This may fail (and that's OK)

This may fail (and that's OK)

When my last company failed in 2018, I felt broken. I had just spent nearly six years of my life working towards something that ultimately amounted to nothing. At least, that's how it felt at the time. From a strictly business perspective, the company was a complete loss. Despite having conversations with several potential acquirers, we were unable to sell the company and I was forced to wind up the business (more on that later).

Although I was briefly overcome with depression and anxiety from losing not only my family's only source of income, but having cost other people their jobs and investments too, as the company's founder and CEO I was not ashamed of the outcome. I was disappointed. I was frustrated. I was tired. But I was not ashamed. I knew that I had tried every possible avenue to ensure the success of the company I had cofounded five years earlier. I was proud of that no matter the result.

I can recall attending local startup events shortly after the news of the company shutting down went public, and people seemed surprised to see me. It was as if I was attending a funeral for a close friend or family member of mine and everyone expected me to be in tears. But I wasn't. I was grateful for others' consolation during this time, but I told them the same thing I've told you: I am not ashamed of the outcome, and I will not go into hiding because of it.

In hindsight, I believe this experience was transformative for me personally and professionally, because it changed how I think about failure. For most of my career up to that point, I viewed failure as something to be embarrassed by. As a competitive person, I believed if you didn't win, you lost. In my mind, failure was not an option. It wasn't until my venture-backed startup failed that I accepted failure as part of the process.

In fact, I wished the company had failed sooner! I'll tell you why in another post.

So I flipped the script. Rather than quietly disappear into obscurity or leave town as I had seen so many founders of failed startups do, I embraced the failure. Within months of having to announce the closure of the company to our employees, I spoke publicly about the experience at a local event. The presentation was even streamed on Facebook Live for anyone to watch. As I took the audience through the various reasons why I think the company failed, I did so as someone wiser than the person who started it.

When starting anything new, failure is a very real possibility. The fear of failure in anything we do can be paralyzing. It's one of the reasons why so many of us are afraid to even try at all. Don't get me wrong, failing sucks. But it can also be liberating if you start viewing failure as an option, a disproven hypothesis, or simply an opportunity to learn something the so-called "hard way". I think this quote from Winston Churchill sums this up perfectly.

"Success consists of going from failure to failure without loss of enthusiasm." – Winston Churchill

Now nearly three years out from the biggest failure of my adult life, I continue to rely on those lessons learned in my role as a product leader at a Fortune 500 company. Although I'm not a startup CEO these days, I find that many of the decisions made (or delayed) at a large company are influenced by the fear of failure. Whether it's trying new features or running A/B tests to optimize existing ones or simply removing something most customers no longer use, the fear of failure is pervasive. But it doesn't have to be.

To overcome this mentality in a product organization of more than 200 product managers and product designers, I've simply started telling teams that failing is OK. In fact, it's encouraged! That's how we'll learn, improve, and innovate for our customers and the business. If we are not willing to fail sometimes, then we'll fail anyway because we'll move too slow in a futile effort to achieve perfection. The key is to learn from the failure with as much objective evidence as possible to answer the question, "Why?".

A colleague (who is too kind) recently told me "If you happen to offer a course of explaining business value or 'the why', I'll be first in line." Their feedback and my reinvigorated desire for a creative outlet inspired me to start writing. Although I've advised startup founders and mentored others over the years, I've never formally shared my knowledge through my own writing. It's always been on phone calls, in meetings, through e-mails, or the occasional text message.

Today I'm starting my personal website for the first time since owning this domain name for nearly two decades. I'll be sharing long-form essays on startups, technology, product management, and controlled experimentation – topics that I find fascinating and have learned about while building Internet products and businesses since the early 2000s. I may also periodically provide in depth analysis of products or companies that I find interesting or important.

My goals in doing this are simple:

  1. Document what I've learned in one place so the knowledge I've gained through experience is not forgotten over time.
  2. Create value for others by sharing what I've learned while starting companies, building Internet products, and leading others.
  3. Force myself to never stop learning so I always have more interesting content to share.

I plan to publish at least once a week. If the type of content I've described sounds interesting to you, please subscribe to receive new posts delivered directly to your inbox so we're not at the mercy of algorithms. You can also follow me on Twitter or LinkedIn. If I can help someone avoid the mistakes I made as a first-time entrepreneur, inspire companies to choose data over intuition, or simply help a product manager hone their craft, then I will consider this effort a success.

In starting this website to publish essays on topics that matter to me, I accept failure as an option. Maybe I will find it difficult to consistently come up with ideas for new content. Maybe I chose the wrong platform to publish on. Maybe I will struggle to drive awareness and traffic to this website from my network. Maybe I'm not a good writer. Maybe no one else will want to read what I write.

This too may fail, and that's OK.