How I Recovered from Losing My Startup’s Technical Co-Founder

Filipe Castro Matos
Altar.io
9 min readJun 26, 2024

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Embarking on the journey of building a tech startup from the ground up presents a unique set of challenges, especially for non-technical founders.

The pivotal question that looms is: how do you bring your product to life? Essentially, you’re faced with three paths:

  • Partnering with a tech co-founder
  • Hiring talent (be that senior or junior)
  • Outsourcing to a software development agency.

Drawing from my own ventures as the founder of a tech startup, a B2C eCommerce startup in the wine industry, I can share a thing or two about that process that can help you avoid a world of pain.

The end goal of our startup was to help users understand and discover the right wine for their taste. The challenge was to connect a traditional and offline world like the wine industry with an advanced digital experience to not only purchase but learn more about wine.

As you can imagine, my co-founders and I were mostly involved in the operational and marketing side of the business but we rapidly understood we needed to provide an outstanding digital experience to differentiate ourselves.

When it came to finding the right tech stakeholder, my journey wasn’t just about making a choice; it was about sitting down with my co-founders and navigating through all three options I mentioned above.

This has given me an in-depth insight into the advantages and drawbacks of each route. I left the experience with a comprehensive understanding of what it takes to find the right technical partner.

In this article, I’ll share what happened when our tech co-founder left, and what we did to ensure we kept our startup on track.

Moreover, I’ll dive into actionable advice on how you can navigate this particular challenge in your startup.

Partnering with a Technical Co-Founder

For many startups, the quest for a technical co-founder or Chief Technology Officer (CTO) is normally the most popular starting point.

Opting for a co-founder route is often seen as financially advantageous because it allows for the allocation of equity in lieu of upfront salaries, making it a cost-effective strategy in the short term.

Additionally, many top startup accelerators argue that this is crucial for the future success of the company. However, I have my reasons to argue against this statement. At least, I believe that this is not the right option for every tech startup — but we’ll get to that in just a second.

Here’s a breakdown of the considerations and challenges that come with going down this route.

Benefits of Finding a Tech Co-Founder

  • Equity Over Salary: By offering equity instead of a traditional salary, startups can secure essential technical expertise in a more financially manageable way. This trade-off is particularly appealing in the early stages when cash flow is tight.
  • Shared Vision and Workload: A tech co-founder who aligns with your startup’s goals and values can divide the entrepreneurial burden, easing the workload and fostering a partnership geared towards mutual success.
  • Building a Foundational Relationship: Creating a solid alliance with someone equally invested in your business’s future can offer invaluable support and insights.

Challenges of Finding a Tech Co-Founder

  • Scarcity of Suitable Candidates: Technology professionals are among the most sought-after and well-compensated globally, which can make the equity-for-work proposition less enticing for potential tech co-founders facing the allure of lucrative job offers elsewhere.
  • Communication Gaps: Divergences in the ‘language’ spoken by business-oriented and tech-savvy founders can lead to misunderstandings, misaligned priorities, and ultimately, to challenges in cohesively driving the startup forward.
  • Evaluation Challenges: Assessing the tech co-founder’s work can be daunting without the necessary technical background, making it difficult to judge the adequacy of their contributions towards building a Minimum Viable Product (MVP) and scaling the startup.
    It’s also important to note here that just because someone has a huge, winning venture in a specific industry or area on their CV doesn’t necessarily mean they will be successful in your venture.
  • Cultural Fit Concerns: Ensuring that your co-founder is a good match for your company’s ethos is critical for maintaining a harmonious and productive working relationship.

Reflecting on My Experience

In the initial phase of my startup, we partnered with a tech co-founder whose expertise and passion for our product were unmistakable.

Regrettably, his tenure with us was brief; he left after three months for a more lucrative salary offer. This situation underscores the competitive nature of the tech talent landscape, where the allure of higher salaries can often eclipse the value of equity stakes, posing retention challenges for startups.

But even before he left, other challenges were already arising. It’s easier to say this today, but our MVP was not the ideal MVP because of some communication misalignment between us.

The eCommerce platform we used (Magento) was the best for a later stage of the company. However, it made us lag more than anything in the beginning. And because he was the only tech guy in the company and he had already built a similar online store, we trusted him blindly, failing to evaluate him properly.

Also, we didn’t have enough time to understand if there was a complete cultural fit. Something that I still recommend to this day is to try to find co-founders (and not only tech co-founders) with whom you have already worked before. I also feel this had a big impact in a later stage as we were discovering how to collaborate during our startup journey, which is not ideal.

Guidance for Your Startup Journey

Embarking on the search for a tech co-founder requires a strategic approach. It’s vital to conduct thorough due diligence, ensuring there’s a strong alignment of vision, values, and expectations regarding the equity split, roles, and responsibilities. Open and honest discussions about these elements can lay the groundwork for a lasting and mutually beneficial partnership, balancing the immediate benefits of cost savings against the long-term considerations of equity sharing.

Working with a Software Development Company

Following the exit of our tech co-founder, we pivoted towards engaging a software development agency. This decision was instrumental in propelling our product development forward efficiently, sidestepping the necessity of recruiting a full-time developer.

