Finding Your Perfect Cofounder

You may have read in articles or heard in discussions that a relationship with a co-founder is kind of like a marriage. Both yes and no. Yes, it is true in terms of how a relationship develops in a movie, where there is a honeymoon phase, gradual discovery of the other person, some frustration, a long evolution, and, if you're lucky, an equal, fulfilling relationships, support, and other good things.
However, the similarities are only superficial because the dynamics and essence of these relationships are very different from marriage because they are driven by much more specific goals.

TL: DR When I decided to radically change my activities and launch a startup despite a lack of connections and experience in tech, I reached out to the few people I knew in the field. However, every attempt to find the right cofounder failed in some way, affecting the success of the projects I started. I needed to figure out how to find the right person to help me successfully launch my next startup, which is a part of my personal mission.

I
I'm an art director/creative director/strategic marketing guy turned startup founder, previously started two startups (both failed). I decided to leave my previous professional life behind and launch my first startup a few years ago. My job had almost nothing to do with tech. And I found myself in a situation where I had an idea and a desire but no resources or knowledge to put it into action.

This didn’t stop me, I searched for information and quickly realized that a good technical cofounder would be extremely beneficial in launching a successful startup. But where do you get one, and what kind of person should it be? It was only clear that it had to be someone in charge of the development.

I reached out to the few tech people I knew, and voila! I was introduced to a potential cofounder. Only one. When he realized that a serious commitment was required, he left before we even began development, and I'm alone again. I spent another couple of months looking for a replacement, but it was futile.

Eventually, I was able to get the app up and running by hiring an external dev team. Sure, I recognized that this was not the best option for a variety of reasons: it was expensive; it was difficult to expect a strong involvement in the product's creation, and the connection with the project and the funder was solely based on financial interest.

I began the next project on my own as well, testing a few basic hypotheses. Because I did not intend to hire an external team this time, I began looking for a cofounder once again. I found him on one of the internet forums. After a few months, it became clear that there was an issue with a lack of commitment as well as skills.

After a while, I invited another developer who was on the same hackathon team as me. He was far more productive than the previous one. We eventually decided to pivot because we discovered a new promising niche where we could apply the same technology. Then the pandemic struck, rendering our efforts futile. Most importantly, it turned out that our goals, relationships, and ability to work through challenges were not on parallel tracks.

A few days later, I sat down and thought about what deeply important problem I had that I desperately wanted to solve but never did. The answer came to me almost instantly: chronic procrastination. I did some quick research and discovered that the same issue affects a large percentage of people around the world.

While researching, developing an MVP, and validating hypotheses, I realized that this was it. The problem itself, as well as this entire field (psychology/neurosciences), are not only exciting but also completely align with my inner motivations and goals (some would call it a mission).

With very promising MVP results in hand, I (yes, once again) decided that now was the right time to bring in a tech cofounder. The search was finally narrowed down to four sources: my network, subreddit r/cofounder, Y Combinator Co-founders Match, and this thread on Indiehackers. I wrote a short intro about myself, the project, the stage I'm currently in, and who I'm looking for.

To have a clear reference point, I sat down and asked myself, "Ok, who would be my ideal co-founder, and what qualities seem important to me based on my previous experience?" I did a document on which I relied during my search. It was important for me to write down all of my thoughts on this rather than hope that "I understand everything anyway."

After that, I placed a new post in the above-mentioned communities and started browsing YC CF Match profiles.

II
A few dozens of people from around the world responded.
Many of them were talented people and strong developers with extensive work experience, including CTO positions in other startups.

All in all, after discussing the terms, the trial period, the areas of responsibility, and our expectations of each other, we started working on the product with one of the candidates.

Now fast forward a few months. We went through a bunch of situations, including the honeymoon period, three or four crises, and the product's evolution. As I reviewed our results and the dynamics of our relationships, I realized that it was probably best for the business and for both of us to go our separate ways.

The two main factors that led to this decision were my cofounder's lack of interest in the problem the product solves and psychology in general, which resulted in poor performance as well as a lack of common interests and themes to discuss. This may sound harsh, but I believe we should have split up much sooner.

III
As I progressed through this quest and analyzed my actions and outcomes, I came to the following conclusions:

0
Setting up meetings with multiple candidates is worth the effort. One person, even if they meet some criteria, is not a choice; it is self-delusion, which will manifest sooner or later. A startup is a long game, and it's worth taking the time to find and communicate with the right people so that I don't have to start the process all over again, possibly at a time when it's completely unnecessary.

1
Homework is crucial. It involves learning the fundamentals of the business I'm running, such as the market, the state of things, the method of company development (venture capital or bootstraping), and the roadmap.

The other part may be more tricky – it is about understanding myself, my values, and motivations, assessing my resources, evaluating what the business requires now and in the medium term, and determining what type of cofounder I should seek.

2
A thorough review of each potential cofounder (it is assumed that this is a stranger from the Internet). What and how he/she says, what he/she asks, what values he/she communicates, how he/she reacts to specific events and changes, the degree of involvement in the problem, and the creation of the best product.

It should be given no less attention during the joint work. And this assessment should be done as frequently as possible, perhaps once a week. If problems are left unattended, they tend to worsen.

As a founder swimming in uncharted waters, I should do the same with myself.

3
Red flags. These can be any signals that cast doubt on a person, his/her qualities, goals, intentions, or values. Ignoring them is a ticking time bomb in business and relationships.

4
Hard skills. They are difficult to assess for a non-technical funder, and vice versa. You could enlist the assistance of someone you know who is knowledgeable about the subject. However, there could be a difficulty: this is not a typical job interview, and there is no one who can share the responsibility. It makes sense to search open sources for information, such as GitHub. In general, it is beneficial to be attentive and creative. All of this, of course, will not give guarantees, but still.

5
The person who invites the cofounder automatically becomes a leader. So, it's crucial to exercise leadership. Of course, it's not about being the alpha. This role may shift over time, but not in the initial phase. Taking responsibility is an essential part of leadership.

6
All of this leads me to believe that empathy, self-discipline, attention management, calmness, and clarity are a founder's best friends. In addition to the well-known qualities and skills that everyone is familiar with.

IV
Andreessen Horowitz's Marc Andreessen claims that approximately 50% of cofounders divorce, yet the firm prefers to work with teams of 2+ cofounders.

I don't think a cofounder is absolutely necessary for everyone. Many super-cool solo founders have built fantastic products and businesses. With a clear vision and some personal qualities and resources, you can get far enough with an external dev team until you have one of your own. However, I think that starting a startup is somewhat similar to climbing a difficult mountain in that having the right partner in the bunch motivates you to move forward, look for and find better ways, express your best qualities, learn new things, and learn to trust. In other words, it greatly increases your chances of reaching the summit.