Have You Ever Failed?

As I was going through my morning information routine, I noticed a number of articles that I’d put in the “how to not fail” bucket.  I read a few of these and noticed a consistent tone of “failure is bad – here’s how to avoid it.”

Throughout my life and career I’ve failed at many things, large and small.  I view failure as a fundamental part of every entrepreneurial endeavor, whether it’s a failed project, hire, partnership, relationship, lead, customer, or even the entire business.  One of the great things about entrepreneurship in America is that failure is an accepted part of the cycle.

I used to say something like “one of the great things about America is that failure is acceptable.”  When great people fail, they acknowledge it, learn from it, get up, dust themselves off, and get back at it.  If you accept reality, you can fail gracefully and hopefully learn something from it.  It’s never fun – and it can be really stressful / painful / emotionally hard – but it’s a part of learning, evolving, and growing stronger and better.

While I fail at stuff regularly, I’ll never forget the deepest cycle of failure I’ve been in to date.  As the Internet bubble popped exploded, company after company that I was an investor in failed.  As I grappled with this, I felt like I had been run over by a truck.  After I got up, a steamroller came and flattened me.  As I was peeling myself off the ground, the steamroller backed up and smushed me again.  Then, I realized I was lying on top of a hole and the top fell in and I tumbled down to the bottom.  As I was looking up at the sky, some jerk came into view, poured gasoline onto me, and then dropped a flaming stick on top of me.  By the summer of 2001, I realized that ever day had been worse than the previous day.  I no longer got up in the morning and said “ok – today will be better than yesterday”; instead I resolved myself that every day would be worse, until it eventually got better.  Then 9/11 happened.

I hung in there, kept getting up every day and doing my best, working hard to make informed and intelligent decisions, and helping all of the companies I was an investor in however I could.  A few more failed, but a nice number survived and ultimately thrived.  Things eventually got better.  And I learned a lot.

In my world view, the best leaders understand that failure is an integral part of things.  The cliche “fail fast” is one of my favorites.  When things aren’t working, deal with it.  Another is the famous line from Atlas Shrugged “Nobody stays here by faking reality in any manner whatever.”  Denying that failure is part of our existence is akin to faking reality.

While I accept “the experience of failure” feels “negative / crappy / depressing / hard / sucky”, I don’t believe that “failure is bad.”  Deal with it, learn from it, pick yourself up, and try again.

  • Andreas

    Love your article Fred. I just failed to get a job after working as an intern at a venture capital. Now i am trying hard to get a job again. One month i could not really motivate myself but now i am into it again. Your article really helps!

    • Thanks – glad you like it.  Keep at it!

  • Eric WIllis

    Great post and that line from Atlas Shrugged is one of my favorites as well

  • Drake

    Brad, I couldn't agree more. Never fail translates into fear of failure which stifles optimism, opportunism and exploration. If you embrace failure as part of the learning process, you can over the ego and get to solving problems and iterating to success– ie fail fast, recover quickly.

  • AnnaMerkin

    It's an interesting perspective. I think that as part of our educational and social experience, more people in the U.S. particularly should be encouraged to try new things and release the stigma of failure when it's the result of an earnest, thoughtful attempt (as opposed to recklessness.)

    Interestingly enough, as an African-American working in the tech startup world, I've come to believe that one of the reasons that there are few African-Americans in the tech startup sector has as much to do with low rates of education in engineering/science-related disciplines as it has to do with a generally conservative disposition that eschews failure due to the perceived lack of any safety net or ability to recover. That is, a college or graduate education leads one to think that it's incumbent upon the individual to pursue the recently-traditional version of the American Dream: suburban house, car, kids, and great career with a "stable" company or organization. I'd like to see more African-Americans and people in general embrace the necessary risk tolerance associated with growing, innovating, and exploring.

  • Most of the time I fail as far as I can tell. I just need one success to break this vicious cycle:) just kidding. Failure in my eyes is like any other part of the journey and usually the most educating ones.

  • andrew

    Failing made me stronger, smarter and hungrier. I am now thinking more clearly than ever and I get it. I am almost second guessing myself because I feel I know so much more. If I didn't fail early it wouldn't have put things in perspective.

    If you haven't failed, you have little experience. Failure is just expensive training.

  • Over the years, I've read a lot of posts with "failure" in the title, and most try to spin a failure into winning if you can learn/persevere from/through the experience.

    While I agree with the basic premise, you know what its like to fail. You don't want to hear this sh!t. The nature of competition is to want to win. Failing to win usually means you lose, and losing sucks. You try to understand why. Rarely is there one moment you can look back at and say, "that's when I fuc$ed up". The US economic downturn is a perfect example of this.

