The False Entrepreneurial Failure Mantra


The Failure Mantra

Embracing failure is one of the first things you are all told to do once you set out on your first entrepreneurial effort.


Because the odds are stacked against any new business. The odds of the business being open after 5 years are less than 40%, but this doesn’t tell the full “failure” picture, as a heartbeat does not denote a success.

Failure, and its teaching benefits, are a mantra deeply engrained in the American startup culture.

Let’s look at what two of the most important entrepreneurs of our time had to say on the subject

I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life

-Steve Jobs

 Reward worthy failure – Experimentation.

 – Bill Gates

Failure was something each actively embraced for themselves, but obviously led their organizations to limit.

We aren’t supposed to seek failure, but what we are to do as entrepreneurs is to destroy any fear we have of it, and learn to use it as an education.  Our job is to strive for success, even in the face of this dark enemy. When it comes ringing, like a death knell, we must have the courage to tell it to pass on, we aren’t dead yet.

Failure is more powerful than any MBA program you could ever enter. It is the catalyst for Eric Ries’ Lean Startup concept, where you fail fast, and iterate off those losses and turn them into wins.

And yet, I put it to you that today many of us have lost site of the importance of this concept in the entrepreneurial landscape.

An Illustration of Our Fickleness

I am going to use Kevin Rose as a quick example.

In March, him and his team at Milk were “acqui-hired” by Google, and the sentiment of many was expressed by Chris O’Brien at the Silicon Beat when he wrote:

“Embrace failure” is the first thing anyone will tell you is the secret to Silicon Valley’s success. There are other things of course, but that’s likely the first thing that will pop out of people’s mouths.

But as important that philosophy is, the news today that Google had “hired” or “acqui-hired” or “whatever-hired” Kevin Rose seems strange and depressing.

The slow descent of has painted Rose as a failure in some people’s eyes. These people forget the impact that site had on social media’s development, or the fact that he was less than fully active as it started to descend, in almost everyone’s eyes it was his fault.

What the masses expounding on this topic also forget is Rose’s knack for knowing what will work. Beyond Digg he co-founded Revision3, which sold to Discovery Communications for a rumored $30 million. And then there is his investment record:

  • He was a part of Twitter’s Series B in 2008
  • He was an angel investor in FourSquare
  • He was involved in Square’s Series A
  • Other investments include Zynga in 2009, Path, and Fab.

And despite all of this there are still people who paint him into a corner because of the decline and death of one company. How has he performed against the average successful entrepreneur in the Valley? How important was his most visible failure to the growth of social media?

A better question, if Steve Jobs never returned to Apple, what would his legacy have been? Is his departure from that company his most defining moment before his return, or is the mark he left on the world in Apple’s early days?

The most interesting thing I read in August was the speculation on Mark Zuckerberg’s need to step down as CEO of Facebook, as if the over valuation of that company falls on his plate. How does the failure of that stock to hold up change anything we know about Facebook?

The Rub

And so here is the rub, if you succeed long term, your overcome failures will be something people give merit too as what shaped you for success, and as long as success evades you those same failures are what people will point to as your incompetance.

The failures don’t change, the end results change our perspective on the failures.

My Personal Experience

I  have failed more than I have succeeded in my entrepreneurial career. Obviously I am not even in the same realm of entrepreneur as the men I have previously mentioned, but my own experience is the easiest for me to pull from.

I began on this road in the Summer of 2008, so I am in the fifth year of growing businesses.

I have made a large amount of mistakes during this time, and upon reflection the last two years have been the most condensed amount of these issues. But I am still standing, still growing, and still learning.

In the last twelve months, I began a new chapter of my life with SteelCast, and closed another chapter with my leaving BlueGlass completely in the Spring of this year. We started SteelCast with 4 projects, and today 1 of those projects is alive and growing, but it’s still in the fragile stage in its startup lifecycle where sales growth is our key strategic focus . Hua Marketing merged into CopyPress due to a strategic need and market changes, and 1 out of the other 2 projects is in a reboot.

tl;dr The last 12 months have produced more failure than success

For me this has meant failures on the personal and professionals sides of life. This post isn’t the place to get into all of the loss, but it is safe to say that the last 12 months have come as close to breaking me as any other time in my life.

But what about the wins? We have grown CopyPress’ revenue by over 550% year over year for August. The company currently employs 16 full-time staffers and a few hundred contractors through our crowdsourced software. We have weathered the changes with how search and social media handle content, and improved.

The most difficult thing I have had to learn to do this year is focus on the success and learn from failure. It is the only thing that has kept me going.

My failure based lessons include:

1) Partnerships are important, but the right partnerships are more important.

2) Having 90% of your revenue coming from 1 source is a poison pill.

3) Your ethics do not apply to other people’s actions. Verbal commitments are useless. (this is a rookie concept, but still made several mistakes around this concept).

4) Being on the same page with your investors about focuses is vital, don’t assume they see your vision.

5) Most people will never share the level of passion you personally have for your project.

6) If someone is not a fit for your culture you must act quickly to remove that individual for the good of the whole.

7) Outside influences will effect your business, you must be able to pivot if needed, and not get sidetracked and use those influences as an excuse.

8) Risks must be weighed, calculated, and then acted on. Hindsight is 20/20, but a failure from taking a risk cannot be something you define yourself by. Everyone makes bad decisions, move on.

Has this experience soured my personal belief in the importance of embracing failure and iterating off of the lessons towards succes? NO.

Regardless of what the people around me believe, my vision is steadfast on what our projects are becoming. Other people’s perspectives are just that; other people’s. I personally cannot let how other people define success and failure change my focus, or alter my course.

