Four Reasons Every Entrepreneur Needs a Mastermind

It was while interviewing Dale Carnegie for a small newspaper that Napoleon Hill landed a writing gig in 1908 that changed not only his own future but created the concept of the mastermind which became a tool for success for generations to come. The reporter was asked by Carnegie to survey over 500 men – and a few women – many of whom were millionaires and were considered among the most successful individuals in the world. The task took Hill twenty years and culminated in a report that filled several volumes of work and outlined the commonalities of experience and process among those he’d surveyed in hopes of creating a path of success for future entrepreneurs to follow.

While Hill is credited with penning the first published concept of the mastermind, the practice of engaging with a tight circle of trusted advisors dates far before his definition to as early as the legendary Knights of the Round Table who advised King Arthur. And, in fact, many of the innovative ideas put into practice as part of the New Deal which many historians believe were responsible for stopping the downward spiral of the U.S. economy in the 1930’s were the result of the mastermind group which advised then-president Franklin D. Roosevelt.

123Over a century has passed since Hill described the role and value of the mastermind, and still today it is a very powerful tool for entrepreneurs. As part of our goal to empower women entrepreneurs and inspire them to think bigger, bolder and better, my cofounder of Hautepreneurs, Jessica Eaves Mathews and I established a mastermind for our group. We meet with a small number of fellow women entrepreneurs once a month, and I have learned first-hand the value of accessing trusted collective knowledge, experience and creative thinking.

Here is why every entrepreneur needs to be a part of a mastermind:

No Complacency Allowed

As the founder of a company, every day is filled with demands and needs coming fast and furious from a multitude of directions, including customers, employees, vendors, investors and beyond. It is easy to allow your time to be consumed with addressing issues as they arise and to not to push ourselves into new areas of growth – the very thing that must happen if we are to stay relevant and capture more of the market. Meeting with a group of peers who all live with the same level of demands means that you will likely get very little pity or license to go easy on yourself. Whether you are afraid to embrace the risk of growth, face the upheaval of firing an entrenched problem employee, or of forcing yourself to slow down to gain proper perspective, a mastermind group will push you beyond complacency and auto-pilot, challenging you to address problems, step up your game and lead with more authority and courage.

Safe to be Vulnerable

There is this scene in the movie You’ve Got Mail where a famous author comes rushing into the book store worried about the possible loss in business due to a new big-box book seller opening nearby that could mean the little store might be closed before her upcoming book signing. The accountant puts on a brave face and declares, “No difference!” despite it being patently untrue. As an entrepreneur, we quickly learn that it is imperative to put on a brave face, wear our courage with a smile, and push forward into the future with all confidence despite living dangerously close to the edge of failure. We often feel isolated and alone, because we can’t let our guard down and talk about the moments when we are terrified that perhaps all we’ve done is build an intricate house of cards that will come tumbling down at any moment. These are the moments of fear and self-doubt that only another entrepreneur can understand. When members of a mastermind are bound by a legal NDA (non-disclosure agreement), there is an incredible freedom that comes with that level of trust. We can talk about the fear, about how close we’re pushing to the edge, about the level of risk we’re living with. And what we discover is that we are far from alone – that every entrepreneur out there is living with more risk, more fear, more worry and less runway than anyone else might be willing for. And sometimes, in the shared experience of learning we are not alone in our fears or in our willingness to take calculated risks, we can begin to accept that our reality and our choices are not so crazy or stupid as they sometimes seem at three in the morning when we haven’t yet figured out how we’re going to meet the lofty goals we’ve set for ourselves and our company.

Access to Variety of Expertise

The best masterminds are organized with a similar level of success and drive but from varied backgrounds and industries. When you seek the advice of others within your industry, you can begin with a higher level shared knowledge that makes it easier for your peers to understand the nuances of your current challenge, but what it won’t get you is the fresh perspective that comes with entrepreneurs who work within a very different industry and approach your challenge from a unique history and experience. When you can tap into the varied experiences, expertise and talents of successful entrepreneurs in different industries, you’d be surprised at the creative approaches that are suggested that often solve your problem in a way you would have never thought of on your own.

Steel Sharpens Steel

For a mastermind group to deliver the most value for all of the members, it is vital that the group be of similar levels of success with similar goals for growth. If the group includes a mix of powerhouse, highly driven leaders and more casual business owners, the friction of values will eventually lead to all of the members feeling that the group is not delivering enough value for the time expended. The leaders will feel frustrated and those who are happy with less pressure will feel disrespected. When the group is created with careful consideration of pairing the level of goals and intensity of drive among the individuals within the group, and when it is kept small enough for each in attendance to have enough time to feel heard and supported, the members will leave with a clarity of focus that only comes from steel sharpening steel.

Being a part of a mastermind where I can bring the unique challenges I have encountered as our team grows APPCityLife into a global platform – and where I can draw from my own experience to shed new light on the challenges of my fellow members are facing – it has helped me understand the real value of making ourselves accountable, vulnerable and available to our peers. With the right kind of mastermind, entrepreneurs gain a level of support and safety that is rare within the startup world.

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