The Co-Founder Courtship

Co-founding teams from Wistia, CodeSee, Pandium and Rubicon MD

Recently, I was listening to the Huberman Lab podcast where Dr. Huberman interviewed Dr. Buss, a founding member in the field of evolutionary psychology and Professor of Psychology at UT, Austin, whose research centers around How Humans Select & Keep Romantic Partners in Short & Long Term Relationships. In the podcast, Dr. Buss describes his research on how people select mates and the dynamics of courtship. While the podcast was focussed primarily on heterogeneous relationships, marriage and monogamy, I couldn’t help but think of the parallels with co-founder relationships. My brain is in the entrepreneurship space most of my waking hours, after all, and it made me think about how many entrepreneurs I know are looking for co-founders, yet many don’t appreciate that this is a similar courtship to mating and partnership. 

Many entrepreneurs believe they must have a co-founder and some are pressured by investors to have a particular type of co-founder. The conviction to have a co-founder is often based solely on complementary skills and experience vs. the softer, and often more important, relationship criteria. While there are some working papers out there, I have yet to see definitive research that proves whether one absolutely must have co-founders vs. going it alone as a solo founder. This is a highly subjective situation dependent on many factors; some of which I’ll discuss below. 

Do you need a co-founder?

I’ve worked both for and with hundreds of entrepreneurs in the last few decades and on the topic of co-founder relationships, my observation is that each situation is highly dependent on the chemistry, the experience each brings into the relationship, leadership styles and many other internal and external factors. While having co-founders can de-risk the business and/or complement skills, forcing these relationships can result in bad “marriages” that create more harm to a business than help. Certainly, when a great match happens it can be magic, but just like any marriage, one should not enter the relationship rashly.

When thinking about whether or not you need a co-founder, consider:

  • How could a co-founder balance your skills and experience? For example, if you are a technologist, but lack management or operating skills (marketing, sales, etc.), you may benefit from a more seasoned business leader as co-founder who’s seen the movie before. While many operating skills can be learned, early stage founders may underestimate how critical these skills are to have early on and rookie mistakes can set back (or kill) a business before it’s barely out of the gate. Read Khalid Halim’s thoughts on Hypergrowth and The Law Of Startup Physics for more on this point. Conversely, expertise and experience can be additive to the business without a co-founder title and compensation. Unless you are doing hard science that is your core business, building a business that is technology-forward or relies on tech to some degree is not nearly as hard as it once was. Having a strong first-hire who is technical can suffice; the same holds for someone with strong sales, marketing or other operational skills.
  • Is domain expertise critical for your venture? Unless you are already the expert in the particular field your venture intends to address, you may need a co-founder with domain specific expertise. Having domain expertise will not only inform the product strategy, but will also help the venture gain credibility in the market and potentially open doors on the sales side. Investors may expect or even require there be a domain expert on the co-founding team, but similar to the point above, you may also be well served with a first hire or even an advisor who could serve you in this way vs. a co-founder.
  • Most importantly, ask yourself whether you value partnership, shared risk and collaboration with others. It can be great to have someone to brainstorm with, share the workload and to commiserate with during your journey, but having co-founders – like a committed personal partnership – is also a big test of your ability to be vulnerable, handle conflict and willingness to compromise. There will be many times your co-founding team will disagree on things – from product and hiring decisions to operating procedures and a fundraising strategy – and how you process these decisions together is fundamental to a healthy co-founding relationship. Self awareness, a willingness to lean into conflict and ability to thrive in ambiguous situations will be critical in a co-founding relationship. If you question whether you are up for sharing these experiences with one or more co-founders, you may need to do some introspective work before taking on a co-founder or, perhaps, go it alone.

Anyone thinking about having a co-founder must go beyond the skills and experience aspects and consider the fact that they are entering into a deep, personal relationship. Whether it’s because you couldn’t find “the one” and time is of the essence or because you are self aware enough to know you are better off going it alone, taking the solo route is perfectly doable by rounding out your team with necessary skills and expertise. You might also consider a second in command (COO, CTO, etc.) who plays a key role in the business without the official co-founder title and compensation. These individuals can still receive founding team worthy equity grants and, in earlier stage businesses could be anointed as “co-founder” down the road if the relationship blossoms over time.

The Co-Founder Courtship

If you’ve decided that you really want and/or need a co-founder, you’ve basically decided to seek a mate for a long term partnership. Just like a personal relationship may result in children, big financial decisions (like buying a house), running a household, etc., a co-founding relationship will force you to commit to how you will nurture employees, manage finances and run your business. There are big decisions to make – “how will we educate our kids?” is similar to “what kind of company culture will we have?”. There are philosophies on which to reach alignment – “where will we raise our family?” is similar to “will we have a home office or remote-friendly work environment?”. You can’t have a few coffee meetings with a prospective co-founder to discover how you will answer these deeper questions. It’s a courtship and despite the urgency you may have to get going with the venture so you can raise money, hire people, etc., I can’t emphasize enough how important it is to nurture these prospective relationships.

