The Real Problem With Being a Solo Founder and How to Overcome It

The Real Problem With Being a Solo Founder and How to Overcome It

Everyone will warn you against being a solo founder, but it’s not as impossible as you might think

The Real Problem With Being a Solo Founder and How to Overcome It
Photo by Benjamin Davies on Unsplash

When I was a new founder, I remember experienced people in the entrepreneurial world constantly warning me that I couldn’t be a solo founder. According to them, solo founders couldn’t succeed.

For years, this was the advice I believed, too. When I got more experienced and began advising entrepreneurs, I always warned the ones working by themselves of the same thing. I told them they needed at least one co-founder. I reminded them that even Elon Musk and Mark Zuckerberg had co-founders for their first ventures — Musk, his brother, and Zuckerberg… well… there’s basically an entire movie about him sparring with the people who helped him launch Facebook.

The reason the entrepreneurial community advised me against starting companies by myself, and the reason I always gave the same advice to other entrepreneurs, is that startups require too much work. A single person will struggle handling everything alone. Nor should they want to. Having at least one co-founder is what helps most entrepreneurs navigate the stresses and challenges of building startups. When you’re building a new company, every day will feel like a fight for your startup life, and having co-founders battling alongside will help you keep going as you confront the inevitable challenges and setbacks.

And yet, despite the difficulties of being a solo founder, I’ve encountered a decent number of entrepreneurs during my career. Not tons, but it’s clearly possible. What’s the secret? Are some people just more efficient and talented? Are they able to do more in their 24 hours than “normal” people? And do they not need support from close collaborators in order to persist despite enormous difficulties? Simply put, how do some solo founders defy the odds and build huge companies by themselves?

I recently had an opportunity to speak with someone who successfully built and sold his company as a solo founder. His name is Jesse Lipson, and he bootstrapped his first tech company — ShareFile — to a $43 million exit. Sure, $43 million isn’t an enormous exit by VC standards, but that’s because VC-backed companies need bigger exits in order for everyone invested to get large enough returns. In contrast, imagine being the solo founder of a bootstrapped company that sold for $43 million. Not a bad outcome, right?

In order to accomplish the same thing, you’ll have to figure out how to overcome the real challenge of starting a company by yourself, and that challenge isn’t what I always used to think.

* Jesse’s story is based on a podcast interview I conducted with him on April 21, 2022. Quotes have been edited for clarity.

Yes, building startups by yourself is difficult because it requires lots of work. And, yes, building startups by yourself is lonely. But, when we apply a bit of logic, we can easily see how those kinds of problems don’t actually explain why solo founders are less likely to succeed. After all, solo founders can hire other people to work for them, and those people can help them get things done while providing encouragement and support.

Since solo founders can hire the help they need, the real problem with building a company as a solo founder has nothing to do with lack of people or lack of support. The real problem with being a solo founder is that solo founders don’t have any checks and balances on their decision making. Instead, solo founders have final say on the most important decisions their companies make, and they have to make those decisions entirely on their own. Unfortunately, no matter how smart people think they are, none of us are smart enough to always see the flaws in our own logic. This, more than anything else, is why solo founders tend to fail.

Luckily, knowing solo founders struggle because they lack additional perspective when making important decisions is also what tells us how to succeed as solo founders. The key to being a successful solo founder is finding ways of making good decisions on your own.

In other words, if you want to be a successful solo founder, you have to figure out how to make the right decisions by yourself. That’s not an easy task.

Yes, consistently making good decisions by yourself is hard, but it’s not impossible. And the story of Jesse Lipson and his company, ShareFile, shows us how to do it.

ShareFile, in case you’ve never heard of it, is an enterprise SaaS platform for file sharing and storage. Think of it like DropBox, but for big businesses who want a white-labeled version for themselves and their clients.

In general, B2B, SaaS software startups require multiple founding team members. At the very least, they need someone to build the software and someone else to sell it and support customers. But that’s not how Jesse operated ShareFile in the early days. Instead, according to Jesse, he did everything by himself. When we spoke, he told me:

“I actually had 1000 customers before I hired our first full time employee… That made for a very busy first 18 months…. I pretty much had to carry my laptop around with me everywhere I went, including, for example, if I went to dinner with my wife because if the system went down, then it was going to be down until I brought it back up.”

As Jesse explains, being responsible for acquiring and supporting 1,000 business customers by himself — including developing and managing the software — required tons of work. But it also had a critical benefit. Because Jesse was the developer, salesman, customer support person, he always knew exactly what needed to be done. He explained that:

“I actually read every support ticket up until we had 15,000 customers. And, because I was forced to read customer requests, it helped me really understand the pain points of customers… and it gave really good insights into every function in the business and helped me develop empathy and discipline for the fact that I had to be focused on the customer impact and the pain that customers were feeling.”

Jesse’s story shows how managing customer support for ShareFile as it grew was critical for helping him make decisions. It meant that, even though he was a solo founder, he wasn’t making decisions on his own. Instead, he was using his direct engagement with customers to make decisions that were best for them regardless of what he might have personally thought. In a sense, his customers were like his co-founder.

This is the strategy you’ll need to leverage if you want to be a successful solo founder. As a solo founder, you’re going to have to make every important decision about your startup, but you won’t have to — and shouldn’t! — make those decisions alone. Instead, stay as connected with your customers as possible and make your decisions in partnership with them. If you listen carefully to what they have to say, your customers can be the best co-founders you could ever hope for.

Listen to Jesse’s entire story by searching for “Web Masters” on Apple, Google, Spotify, Stitcher, or wherever you listen to your favorite podcasts.

Go to Publisher:

Entrepreneur's Handbook – Medium

Author: Aaron Dinin, PhD