As both a seasoned entrepreneur and an investor myself, I’ve lost count of the times I’ve heard the advice dolled out to new or would-be-founders to “fail fast.” In theory, this platitude is meant to serve as a guidepost for their strategic decisions and urgency. And yet, in my experience not only is it unhelpful, it’s actually detrimental. 

For one thing, failure is inherently subjective. Even in seemingly unquestionable circumstances of failure, like running out of money, companies have found ways to live on. Furthermore, when offering it as a straightforward litmus test, it further falls apart in the complexity between  personal failure and enterprise failure. Let alone the ambiguity of perspective. In whose eyes should you fail fast? Your own, your investors’, your advisors’, your customers’, your employees’? Therefore, this trite euphemism becomes more of a beacon of anxiet y rather than a reassuring northstar. 

The inclusion of the qualifier fast is also confounding. The average startup (that survives) takes five years to reach Series A. Is that our definition of fast? How many times have you seen the entrepreneur's journey chart - the one with the ups and downs - that’s often accompanied by the adage that in the lows one just has to power on to get over the hurdle and onto the implied success at the end of the path? When I recall the journey I’ve traveled in launching businesses, my forward progress was not always evident with each passing day. Indeed, if I’m being honest, there were plenty of periods where eminent “success” felt anything but certain. For a founder in the throes of launching a startup, which of those inevitable low points should they assume to be a failure compared to a point where they must redouble their efforts and apply “grit”?

We all want to avoid wasting time and money; both are finite. But once a company gets formed, or takes investment, or secures its first customer, a natural flywheel of forward momentum pulls it onward, but not always upward, independent of its financial results. With additional stakeholders in the mix, the success (or failure) is now personal to many - with the added shame and consequences of disappointing performance. In fact, there becomes an “anti-fail” mindset. Whether it’s an extreme bias to "push through the adversity" even when faced with diminishing returns or to try and execute a "pivot" based on the most recent customer data and insights, the psychology of business development naturally resists admission of failure. If you have been there, you know. And our culture loves to fetishize these gritty moments, especially as part of the hero's journey narrative that we tell retroactively from the unanimous successes (enter the now cult-like celebrity status of certain business leaders and their unflagging determination and refusal to fail.)  

To be clear, in the face of all of these strong forces pushing towards perseverance, it’s awfully tempting to resort to a pithy directive, like “fail fast” as a counterweight. And without question, sometimes it does require bravery and leadership to cut one’s losses and admit defeat. But, in truth, rarely does this realization come from such casual advice, even if it’s given frequently.

Instead, I believe the more helpful advice we can offer as investors, mentors, fellow co-founders, and entrepreneur ecosystem players, is the steadfast faith in measurable data and the unflappable commitment to measure and assess. Where failing fast is subjective, data is quantifiable. And data need not always be financial. In fact, for an early-stage company, financial data may be the least valuable. That said, the insights that are valuable in guiding a company need to be measurable over time to help identify weaknesses as well as opportunities. In this space, advisors must be courageous in helping founders seek the collection of that data and then offer the support and candor to help analyze it, especially when it points towards an end. Staying in the 0s and 1s of metrics not only removes the ambiguity of emotion but also dampens the crash of personal defeat.

Shouting "fail fast" into the wind diminishes the complexities that startups face. It ignores the myriad of emotions and external forces at play, and blithely downplays the very real personal and financial repercussions that failures bring. Instead, we need more people to step up to help founders realize they are in trouble before they get there by being proactive, measured, and analytical. 

It takes incredible courage to take a risk and start a company. We, as startup stakeholders, owe founders the same bravery in helping them evaluate their progress quantitatively, including, if it comes to this, offering companionship and acknowledgment to them when those outcomes make it clear that the risk won’t pay off.