From my response on the Yabbly Startup Survivor Challenge: What was your worst/darkest moment in your starup experience, and how did you get through it?
Now that’s a great question!
In the Lucky Oyster office, on the wall between our two whiteboards, we have a copy of Anna Vital’s “How to Never Give Up” infographic (seebit.ly/1fMDu8L). She qualifies the lowest point in the graph, “the dip”, as follows: “right before success, you will face the worst.” In our field, successes look like blazing flashes of light, but we all know that in reality they all go through dark, dark days, and generally just before their ascendancy to greatness.
My darkest moment in a startup came just shy of a decade ago. Because of disagreements with and between my partners/investors, we found ourselves with almost no operating capital, having walked away from a $4m investment. Because of this, I had to lay off three engineers, close up the office we had been subleasing, and I–the only full time employee remaining–moved my workstation onto a crowded conference room table in my Mom’s office. My partners, both incredibly talented product thinkers and deal makers, were not only upset with each other, but literally on two different sides of the planet, neither local to me.
Firing up that workstation, I realized that from that moment, I’d likely be the sole tactical driver of the business for quite a long time. And while I’ve always loved wearing many hats in a business, the idea that I was quite literally on my own, having taken a bunch of steps backwards from a traditional growth trajectory, was pretty devastating.
A few things kept me going. First, I truly believed that what we were doing was innovative, important, and could really enrich the lives of our users. I also continued to love the work: it was technically challenging, but in ways that were solvable with creativity as much as engineering horsepower. I also knew that if we kept at it, we could organically build a sustainable business, with great revenue and high margins.
For support, I also turned to my partners. And it turns out that making it through the worst is an incredibly powerfully way to cement and enrich working relationships. Both brought just what we needed at that point to the table: enough working capital to get us to a sustainable point; introductions to partners and advertisers; and much more. But really, it was their continued faith in me and the business that helped keep my spirits alive. I turned their faith into my mission.
For a long time, things were difficult. Every day, I sat at that workstation, and I hammered. If it needed to get done, it was solely up to me. And looking back, it was one of the most productive periods of work I’ve ever had.
Slowly, we got back on a growth trajectory. We brought on someone to help us operate, and then a business development resource. Our traffic and revenue grew. We licensed our platform to a large publisher. And our product footprint grew larger every day. In the end, we were acquired for more than the post-money valuation of the financing from which we walked away.
The story ends well, which is a Good Thing, but what I take away from those dark days is far more important: the knowledge that it’s ok for disasters to befall a business, and that contractions in the typical growth trajectory of a business can be leveraged to focus the team that remains, and slingshot the endeavor back into ascendancy and ultimately, success.