This week we had a meeting about a pivotal strategic change in one of our CopyPress offerings, and when our COO Stefan asked me, “Are we sure we want to pull the trigger on this?” I could see the memories of the past 12 months playing out in his mind. My response, “If we fail, we are going to fail doing what we know is the right thing for the company based on our vision.”


When you are an entrepreneur, often times more people are cheering for you to fail than succeed. Not the type of failure that breeds growth, but the type of failure that breeds death. As much as we love a success story, in many ways we still love to watch train wrecks even more.

The best advice I can give is: Don’t listen to any of it

Be willing to take risks, but be smart about weighing risks ahead of time. Utilize the Lean Startup concept, and fail quickly and fix it quicker. You will scab your knee, you will bandage it, and you will scab it again. Rub some dirt on it and get back up. Eventually if you have the stamina you will succeed, perhaps not in the way that you thought you would when you set out on the journey, but that isn’t in your control anyway.

In so many ways the path to success is a marathon, those that can endure the longest will win.

The other largest take away from the last 12 months for me is that the experience is as valuable for me as the result, and I think that is the true trait of an entrepreneur. Can you learn to love the rollercoaster? Can you yearn for the painful education of iteration? Can you become so focused on the idea that your WILL WIN that nothing else that happens can deter you?

Failure and success is something we can only define for ourselves. Other people can try to label our actions, but when all is said and done in this life only we can count up our score.

Here is what some other important people have said about failure:

Failure is the condiment that gives success its flavor.

- Truman Capote


I don’t know the key to success but the key to failure is to try to please everyone.

- Bill Cosby


I’ve missed more than 9.000 shots in my career. I’ve lost almost 300 games. 26 times I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life, and that is why I succeed.

-Michael Jordan


I don’t believe in failure. It’s not failure if you enjoyed the process.

- Oprah Winfrey


 A failure establishes only this: that our determination to succeed was not strong enough.

– Bovee


I have not failed. I have just found 10,000 ways that won’t work.

– Thomas Edison


 Don’t fear failure so much that you refuse to try new things.

– Louis Boone


Failure can either be a stepping stone to success or a stumbling to defeat.

– Ron Holland


Greatness is not achieved by never falling but by rising each time we fall.

– Confucius


Sheer persistence is the difference between success and failure.

– Donald Trump


The greatest failure in life is to stop trying.

– Napoleon Hill


I can accept failure, everyone fails at something. But I cannot accept not trying.

– Michael Jordan


Failure is just a resting place. It is an opportunity to begin again more intelligently.

– Henry Ford


I have had all the disadvantages required for success.

– Larry Ellison


I’ve learned that mistakes can often be as good a teacher as success.

– Jack Welch


All my life, people have said that I wasn’t going to make it

. – Ted Turner

15 thoughts on “The False Entrepreneurial Failure Mantra

  1. Well put Dave. Reminds me of one of my first bosses who started his business out cold-calling probably 50 years ago by now. He did the math and figured out every time someone said “No”, he made $0.25.

  2. @Andrew – I love the idea of creating KPIs around your success and failures as a way to keep focus on the end goal

  3. Along those lines, every day working for yourself is a whole helluvalot of bank:
    - you’re not part of someone else’s “aging workforce” that WILL eventually be dumped
    - you’re not a worker under a boss who thinks “my employees are here to make me rich”
    - you’re not a drone doing what someone else thinks you should do for them, for some reason no one knows
    - you don’t have to believe (or pretend to believe) someone else’s vision, because you need your job
    - you’re not forced to re-invest into a system you don’t believe in (corporate ladders, retirement savings, professions, etc)
    - you know in your heart (and can sense the freedom it reflects) that if your own judgement it’s time to shift direction, you could, and would for the right reasons

    I’m not a believer in the focus on “failure” (not even acknowledgements that failing is winning). The main reason is I have very little respect for those who seem to value that stuff. Usually, those people are either in the way (of innovative thinking) or part of the problem (that stifles creative expression and innovation) or are themselves parasites living off the sweat of innovation. In that last case, what value is their opinion after all? I might need their money, but not their opinions. And if I can’t have one without the other, well, the search for partners continues.

    Here’s what I do, and here’s some stuff I’ve explored/tried, and I’ve learned a lot, and I have a lot more to learn., and I LOVE TRYING AND LEARNING — it’s what defines life for me. Who give’s a shit if someone else thinks it’s a success or a failure?

    Thanks for the invitation to “speak my mind” Dave.

  4. John -

    As always I love your perspective on things. I really agree with the idea that people that get hung up on the BS of “success now” stifle innovation, because it is true. You can’t cry for 100% success and cry for adaptation.

  5. Thank you SO much for this Dave. It’s a perspective that I really needed right now because lately I’ve been feeling defeated.

    Most people probably haven’t noticed, but I’m not as ‘out there’ as I used to be. I haven’t blogged about links or SEO In over a year. I hardly tweet anymore and can barely bring myself to update facebook. This is because I feel like a failure. After 3 yrs in business, I’m still struggling financially, still spending all of my time working (when I can bring myself to open my laptop that is), and most importantly, I’m missing out on life. The SEO game has gotten more complicated, and where it comes to link building, clients are getting exceedingly harder to please. Expectations are huge but budgets are small and deadlines are tight. Couple that with all the other stuff that comes with operating a biz, and it’s enough to make a person go batty.

    Not sure if any of this is making sense. It’s 2am, I’m still working and I need coffee.

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