On the edge of quitting

When I started on my entrepreneurial adventure, I didn’t think it would end like this.

Two out of my three partners left in a span of ten months. Over half of our staff left in less than twelve months. And, I was burning out.

I was watching nearly a decade worth of work start to collapse. My company was severely suffering, and I didn’t know how to save it.

My confidence had dissolved, and I began to wonder if what we had accomplished up to that point was just a fluke. I doubted myself, my abilities, my worth.

To make matters worse, we didn’t have new work coming in, and we were pulling cash from our savings.

Let me give you some history before we go on.

In 2008, I stepped out into the world of entrepreneurship. I believed that the possibilities were endless, and the only things I needed were hard work and luck. I hoped to do something in the intersection of strategy, design, and technology since it fascinated me.

My first client hired me to redesign a website for his small hotel in Northern Ireland. However, I was neither a designer nor a developer. I was just a guy with an interest who had no idea what he was doing.

Then, I remembered that I met a developer who created websites. He and his wife worked as a team. He built the sites that his wife designed. I asked him if he wanted to work on this project, and he said yes.

A year and a half after that project, we formed a partnership.

By 2013, with two additional partners, we built a full-service creative agency that employed a team of sixteen full-time makers and creators.

We built the company on the mission of producing great work for good organizations, serving clients who were making a difference in the world. It sounds super altruistic and borderline cheesy, but the idea inspired us.

We also committed ourselves to creating internal projects, ventures we found compelling.

We built an online publication called the St. Louis Curator. We loved it. But love doesn’t always make a venture monetize. So, we decided to end it. As a result, our team of copywriters left.

A couple of months later we launched an iPhone app called Smap. We spent eight months developing it. We believed it would beat Yelp at the place finding experience. I quickly saw the foolishness of that notion.

After Smap launched, it didn’t get close to the response we wanted. Our marketing efforts and budget were too light. We had already risked about $150K of our capital and couldn’t invest more time and resources on it. The app was pulling us too far from our primary business.

Smap and the St. Louis Curator both failed. That combined with my shortcomings weighed heavily on me. And, I didn’t foresee the effects they would have on our company.

A host of people, aside from the copywriters, left our team. The entire design team, including our creative director, except for one designer, our film team lead, a project manager, and all of our developers except for one exited our company.

Over 55 percent of our personnel left.

Things got darker for me. The thought of quitting crept into my mind. I had thoughts of just closing up shop and slinking into some job just to make a paycheck. I focused on my shortcomings and bludgeoned myself by replaying them in my mind.

I was supposed to lead, but, in the midst of all of that, I couldn’t lead anyone. All I could do was survive, try not do anything too stupid, and pray.

Despite it all, some people stayed. They are great, talented, reliable, trustworthy, and kind people. And, I wondered, why they would choose to stay when so many others left.

But, I knew that focusing on the past wasn’t going to help the company with its future and those who decided to stay. I had to face my insecurities and move forward one small step at a time.

We still had clients who needed us. And, we also won a couple of significant new ones. I saw movement in the right direction. Not only did we start to see a little bit of momentum with clients, but also our team started to gain its footing as well.

We promoted our director of photography to the film team’s lead and the lone designer to creative director. They started to take on new responsibilities and rose to the occasion.

Our creative director and I went to Nashville to attend a branding conference hosted by Brand New. Some may have said that a conference isn’t a good way to spend money when it was scarce. But, investing in our people felt like the perfect way to help the company look ahead.

He learned a lot. And, I healed a lot. Getting away, spending time with him, and hearing about the work and process of other designers, helped me see the possibilities again.

Our one man technology team desperately needed help. My partner had far more work than he could handle alone, and help came just in time. We were able to recruit a developer from San Francisco. He filled a much-needed gap and improved our morale.

Some point along the line, work became fun for me again. The team was working well together, and we focused on creating great work and how it can be improved. I stopped wallowing in self-pity and started to think of ways of growing the company and cultivating our culture.

I kept on waiting for more people to leave, but this core group of people hung in there. We even seemed to be creating better work than we ever had, and we waited to see what else would happen.

I started to hustle. I took any meeting that had an appearance of potential benefit for the company.

Then, toward the end of the year, we got some random email from a person whom we helped years ago. They said that they had a significant design and branding project. I drafted a proposal, pored over it to make sure it was perfect and sent it to them.

By the end of the year, in a span of a week, we won that design project and a few other engagements, including one for digital marketing. In a matter of a week, we found work that would set us up for the next six months.

We expanded our team and brought on a senior and junior designer. Our office was buzzing again.

It appears that the storm is over. It was the darkest time I have ever faced as an entrepreneur. I know that I’m not the same and much of my naivete has been slapped off of me.

But, even though I still feel like a failure at times, I am hopeful again. I don’t attribute our resilience to my leadership, and I certainly don’t think I guided us out of our troubles.

I believe what got us through was purely divine grace and the people who decided to stay with us. They didn’t give up. Instead, they came into the office day in and day out and worked. They, as a collective whole, steadied our company.

When I was too weak to lead, new leaders rose to meet the uncertainty and forged a way forward. When I wanted to quit, they worked. And, as a result, we are moving forward into the future.

Looking back, I have come to realize that what looked like the end of our company, wasn’t really the case at all.

It was our new beginning.

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