Red Flags in Startup Co-Founders: Lessons Learned from a Technical Founder's Journey

Published: at 05:07 PM

Introduction

Beginning a project or startup is super exciting, everything is roses and sunshine at the beginning, everyone is super motivated and you’re ready to take on the world.

As a technical founder, choosing the right co-founder is crucial. This article aims to share insights on potential red flags to watch out for when selecting a co-founder, focusing on the perspective of a technical founder.

Why am I writing this?

There are TONS of articles out there on how to choose a technical co-founder, but really few on the opposite scenario.

This article is written in the hope that someone in a similar position will read this and make better decisions.

Why focus on the red flags?

I could’ve written “How to choose the best co-founder” but I believe going the opposite way will prevent you from making mistakes and, therefore, naturally gravitate towards the right choice.

Word of caution

Every project, situation and person is different, so don’t take this article as a rule, but rather as some pointers to help you make a better decision.

1. Do not rush it!

As a technical person, you will be sought after.

There’s a massive under-supply of technical talent in the startup world, which means you’ll have plenty of people wanting to start a business with you. It’s exciting, and you might be tempted to jump on the first opportunity that comes your way, but don’t do it.

Many people have the mindset of, “I’ve got an idea, I just need a tech person to build it.” Be careful not to get swept up by the excitement and flattery of someone wanting to work with you.

These kind of people, more often than not, are really good at selling themselves, they know how to portray themselves in a way people want to work with them.

Take your time, ask questions, and do your due diligence. Don’t rush into a partnership just because someone with experience is interested. Weigh your options, talk to other people, and really think about whether this is the right move for you.

2. Do you really need a co-founder?

As tech founders, we have the skills and tools to build a product ourselves. What we might lack is the business knowledge to turn that product into a successful company.

But remember:

The first step of a startup is to validate an idea.

That means creating something, iterating fast, and getting feedback. This is something I believe every tech founder can do on their own.

Bringing in a non-technical co-founder too early might not be the best move. Ideally, they shouldn’t come in until you have a validated product or even product-market fit.

This can cause pressure from the non-technical side to the technical side, as they will be sitting, waiting for an MVP to be ready so they can start doing what they do best. This can sometimes take months.

Before rushing to bring on a co-founder, ask yourself if you really need one at this stage. You might be better off building and validating your initial product solo before involving someone else.

You might feel the urge to establish a legal entity right at the start—thinking it’s a sign of commitment and progress—but this can be a huge mistake. Forming a company is a huge commitment: it’s not just about paperwork and legalities; it costs money and takes time—time that could be better spent on building your product.

Creating a company with someone early on is like marrying someone before even dating them. You don’t know yet if you’re compatible, if you can work together, or if you share the same vision. Words are cheap; it’s actions that reveal whether you and your potential co-founder are actually a good fit.

Don’t rush into forming a legal entity. Focus on validating your product and ensuring that you and your co-founder can actually work well together before making such a big commitment.

4. Negotiate the divorce before the marriage

Before diving into building a company or even a product with a co-founder, you need to have a clear agreement on what happens if things go south. This is usually called a shareholders agreement. It’s crucial to have this in place before you start working together.

Take the time to find a lawyer and draft a document that protects both the company and the founders in case of disagreements or a breakup. It might feel like an unnecessary formality when everything seems positive, but it’s essential for avoiding chaos later on.

I’ve known of co-founders that push back on this. If that’s the case, it’s a huge red flag, as this not only protects each one of you but also the company, plus it has the benefit of bringing everything on top of the table.

Don’t skip the shareholders agreement. Protect yourself and your company from the beginning so you’re not left scrambling when things don’t go as planned.

5. NEVER Split Equity 50/50

This is a big one, and it happens far too often. Splitting equity 50/50 sounds fair at the start, but it’s actually a huge mistake. NEVER do it.

A 50/50 split can become a major blocker for decision-making because when disagreements arise—and they will—neither of you has the final say.

In any startup, there’s always someone who puts in more work or has more initiative, and that person should have more equity. Wait until you have something tangible before dividing equity. If you’re bringing someone in later, offer them a smaller percentage and increase it as they prove their value.

Never split equity evenly — someone should always have a slight edge to keep things moving forward.

6. Go on dates

When starting a business with someone, it’s important to get to know them on a personal level, not just a professional one. If you only interact during work, you’re missing out on crucial insights into their values and personality. Taking the time to grab a beer, hang out outside of work, or just chat casually can reveal whether you’re truly compatible as co-founders.

It’s like this:

You wouldn’t necessarily want a friend to become a business partner, but you’d want a business partner to be someone you could see becoming a friend.

Be aware of the situation and ask yourself:

If it was in any other situation than business, would I want to be near this person?

If the answer is no, take it as a big red flag.

