My Startup has 30 Days to Live

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Years ago, one of my investors told me that the life choice I was making when I was setting forth on my startup journey would change me forever. It would make others think I was reckless. It would make me feel dangerous, capable and ready for action.

After writing my last post here, I’ve been in the shadows. From the shadows of the startup ecosystem I built a team, then product, and it grew and grew and grew.

I’m building something I love, with people that I love, for all the right reasons. This time, I’m going to win.

I won’t self-promote here. I just want you all to know that there is indeed life after a startup death. There is redemption. You too will survive and you too will enjoy the ride even more the second time around.

In two days, I begin anew in a senior management role, though firmly outside the startup ecosystem. I’m thrilled to have a clean slate and happy to be so employable after such a colossal fuck up. Though, the learnings were indeed real and have made me a better man.

The past month has been a torrent of emotions, a series of lows, each lower than the last as I retreated into a shell, neglected my health and came to terms with our only chance at a strategic acquihire ending with a shitty skype chat where we were told we just weren’t good enough to work with the successful valley startup in our space. It was a blow to the work we did over the last two years as well as to those who had invested in us as people, whether financially or emotionally.

We have been threatened with legal action due to our gradual shut down, we had a support organization breach contract and tell us, “just give up, do you really want to fight this”, and have been up close and personal with the true filthy face of the world that on the outside celebrates failure but in reality treats those that are suffering through failure inhumanely, because they can.

It’s over. But you’ll never know. The service continues to run, but communication is slowing down. It’ll continue to slow down gradually, until you get annoyed and lose interest. Churning away to the next big thing to hit tech crunch. Which hopefully, will have a fate better than ours.

I’m not going to reveal my identity, because it does you all a great disservice. Let these words and these memories resonate (or not) not because of who I am but because of who we are. At some point in your life, entrepreneur or not, you will fail and do so spectacularly.

You’re not alone. It’s going to hurt more than anything you’ve ever felt before. It will try to destroy you.

But it won’t.

Thank you, everyone. For your words of support, your introduction, and spirit of perseverance. I am forever grateful that your voices helped me through this awful experience.

I’ve often heard that in our final moments, our life starts to flash before our eyes. I’m still not sure whether this is a fictional construct that has become ubiquitous or some neurological effect. However, I do know that over the last 24 days I feel like I’ve experienced a lifetime of trials, failures, successes and emotions as I came to terms with the fate of my startup.

I am The Blerch

When I first sought catharsis through this blog I felt completely and utterly alone. I always knew that statistically this outcome was the most likely and the prospect of failing to execute on my vision due to an externality didn’t frighten me. What tore me apart that in the middle of the night was the responsibility I felt toward people who had shared in my vision and took part in clarifying it and building it with me.

What would failure mean for them? Would their careers really recover from the sacrifices they made chasing this dream? Would failure of a business sever friendships and relationships the way the reading of a will can tear a family apart?

The Musketeers

Paralyzed by my worries, I had forgotten one important thing about the team I had built. It had heart. 

I was careful not to build a team of mercenaries who toiled for riches or fame. I had passed on hiring great engineers that lacked humility and thought their github profiles made up for it. Instead, I hired nice people who worked ridiculously hard and got things done. And they did, over and over again.

So when I called a meeting and gave everyone a long, hard look at our financials. I was the only one with the quiver of sadness in my voice. My team stepped up, re-affirmed their alignment with our shared vision and made a ton of sacrifices to ensure we can continue executing it. 

This passion is what being elite is all about. These are people that can independently step up and save anyone or anything when the outlook looks grim. These people are not employees. They’re not co-founders. They’re humans. Great humans.

Going Big or Going Home

We didn’t go big, and looking back on it all, it was clear to me that we almost always wanted to go home. We just knew that we couldn’t really do what we wanted to do alone. Not if we wanted it to really matter.

Of all the meetings I’ve had this past month, only one man has been able to understand the importance of my vision because he shares it. He’s successful, but gets like I do, that it can’t be measured in dollars or power. His mission is one my team believes in and I wouldn’t have had the chance to connect with him if it wasn’t for the intervention of someone I admire. I’m blessed to have been able to find this connection now, before it was too late.

My team now has a chance to live on in some way, the mechanics of which really don’t matter to any of us. What does matter is that I know that we are among others whose motivations stem from the same place as our own. This kind of alignment is rare and is the only way that I could be so hopeful that my team will now be able to do the best work it ever has. I don’t know what will happen over the next few weeks, but I do know that I’m not scared anymore.

It’s gonna be alright.

I wish I could write about how I capitalized on a once-in-a-lifetime moment, using it to find some way to save my team and this company. I wish I could tell you about how I begged and pleaded my way to a soft landing, allowing my team to bring their awesome talent at building and creating to a company that would really be able to make these talents shine.

Instead, I’m writing about the latest in my personal stream of fuck ups. As much as I’ve written about accepting the 30-day prognosis, I really don’t want to. My desire to find a safe landing is offset by the desire to stay true to who I am and what we were out to solve. We made some bad decisions along the way but there is something here, I just wish we had the time to figure out what it would be. I also wish I could tell how much time I’d need, how much it would cost, and how I’d make it work. If I knew, then I’d have a real plan.

How do you fail with dignity when people depend on you?

For the past 2 years, it seems that all i’ve been doing is selling dreams. Sometimes, the hunt felt incredible, other times it left me drained and beaten. Nothing was more thrilling than selling my dream to myself to build up the courage to look my boss in the eye and tell him that I’m leaving (and stare back as he threatened to ensure that I’ll never work in the industry again if I needed to), or selling our product to early clients and the press that gave us the liquidity and reputation we needed to get noticed. Every time I heard “No", I tried twice as hard and it usually resulted in a close.

When we raised our seed round, I spent months pitching, pitching and pitching again. We played along through coy games over email and LinkedIn as investors tried to establish negotiating leverage for themselves through their communication patterns. Intros, recon, sizing up and an over abundance of assholes were my day to day. At night, my wife would tell me how this was changing me, we were fighting more then, a lot more. Despite having lived through and participated in M&A and financings before as an employee of a BigCo., I had begun to think that this is how the world really worked. That it was normal to be strung along with smiles and to string others along the same way. These were some of the darkest times for me and the ones that created the greatest rift in my marraige. Thus, when we closed our round I was elated and ready to do what I do best.

Same shit, just more shares on the table

That darkness I felt then is back now as I work towards this acquihire. Once again, we’re being courted by men who use an abundance of designer hair products. Men who’ve seemingly forgotten the struggle and are intent on toying with their prey. Both those that have approached us and those who we’ve approached have acted similarly, circling our bleeding body in the water, perhaps to sadistically toy with us. Though likely, they’re doing what I did when I last was involved in an M&A - waiting until the lights go out before looting.

In the meantime, we are plugging away and keeping the ship afloat. Making ridiculous sacrifices as we try to play a game of chicken with a much larger and apparently much meaner adversary.

So, how do you fail with dignity when you’re responsible for a team of talented, educated, and accomplished builders?

You sell them to whoever is kind enough to be the first who takes your company out back and shoots it.

Dignified, isn’t it?

Yet these days, it’s what I pray for.