How I Felt When My Startup Failed

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Call me crazy, but I truly believed that my first startup would make it big. I believed that my co-founder and I were the only ones that could make this idea work. That is the level of crazy you need to become a startup founder.

That’s a good thing, isn’t it?

If you don’t believe in yourselves and your company that deeply, you won’t live and breathe your startup. Without that level of belief, your startup will most certainly fail.

There is, however, a downside to that level of belief. If your startup does fail, it calls into question the very core of your self-esteem. You were the reason that the startup was going to succeed, so you must be the reason that it failed. You must be the failure.

And most startups do fail. Mine did. There’s a good chance yours will, too. You need to be emotionally prepared for that to happen.

I’m hoping that — by walking you through my thoughts and emotions during the last days of my startup — I can help you in these preparations.

Ready? Let’s start at the beginning of the end.

Deny, Deny, Deny

What was the first sign that we were going to fail? I have asked that question of myself thousands of times by this point. Truthfully, I still don’t know. I do know that I missed several of the early warning signs.

Actually, missed is not the right word. I chose to ignore many of them. I couldn’t let my belief in the company falter. Denial is a scary thing. You know what is happening — in my case, the fall of my company — but you convince yourself that it can’t actually happen if you don’t admit that it is happening. You come to believe that you are holding off the inevitable by sheer force of will.

Whose Fault Is It?

After denial comes anger, right? It’s not quite that simple. I was in denial and feeling angry all at the same time. The following stream of thoughts was running through my head at once in a jumbled mess.

The company is fine. Even if it’s not fine, I’m doing everything I can. It must be someone else’s fault. The market is bad, so that could be it. Is my co-founder really pulling his weight? I can’t let it be my fault.

In my head, I was putting together a list of reasons why my co-founder would be to blame if anything went wrong. The partnership between co-founders is crucial when things get rough, and here I was looking for the nearest bus to throw him under.

The denial I could live with, but this was unacceptable. I had to let that anger and the desire to assign blame go if we were to have any chance to survive.

Most of what I wanted to blame him for was beyond pointless. It had to do with his level of experience, his connections, and other aspects that were beyond his power to change. These were aspects that could influence my choice of co-founder for my next startup, but I knew they had to exit my mind for the time being.

Even for the things that I believed could change, I needed to shift the perspective. Blame is toxic. Instead, I needed to make it about change. I had to be honest with my co-founder about what was going through my head, but only in so far as it led to a path forward.

Can I Buy a Pivot?

Denial morphs easily into bargaining. It’s the mindset shift from nothing is wrong to nothing is so wrong that I can’t fix it. I became convinced that a pivot would fix everything. The company couldn’t die as long as we were willing to pivot.

Pivoting is not a bad idea. It’s the reason Slack is still in business. But a pivot needs to be controlled, and I was out of control. The early pivots were fine. They involved solving somewhat different problems in the same space. Often they were as simple as expanding a single feature to become the new core.

As our desperation grew, so did the lengths that I would go to make a pivot work. I went as far as suggesting we built add-ons for a real estate CRM. That would have been great if we were in real estate software, but we weren’t. We were a data platform for chemical plants. Try to figure out that leap.

We had a long runway due to funding that we had acquired just before the COVID pandemic. This made it very hard to imagine that giving up could be an acceptable alternative to a pivot. But our target market was postponing all capital expenditures. Any pivot would have to leave them behind.

My co-founder and I had gotten together because of our joint backgrounds in chemistry (chemical engineering in his case) and analytics. If we were talking about leaving one or possibly both of those aspects behind, did it even make sense for us to continue together? In the end, it didn’t.

I had no customers, no product, and no co-founder. There was nothing left to bargain with. I was ready for the next stage.

Nowhere to Run


The ending had arrived. Our company was no more. All my life I had wanted to build my own company, and now it was gone. My startup was a failure. I was a failure.

I don’t know what I would have done without my friends. My co-founder and I stayed in contact, talking often about what we planned to do next. My girlfriend was a constant source of emotional support. I had a system in place that allowed me to cope.

But it still hurt.

I told myself that I was a serial entrepreneur, so this was just a stepping stone. I told myself that investors prefer second-time founders. I told myself that this wasn’t my dream startup anyway. I don’t know why I thought any of that would help.

I started jumping into other projects as quickly as I could. I applied for jobs at various startups, took a course on affiliate marketing, and renovated my Upwork profile. I needed something to go right in my life. I needed to be a success at something. But desperation is not the solution to despair — it’s just another symptom.

I couldn’t put the intentionality I needed behind any of these ventures. To do so would make it a real attempt. Real attempts can lead to real failure. I couldn’t let myself fail again so soon. Instead, I gave each of them a bare minimum of effort, which of course didn’t go well.

One question kept rising to the top of my mind above all others: “Did everyone else know I was going to fail before I did?”

I became convinced that my friends and family had just been indulging my fantasies. They never really thought I would succeed. In my mind, I had been a child pretending to be a businessman, and everyone else had just been playing along.

The greatest power depression has is its ability to make you isolate yourself. Depression knows that your support system is its greatest enemy, so it tries to get you as far away from them as it can. I know because that was exactly what happened when I sunk into depression after my divorce.

What kept me from giving in to these thoughts was some combination of my previous experience with depression, my girlfriend and close friends, and my writing. Putting my thoughts down on paper was a huge boon to my mental health. It’s much easier for me to sort through my thoughts and feelings when they are in print. It’s hard to hide from feelings that are staring back at you in black and white.

Final Thoughts

The stages of grief aren’t as well delineated as an intro psych book would lead you to believe. They don’t occur in order, and getting through a stage does not guarantee that it won’t come back.

I’ve accepted the loss of my startup, but that doesn’t mean that I’m over it. When I tell others this story, it can still bring up feelings of denial, anger, depression, and more. Writing this article is my latest attempt to find the lingering feelings that I still need to deal with.

The hardest part is that startups don’t die instantly. I started this article either 6 hours or 2 months after the death of my company, and I’m not really sure which to call it. Long goodbyes truly are the hardest.

Here’s what I do know: 6C Solutions will always have been my first startup, but it will not be my last. I’ve tasted the adventure of startup life. I’ve felt the rush of the highs and the pain of the lows. No matter what my next step is, I will be back for more.

I will bring the same enthusiasm to my next startup as I brought to this one. If it fails, I will likely feel the same level of loss all over again.

I am prepared for all of that — or at least as prepared as I can be.

My second startup will be the big one. And if it isn’t, they do say the third time is the charm.

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