Failing and Other Uplifting Anecdotes

Josh Carter
6 min readJan 5, 2019

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****THIS POST WAS ORIGINALLY WRITTEN IN THE FALL OF 2017 BUT NEVER PUBLISHED. UNTIL NOW****

It’s Monday morning and I am having a hard time getting myself out of bed. My alarm is set, but it’s not because I have a job to go to. It is my daily routine of waking up my kids to ensure they get ready for school. The sun is struggling to start the day and I find myself empathizing with it as I waddle my way to the kitchen to turn on the coffee maker. Checking my phone is futile, but I do it anyway knowing full well there are no emails of substance, no texts, or no missed calls. My phone, email, and my life as a whole is just as quiet as my house is in the early morning hours. It is a deeply lonely feeling.

Three months before my email’s inbox was a bevy of activity. Calls and texts came in at a regular cadence as I worked to build a backend as a service startup that we had taken through Techstars the summer before. My calendar was filled with meetings meant to grow our business and ensure we were putting it on a path to success. My travel schedule was full and I was racking up those frequent flyer miles as I worked to meet with investors, network at substantial events, and sit with business leaders to help grow our business.

Now, I won’t go into great detail as to why all of this stopped. I am sure there are lots of opinions about why BrightWork failed and I do not think litigating it in some random blog post would be the appropriate venue. I will just say that I have spent a lot of time trying to understand what I could have done to mitigate our failure. I spent a lot of time Monday morning quarterbacking every step and misstep we made to get the company to a point in which we just could not steer away from failure. And what conclusion I ultimately came to was that people will always be the most important asset of any early stage company.

Without the key people who understand the different elements of a business, without surrounding themselves with the right mentors, and without finding people who have the stamina to weather the ups and downs, you will always find your business on a path to failure.

As I sipped my coffee on this cold fall morning, the thoughts of what we could have done better drown out the faint voices of the morning news which seem inconsequential right now. My son tells me to have a great day as he walks out of the front door to head out for his day. I can’t help but envy the fact that he is going to have a full productive day at school while I sit at home trying to find a path back from this deep sense of failure that has been eating away at me like a virus. The feeling is paralyzing as I stare blankly at my screen and continue to seek some sense of purpose. I have failed those that rely on me and I have to find a way to put on a good face for my family and friends. Today, it’s nearly impossible. The voice in my head that is typically optimistic is eerily silent lately.

About midday I make my way back to my bedroom because all I want to do is sleep. Getting up and doing anything is difficult and it’s beginning to take a toll on my health. I can feel it. I am gaining weight, feeling sluggish all the time, and finding comfort in food is not helping. My smile is gone and it’s something I am keenly aware is impacting my ability to progress as a person. I am feeling my age more and more with every empty day that passes.

At some point I had to find a path forward. It helps that my daughter wants to play and spend all her time with me. Her smile is contagious and it helps me to find light in the dark that is consuming me every day. Whether it’s playing pretend tea or her begging me to take her outside, her pure innocence is giving me the ability to find my joy again. She does not know it, but someday she’ll know how profound she was at such a young age in helping me find a way to move passed the misery I have felt through the summer.

An event is coming up that I have attended a number of times and I am excited that their leader, Charlotte Creech, has asked me to be a mentor and also speak about my journey. I ask if it’s ok if I talk about failure. Suddenly I have an inner sense of purpose again. It’s not a big event, but it is a community I am passionate about and I am eager to share with them what happened to our business. Not sure why, but the feeling that the story could help others going through the threat of failure is helping me turn the corner and helping me find the light again. The event is Patriot Boot Camp and, at the time, I did not know that just a few months later I would be put in a position to help lead the organization.

The talk is profound. It is an open forum filled with incredible people who have gone through extraordinary circumstances to get to the Denver event. Some have seen battle in Iraq and Afghanistan. Others have fought their way through PTSD to build a company that helps them find purpose. My story clearly resonates as more people tell me their stories of struggle, going so far as to share with me their past desires to harm themselves because the fear of startup failure was eating away at them. For me, this was an awakening. This talk was more helpful to me than it was for them. Here I was standing up here telling these people that it’s ok to fail and that they are not alone. But really I was just telling myself that in a room full of other people.

Going home the next day from another exhausting three-day Patriot Boot Camp event, I was left with a greater sense of purpose. This community, which had already given me so much, had given me my smile back. It had given me my purpose back. It had taken something so profound as hearing someone struggling worse than me to put it all into context and realize that I needed to pull myself up, stop feeling sorry for myself, and use my experience as an example for others who were going through similar struggles.

Building and growing a startup is one of the hardest things you can do as a person. When the times are good your phone and email are full of life. People want to connect with you. They want to find a path to build on your success. However, when the times are bad you are on an island. You are by yourself. And when this happens it is important for you to realize it quickly and find an outlet for your stress and anxiety. Whether that is finding a therapist, finding other founders to connect with, or just simply working to reconnect with your friends, you cannot allow your failures to define or consume you.

Failure is our greatest teacher. It reminds us that we are not perfect. It is also something to be shared with the community.

We do not spend enough time talking about the mental impact that goes along with being a founder. It took me a long time to come to the conclusion that I was depressed. Deeply depressed. Dangerously depressed. I had to be honest and mindful about my own feelings and find a way to get out of it. It’s not easy. I honestly still struggle with the feeling of emptiness and failure. I don’t know that I will ever shake that feeling. I just know that I have a wonderful network of people who I call friends and family who remind me that I am loved.

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Josh Carter

Serial Entrepreneur, 1859 Ventures Principal, ex-WeWork Labs, ex-Twilio, ex-BrightWork (CEO), US Navy Vet