Learnings from “co-founder dating”

Timo Luukkola
5 min readApr 12, 2024

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Two months ago, I shared on Linkedin that I’m going to build something new. Same time I shared my early ideas and started my co-founder exploring journey (some refer to it as “co-founder dating”). I was pleasantly surprised by the number of people who reached out to me. My somewhat cryptic posts appeared to resonate with people.

Shortly after my previous post, I was contacted by a person with complementary skills and shared interests in the problem field. We somewhat knew each other through mutual friends and associations. We started by having lunch together, then began meeting several times a week. Eventually, we had a shared table at Startup Sauna.

We used the Minimum Viable Test (MVT) Process, the alternative to the more commonly known MVP (Minimum Viable Product). Having a shared interest in personal data and individual empowerment, we started to brainstorm, research the market, and write down dozens of concepts, to find those risky assumptions.

An MVP is a basic early version of a product that looks and feels like a simplified version of the eventual vision. An MVT, on the other hand, does not attempt to look like the eventual product. It’s rather a specific test of an assumption that must be true for the business to succeed.

The idea evolved from one meeting to another: Personal AI coach → Bank of your data → Platform to integrate your data to services → Personal AI assistants → JARVIS → Personal data platform → Product Discovery Assistant …

I can say, the process was anything but easy and hardly pleasant. Jumping right to building and seeing code turning to interfaces and functions is way more pleasing than trying to kill your concept already to whiteboards with intellectual honesty. The feeling of just getting over it and focusing on building measured resilience, but too many startups fail to think through what they are rushing to do.

As our background differentiated, we approached the problem from strongly different directions. I thought of the problem more from an individual and product point of view, while my co-founder focused more on the technological side and traditional business needs. Starting at different ends sounds perfect deal, but also makes the process cumbersome. I soon noticed that the hardness was more due to differences in viewpoints; what is sufficient impact, what individual empowerment means, what we want to accomplish, and what kind of business we aim to build.

1-month founder dating & break-up

There started to be signs of our differences, that might become a problem in the long run. We read the same documents through two different lenses; while I was more consumer-focused, my co-founder looked at things more from a business perspective. We conducted an exercise multiple times where each of us wrote down our thoughts on Notion individually, and then compared them to see if they matched. Often, we found that there were shared themes but different tones in the voice. We realized that we were heading towards creating a Frankenstein product, with too many compromises.

We have all learned that “we shouldn’t build companies with homogenous backgrounds”. However, studies have found that the greater the heterogeneity among executive team members, the greater the risk of interpersonal and affective conflict and the lower the group-level integration (Wasserman, 2012). Heterogeneous cofounders may run into early problems if their differences result in incompatible working and communication styles. Those tensions are most likely to flare up when the team is facing decisions that could make or break the business.

We liked each other as a person. We learned from each other, showing new ways of thinking and working, challenging our “intellectual honesty” and we had complementary hard skills. However, our values and aim for impact we not aligned, our dream roles in the founding team overlapped too much. I was somewhat nervous to bring it up, but I soon discovered that during the holidays, we had both independently arrived at the same conclusion: Building two different success stories is more beneficial than building one together.

Learnings

For those thinking about the founding team, hiring, and investors, the book The Founder’s Dilemmas by Noam Wasserman has good insights! I like the way it is written. First, possible options are shared, then statistics on how founders tend to choose are looked at, and finally, the pros and cons of each option are listed. I found it very helpful when dealing with co-founder fit.

Co-founder questionnaires, like “50 Questions to Explore with a Potential Co-Founder” are good tools, until you blindly follow them. While the co-founder fit looks good on the paper, reality can prove it wrong. Nonetheless, the questionnaire attached is helpful for self-exploration (I completed it last year). I believe that some of the topics in the questionnaire should be discussed before working together (commitment, motivation, values), while others can be addressed once there is a better understanding of the concept.

👉 Start with simple questions: do we share an interest in the same field or problem at hand?

👉 In the beginning, it’s important to discuss your level of commitment, motivations drivers, and core values for working on the startup.

👉 Work together (a month at the minimum) to get to know each other. Don’t establish a company, think of it more like common unattached brainstorming.

👉 It's tempting to choose the easiest option, but that's not always the best long-term strategy. Embrace the pain of hard work, but only until it pays off.

👉 Talk about your wishes early: are you after a big impact or a big paycheck, what role makes you excited every day, what are your non-negotiable values…

👉 If you find discussions raise values often and those discussions are hard or not fully in line, take it as a warning sign. Shared core values are important for success.

👉 Avoid a lukewarm compromise in roles and responsibilities. It kills enthusiasm, increases confrontation/dissatisfaction in the future, and ultimately kills the company.

In the end, building the company is already hard without a complicated founder relationship. Founders should work together against challenges at hand and ahead, not add challenges to the road.

What next?

As a founder, I learned a lot. I understood the importance of shared values and soft skills in addition to diverse skill backgrounds. I’m more aware of what kind of company I want to build, and what kind of people I want to be surrounded by, I know way more about the industry than before and I had the privilege to learn thinking this problem from a different perspective.

I’ll continue building the team for this idea stage company, which got the working name “Zero”. If you are interested in following the journey of Zero, you join the inner circle at withzero.io. Team building is on, reach out to me on LinkedIn.

Cheers! 🕺

Wasserman, N. (2012). The founder’s dilemmas. The Kauffman Foundation Series on Innovation and Entrepreneurship.

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Timo Luukkola

Founder at Stealth Startup, prev. product lead at Wolt, and university graduate from Finland. Had a creative break, now building the next startup adventure.