Go on dates with your potential co-founder. These personal interactions help you understand who they are beyond the business setting, which is key to building a successful partnership.

7. Unclear roles and responsibilities

One of the biggest issues in early-stage startups is when co-founders don’t clearly define their roles and responsibilities. This is especially true when one co-founder is non-technical—they may start treating their technical co-founder like an employee rather than an equal partner. Make sure roles and boundaries are clearly defined from the start, and respect them.

Here’s what to watch out for:

If your co-founder keeps on checking on your work and progress, they might be seeing you more as an employee than as an equal.

Be clear about roles and enforce those boundaries to avoid unnecessary conflicts and power struggles.

8. Premature Fundraising and Misaligned Financial Views

One of the first things you need to align on with your co-founder is how you plan to fund the startup. Are you going to bootstrap or raise money? Be very clear and stick to that decision from the outset. Misalignment on this issue can lead to serious problems down the road.

I’ll keep my opinions on VC money for another post, but my key takeaway is that you should do your own research, a lot of people want VC money for the sake of it without any good reason, even before they hit Product Market Fit.

Make sure you and your co-founder are aligned on your financial approach from day one. It’s not just about getting money—it’s about making sure your financial philosophy and strategy are in sync for the long haul.

9. Co-founder background check

Let’s be honest, if you’re looking for a co-founder, you’re probably not the best at doing what you want them to do. So it’s hard to assess if they’re any good at it. Here’s what you should do:

  1. Get real experts involved: Find people you trust who actually know their stuff in the field you’re hiring for. Get them to quickly interview your potential co-founder. They’ll know what to look for and what questions to ask.

  2. Start with a trial run: Begin working together without any formal commitment. See how they work, how they think, how they solve problems in real situations. It’s way more revealing than any interview or reference check. Don’t get hyper focused on product and take the time to do this.

  3. Stay engaged across the board: Even if you’re delegating, keep tabs on all aspects of the business. Don’t check out just because you think someone else has it covered.

  4. Set up regular check-ins: Establish clear milestones and progress reports from the get-go. It’s not about micromanaging—it’s about making sure you’re both on the same page and meeting expectations.

Make sure you and your potential co-founder are aligned on how you evaluate skills and performance from day one. It’s not just about finding someone who looks good on paper—it’s about making sure you have compatible working styles and can actually deliver results together.

Take the time to really get to know them in action, not just in talk. A thorough vetting process upfront can save you from major headaches down the road. Trust your gut, but back it up with solid evidence of their capabilities.

10. Make sure your co-founder can actually get their hands dirty

A co-founder can look great on paper. They can have loads of experience in the corporate world, or be a bigshot manager at some big company, know how to handle people and projects. Sounds perfect, right?

Wrong.

What you might not realize is that a person with such a profile is used to delegating tasks, not doing them themselves. In the corporate world, that’s fine. In a startup? It’s a disaster waiting to happen.

Startups need someone who can roll up their sleeves and do the nitty-gritty work, especially when you’re just starting out. It’s not about fancy titles or managing big teams—it’s about getting things done yourself.

When you’re looking for a co-founder, don’t just focus on their fancy titles or big company experience. Ask yourself:

  1. Can they actually DO the work, not just oversee it?
  2. Are they willing and capable to learn new skills on the fly?
  3. Do they understand the difference between running a department and building something from scratch?

Remember, in a startup, everyone needs to be a doer. You want a co-founder who’s ready to get their hands dirty, learn on the go, and do whatever it takes to make your vision a reality. Don’t settle for less, no matter how impressive their LinkedIn profile looks.

11. Do not hesitate to ask others

If you take anything from this post, let it be this: do not hesitate to ask others for their opinion.

Bring experienced friends and mentors into the mix. They might see red flags immediately, ask questions you didn’t think of, and give you advice you need to hear.

Final words

Always remember, even if the journey proofs stressful and painful, those are the times you will learn the most from. Hopefully by reading this article I have helped you in you journey.

A couple of extra notes to keep in mind:

  1. Trust your gut: If something feels off, it probably is. Don’t ignore your instincts just because you want things to work out.

  2. Careful with the sharks: Be wary of narcissistic people who look great on paper and know how to sell themselves. They might seem like the perfect fit, but they could be hiding some serious red flags. Don’t get blinded by their charm.

  3. Be aware of your surroundings: When you’re starting out, it’s easy to get tunnel vision and focus only on your product. But remember, your co-founder is just as important as your idea. Take the time to vet them properly and make sure they’re the right fit for you.

  4. Don’t rush into anything: Contrary to what VCs might tell you, building a startup is a marathon, not a sprint. Take your time to find the right co-founder, even if it means saying no to some tempting offers along the way.

I’ll leave you with a question:

If you have an idea, you have the knowhow, the business model is based in the product being brought to life, and the rest is easily accessible and/or can be easily delegated… do you really need a co-founder?