does breaking the rules make you a good entrepreneur?

ImagesFred wrote a post about the Womens Entrepreneur Festival posting his favorite panel which was the Makers panel.  I loved that panel too.  Five super bright women who have thriving businesses around products that they have created.  Each of them built companies around something they were passionate about which makes for a great entrepreneur.

The comments are worth reading starting with one that says women are not socialized to be mavericks but to follow the rules yet we are all in the system together.  I spoke about this at the kick-off speech that I gave at the Womens Entrepreneur Festival and mentioned it again at the White House panel to promote women led small businesses.  Women need to jump in the game and not spend so much time crossing their t's and dotting their i's until they get it right.  Businesses are never right.  They are always moving forward and sometimes backward.  They are always evolving and so what is right today might not be right tomorrow.  Sometimes you just have to take the plunge and for whatever reason that seems to be something men are more comfortable with.

So does breaking the rule make you a good entrepreneur?  We were all asked at the White House panel I was on by Arianna Huffington, when did you know that you were going to be an entrepreneur?  Truth is, I always broke the rules.  Even while I worked for a large company at the beginning of my career, I very much felt like a lone ranger.  I definitely was great at leading the pack but I wasn't so great at following the rules. 

I chaired a non–profit organization for a few years.  I remember we had a board meeting and were discussing how we were going to undertake a particular project.  One board member, who had been in the non-profit world for years said, "you can't do it that way because that is not how they do it in the non-profit world."   Needless to say, I replied that we were not going to do it the way you are supposed to do it but the way we think we should.  In the end, our way was hugely successful and that NY organization is now a global organization. Did we break the rules, yes.

I always broke the rules but rarely got caught.  Do those skills come inately or can they be taught?  How can we teach our daughters to be whatever they want to be and understand that rules are sometimes meant to be broken or at least be disrupted.

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Comments (Archived):

  1. Rohan

    By teaching them to ask 2 questions when they see a situation – – Why.. to understand why things are the way they are.- Why not.. to consider what the alternatives/possibilities could be. And we can only teach them as such if we do this ourselves, I guess.. consciously or unconsciously.

    1. Gotham Gal

      great questions to ask.

    2. Andy Ellis

      I break rules fairly often when it serves me but after the fact wonder at my motivation: Do I consider myself to be part of an intellectual elite for whom the rules don’t apply? Or am I okay with everyone skirting regulations when it suits them that may (taken to an extreme) lead to a culture of entitled anarchists?I don’t particularly like either option and I think that your (Rohan’s) two questions are the only way to properly frame rule-skirting behavior. The mentality that a certain situation should be exempt from a broad, cumbersome rule is likely a much healthier outlook than any one person taking the attitude that ‘the rules don’t apply to me.’I think the tone of a lot the reactions here are more geared toward stereotypes and societal expectations than rules within anything specific. I’m unreservedly okay with disregarding those traditional notions when common sense can prevail.

      1. Gotham Gal

        obnoxious self-serving pretentious people that think the rules don’t apply to them is wrong on so many levels.thinking about business or a recipe or a way to analyze data differently is how rules should be broken daily.

        1. Andy Ellis

          I totally agree and I am perpetually asking myself whether I’m doing unconventional things for the right reasons.For me, I worry about the potential for a slippery slope.

          1. Rohan

            I’ve done it so many times simply because I tend to be impatient. Eventually, 50% of them made sense and 50% of them didn’t and that resulted in a lot of time wasted. Learning to ask the ‘why’ question first these days!

          2. Emily Merkle

            With you. You say impatient – I am in spades. I have found that (very rarely mind you) if I understand the reason for the “rule” as is, I can typically come to the conclusion that it does apply to most foreseeable situations, and if I put on my thinking cap tight, I can come up with a way to reach my objective without breaking the law, breaking the law. When in doubt, literally ask why. 

          3. Rohan

            Exactly. It’s happening with age.. and some maturity.. haha

  2. William Mougayar

    Determination is what makes you do creative things. Rules can be (and should be) bent and adapted to fit your own agenda, and when an entrepreneur is laser-focused on their goals, nothing can stand in the way of reaching that agenda. It’s ok to break the rules, as long you don’t break the law. 

    1. Gotham Gal

      agreed. breaking rules is one thing, breaking the law is another

      1. William Mougayar

        I would add…If an entrepreneur is not breaking some rule, they aren’t trying hard enough. You have to break the mold to make a new kind of cake. Sorry if i keep coming up with these food analogies 🙂

        1. Gotham Gal

          its either sports or food. i like it.

      2. Guest

        I would add…If an entrepreneur is not breaking some rule, they aren’t trying hard enough. You have to break the mold to make a new kind of cake. Sorry if i keep coming up with these food analogies 🙂

    2. Guest

      Depends on the law William.  😉  I was taught by my mother to break rules quite early in my life.  She taught that lesson by example.  Unfortunately for her when I was growing up the rules I was breaking were hers. 