    I'm young, (29), and I've seen grown men act like complete babies when they lose. Just the other weekend, I played a game of Taboo with a group of friends, one of which is a super talented corporate executive. When it was his turn to have my team guess the word he was reading, without saying the words he's not allowed to use in his description, he got nervous and totally blew the round. He then lost it, threatening physical violence on the opposing team members that were assigned to catch his violations, and it ruined the atmosphere from then on. He also never apologized the entire weekend.

    I've also witnessed youth act with the maturity of someone twice their age. My cousin has two twins, both 8 years old, and their older brother, age 11. I gave them each one R/C helicopter each for Christmas, and the choppers have invisible lasers that can shoot each other down. One of the twins had his chopper shot down and crashed his into a very tall tree. His brothers wouldn't stop playing with their helicopters to help him get his. After crying for a 1/2 hour and whining to his brothers to let him try flying theirs, he came and got me for help. I got several tennis balls for him, and after many attempts, he finally knocked his helicopter out of the tree and was elated when he began flying again. 5 minutes later, his older brother crashed his on the roof, and displayed the same immature tantrum. This time, however, the younger cousin who had crashed his immediately landed his, and to my surprise, thought to use a water hose to lasso and rescue his older brother's chopper.

    When you're failing, it sucks, and your reactions are expected to be poor. Taking responsibility for your actions, and having the conviction and courage to do what needs doing will define you to yourself and everyone around you.

  • Success comes out of failure and not giving up. LOVE your article!

  • I would venture that if you haven't failed, you're not trying hard enough. Ultimately, the people who challenge themselves continually end up hitting that wall where their ambitions are unmatched with their ability. It is one's ability to learn from those failures and carry on that distinguishes successful people from the others.

    The interesting thing is also in the example you bring up. Like you, I failed (or "didn't succeed" which I consider a better point of view as it forces me to try again, using the learning from the previous failure to adapt my approach) during the dotcom crash. The interesting thing is, that crash actually prepared me much better for the current financial crisis. The sense of panic that existed during the last cycle as our whole industry was undergoing creative destruction seems gone nowadays, replaced by a more positive attitude that will result, hopefully, in a better riding of the current tumultuous waters we've encountered.

  • Currently I am feeling like you did in 2001. Business and financial lives are a disaster. I would have been a far greater success in life playing drums on Pearl St. for the past 3 years. But I did build a nice house and pull of a wonderful Bar Mitzvah for my son.

    I quoted Atlas Shrugged on your blog last week.

  • While each day is tough, it will get better.  Just keep reminding yourself of that.  Plus, it sounds like you have a kid you love which is a great accomplishment in and of itself.

  • Brad
    I agree. Basically you don't learn anything or build reslience unless you fail. I Wrote something of a similar vein for Inquisix on this: http://inquisix.com/blog/2008/11/12/do-the-hustle… Tenacity is a key component to both being a hustler and success, failure is inevitable, what you do after is what matters.

    Another note, bummed I will miss meeting you at SXSW, would have totally broke bread. Let me know if you find yourself skipping through Boston anytime soon…

    T: TheBetsy

  • Great article.

  • I’m in Boston a bunch over the next six months because of TechStars Boston, a few investments we have there, and MIT stuff I’m doing.  Look for my travel on twitter and ping me when you see me there.

  • David Leffler

    I know that studies have been done that demonstrate that the most important factor as to how well a person will do in life is not how talented they are, but how well they recover from failure. That pretty much tells you that almost everyone has to face failure sometime in their life, and the most important aspect of this is not the nature or extent of the failure but how well you recover from it.
    As for the current economic climate, my business law practice is very active right now, so much so that I feel like I am living in a parallel universe, and certainly I hope that it continues this way. What that says for others is that there is economic activity out there, notwithstanding what the stock market is doing, and you should get up each day with the purpose of creating something new and connecting up with that activity.
    After all, being an entrepreneur is about taking a stand on something which you have developed, and not being dissuaded by every contrary wind, whether it be people that say that it's never been done this way before or by the past six months of bad news that we've been reading in the paper.

  • You're on! Look forward to meeting you in person and hearing all about how The Brad Feld (iPhone) Experience is going and Tech Stars.

  • As a budding entrepreneur getting ready to graduate from b-school this post is inspirational. Good lesson for a lot of us who are scared of failure to wrap our heads around.

  • Eric Remer

    Love your blog and couldn't agree more. Incredibly refreshing and authentic. Another question would be: what is failure? Is it some set of expectations (whether yours or others) not met, or is it not living a particular part of your journey according to your true nature? I would argue that whether you perceive failure as good, bad or indifferent, true failure only occurs in the latter.

