From February to April 2024, I worked with two engineers (whom I connected with on the YC co-founder platform) to find a compelling problem space, attractive market, and product concept with the goal of co-founding a company together.

The two engineers had impressive academic and professional credentials having worked at all the big tech names but they had limited exposure to real-world business problems. However, they were eager to learn. I led them on a seven week journey of customer discovery and provided them access to my network. We spoke to many customers and honed in on where we wanted to focus our design and development efforts. We found a technically challenging, high value business problem that everyone on the team was excited to work on (AI Infrastructure to Automate Data Pipelines).

We then took this problem area and applied to well known incubators. We got to the final rounds of a couple and also received a YC interview for the Summer 2024 batch. However, we decided to part ways minutes before receiving the invitation to interview for YC.

What happened and where did we go wrong?

When we first connected, we thought we covered the basics of co-founder compatability. We aligned on controversial questions related to roles, responsibilities, and equity ownership. We aligned on our mutual interest areas and why we wanted to start a company. Basically all the easy, perfunctory topics.

All seemed great. However, as soon as we got into the weeds of product development, working with customers, and staying accountable to each other - we realized that we were actually quite misaligned. Here are some of the takeaways from my experience:

Takeaway 1: Build together (ALOT) before applying together

My co-founders were really keen on getting into a respected incubator. As the CEO and non-technical co-founder, I was happy to try to weave a great story, problem, market, and product idea to convince incubators to bet on us. We were able to do this decently well, given the credentials of the team. However, at some point, getting into an incubator became more important than building a product, business and team. This really obscured several underlying team issues. Collaborating on an incubator application is not a good way to test a team’s ability to collaborate and execute. The only way to pressure test the collaboration is to build something together that has some stakes to it. To give ourselves some credit, we did try to test this but it only took a week and didn’t have sufficient stakes.

Takeaway 2: Regularly reassess founder-market fit

As we narrowed in on our problem and market space, we did not regularly reassess whether we had the right set of experiences, skills and network to be successful in the market we were targeting. We had the right hard skills across each of the functions in engineering, sales, product, and marketing, but I wonder whether our team had enough overlap in experiences to be able to succeed. When I had initially been searching for co-founders, I was looking for people with very different experiences and skills than mine. However coming out of this experience, I have realized that some degree of overlap is critical to establish a shared language and way of working that otherwise needs to be learned (which I address in my last takeaway).

Takeaway 3: Founding teams are much more fragile than I had imagined

I did not fully appreciate how fragile a team is at this stage. No external force holds it together beyond each individual’s commitment. I have worked successfully on many teams. I’ve been on challenging teams and helped turn them around into high performing teams. So when I began to see potential issues with our team’s compatibility, I felt confident that I could make it work because at frog, we were literally trained to adapt to differences. I’ve now come to realize that the cohesion of those teams was actually maintained by the underlying structure of the existing organization, frog. Here in the fragile state of early entrepreneurship, there was nothing. So when the first issues start appearing, the force wasn’t strong enough to keep us together.

Moving Forward

I’ve reflected on some of the characteristics I’m going to look for in co-founders if I continue to pursue entrepreneurship. I’ve created a framework which is comprised of four layers: Velocity, Foundations, Grit Orientation and Founder-Market fit.

Here are a few questions that I plan to ask myself every time I evaluate a potential co-founder. I also hope that a potential co-founder asks me the same questions.

Velocity

Shared perspectives on the pace of progress.

• Learning How fast and willing are you to learn?
• Execution How quickly can you execute?
• Decision-making How quickly can you make decisions?

Foundations

Shared ideas around passion, purpose and practice.

• Shared Passions: What are you interested in building? What are your domain interests? What problem areas do you want to solve? What industries are you interested in?
• Shared Purpose: Why are you starting a company? What do you think about the responsibilities of taking on venture capital and what this entails?
• Shared Practices: How do you collaborate? How do you express and get feedback on your ideas? How do you plan? What keeps you accountable? How do you share your work?

Grit Orientation

Shared characteristics necessary to break through barriers and follow through on commitments.

• Perseverance: Can the team adapt, take initiative to move projects forward regardless of obstacles and without external prompting?
• Commitment: How committed is everyone and how is this commitment reflected in personal sacrifices?
• Resilience: What is the level emotional strength to endure stress and challenges without breaking focus?

Founder-Market Fit

Alignment between the team’s assets and the needs of the target market. Complementary but also overlapping.

• Professional experiences: Does the team have professional experiences valuable to the target market? Have they seen similar problems in prior roles? Do they know the competition? Is there sufficient overlap in experiences across the team? What is their exposure to the various functions of a business?
• Hard & soft skills: Does the team have the range of hard and soft skills to build a solution for the market? Different technical skills, marketing/sales skills, customer relationship etc?
• Network: Does the team have relevant networks of potential customers, employees, and partners to succeed in the market?