Zero to Half a Million: Year One Lessons in Entrepreneurship

In 2017, I shared a lot of thoughts, ideas and tactics for successful content marketing. But, that entire time, I was also experiencing my first year of entrepreneurship.

In December of 2016, I launched my content marketing agency, Optimist. We set out to help startups, agencies and nonprofits use content to drive traffic and grow their business.

Over the course of 2017, we grew from just an idea to a full-blown team of nine contractors with six long-term clients. We went from zero revenue to half a million in annual run rate. It felt great.

There’s still a lot of work to do (our new goal for 2018 is to hit $1.5 million annual recurring revenue). But, for my first article of 2018, I would like to take a step back and share some of my own personal lessons.

As a first-time entrepreneur, I learned a lot in just 12 months. I think I’ve become more confident and also more humble. I’ve come to see (first hand) the true importance of surrounding yourself with the right people.

So, I’m going to share a few of the biggest lessons I learned from my first year of entrepreneurship.

Lesson #1: Set clear goals for yourself

Right from the outset, I had a pretty big vision for Optimist and the kind of company we wanted to build. I set a goal of building a $1 million (ARR) content marketing agency, then I published that goal, publicly, right on our blog. I vowed to keep score and share it with our readers.

This was huge for me because it gave me a lot of external accountability. People were watching.

That may not be the right mechanism for you as an entrepreneur or your particular startup, but I think that you should still set clear goals for yourself and put them in writing somewhere.

As you get into the weeds of building a business, it’s easy to get tired and distracted by all of the stuff that’s happening. But if you have goals, you can use them to remind yourself to focus most of your time and energy on the work that is going to help you achieve those benchmarks.

Related: 7 Lessons for Aspiring Entrepreneurs

Lesson #2: The path is generally not linear

There were a lot of ups and downs throughout the course of our growth in 2017.

Right out of the gate, we had a bunch of opportunities and revenue coming in. But, I struggled to convert that into long-term cash flow and work for the team.

It wasn’t until August or September that I focused on really digging into our sales process, refining each step and creating a better pipeline for new business.

Talking with other entrepreneurs, I think most companies go through this same process: periods of growth, stagnation and shrinking. There are a lot of variables to figure out and that means that most businesses won’t have a perfect, linear path to their goal.

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Lesson #3: Admit when you’re wrong; seek opportunities to improve

Most people go through life wanting and expecting to do everything right. No one likes to feel like they’ve made a mistake, right?

As a result, people hate to feel like they’ve done something wrong. In fact, most people will do just about anything in their power to avoid it.

But, as an entrepreneur, I think that failure, and learning from failure, is the most important part of the process. The key is to identify the places where you’ve made a mistake as early as possible and then figure out how to fix it. In other words, don’t wait until those mistakes manifest themselves in big, terrible ways.

Instead, take a hard look in the mirror every day, week or month. See what parts of the business are working well, but also really analyze the stuff that doesn’t seem great, including places where there is frustration, anxiety or friction. Then, try to figure out how to fix that problem and inch closer to the “right” answer.

In the grand scheme of things, entrepreneurship is one big experiment. You start with an idea of what will work and then you go out and test that idea every day. Sometimes it works, sometimes it doesn’t.

The key is to remain humble enough to admit when it doesn’t work but be dedicated enough to keep trying.

Here’s to even more learning in 2018.

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