Russ Heddleston Contributor

Russ Heddleston is Head of Commercial, DocSend at Dropbox.

More posts from this contributor Essential Steps to Thrive and Survive in Fundraising Pre-seed round funding scrutinized: is VC pandemic here to stay?

Every journey into entrepreneurship is unique. I find the world of startups fascinating because the desire to address a problem or need — often one you’ve struggled with — is just too tempting to resist.

As a solo founder, facing that problem alone can be daunting but also liberating. Alternatively, starting a business with co-founders can be productive but it comes with its challenges.


When I started DocSend, I never had to consider whether I wanted to be a co-founder because I knew I wanted to build a company with two specific people I liked personally and respected professionally. But for many entrepreneurs, whether you can handle that challenge alone or want a co-founder by your side is not easy. It’s understandable why.

Going solo can give you more control and freedom to run the business the way you want. It also means that you are the only one responsible for pitching VCs, leading board meetings, staffing a team, and making important decisions.

While a solo founder can bring in executives and managers to help with this work and these decisions, co-founders can balance the leadership team. They can bring different areas of expertise, professional networks, and shared responsibility.

While the data shows that solo founders are raising more money, a holistic approach to understanding your gaps and how to fill them is imperative.

If you’re starting a business or currently running your startup all by yourself, here are four things to consider when hiring a co-founder (or not).


Every entrepreneur must objectively assess his skills and determine whether his abilities are sufficiently rounded to run a business independently. If you’re not tech and starting a technology company, you may need to find a co-founder to fill that gap or, at the very least, a strong engineer to lead product development.

Even if you are technical and can start coding from day one, you should consider other key business areas and decide whether hiring a co-founder with expertise in those areas will enable you to create a viable product, market traction, and revenue to come faster.

I contacted my network to see what they thought of the decision. I recently spoke to Aneto Okonkwo, co-founder, and CEO of Chatdesk, about why he decided to hire multiple co-founders. He said that different areas of expertise are big drivers.

“I thought about the different features needed to make Chatdesk successful. As we bring together technical and personal human support, it was important to establish three functions: technical, operational, and sales. I knew that if everyone could own territory, it would help us achieve our mission,” he said.

The number of founders on your team can also affect the success of your fundraiser. Our analysis found that solo founders had the most success with fundraising, with an average of 42 investor meetings and an average of $3.22 million, compared to companies with four or more founders, which landed an average of 30 conferences and raised an average of $1.7 million.

While the data shows that solo founders are raising more money, a holistic approach to understanding your gaps and how to fill them is imperative.

Founder vs. Co-Founder


I have been blogging since August 2011. I have had over 10,000 visitors to my blog! My goal is to help people, and I have the knowledge and the passion to do this. I love to travel, dance, and play volleyball. I also enjoy hanging out with my friends and family. I started writing my blogs when I lived in California. I would wake up in the middle of the night and write something while listening to music and looking at the ocean. When I moved to Texas, I found a new place to write. I would sit in my backyard while everyone else was at work, and I could write all day.