      1. Gotham Gal

        that’s good. my father used to say, “i don’t care what you do but just don’t get caught”. not exactly heartwarming words from my father but what he meant was break the rules, push the envelope and always been challenging the system.

        1. Emily Merkle

          I have been a law/rule breaker from the start. I find that it is simply another way of saying that you choose to explore the world by testing limits and feeling out boundaries. Question and be curious. 

    3. Emily Merkle

      i would add don’t break the code of human decency…and basic respect.

  3. andyswan

    OK I might get all kinds of ostracized for this….But there ARE differences between men and women (generally…exceptions all over, blah blah blah).Women are nurturers by biology.  Nurturers tend to perform much better WITHIN the rules.  Experimental and innovative mothering is pretty likely to result in bad things.Men, on the other hand, are innovators by biology.  They are more likely to hunt, to gamble, to risk failure for the prize…they were born to compete with one another to “bring home the bacon.”   Experimental and innovative rule-breaking in hunting and defending— that could pay off big.Note, I am NOT saying that women shouldn’t be entrepreneurs….In fact, I believe exactly the opposite.  My daughter and I set up “businesses” at every opportunity and I love that she is seeing the world through the prism of self-reliance and innovation.What I am saying is that when you’re looking at a broad swath of society, don’t be surprised that more men wind up as rule-breakers….whether that means successful entrepreneur, binge-drinking homeless gambling addict, or prisoner.It’s up to us as parents (and yes, members of society) to “break” the biological rules (in a safe way) that might hold our kids back…and I applaud your efforts in this arena, both personal and professional.

    1. Gotham Gal

      Andy…I agree with you. There is something to say about nature vs nurture. As parents of daughters, we need to focus on our nurture role to get them to push themselves to get out of the box of nurturing and doing more risk taking.

      1. andyswan

        Yes!My wife is a little more concerned with reigning our son in at the moment LOL

        1. Gotham Gal

          i got a good chuckle out of that.

        2. Lisa Mogull

          In my observation boys tend to take testosterone-fueled risks while girls tend to take more calculated risks and are more aware of the cost of failure.  Thus they are more likely to assess the risks before they break a rule.This seems to be true with young entrepreneurs.  The young men I’ve met are more likely to bet it all while the young women are more likely to have a plan B even though they don’t differ in their level of commitment or vision.I once got chewed out by my male boss for breaking a rule (I had good reason).  When he complained to the female higher up she said “she did the right thing and that’s why we hired her.”  She nurtured the right ethic. He didn’t. I respect her authority and not his.Gotham Gal I agree with you but think the key is to convince/show our daughters that nurturing and calculated risk-taking go well together and the combo is unbeatable.  It’s much harder for a woman to make it to the the top but the ones who do and who are nurturers create more loyalty.  That’s one of the many reasons women make great leaders. 

          1. Gotham Gal

            women that are nurturers and break rules just rule.

          2. Emily Merkle

            I admire women and men who nurture by mentoring – but more so, by walking the walk. Against the light.

    2. William Mougayar

      I think (most) women might be more calculating and cautious when breaking the rules. 

      1. Emily Merkle

        depending on how impactful breaking the rule is, a little caution is advised at times.

    3. Rohan

      Agree.There’s also something about the ugly half being naturally responsible to ‘bring home the bacon.’If we look at animals and birds.. the males are generally ‘better looking’ i..e the ones with beautiful manes etc etc – peacocks, lions and the like.  And humans are the among only organisms where the males are uglier. (Okay.. George Clooney may differ but really, it’s a no contest)

      1. Emily Merkle

        I like brains. Brains are pretty.

  4. PMarchetti

    You can learn to break the rules.  I was a rule follower growing up, but became a rule breaker after I started working in corporate America.   That trait led me to becoming an entrepreneur.  Interestingly though, I don’t think this trait serves me well in fundraising for my venture because the VC world likes innovative ideas, but likes people to follow specific rules on how to be introduced, pitched, etc. 

    1. Gotham Gal

      maybe you are talking to the wrong VC’s?

      1. PMarchetti

        I’m finding that personal introductions from another investor, VC, or organization are the best way to get the meeting or pitch…. which is fascinating in a digital world.  Meeting those connectors offline is key. I’ve heard numerous VCs say that although they accept pitches online, it’s almost never who they choose to fund.   Breaking the rules and approaching investors directly seems like a breach of etiquette and doesn’t work for many of them.   I do like Twitter for following folks so I can better learn what interests them, but proper intros seems to be the key for me. 

        1. Gotham Gal

          interesting.

        2. Emily Merkle

          I think etiquette takes a backseat if you have done your due diligence to interface and engage individuals that may be of strategic help to you, you to them, or both. I think, for me, I am most comfortable being referred to a VC or really any potential partner by someone who knows my work, knows me, and feels 100% comfortable introducing me. It can take years to build that rapport and rep. with someone(s). I have no qualms contacting someone I think I can bring value of some sort to. Yes, you seek funding, but without the Venture there is no V in VC. Yes there are many VCs who are fonts of experience and wisdom whose blogs I love to drink at and whose portfolios I stalk … but I do not think any businessperson who is ultimately worth working with would decline a promising opportunity because the entrepreneur had the gall (!) to contact them directly. Etiquette be damned. 

