It Pays to Embrace the Embarrassment of Failure

Lionel Messi, one of the best soccer players of all time, famously said, “It took me 17 years and 114 days to become an overnight success.” When I decided to leave Google and start my first company, a number of people casually mentioned that I was committing myself to a 10-year journey at a minimum. My younger, significantly less grey-haired self brushed off those timelines with the incredulity typical of a teenager: Surely, we’d be able to do it in a fraction of the time. August 2022 will mark 10 years since I walked out of the Googleplex, away from those free lobster lunches, to start a company. Eight of those 10 years were spent in the dogged pursuit of achieving what’s known in the tech industry as “product-market fit” (PMF), which is roughly understood to be building something that people actually want and are willing to use and pay for. It’s as easy as summiting Everest in a snowstorm. I’ve been reflecting a lot on those first eight years in the PMF trenches. Achieving PMF is a delicate dance that requires mastering one behavioral trait: The ability to change your mind. It’s fascinating to see how the same concept goes by different names in different industries and carries ranging connotations. “Pivoting” in tech is good, “flip-flopping” in politics is bad. But this lengthy and arguably foundational stage requires that you get really good at acknowledging when you’re wrong and course-correcting accordingly. The company I started when I left Google was an e-commerce company, which evolved into a type of customizable Etsy and eventually shimmied into the creative analytics space, within which we tried 13 different products over the course of three years until one finally stuck. It was exhausting but exhilarating, now that I look at it from the safety of the rearview mirror. Much like raising young kids, I didn’t realize how much fun it was until I was way out of that stage. It’s Time to Start Measuring ‘Return on Creativity’ As marketers, we don’t pivot enough. It requires a type of constant introspection and self-awareness that’s grueling in the best of times and completely debilitating in the worst. “How can I be wrong about this, yet again?” And rather than sweeping under the rug the fact that something you tried didn’t work as intended, hoping no one notices, pivoting requires that you shout about it from the rooftops to refocus everyone on the arduous effort of trying again. And again. And again. Our individual avoidance of the pivot is influenced by most companies’ general attitudes towards failure; it's always bad, avoid at all costs, slap on the wrist and career purgatory. But that fear of failure, which inhibits our personal ability and willingness to try and therefore to learn, is like a poison pill with a slow and gradual release that eventually sends you into corporate obscurity. Now is a really good time to get good at the pivot, however big or small, and introduce it into our ways of working. There’s uncertainty all around us, which means there are tons to learn. From the deprecation of third-party cookies to the instability in the financial markets that will disrupt consumers' purchase decisions and patterns, there are miles of uncharted territory to navigate. Simply put, those who learn the routes first are setting themselves up to win. There are 3 lessons I’ve learned from hundreds of pivots. Wed yourself to the goal, not the idea Frame everything as a learning experiment that’s a stepping stone to the larger goal you’re trying to achieve, which it is but we don’t often talk about it like that. That means even null hypotheses are data points on your largest quest for figuring out how to make something work. It’s like a puzzle that’s slowly coming into view. Things that haven’t worked, or that you can confidently say you were wrong about, increase your ability to see the bigger picture. Practice saying 'I was wrong' and see what happens I remember learning as a kid that if I admitted to doing something wrong when my parents asked, rather than denying and blaming the dog, I’d usually get off scot-free. Extra points for taking responsibility, my parents would say. This is a bit like that. Saying you tried something and it didn’t work, and providing ideas of what we can try next to continue peeling back the layers of discovery, reeks of confidence. Gravitas. Leadership. And those are the kinds of traits that every promotion committee looks for. Measure everything Experiments are useless without a data framework to help you understand what you really learned, and turn the data from your learning experiment into an insight that can shape future strategy. Every failed idea and product iteration we had eventually brought us here, to a place where a little e-commerce company with no office space and bootstrapped from my meager Google savings is now active in 130 markets, used by over 5,000 brands and is at the forefront of applying creative data to marketing measurement. It might have taken nearly a decade, but truly transformative things always do. It’s Up to Brands to Bridge the Gap Between Art and Tech