The Pivot Diaries, Ch. 1: 100 miles an hour into a brick wall


On June 18, 2017, I hit the send button in MailChimp on the most vulnerable email I’d ever sent to our subscribers. I wanted to share it here, and talk a bit about why we decided to do that:

Have you ever been in a situation where you know you’re not on the right path, but you keep going anyways?
The more I think about it, the more I realize how prevalent that behavior is.
But you know who stands out to me, who I’m secretly jealous of? The people who own up to their mistakes, slam hard on the breaks, and steer into a different, hopefully better path. You know the type. They’re the ones who are normally saying the things that everyone else is thinking, but are too embarrassed to admit. In today’s world of over-hyped everything, to me they seem kind of like heroes.
Why am I talking about this?
Well, not to be vain or overambitious, but I am actually hoping to be one of these truth-speaking heroes from this day forward.
Case in point:
All of you are getting this email because at some point you either signed up for our service, or we demoed it to you.
Most of you, however, are not using the platform that we built.
And that’s okay.
We realized a while ago that the platform as it is would just not be a good enough solution to a big enough problem for most people.
Right now we’re in the middle of what you would call, well, a pivot.
Where will it take us? I wish I knew :)
Hopefully it will lead us to solve a problem where we can use the skills we’ve sharpened over the time we spent on Wombat until now.
But I do know that in order to properly see where we should go, I’ve had to shed so much of my ego (even though I thought it was already non-existent). It feels wonderful — exhilarating and gut-jerking all at once, like a Drop Tower at an amusement park.
Knowing deep down inside we were going the wrong way and no amount of good copy writing, web design, or Facebook ad spend was going to fix it was causing a lot of distress for me. Now everything is out in the open internally with our team — we talk about where we are and what we’re looking for quite openly — and I want you to be a part of our journey, as well.
To our existing betas, thank you for putting your trust in our team and our technology. We’re going to keep the Wombat machine running for now, so you don’t have to worry about any changes just yet. We’ll let you know in advance when we decide to pull the plug on it completely.
I’ll update all of you when we have new big insights, breakthroughs, and share in our frustrations.
What do you think about this? Do you have a similar story from your professional life? I’d love to hear it — just reply to this email if you have a story you want to share with me.

I didn’t know what would happen, if we would actually get any responses, but we did. It was the first time anyone had ever hit reply on one of our emails. And the responses we got were so moving.

People told us they had gone through similar adversaries in their startups. Some encouraged us, saying they know we’re going to rock. Others gave us advice.

In parallel we started noticing that the more public we were about the moves we were making, the more people around us started asking us questions about it, regarding us as knowledgeable, wise, even expert, and eager for any bit of information we could give. It felt so strange, because the failure of the previous model had stung so much. We did not know that we had anything to offer, but there it was, all those replies and all these people coming to us for advice.

It was pretty incredible, but I was kind of too overwhelmed to notice it at the time. In fact, if there’s something to be said of the pivotal time of a pivot in a startup’s life, it’s that it is totally overwhelming. The bigger the disconnect there was to begin with, the bigger the pivot, and the more unsettling the whole thing is.

But I’m getting ahead of myself. Let’s start at the beginning.

We only ever hear about the successes.

Let’s start with the one obvious truth people don’t care to admit: no one talks about their failures from a point of failure. And I believe we all lose for it, because we’re getting a tainted hindsight view of what happened.

Maybe it’s our fault as a society for glorifying success. We might talk a big talk about #failingfast and revering our mistakes as catalysts for growth, but what we really want to hear is a turnaround story — someone who failed, but overcame, and ultimately succeeded.

That certainly weeds out a lot of useless stories with nothing to be learned from, but it also excludes a lot of valuable lessons that we could all gain from, even if the people who learned those lessons through hard mistakes didn’t end up rising above and reaching the epitome of success.

The birth of The Pivot Diaries.

Part of the reason it took us so long to come out about what was going on in the company is exactly that — what right have we to summarize our “lessons learned” for others, if we’re in the thick of it struggling just like them, if not more? Who are we to speak not from the heights of startup success, but from the rock bottom of the lurch we had found ourselves in?

Another part of it was, of course, the overwhelming reality of just trying to frantically save our ship. Who has time to keep a diary of this madness, anyway? But keep one we did. Not anything fancy, but the writer in me was taking notes, naming chapters, making up back stories for contributing characters, and making baseless decisions about what details would be foreshadowing. It was a sort of coping mechanism for me as CEO, turning my small team into the underdog protagonists of a story that will have a happy ending.

Now, our story is far from over, and we are not at all (yet) speaking from a place of great success. But I’m finding the time to write, and while the memories are still fresh in my head, I want to share them with you.

Because even though every successful person will tell you there was a pivotal failure almost directly responsible for that success, we as an audience are left to guess what happened in between. Between the moment they realized that with the current trajectory, they’re screwed, and the moment where they feel confident enough to tell everyone about it, there’s a twilight zone shrouded in mystery. And I believe that when someone recounts their story from a place of success, that story is already tainted and skewed.

If you think everything happens for a reason, you’ll find reasons and patterns to show exactly how failing at A led you to succeeding at B. But that story, albeit inspiring, is completely useless to someone deep in A creek without a paddle struggling to make sense of it all. And the further away the failure is, the more sense the chaos it breeds seems to make in retrospect.

My goal here is to untangle the thoughts and events happening in the midst of that chaos, without losing sight of the chaos itself, because it is so real.

In the next chapters of our story, I’ll talk about…

  • How we discovered we needed a pivot
  • How we discovered we did not need a pivot, but to build a whole new company
  • How other people react when you don’t show remorse about failing
  • What is the process we used to find the next best thing to do, and why it wasn’t really a process
  • How we built three different companies in two hours
  • How we got an investor panel to talk about their feelings in a conference about empathy, and how we set up a meeting with a roomful of investors so they could crush our dreams
  • How we became VCs ourselves

…And so much more.

I hope you’ll stick around to share in our experience as it unfolds. And I hope that by keeping an honest record of what’s happening, another startup can avoid some of our pitfalls, try to recognize some possible small wins, and feel a little less lonely in the wilderness of the pivot.