          1. Gotham Gal

            i’m with you emily. i get blind emails all the time and i truly try and answer each one ( and meet with many of them )

          2. PMarchetti

            I appreciate the advice.   I’m working to make the connections and researching the VCs that I think would be the best match.   I also imagine that if I do my due diligence and approach the right VCs directly… they’ll see a strong reason to meet.  

          3. Gotham Gal

            agreed

  5. rebeccastees

    An older wiser business woman taught me”Better to ask forgiveness than permission”The trick seems to be building relationships that can tolerate and support rule change. Sometimes breaking a rule means that you’ve outgrown your status.My Dad told me that as an artist I was a social outcast. I think women suffer worse consequences for breaking rules.I’m thinking of a the five letter B word and the for letter S word.Joanne, can you make a list of rules you’ve broken?  I’d like to read it!

    1. Gotham Gal

      Better to ask forgiveness later. Agree.My list would take years to compile

    2. Emily Merkle

      i think you just need respect and communication. sounds simple – not so though…

  6. andyidsinga

    ive occasionally observed my daughter breaking the rules ive set out for her ..but couldnt bring myself to bust her after realizing how lame they were 🙂

    1. Emily Merkle

      yay!

  7. Emily Merkle

    I think that the question “can you teach people to break rules” is better understood as, can you teach people how to objectively and holistically evaluate the cost-benefit of choosing to break a rule rather than follow it. The answer is yes, it can be taught, though not in a vacuum. Avoiding “getting caught” should be taught in the sense of – if you choose to break a rule and your choice to do so results in a negative outcome that is directly tied to violating the rule, make sure you have done and can ably demonstrate the due diligence process you went through to arrive at the decision to buck policy. I do not encourage sneaking around by any means. In fact, it sometimes helps to make a point – with some degree of visibility – and a case for needed policy change by demonstrating that breaking the rule at hand led to and can reliably lead to positive outcomes. Remember that it is not a “crime” if you don’t get caught…spoken by a born rebel.

  8. awaldstein

    I never think about breaking the rules or not. I think ‘just doing it’ regardless of whether logic supports you drives this harder.Is it logical to think you can disintermediate a traditional biz by reducing the cost of a service by 10x and still making money? Nope but it happens.RIght now, with a food startup I’m involved with the margins just don’t make any sense. The idea does and my gut says go. Breaking rules or just doing it. Maybe the same thing.

    1. Emily Merkle

      If it makes sense and your gut is screaming go – absolutely. I am a big believer in gut. But some people are not. Just doing it may work for us but does not make sense to / convince / land everyone. I have learned the hard way that, as a chronic maverick, I often take an unorthodox route. If I spend some time charting my decision process and document the indicators that made sense to me and led to my deviating from “plan”. I was thinking more about staring down traditional VCs, bending age and gender and all stereotypes in the space, and being prepared for blowback 🙂 it has happened. I try to be ready.

      1. awaldstein

        Thanks for this Emily…I’m a huge believer personally for my own projects and in my advisory business in proving the behavior and then making the leap of faith to a model.It’s really hard, no impossible to prove that something will become large, like the expected scale of a marketplace. It is possible though to figure out if you’ve captured a behavior that works. Early communities even built around prototypes can give glimpses of this.If I can see that, then I can or sometimes convince others to take the leap with me.

        1. Emily Merkle

          I love leaping. 

          1. Gotham Gal

            Me too

        2. Emily Merkle

          I have worked on many things that are not “large” but are meaningful to me from a philosophical standpoint – I have to feel it and be honest and ethical to do the best I can by my partners and all involved. Meaningful and lucrative. It happens every day. You are right – key to be a student of human nature and enhance the experience.

  9. pixiedust8

    I sort of struggled with the definition of “rule breaker,” perhaps because I’ve worked in many corporations where there wasn’t a way to break rules without being actually fired. I’ve protested the rules many a time, but because of the very structured process, there wasn’t a way to go around it with serious repercussions. I have designed new processes. Not sure that just means I’m not a “rule breaker” or I have just worked in industries where that is strictly discouraged. In any event, my frustration with all the bureaucracy is why I’m rethinking what I do for a living. 

    1. Gotham Gal

      follow your heart

    2. Emily Merkle

      Christ. I am not bureaucracy material AT ALL. Feral and I do not play we’ll with others. Hard to find people who get that value and intel and the ability to rock are not diminished by a visceral life-threatening reaction to trying play politics and power struggles eesh.

      1. Emily Merkle

        People think you don’t exist If your company or very niche but awesome underground market is not featured in Mediapost.Some crazy fun money making big ball playing goes on with zero fanfare. Even the biggest dogs play – but you’ll never hear it from them. Or me 😉