    We have never met, but a good friend of mine, Bill Flagg, always sings your praises. Love the Atlas Shrugged quote.


    • Eric – nice thoughts.  I agree with the deeper version of failure: “not living a particular part of your journey according to your true nature.”  It’s a powerful construct if one can get their mind around it.

  • I am having more and more discussions on this topic with my entrepreneur friends. We all know academically when failure is imminent but we lack the balls to admit the failure and walk away.

    I have two young children who have just finished celebrating the birthday of Dr Suess. This has allowed us to reread some of the great books he's written. Yesterday happened to be Oh, the places you'll go, in which we get the sage advice, "I'm sorry to say so but, sadly its true that bang ups and hang ups can happen to you." It goes on "You will come to a place where the streets are not marked. Some windows are lighted. But mostly they're darked. A place you could sprain both your elbow and chin! Do you dare to stay out? Do you dare to go in? How much can you lose? How much can you win?" (I could go on and on, the Dr. really nails it in this one)

    This is in a book aimed at graduates! How quickly we let that lesson get drowned out.

  • There is a great academic argument (that means there is no right answer) on this topic. The scenario is you have narrowed the pool down to two CEO candidates for a startup- both qualified and both with similar and acceptable experience. The key difference between them is one was successful with their startup (and sold it or something) and the other failed.

    The obvious answer is to select the one that was successful. However, there are so many situations where the other one may indeed be more qualified. Why did his/her startup fail? What did he/she learn from it? Why did the other one succeed? What did he/she learn from their success? The fact is many startups have to bet everything at least once or twice a year – sometimes you get it wrong.

    It is a great conversation and one similar to the one living in this thread. The point is experience is critical to success – sometimes that experience comes at a great cost. Sometimes that experience is wasted on fools. Generally speaking, the more experience the better the candidate – or he/she is fool and will kill your company. Can you tell the difference in a few hours of conversation?

  • My favorite CEOs (and entrepreneurs) are those that have both success and failure in their past and can talk eloquently and thoughtfully about both, especially the lessons that they learned.

  • Michael Gates

    Thanks Brad I needed that!

    I left a lucrative career in investment banking to pursue a life long dream of opening up a restaurant lounge in Manhattan. Suffice to say, the business eventually failed and it completely wiped me out personally – and I mean completely. Though my failure has been an extraordinarily painful and embarrassing process, I've learned a hell of a lot. I'm very thankful as it has made me a stronger, wiser, more humble person. Going forward, in my future business endeavors, I'd much rather go into business with a partner who has experienced their own failure at some point and learned from it, rather than team up with someone who is green on the failure front. You gotta have that notch on the belt.

    Thanks again!

  • Thanks brad. Just the other day, my buddy and I were talking about how everyone says its ok to failure, but they fail to mention that it continues to suck.

    Funny thing about black holes is that you are completely lost, without hope, all momentum turned inertia, no friction to get anywhere, flailing helplessly in oily, suffocating, darkness and then…


    the light switch flips and there you are you are standing in your room, unshaven, out of shape, but otherwise completely health and capable, just wondering why you are still in your PJs at 1130am. and then you get moving.

  • Failure is all about perception(so is the rest of your interpretive life). What you perceive as failure becomes failure. Your failure may be someone else's success and isn't success just another perception and fantasy of the mind. If you decide something is a failure, then you now get to define yourself as a failure and "enjoy" the indulgence of anger, sadness, and pity that the ego thrives upon.

    Ultimately though, how do you define the instant of failure? When was the exact moment that you failed? Was it layoff number 1, number 20, number 800? Was it when the stock price hit 20 cents or was it when it dropped to $30?

    In what moment were you a success? Where does success end and failure begin? When you created a brilliant piece of earth changing software were you a success? Did you become a failure after 6 months of miserable sales or were you a failure when you hired the wrong marketing guy?

    Ultimately you have decide whether it is you or your ego and perceptions that are in control of how you feel. I realize this sounds overly simplified, but if you really look at yourself and the chatter in your brain, it's the simplest truth you will ever know.

    You can never fail at this moment and it is the only moment you have.

  • This is one of my favorite posts of yours that I've read to date. It seems so obvious that experiencing and growing from failure is a integral part of success – yet its something that bears repeating.

    I've often found myself trying to rationalize the reasons for my failures instead of honestly acknowledging my ownership of them.

    I like what BradNickel said in the comments:
    "Ultimately you have decide whether it is you or your ego and perceptions that are in control of how you feel. I realize this sounds overly simplified, but if you really look at yourself and the chatter in your brain, it's the simplest truth you will ever know."

  • some tip about this issue are welcome and really sorry if my question is very simple. Thanks in advance

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