Herewith a few suggestions on how to court your co-founder(s):

  • Conduct a listening tour by meeting other startup co-founders. Talk with them about their own courtship process. Ask if there were questions they wish they had asked and hurdles they had to overcome early in their relationship. Even the greatest co-founding teams have war stories to tell about stressful situations in their relationships and what they learned from these experiences.
  • Using insights from the listening tour, along with your personal preferences, write a co-founder job description (JD) and include experience, skills and your ideal, softer, characteristics for this person. If you already have someone in mind, try to stay objective and not write this JD to ensure they can fill the role (confirmation bias). Use this as your guide as you meet prospective co-founders and adjust as you go. It’s very likely that the more prospects you meet, the more tweaks you’ll make to that JD and finding “the one”.
    • NOTE: If more than two of you are thinking about becoming co-founders, do the JD method as a “diverge-converge” exercise. Discuss potential roles each may fill and have each of you, independently (diverge) write the optimal co-founder JDs for each role. Once each has taken a stab at this exercise on their own, share these JDs with each other (converge) and discuss where you were all coming from for each role. Not only will this better define each role, but it will allow you and your prospective co-founders to expose perceptions and expectations of each other and how the leadership of the business will play out.
  • Experienced hiring managers know that it is rare they’ll hire the first candidate they interview for a newly created role because they may not be clear on the right fit for the role until they’ve met a few types of candidates. The same holds for co-founders. You may have to test a few potential co-founder candidates before inking a co-founder agreement. Try to meet at least a half-dozen people who may solve for the gaps you are hoping to fill (expertise, experience, chemistry, etc.). Yes, this may mean you are “dating more than one person at a time”, but you’ll be far more clear about fit through this series of conversations.
    • NOTE: Finding a half-dozen candidates may not be easy. Tap into your network, ask prospective investors, former professors, etc. and tell them what you’re looking for. Share the JD. Attend conferences, talks etc. and be clear you are in the market for a co-founder. YC also released a co-founder matching tool that may be helpful.
  • Test the relationship beyond coffee chats and dinners. As noted in the Huberman podcast noted above, relationships are truly tested when the parties engage in experiences that allow them to see more dimensions of their personalities. For example, go on a road trip or partake in an activity that neither of you have done before. See how each of you make decisions together like where to eat lunch or which trail to hike. Even a game of mini golf at a course neither of you have visited or playing a video game together can test how you collaborate and/or handle competition. You might also consider working on a start-up related project together to see how that feels, such as co-creating a pitch deck or conducting customer interviews together.
    • NOTE: If you are considering a first time co-founding relationship with someone you’ve worked with at a company in the past, this does not give you a “pass” to skip this part of the process. Co-founding a business with a former coworker is like going from dating to living together. You are sharing responsibilities you likely did not have when you were colleagues at a business where someone else was accountable for the overall successes and failures and, likely, making more strategic decisions than you were privy to.
  • Have vulnerable conversations. One of the most popular sessions in my course at HBS is the discussion around one’s relationship with money. Most adults have very different perspectives on money and typically this is rooted in deep family or personal experiences, sometimes starting in early childhood. A parent losing a job, having to work at a young age to support family, credit card debt, anxiety about school loans, etc. Understanding how you and your co-founder think about money will give you a lot of perspective when it comes time to raise capital, price your product, pay employees, etc. Similarly, it’s important to talk about any peak moments in past jobs, school, etc. that inform your attitudes about leadership, culture and how products are designed/built, etc. While these conversations may feel very uncomfortable, it’s a step towards a solid working foundation in what will almost surely be a roller coaster of a journey together. Being able to have these conversations also tests how you’ll handle and support each other during conflict and stressful moments. You will have context and better understand where you are each coming from. Most importantly, these types of conversations don’t stop once you agree to be co-founders; they should be ongoing throughout the life of your venture as each co-founder and the relationship matures.
  • Finally, I recommend that prospective co-founders meet each others’ partners/families/BFFs. Not only does this further uncover the broader context of who these individuals are, but it also helps these important people in your lives understand this new relationship you may be entering. So, when you are up until 2am slacking with your co-founder about the upcoming pitch or how to deal with a customer issue, they know who that person is and how they are partnered with you. 
    • NOTE: For those considering co-founders who ARE your partner/family member/BFF, I encourage you to enter with a mindset around taking a personal partnership from no kids to four kids. It brings the relationship to a whole new level. This can be an incredibly rewarding experience for you, but it can also test the relationship to the max. While this person/people know and probably trust each other better than strangers co-founding a business together, it also means there is likely baggage that can create more emotion and triggers around certain issues than the average partnership. I have worked with incredibly endearing and high performing co-founding teams made up of siblings, married couples and BFFs, but I have also seen these types of co-founding teams erode due to irreparable events rooted in their personal history. Do not take this choice lightly. Consider getting a coach early on who specializes in working with co-founders who also have personal history together. I guarantee you will not be able to put your personal stuff in a box outside your business. Personal tensions will come up – either overtly or subtly – and having the support to work through it will be crucial to your long term success.

One cannot rush the co-founder courtship process. The most successful co-founding relationships I’ve seen inevitably end up being far more than co-workers. They are practically family and while that means potentially more emotions are at stake, it’s their mutual understanding and deep respect for each other that allows them to traverse this often treacherous journey. They have mutual trust and are committed to ensuring the success of their business, together.

There are many other articles and videos published on this topic, but a few I like are here and here.

Do you have lessons learned from your co-founder courting and/or working relationships? Please share in the comments!

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