Who Cares About Your Success Story? [Thoughts of a Serial Entrepreneur]


The conversation around someone’s (anyone’s) entrepreneurial success is played out… In the same way Facebook isn’t the cool social platform it was once considered by the younger crowd because their parents use it now and everyone else has an account. The story of success is what everyone is talking about everywhere in startup news, so it’s just not special anymore.



In any given month, there are a gazillion different events in startup communities around the globe talking about success this and success that.

Let’s get real about the situation. Often times the conversation around success is abused  as a platform to market the speaker’s own venture and becomes more of an advertisement than a story meant to pass on learning.

But what if there was something else which did have significant, real world value… and impact? What if I told you it was also shared from a practical point of view like success and that it could show you how to be more successful than someone’s story of success? Can you guess what it is?

“You always pass failure on your way to success.” – Mickey Rooney

Failure! Yes, failure. The thing society has taught us to bury deep down inside, padlock and never share with the world and those around you because it makes you unattractive, appear weak, less likely to succeed in the future and a whole host of other descriptions. Failure is where the greatest value comes from in any experience, not the success story. It is where the learning takes place.

“There is only one thing that makes a dream impossible to achieve: the fear of failure.” ― Paulo Coelho


The meaningful, real world value in a success story only exists *if* the specific path, method or insight can be replicated in your specific scenario (all variables being identical and that is the catch) and even then many times may not yield similar results. Sure, there is the inspiration side of that or you get the rare instance where someone heard something one time and applied it and hit pay dirt but honestly, more times than not, it doesn’t happen. So it can be argued success’s biggest value then comes from the inspiration.

Failure is the “next thing” for our startup ecosystems. And I am not talking about everyone out there who says they are being open and talking about their failures when really they are just humble-bragging.

By the way, what is a humble-brag?

It is a term coined by comedian and Parks and Recreation writer/producer Harris Wittels, it’s the kind of story or statement that tells the world how great your life or experience is, but then downplay it under the guise of humility or self-deprecating humor. Humble-bragging about your failure stories is, in this instance, ironically a failure in talking about failure.

“Success represents the 1% of your work which results from the 99% that is called failure.” – Yoichiro Honda


The conversation of failure, more than anything else right now will evolve and push us to be better all around entrepreneurs and communities. Failure is a defacto part of life as well as startup – it cannot be avoided entirely, but it also happens to be where real learning takes place and is what most people are not really talking about as often [or openly] as they should be.

All of this is not a suggestion that you should wear failure as a badge of honor, because failure alone is not the thing to be proud of… you still want to succeed ultimately but failure is the catalyst for change in the community and what comes right after failure is what you should wear as a badge of honor and be proud of. The fact you can identify the exact fail point, then identify where/why that occurred and finally what you changed about yourself, the operation or whatever, so that fail point specifically does not occur again or at least has a much higher likelihood of not reoccurring, is. That is what you want to be proud of when talking about failure.

“Smooth seas do not make skillful sailors”

As an investor for example, I don’t want to invest in the person who tells me they have had little to no failure. That is an indication of one of two scenarios: a) you aren’t trying hard enough or doing anything truly innovative, or b) your not being 100% truthful with me. I would rather invest in someone well thought out, with good resources that give me confidence in their execution going forward and that they have weathered the failure storm at least once.


If you fail and come back better than before, that is an entrepreneur I can get behind. Let’s start talking more about failure and the lessons learned with our local communities and sharing the wealth of knowledge that is still very much untapped. After all, going by current metrics, there should be nine times as many outright failure stories in startup and we all know everyone at some point in their life has or will experience it. There are plenty of examples to share… they are all around us.

Peter Sinkevich


Peter is a New York based serial entrepreneur with several years of financial and startup experience. His current projects include an early stage investment fund called Stamford Venture Partners and two stealth startups. He has served as a formal advisor for over 100 startups during his career.