Should you Find a Cofounder for your Startup?

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When you decide to start a business, you have a tough decision to make…well, you have an endless amount of difficult decisions to make…but this one will directly impact the initial founding.

Do you find a cofounder or do you start it on your own?

In this column, we’ll examine this particular question from both sides of the coin and I’ll provide how I’ve handled it throughout my entrepreneurial journey.

Things to Consider when Thinking About a Cofounder

1. Do you trust them?

With a cofounder, there has to be trust. This is someone that you will be working with for the indefinite future. If your ideals don’t align and you question their judgement, keep dating until you find the right one. As with any relationship, trust will allow you both to reach your end goal faster and with greater passion.

2. Do you need a cofounder?

All entrepreneurs will answer this question differently. Unless you have every skill necessary for a successful founding team, I advise to highly consider seeking out a cofounder. Having a cofounder makes the ride of building a business more enjoyable and you always have someone that can motivate you through the hard times.

3. What are your strengths and weaknesses?

The trickiest part about finding a cofounder is to not find and pick a clone of yourself. It’s important to conduct a self-evaluation exercise before starting the dating process. You want to focus on what your strengths and, more importantly, weaknesses are so that you can find a cofounder that complements your skill set. If you decide to add a cofounder to your team, you want to make sure they are taking your business to a new level.

4. Can your cofounder be one of your friends?

This is an extremely difficult question. Again, entrepreneurs will have their own theories on how to approach working with friends dependent on past experiences and advice from their mentors.

I advise to evaluate a potential cofounder the same way regardless if they are your friend or not. If they meet all of the key criteria of skill sets that you are looking for and they are serious about the business idea, tyou should not rule them out.

However, don’t invite just any of your friends to start a business with you because you both think “it will be fun.” A cofounder has to be someone that is as serious as you are about the long term growth of the business. If you put yourself in a situation where your cofounder is not as serious, you’re setting yourself up for failure.

5. How will you split equity?

Although it’s not what you want to talk about in your first conversation with a potential cofounder, you need to know how much you are willing to give up of the company for this cofounder. Properly splitting the equity with your cofounder and setting clear expectations with a founder’s agreement is a key step to starting your business partnership. Don’t overlook this aspect of finding a cofounder even though it is a tougher topic of discussion.

6. Where do you find a cofounder?

First, look inside your immediate network…friends, family, colleagues. Do any of them meet your minimal criteria? If they don’t, start networking. Find meetups where your cofounder may attend and put yourself out there. Third, perform research on LinkedIn and invite a few to get coffee.

Just keep this in mind…if the people you meet aren’t the perfect match, they may know someone that would be.

7. Can you see yourself working with this person for at least 5 years?

If the answer is “No”, move on. You want your cofounder to be someone that you see yourself growing with. It’s very much a relationship!

Potential Disadvantages of a Cofounder

  • loss of equity
  • future personal issues with decisions
  • the wrong pick skill wise
  • discontinued interest over time

Advantages of a Cofounder

  • having two people passionate about growing the business
  • adding strengths to cover your weakness
  • a soundboard for new ideas
  • able to get more done faster

My Entrepreneurial Experience with Cofounders

Landscaping for You

When I started my first business at the age of 16, I decided to fly solo. I hardly knew anything about business and I was looking for a way to make some extra money. Without even knowing it, I decided to play on my strengths.

I had learned a ton about landscaping from working multiple summers with my cousin. He owned his own landscaping business that he started when he was in high school and I loved how he had created his own company.

For my first business, not having a cofounder worked out because it was a very small business focused on only 10 lawns in my neighborhood. I didn’t have visions of turning it into a massive company and I was able to manage the operations with my own schedule. Had I created a vision of building the business into a lanscaping empire, I believe that a cofounder would have been the right move.


When I first started working on Portlight as a junior in college, the business had already been started. It was running, but my eventual business partner was seeking a cofounder. I just so happened to be seeking an opportunity to start another business. The stars aligned.

After proving my worth and reliability by putting in the hours to learn everything that he had built, I became a cofounder of the business with a new vision for where we could take the company. The Portlight team eventually welcomed a third cofounder as we expanded in our senior year of college. It was another hungry entrepreneur eager to build his first company.

The three of us have been running the company together for the past 5 years and we’ve been able to divide our friendship from being business partners. How did we do it? We set clear expectations in the very beginning and made sure that the business always came first. We made a strong separation between our friendship and our business partnership.


It has always been a dream to make a positive impact on others through my writing. I have been writing privately for over 8 years and I’ve been waiting for the perfect opportunity to make my writing and thoughts public. When my cofounders and I decided to scale down our operations at Portlight, I had a significant amount of free time.

Before the ideas of FreeeUp and eCommetize became a reality, I spent my time writing about my experiences as an entrepreneur and building ConnorGillivan.com. While the site does not generate any income today, I still consider it to be a business as I am making investments — time and money — to keep it running and growing.

As I started the business, I made the decision that this one would be focused on my writing. Given that all of the content would be created by me, a cofounder didn’t make much sense.


The idea for FreeeUp started in the early summer of 2015 as my business partners and I brainstormed new business ideas. We were still fully entrenched in Portlight, but we were starting to consider new ideas once we had successfully scaled down Portlight’s operations. Nate, my cofounder with FreeeUp, was passionate about the idea and so was I. We had the chance to share ideas and in early Fall, we set out to start the company.

Working as cofounders came naturally as we had started Portlight together and we knew each other’s strengths and weaknesses extremely well. When forming the initial structure of FreeeUp’s operations, we were able to place ourselves easily into different areas of the business where we would both excel.

We’ve been at building the business for almost 6 months now and we’re working together better than ever. Each of us have our roles that drive the business forward and we meet everyday to share ideas on how we can continue to grow.


Coming a few months later was the initial idea of eCommetize. I was traveling with my girlfriend in Chicago and she introduced me to someone that she worked with who happened to own his own website. He had created the site 7 years ago and had turned it into a community of over 200,000 readers with over 500,000 page views per month. I shared my background with Portlight and a spark flew.

He had always wanted to add an online store to his site to sell products to his readers. I knew how to build and run eCommerce businesses. A relationship was formed and the idea for eCommetize started.

As I finished the online store for my new connection, I started to think about the idea of turning it into a business where we found other online influencers that wanted stores on their sites. I dug into the idea using my Four Pillars of Startup for a few weeks and realized that there could be something real.

Wanting a second pair of eyes on the idea, I got together with my other cofounder from Portlight and shared what I had come up with. As I spent hours creatively brainstorming the idea with him, I remembered how well we worked together and how helpful it was to have a different mind at the drawing board.

After careful consideration of our strengths and weaknesses, I made the decision that I wanted Zack to become my cofounder. I invited Zack to start eCommetize with me and we’ve been at it since January 1st.

My Final Words on Cofounders

If you are deciding to start a company and want to find a cofounder, search for someone that is going to challenge you to become a better entrepreneur. Both of my cofounders think differently than I do and push me to think outside of the box everyday that we work together. At first, it was frustrating to always be questioned on every topic, but we eventually reached a point where we knew that the constant challenging was only to make us all smarter. Find a person that can push you to that limit.

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About Connor Gillivan

In the past 10 years, I’ve started 7 businesses & built two to $10M+ in annual revenue, teams of 30+ & an exit in 2019. Today, I run SEO & growth for my 4 B2B companies while teaching millions how to make SEO simple.

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