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I Joined and Failed My First Company Within a Year, and That’s Okay

The invaluable lessons I learned from failing my first entrepreneurial venture


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Kenny C

3 years ago | 9 min read

Last year in May, I decided to join my friends’ company as a Member of the Board. The company was a Virtual Reality event center that served as a place for people to play and experience VR.

It launched right in the heart of the city and immediately became a topic of discussion all around the city.

I had been following their journey for a couple of months and finally felt that I wanted to join them. It felt truly inspiring.

I pitched them the idea of helping out with marketing strategies and business development; I had a vision of the direction I wanted to take the company. They happily accepted my proposition, and within a month, I joined them as a new Member of the Board.

My primary responsibility was to oversee the long-term strategies while my friends handled the day-to-day business operations. We achieved a lot during my time in the company, including:

  • Getting featured in local newspapers and several websites describing us as a Must Visit Place;
  • Creating collaborative opportunities with local restaurants; such as an after-work all-inclusive package with entertainment, food, and beverage;
  • Starting a podcast about Virtual Reality to promote the company further;
  • Establishing collaborations with conference centers and hotels as an event alternative for companies and organizations; and much more.

We worked hard on trying to take the startup to the next step in its journey. It was so much fun to work on a mutually shared goal with your best friends.

However, it did not last long until reality set in. Slowly, the many problems and inconsistencies of the company started to rise to the surface. We had many issues, most of them concerning solvency. It all seemed possible to overcome given enough time.

And then COVID-19 hit.

After the Swedish government’s official recommendations came out regarding social distancing, we were on the edge of bankruptcy in a couple of weeks.

Through tenacious negotiations with our property owners and cutting costs in all areas we could afford — we managed to stay solvent in end, if just barely.

At the moment, it felt like a victory. But looking back at these few months, there were a lot of circumstances leading up to our near-bankruptcy. It felt inevitable that we would not last, even if the pandemic had not hit.

I’ve been thinking quite a bit about how my first real entrepreneurial journey turned out. Even though I vividly see the many successes we built up under the brand, the failures are where I draw my most invaluable lessons.

Hopefully, if you are starting as an entrepreneur, there are a couple of tips here that you can take with you.

Clear Communication is King

In an early startup, you are almost always working closely with a few people. Ours was no different. We would speak with each other 24/7 about small decisions, changes to the business, improvement suggestions, and so on.

However, and here the lesson lies, we would do most of our communication by texting. Essentially we would have a chat group where everyone would write anything and everything about company-related topics.

Now — before I continue any further, I am aware of the tremendous benefits of texting as a means of communication. It is an excellent way for shorter conversations, announcements, or smaller discussions.

When it comes to hard decisions requiring more in-depth discussion between your fellow peers, not so much.

On more than one occasion, I found us starting to quarrel and argue about small issues that we could have solved through a quick call. The problem would often lie in our different texting styles. A message without ill intent could spur disagreements and bring out unnecessary irritation and anger.

Another problem regarding texting was that context and red threads were occasionally buried in walls of texts. On good days, communication in our chat group was clear.

On bad days, our discussions could range over a dozen different topics and business decisions that needed to be taken — cue more misunderstandings.

Eventually, I decided to leave the chat group altogether. It gave me a better sight of the bigger picture, and I could solely focus on discussions that would significantly affect the company. If we had important decisions to take, I would be present during formal board meetings. Otherwise, I was available on the phone.

It gave me the perspective of the role I played in the company. The everyday decision-making that I thought I needed to be involved in — well, it turns out I didn’t need to be involved in them.

In my newest venture, my business partner and I have it, as a rule, to take calls as often as possible. In the end, it leads to fewer misunderstandings and better discussions in general.

Go for the Big Ask

A tremendous burden for the company was the rent. It was located in the city center, and thus our location was perfect for attracting curious bypassers. However, with that came a matching rent.

We had been given beneficial terms from our realtor, which we could live up to; until COVID-19 hit, that is. Suddenly, we were in a deep crisis as our revenue was drastically dropping.

We quickly realized that we needed to talk to the property owners regarding the rent. The coming months were crucial to the company’s survival. We were hoping that the pandemic would blow over and that the market would slowly recover. In the end, we thought we just needed more time.

Of course, they were in trouble as well and had gotten directives from their management to standby and wait for the chaos to settle. So our propositions to discount our current rent and the possibility of relocating our business got rejected. The option left, was to ask them to terminate our leasing contract immediately without any damages or liabilities.

