Three Non-Negotiables in Choosing a Cofounder



I started my first two companies without a cofounder. Doing so has some advantages: you can move swiftly, you don’t have to shave or be civil (at least until you get your first coworker or customer), and someone who cares less about your business than you do doesn’t hold you back.

But having the right cofounder has even more advantages:

  • It’s hard to do—and impossible to be good at—everything. The right cofounder brings not just more work capacity, but skills, knowledge, and other resources complementary to yours.
  • You will need to collaborate with team members as you grow. Having a cofounder lets you immediately start building skills in teamwork, achieving consensus, resolving conflicts, and creating a positive work environment.
  • The right cofounder challenges you, making you stronger, and boosts you up when you are down. And vice versa.

Choosing your cofounder or cofounders may be the most important decision you make in your venture. It is a high-risk, high-reward decision: the right co-founder propels you forward; the wrong co-founder can destine you to failure. Here are three “non-negotiables” to look for in a co-founder.

1) Character

Think of character as overall human quality. Larry Reed, president of the Foundation for Economic Education, lists 9 qualities that he sees as most important to character: honesty, humility, responsibility, principle, self-discipline, courage, self-reliance, optimism, and long-term focus. Characterfirst.com lists 49 qualities, adding such attributes as attentiveness, compassion, creativity, flexibility, generosity, initiative, patience, and thriftiness. You decide which of these qualities are most important to your venture and in your cofounder, and how much weight you place on each quality.

Whichever character qualities you emphasize, recognize the importance of both inward values (attitudes) and outward actions (behaviors). I define character as inward values and outward actions that mutually determine and reinforce each other.

Character is independent of you and your mission. The cofounder who embodies character will continue to add value no matter how your organization grows and evolves.

2) Fit with You

Your co-founder’s fit with you has two parts: trust and complementarity.


Trust is the most essential aspect of the fit between you and your cofounder. Trusting your cofounder means that you and your cofounder are confident that each of you will

  1. Do (or perform or deliver) what you say you will do or have committed to, to the extent that circumstances are within your control or power to do so; and
  2. Act with your and your business’s best interests in mind.

The first one implies that you each have the skills and other means to fulfill the commitment and do not overcommit. If a situation cannot be controlled, you may not know what the other person is going to do, but you have confidence it will be the best the circumstances allow. Both numbers 1 and 2 imply an alignment between intentions and actions. The more uncertain the environment and the more independent judgment required by either cofounder, the more valuable is 2 than 1. Your consistently fulfilling your commitments and acting in your cofounder’s and your business’s interests is the best way to build trust and confidence in each other.


Two people with identical resources and advantages bring more manpower to your venture but no new ingredients. So your cofounder’s skills, knowledge, and relationships and yours should be complementary, which according to the dictionary means—“combining in such a way as to enhance or extend each other’s resources and advantages.” The skills, background, and relationship network of Dickey Singh, my second company’s CTO, and mine were highly complementary: computer and software engineering for him, consultative sales and product management for me. We ended up co-founding my third company together.

3) Fit with Your Mission

If you and your cofounder can find or co-create a mission to which both of you contribute something essential, both of you will bring advantages to it and increase your likelihood of success. Plus, both of you are more likely to be passionate about something you’ve created together.

Both of you should ideally contribute something important to your vision, like ingredients in a recipe. Assume that the customer need you satisfy and your business plan will be different, and likely more ambitious, after you and your cofounder team up.

A measure of the overall fit between you and a prospective cofounder is the product of these three factors. All three are essential; if any one of them is absent, the overall score is zero.

FactorIncludes:Relationship to you
CharacterHonesty, passion, perseverance, positive attitude, intelligence, flexibility, kindness . . .Independent of you and your mission
Fit with You·    Mutual trust, respect, and reinforcement·    Complementary resources and advantagesRelative to you
Fit with Your MissionShared passion and visionCo-created with you

As you think about these qualities in potential cofounders, remember: they are wondering about the same qualities in you. What is your character? Can they trust you? Are your skills and other resources complementary to theirs? Can you and they co-create a mission that they can become passionate about? How do they perceive your overall score as a cofounder? Candidly assess these factors from all sides. Getting to know and trust someone takes time. Ideally, your cofounder is someone you have worked with before. You will already have experience with his or her values, character, ups and downs, and how they respond to deadlines and other pressures.

Start-up “speed-dating” events (popular in Silicon Valley) purport to help entrepreneurs find cofounders through a rapid-fire series of meetings with different people, each lasting three to five minutes. Such meetings can help build your network with the understanding that you will have to invest much more time getting to know each person; their skills, attitudes, compatibility with you; and so on. Don’t expect such events to produce a cofounder for you right away.

Your cofounder or cofounders and your relationship with them will affect every team member who comes later and the entire trajectory of your venture. In the words of serial entrepreneur Naval Ravikant, cofounder and coauthor of the VentureHacks blog site, “If it doesn’t feel right, keep looking. If you’re compromising, keep looking.”



Image credit: CC by DonkeyHotey



About the author: John Chisholm

John Chisholm is CEO of John Chisholm Ventures, an entrepreneurship advisory, consulting, and investment firm.  He founded Decisive Technology (now part of Google) and CustomerSat (now part of Confirmit).   He is president and chair of the worldwide MIT Alumni Association and a trustee of MIT.

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