ask yourself.

After asking your prospective cofounders the above questions, ask yourself some of these:

• What skills, experience or personality gaps are there on our team?
• Does this person have a spirit of abundance? Do they believe rising tides raise all ships?
• Is this personal comfortable fundraising and/or asking people for help/resources/money?
• Do I really know this person? Do I trust this person? If not, do they have credible referrals or other past business partners or colleagues who can vouch for them?
• Does this person frequently follow through and do what they say they will do?
• Does this person have access to capital (either financial, professional, social, or otherwise)?
• Have I worked with this person before? Do we have complementary work styles?
• Does this person have relevant experience (either professionally or personally) or are they a subject matter expert when it comes to the problem we are trying to solve?
• Is this person too similar to me? Do we have redundant or complementary skill sets?
• Do I feel safe having challenging, authentic conversations with this person?

Red flags to watch out for.

If you’re thinking about going into business with someone, here are some red flags to watch out for:

• They’ve broken up with other business partners in the past (and speak negatively about them).
• They're your best friend (not a deal-breaker but could prove challenging to navigate later down the road).
• They fight you for control.
• They have a big ego and make everything about themselves.
• They aren’t great listeners and frequently use “me” language vs “we” language.
• They are flaky and frequently miss deadlines or don’t follow through on their commitments.
• They have 9 different companies and side hustles going on at any given time.
• They lack integrity.
• Their expertise is too similar to yours.
• They don't have relevant experience at all.
• They have starkly different values than you.
• They are overly confrontational - or overly passive.

Considering multiple founders?

Sometimes it can be beneficial to have more than two cofounders. If your goals are especially ambitious or you know multiple people who work well together, share values and vision for the company then it might make sense to have 3-4 cofounders.

In that case, it’s important to have very clear, outlined roles and responsibilities. Who is in charge of what? What is the share/ownership breakdown? How are decisions made? How can you make sure people are all working together and at similar speeds/rates?

Considering solopreneurship?

Another option is starting out as a solopreneur, meaning you don’t have any cofounders. This can be a great way to get things off the ground if you have a clear vision and don’t need too much help right out of the gate. Just remember the expression: If you want to go fast, go alone. If you want to go far, go together.

This article was originally published to Cloudburst SBC's Partly Sunny Blog on December 12, 2022.