What Nobody Tells You About Entrepreneurship

Roger Patterson, Founder/CEO of Later and Co-founder of Launch Academy, has worked to positively shape startup culture in Vancouver in his sixteen years as an entrepreneur. Later, his fourth startup, changed life for Digital Marketers everywhere by building the world’s first Instagram scheduler, formerly known as Latergram.

Later was born at AngelHack in 2013 and launched 6 months later to a waitlist of 20,000 people. Shortly thereafter, the founders secured funding from early Facebook investors and grew Later’s user base to over 100,000 before working on the app full-time in 2015.

When we originally reached out to Patterson, we wanted to learn how he built a company that changed the way people used Instagram.

But that was not where we ultimately steered the conversation.

Instead, Patterson spoke passionately about the everyday trials of entrepreneurship and didn’t hold back.

Patterson has a multitude of insights on what it takes to succeed in the cutthroat world of startups. For example, when we asked about the most common mistakes he saw startups making, his answer surprised us:

“The Number One Reason Startups Fail is Because of Loneliness and Depression.”

In an era that romanticizes entrepreneurship and glorifies hard work and sacrifice, this isn't something most entrepreneurs openly discuss. We don’t hear about it because “solopreneurs” tend to work in isolation. Patterson, who worked on his second startup alone out of his house, can attest to this personally. 

“Starting a company by yourself can force even the most confident and stubborn of people into massive self-doubt,” he said.

Thankfully, he pointed to a cure:

1. Surround yourself with other entrepreneurs.

As Patterson saw in the first few months of running Launch Academy, there are unexpected benefits to sharing physical space with other entrepreneurs. Namely, this closeness promotes collaboration and networking, and provides a built-in support system. Entrepreneurs looking to recruit can easily find like-minded people who shared their values and vision.

Aside from working in the same physical environment, entrepreneurs can join meetup groups, get a business mentor, and attend networking events. As Patterson puts it, "Entrepreneurs tend to be inclusive and want to support other entrepreneurs. They have this infectious creative energy and want to help others see the world the way they do. By just being around them, you can feed off of that energy."

If you’re going it alone and are unsure of where to start, the first step is easier than you think.

2. Get a cofounder.

For many entrepreneurs, the prospect of co-founder disagreements is enough to dissuade them from this prospect entirely. However, Patterson views it as a crucial first step to go from concept to a viable business. While the recruitment process can be challenging, the right co-founder will understand your goals, bolster you during challenging times, and fill out the business with strengths you don’t have.  

To find the right co-founder, Patterson stresses that you must take the process seriously. Formulate a plan, interview candidates, and before an inevitable disagreement arises, set your expectations and compile a shareholders agreement to make your relationship crystal clear. This is especially critical if your co-founder is a friend or family member.

Patterson notes, “If you neglect this step, drift happens where people start seeing things differently over time, and the gap only widens. Typically there’s a breaking point and an argument you can’t come back from.”

Once you've built your startup dream team, what else can you do to move from a basement operation to Later-esque "overnight success"?

3. Embrace the advantages of being a startup.

We live in a time where small companies can utilize lean practices to help them grow as fast as, or even faster than, large companies that have been around for years. This is a relatively new development as Western economies move to become more and more "startup-centric." As recently as 15 years ago, every aspect of business used to cost money - from manufacturing, to advertising, and transportation. Now, even if you’re in physical goods, you can outsource, run your business from your house, and utilize free tools to grow your business.  Nimble startups can compete at an arguably equal playing field with corporate monoliths by capitalizing on inefficiencies that pass by these large, slower moving businesses... so much so that large businesses are mimicking startup growth tactics in order to stay relevant.