Advantages of Partnering with a Software Development Agency

  • Speed and Efficiency: Engaging a software development agency can significantly accelerate the development process, allowing you to launch your product without the delays associated with hiring and training a team to work well together.
  • Access to Experienced Talent: These agencies offer a gateway to a diverse pool of skilled developers, ensuring that your project benefits from a wealth of expertise.
    In some cases, these teams will have built dozens of products, knowing the process from top to bottom. Often founders look for someone who had one massive successful venture, which may or may not translate to the second one.
  • Cost-Effective Recruitment: Opting for a software development partner can circumvent the substantial expenses tied to recruiting and maintaining a full-time development team.

Challenges of Engaging with a Software Development Company

  • Selecting the Right Partner: The task of identifying an outsourcing partner that aligns with your project’s needs can be daunting amidst a sea of options.
  • Limited Project Control: Outsourcing may result in diminished direct oversight over the development process, potentially affecting the project’s direction.
  • Higher Development Costs: Although it saves on hiring expenses, outsourcing development work can sometimes lead to higher costs than anticipated, especially in comparison to in-house development.

Navigating Software Development Outsourcing

Our journey with a software development agency proved to be a positive one, enabling rapid and smooth development of our product. Despite this, the financial aspect was more burdensome than initially expected. This underscores the importance of diligent planning and budgeting when considering outsourcing.

Also, once again we needed to trust blindly while choosing the agency. Even if they are friends or people navigating the same community (which was the case), that doesn’t help you to evaluate properly if that specific agency is the best for our specific challenges.

Price was the only criterion we could understand but the most important thing is the ratio between deliverables and the price you pay.

How to Successfully Work with a Software Development Agency

If you’re leaning towards outsourcing your software development efforts, thorough research is crucial to find a reputable and compatible agency.

Clarifying the scope of work, expected deliverables, and a detailed understanding of the financial commitment is essential.

Ensure transparent communication and establish a clear, mutually agreeable project management framework to maintain oversight and align expectations.

This approach can help mitigate the potential drawbacks of outsourcing, paving the way for a fruitful collaboration that propels your startup towards its development goals.

Transitioning to an In-House Development Team

After gaining valuable insights and progress through our partnership with a software development agency, we shifted gears towards hiring a full-time developer a year into our journey. This strategic move was driven by the desire to enhance our oversight of the development process and forge a more cohesive and robust team dynamic.

Advantages of Hiring an In-House Developer

  • Enhanced Control: Bringing development in-house affords you greater control over the nuances of the project, ensuring that every aspect aligns with your vision.
  • Team Cohesion: A full-time developer becomes an integral part of your team, facilitating stronger bonds and a unified pursuit of your startup’s goals.
  • Cost Efficiency Over Time: While upfront costs are higher, investing in an in-house developer can be more economical in the long run compared to continuous outsourcing expenses.

Challenges of Onboarding an In-House Developer

  • Recruitment Hurdles: Finding a developer that not only fits the technical requirements but is also a good fit with your company culturally can be challenging.
  • Financial Commitment: Offering a competitive salary and benefits package is necessary to attract top talent, which represents a significant financial undertaking.
  • Performance Management: As with any hire, there is a need for ongoing management of performance and productivity, ensuring that your developer remains aligned with the company’s objectives.

My Experience Working with an In-House Developer

Our journey towards building an in-house development team led us to a talented developer who became a crucial part of our team.

Nonetheless, much like working with a software development company, the financial aspects of maintaining an in-house developer proved to be more taxing than initially expected, once again highlighting the importance of thorough financial planning and budget management.

Even worse, the performance management was poor because we couldn’t evaluate properly his performance (like with the agency). And because this was a junior resource, he couldn’t improve either. He lacked technical supervision and should have also found a technical advisor.

Guidance for Hiring an In-House Developer for Your Startup

For startups considering the transition to an in-house development team, meticulous preparation is key.

It’s imperative to conduct extensive research to identify candidates who not only have the requisite technical skills but also embody the spirit and culture of your startup.

In my case, we cared more about his product and industry knowledge than his cultural alignment with our team. As we were doing a very particular thing (a new way to choose and buy wine), it was mandatory for us that this person could understand the target audience and the product experience.

However, the thing that eventually failed was, in fact, the cultural fit. He had enough experience to have some responsibility but he didn’t enjoy building things from scratch or by himself.

All of this to say, clear communication regarding the role, expectations, and compensation package is crucial to ensure alignment.

Additionally, devising a structured onboarding and performance review process will help integrate the developer into your team effectively, maximizing their contribution to your startup’s success.

But most importantly, cultural fit cannot be overlooked.

Wrapping Up

Deciding on the most effective approach to sourcing technical talent is a pivotal moment for any tech startup. The reality is that there’s no universal solution; the most suitable choice varies greatly depending on your startup’s unique situation, including its stage, resources, and strategic goals.

Navigating this decision-making process can seem daunting, especially with the myriad of factors to consider.

If you find yourself at a crossroads, unsure of which direction to take, seeking external perspectives can be incredibly valuable.

Engage with fellow entrepreneurs who have traversed similar paths (feel free to reach out to me directly, I’d be happy to help). And don’t underestimate the power of guidance from a seasoned mentor or advisor.

These conversations can offer fresh insights, shed light on potential pitfalls, and provide clarity, helping you to make a decision that aligns with both your immediate needs and long-term vision.

Ultimately, the journey towards building your tech team is as unique as your startup itself. By actively seeking advice, weighing your options carefully, and staying attuned to the evolving needs of your business, you’ll be well-equipped to choose the path that best positions your startup for technological success and growth.

Good luck and thanks for reading.

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Filipe Castro Matos
Altar.io

Writing about entrepreneurship, startups, marketing and one or two things about life.