“It’s more fun to be a pirate than it is to join the Navy”

….. Steve Jobs quote from Sept 1982. Today’s Millennials are the pirates and the forces that are established to defeat can be navigated. The following are six tips on how millennials successfully work the Gen X and Boomer networks that control the resources they need ……

Today’s Entrepreneur…Millennials in the Basement

It’s lonely. The forces around you are telling you to conform, find a job, how long are you going to live in your parent’s basement? You have a dream, a vision, that dream becomes a demon. You can’t shake it. You can’t sleep. Everyone tells you “that’s a great idea” but in the end, no one is willing to get all in with you. At some unspoken level, you get cast out. There is societal pressure to go to school, become an engineer, a businesswoman, a nurse, a dentist or worse than that….get a J.O.B.

My perspective on the challenges of the millennial entrepreneur and the pressures to conform have come from some very rich experiences. In some cases, standing shoulder to shoulder to tackle obstacles and overcome the conforming forces around them. The past couple years I’ve been very privileged to spend hours listening, coaching, and advising talented millennial entrepreneurs that invited me into their aspirations and dreams to build new multi-channel media businesses. What I have learned has helped me garner insights into the differences between gaining traction and total frustration.

The most successful are those that have adapted and adopted. These have become the translators, literally translating generational preference and lifestyle to a Boomer generation sitting on ginormous amounts of cash and resource. Millennial 2.0 applies to this wily group of agile entrepreneurs that have learned that it takes more than a great idea to get funded and sponsorship. My efforts and conversations largely focus on six traits that I believe to be key and characteristic of the success millennial entrepreneur as they tackle that translation …..

1. Clear Vision:

  • They are the Producer, Director, and Main Character in a movie that they can see with amazing clarity. They know the vision output, the ‘end game’, the movie from start to finish. They do not get distracted. They resist the temptation to conform, to move to the comfortable.

2. Bias Toward Action;

  • Speed is Life. A successful entrepreneur once told me “the tooth fairy only comes once and I’m going to recognize it!”. They aren’t sitting around just dreaming. They are doing it. They are continuing to move their dream and vision forward. The successful ones never lose sight of the dependencies and therefore rarely become paralyzed with what is next. Those that struggle don’t understand their own road map and the dependencies and because of their bias toward action, they focus on the noise and not what matters.

3. Outstanding Communication Skills and Charismatic:

  • They can articulate their movie in 5 minutes that gets stakeholders not only interested but already leaning towards motivation and action.
  • They engage stakeholders at all levels with their dogged focus on the goal and ability to ladder conversation up and down – from partners, to programmers, to principles.

4. Ability to See Value and Monetize It:

  • They understand when its time to partner or lead, depending on the value they can bring in sophisticated value chains. They all start their journey taking total control but quickly learn that to be successful, they must fill their skill gaps. The successful ones are constantly exploring the best way to enable and accelerate their plans.
  • They understand the value of scale which comes only with simple value propositions that can be delivered effortlessly and easily executed with a high degree quality, over, and over, and over, again.

So, before moving on, I’d be remiss if I didn’t say that these next two characteristics are where I see the most vulnerability and frequent breakdowns…. 

5. Adopt an Agile Methodology and Lifestyle:

  • These entrepreneurs are working half days. Cool thing is they can pick which 12+ hours that is. Their efforts are not driven by a clock but by fuel in the belly. They don’t see time the same way we do. They have grit and perseverance. They are inspired by the “No’s” they hear along the way. They apply a high level of rigger to their work and have discipline in their schedule but sometimes they get caught up in their own dream and expectations. They demand perfection at the cost of forward movement and scale.
  • Only do the successful ones understand that the methodology used to go to market is a process that requires continuous improvement, not perfection. It applied to their lifestyle as well. They continue to tweak the elements around them and understand what fuels high performance – diet, exercise, sleep.

6. Humility:

  • They course correct quickly because they are open and approachable. They can engage at three levels – subordinate, peer, superior with amazing ease.
  • They understand the world does not revolve around them. They adjust because they know in the tiniest of course correct, personal or professional, comes the nugget that might make the difference. I’ve seen terrific ideas completely blow up because the millennial entrepreneur believes that everyone around them is privileged to be associated with their idea or worse, with them personally.
  • Finally, they hold themselves accountable, understand they aren’t perfect and embrace it. They don’t look to deflect blame or accountability.


In the end, greatest challenge isn’t the lack of talent or drive, it’s time. They are fighting battles on every front, many times alone. They spend a lot of dark cold mornings and late nights writing business plans, scripts, code, and elevator pitches completely driven by vision and dreams. The successful millennial entrepreneur engages and inspires others to fill skill gaps and time. I’ll spend a Saturday morning or a Sunday afternoon coaching and filling skill gaps anytime these ambitious, talented and inspirational leaders are gracious enough to share their dreams and they show up. Always.

So look, if you are a start-up millennial entrepreneur reading this, I’m not going to sugar coat it. Nine out of ten of you aren’t going to get out of their parent’s basement with your current project. If you are out drinking until 6am and sleep through a 2pm call with your mentor, that’s not the kind of discipline investors are looking for in a future CEO or President (or even a housekeeping position). BUT you can improve your odds to be that one successful entrepreneur by adopting and embodying the characteristics above and recognize some key critical points. These critical steps include:

  • The right vision and corresponding value propositions
  • Build a solid and realistic road map
  • Have realistic expectations around adoption and financial returns
  • Build a solid Board and Advisers
  • Find a mentor with solid chemistry so that when you get into battle, you’ll be able to work out of those valley of Hell moments.

In summary, if you have the bandwidth to sustain a protracted effort to launch and the grit to withstand an barrage of forces against you, don’t ever worry about being cast out. After all, today it is the geeks that are inheriting the earth.

About Mike McNamara:

Mike has held C-Suite, Executive and Senior Sales, Marketing, Business Development, and General Management roles with Equifax, Cox Enterprises, WW Grainger, and Federal-Mogul Corporation. Mike has led sales, service and operations organizations of over 1,500 associates and accountable for P&L responsibility in excess of $250M.

Dedicated to giving back, Mike formed The MBAR Group in 2009 with the sole intent of providing pro bono career and business consulting services. Today he coaches a number of high profile media personalities as well as holding advisory board positions guiding a number of multimedia and small business startups.

Mike earned his MBA from Kellogg School of Management, Northwestern University and holds a Bachelor of Science degree from Michigan State University. He is a past chapter President of the American Marketing Association. Mike and family split time between their adopted state of Missouri and family home in NW Michigan where their philanthropic causes include The Kingdom House – St Louis, BACN in Benzonia, MI., and Samaritan’s Purse, Boone NC.

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