While we did discuss this option among us, it got downplayed fast. The idea seemed too far-fetched even to be considered serious. Why would our counterparty agree to terminate our contract? We still had a couple of years left of it, and deciding to terminate our leasing contract meant that they would lose out.

Or so we thought.

In a surprising turn of events — the question was brought up by the property owners themselves. “How about we just terminate your leasing contract by the end of the month?” we got asked during our final negotiation. We were absolutely stunned that the option that seemed to be the least viable, was the option proposed to us.

It just goes to show that you never know your counterpart’s situation or circumstances. Instead, we focused on the possibilities that we thought were viable and serious enough to bring up. We started to negotiate on behalf of our counterparty.

But, this lesson turned out to be invaluable. No matter how unbelievable nor far-fetched your idea seems to be. Well, ask it anyway and see what happens — you never know.

Trust Each Other or Get Nothing Done

We were all new entrepreneurs and were, like most businesses, faced with innumerable small decisions each day.

What kind of marketing content were we going to post on social media? Who was responsible for contacting potential partners? How were this weekend’s events going to be conducted? Who could stand-in this Friday?

Eventually, we worked out a way to take responsibility for different tasks. But, in the end, the entire team was more or less involved in the decision processes — all of them.

Needless to say — it was not effective at all. Every decision was put on the table and scrutinized from a risk-benefit perspective. For a while, we all felt proud that we always managed to take the right and well-argued decision. But the truth was that we probably were busier than we were productive.

As a result of scrutinizing every decision, it took up a lot of time to come to a conclusion. It tested everyone’s patience, and in the best of cases, we were decision fatigued. In the worst of circumstances, we were tired of each other. Most decisions were of no importance to the general order of things. Regardless of the result, the company would be fine.

Looking back, the need to be a part of the everyday decisions stemmed from our insecurities. We didn’t know what we were doing, so it felt safer always to discuss everything first.

However, the truth is that you will never be sure of what you are doing. A hallmark of the entrepreneurial journey is the never-ending path of learning. Some would even say that it is the charm of entrepreneurship to solve all the problems you will undoubtedly face.

Now — there’s nothing wrong with consulting your teammates, and you should probably do it often when you’re a startup. Nevertheless, there needs to be someone that takes charge and ownership of the task at hand. And it is up to the rest of the team to trust that person to be competent enough to finish the job.

Celebrate the Small Victories

The last tip might seem odd, but I would argue that it is just as important as the lessons above. Building a business up from the ground is very difficult. You try and try for many months and years to make something happen without any guarantees of success.

Therefore, it is essential to celebrate the small victories along the way. Sure, you did not make the next Facebook or Amazon (not yet, at least!). Nonetheless, your first sale, your first partnership, your first revenue goal — all of them are worthy of recognition.

Think about it. You managed to create something that other people value. That is amazing in itself and, undoubtedly, worthy of being milestones in your journey.

My current business partner and I joke all the time about different events that we will write about in our future best-selling biography. That lightheartedness is precisely what I think is vital in a company.

Celebrating the small victories boosts the morale of the team. Otherwise, it can be hard to see the forest for the trees. Everyone has a limit for hard they can grind before they get exhausted and want to give up.

While we did celebrate certain milestones, such as the business turning one year old, many milestones just passed us. It is difficult to say precisely how much this affected our morale — but I know that what once felt truly exciting started to feel less inspiring over time.

I believe that celebrating the small victories is how you keep your eyes on the prize in the long run. Because, after all, building a successful enterprise is a marathon.

Photo by Patrick Tomasso on Unsplash
Photo by Patrick Tomasso on Unsplash

Although I describe my first venture as a failure; in reality, the company is still alive.

What is true, however, is that our physical store is no more. Some of the more active board members have decided to try and restructure the concept and try again.

For me, the journey ended more or less after this experience. I am still part of the Board, although not quite as active anymore.

I have decided to take the lessons from my first entrepreneurial venture and put it into my current company’s labors instead.

It’s been quite a journey, and I am glad that I saw it through. Failing your first company is part of the experience of being an entrepreneur. If you have chosen this particular road — be ready to fall many, many times.

Therefore, you might as well just strap-on your boots and brace yourself for the road ahead. There’s nothing that is guaranteed except the process in itself.

And boy — do I love the process.

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