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The Difference Between Winners and Losers

John Doherty —  March 27, 2012
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Do you cringe when someone says “I could have done that”? Whether it is a blog post, a new startup, or a piece of modern art, people say it all the time.

I have come to realize that there are two kinds of people – those who do and those who say they could. Those who win are the doers and those who don’t never move into the realm of the unknown and thus keep saying “I could have done that.”

The point is, you didn’t.

What separates the doers from the could-have-dones? There are a few key characteristics, which funny enough are the same characteristics that I often see being written about as characterisitcs of entrepreneurs.

Willingness to fail through taking risks

Failure is not seen by a doer as a negative thing, but rather as an opportunity to learn and do better next time. You don’t fail, except ultimately, if you do not try. Max Levchin of Paypal, for instance, had four companies before he hit a home run with Paypal (which was valued at $12bn in 2010).

Even VCs are willing to take risks. On average, it seems that 30% of investments exit well, and 40% break even. Flip that around, and 60% are losses. Yet why would a VC keep investing if they never made money? The risk is worth it.

Here are the investments made over the past 5 years by VCs:

And here are the numbers that have exited:

And many of you have seen this graph of SEOmoz’s financials:

And now we see this:

Eagerness to learn

Doers tend to have an uncanny knack for picking up new skills easily (as cited in this article with Richard Branson last week), which is probably why they are willing to take on new tasks and opportunities.

This quote describes the mentality well:

I’m a geek and being in control of everything (to the finest detail) defines me. Not only that, but since I can pick up skills quickly, I think that I can learn pretty much anything. And that’s where we, as geeks, fail.

Part of this mentality as well, I think, is that doers tend to get bored when they do the same tasks again and again. We end up looking for new opportunities that will challenge us. This may appear as being unloyal to some. I see it as an opportunity to enrich your life with new experiences.

Doers are stubborn

We know what we want to do, or at least that we want to work for ourselves or be successful, but we often make challenging followers. We think we are right, and that unrelenting commitment to perfection has led to many successful entrepreneurs. I would also say, though, that the most successful overall are those that do learn to listen to mentors and are open to feedback in their life, which takes humility. Humility is not weakness, but rather an attitude to learn (see point 2).

There have been a few, yes, that have succeeded in ways without humility. Steve Jobs is one, yet even he had regrets about being so stubborn. And many that are humble yet stubborn fail too.

Yet, it’s the stubbornness that makes us get up again. Just recently I read this post about two men that didn’t find the right idea until they had two months of runway left. OMGPOP slaved away for 6 years before their product took off.

Stubbornness wins. Remember:


Does this post resonate with you? I failed in my first startup. I’ll admit it. I’ll write about it sometime. Yet I plan to do it again someday. We can be afraid of failure, yet still do great work. You fail when you try to do great work, but sometimes you hit a home run.

Be a doer.

John Doherty

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I'm the new (as of October 2013) Online Marketing Manager of Hotpads.com, soon to be based in San Francisco. Previous to Hotpads I worked at Distilled for 2 years as an online marketing consultant. In my spare time I shoot lifestyle photography, explore new and interesting food in New York, ski, rock climb, and update my Twitter and Google+ accounts.

11 responses to The Difference Between Winners and Losers

  1. Thanks, John. Reading your post triggered a reminder that all of things I would consider to be the greatest successes, on a professional level, were done with the help of other people. And everything I’ve tried to do by myself has failed miserably.

    My belief is that one of the best ways to mitigate failure is to surround yourself with people who have skill sets and competencies you do not, and create an opportunity for them to buy-in on your vision. It’s a formula that seems to work well.

    • Anthony Pensabene March 27, 2012 at 10:54 am

      Great real-to-life post, John, and sound comments by David above. In marketing, there is so much focus on ‘perception.’ I get it; but, I’m also a real person, savvy about people and reality. It’s not an idle road; professionals get stronger from the help of other professionals and experiences.

      I have some jiu jitsu experience. At the beginning of each class, students line up (most experienced to least experienced), then fold in (the most experienced pairs with the least experienced). It makes for an enriching experience and community for all.

      Failure is the father of success…

      • Cheers Anthony, really appreciate it! Build value and not just perception; that’s my take on it. It’s much easier to market something real than trying to spin a story.

    • Thanks David. Great words here. You must have a team that is behind you. That is how you win!

  2. Great post, and very motivation! I’m curious to know what that annotation says right before the massive traffic spike on the last graph.

  3. John – I love this post. Plain and simple. Your opening captures so much of how I feel and what I want to say to people when they explain to me how they ‘could’ have done things.

    Furthermore this is a prime example of the importance of Alex Hillman’s personal life slogan JFDI and how it takes guts, perseverance, and some serious effort to make things happen.

    I also like the way you cite failure, the way sit should be cited; as an opportunity to learn. This is the probably the single most important question I ask potential hires and immediately separates the talkers from the doers. Doers are not only proud of their failures, they are proud to talk about them, what went wrong, and how they did or will do better next time. Doers do not discouraged, at least not easily.

    Thanks again man, really enjoyed this.

  4. Love this post and topic, John.

    Doggedness goes a long way, but it’s hard to quantify exactly what it is, outside of the outcome, that separates positive stubbornness with foolishly expecting things to somehow go your way when the basics aren’t making sense.

    Intriguing stuff.

    I was personally amazed to see the debt that Rand & Gillian of SEOmoz got into – not that it was some foolishness on their part, but that I was around that community non-stop starting in 2004 and never caught wind of it – Rand believed in what he was doing, that much was obvious, even in the face of that mountain of debt.

    Somewhat of an aside: this definition of entrepreneurship I came across in Inc recently really gets at the root of it: “Entrepreneurship is the pursuit of opportunity without regard to resources currently controlled.” (source)

    Good stuff, man.

  5. Darren Moloney March 28, 2012 at 4:56 am

    Great post, really informative and I rarely go around blog commenting like this but genuinely thank you, it is something I intend to share with our clients.

    PS I also intend to show my wife your headline “Doers are stubborn” – this trait of mine sometimes drives her crazy… maybe now she’ll understand :) )

  6. Very inspirational, and great use of visuals to promote a point. I personally have always been one scared to take risks as I see the mass potential for harm in the world, yet I have been coming more and more out of my shell by looking at all of the entrepreneurs I hold in high regard. No entrepreneur goes out looking for the negatives to find the correct market to start something of his own in, instead they go out looking for the most intriguing thing to them, what they want the most, and think positively in pursuing their goals. Foolhardy some may be in their efforts, yet some are genius in their efforts (ie Steve Jobs) great post man.

  7. Nice post John,
    but let me do a defense of the “oh, I would have done” party, as it is something I like to do for one reason: I am really self critical to what I do, as if I was aiming to perfection.
    But the real reason I consider that from time to time it is a great thing to say “Oh, what if I’ve done that” is a great exercise in order to clear up your mind about what you are now, hence it can help you taking the final decision about what to do now, deciding to change you route and – eventually – break with a carcinogenic way of living.
    Obviously, if then you just spend your time living in a sort of parallel universe of what if, well, then you’re right.