Just DON’T Do It: Five Reasons NOT to become an entrepreneur



The greatest part of my day job as a venture capitalist is the inspiration I draw from watching amazing Founders take a crazy concept, work tirelessly, and sacrifice a ton with the sole purpose of turning a dream into a reality.  I recognize how hard the entrepreneurial journey is – and I know full well of the ups and downs that the job brings.

I fully believe the world needs entrepreneurs more than ever and I try my best to encourage and support anyone who is just crazy enough to jump into the arena and give it a shot.  From my own experience, being an entrepreneur is the greatest job in the world.  Innovation is the key to global progress and entrepreneurs have the potential to change the world, improve communities, create new jobs and solve some of the greatest challenges the world faces.  What job even comes close?

Historically, if someone asked me if they should jump onto the entrepreneurial path I would reply enthusiastically HECK YES…or, I would borrow from the now ancient tagline from Nike –and quickly reply “ Just Do It!!”

But over the past few years I have watched what I would call the “Shark Tank” effect come and bite a lot of entrepreneurs in the proverbial backside.  To me, the Shark Tank effect (or the Buzzfeed click bait effect) means carelessly encouraging anyone to become an entrepreneur without warning them just what they are getting themselves into.  As if coming up with an idea and getting a thumbs up from some angel investors is all you need – the rest is easy.  Like there is a “hack” that will turn your idea into a billion-dollar outcome.

I am not here to discourage anyone from chasing their dreams and I remain a staunch supporter of the power on entrepreneurship.  Some days, watching all the craziness in the world, I am tempted to believe it is our only hope.  However, my current perspective is that any encouragement I can provide about entrepreneurship should come with a warning sign or waiver form before some dangerous adventure.   

 Like one of those signs that surround my favorite ski resort that simply say “Hey, have fun.  Skiing is awesome.  But it is also really dangerous and lots of people get injured and some die.  So, be careful, understand the risk and consider yourself warned”.  

Here are my five biggest “warning” signs as it relates to starting your entrepreneurial journey.  Said differently, here are five reasons to just DON’T do it:

  1. You are not in a good mental place.  Entrepreneurship is really, really hard and the ups and downs are almost impossible to quantify.  Most aspiring entrepreneurs underestimate just how mentally tasking the job will be and there is very little guidance on this aspect of the experience.  You can expect really long work weeks but have you also considered the mental toll?  Make sure you take a look at your current mental state and make an honest assessment.  Do you feel mentally prepared to take all of this on?  
  2. Your support structure isn’t that great.  Starting a business is the loneliest job you will ever have.  All of the responsibility will be on your shoulders.  It sounds fun to be the “boss,” but frankly it is highly overrated.  Take a look at what you have OUTSIDE of your business dream and make sure you have someone – anyone (or thing) – to help you deal with all of the stress that goes with entrepreneurship.  In my book, Mr. Monkey and Me, I devote an entire chapter to (H)elp – why it is important, the risk of overlooking this and specific tips to help entrepreneurs build out their support network.  
  3. Your experience isn’t tied to the business you want to start.  So you want to start a landscaping business but you don’t know a dandelion from a daffodil?  That might be a problem.  Perhaps there is a way to get relevant experience in your field of dreams (pun intended) BEFORE you start out on your own.  This is called “Founder / Market Fit” and it can be achieved by working in your area of interest BEFORE starting out on your own. It might mean delaying your dream for a few years but it may also be the critical knowledge that separates success and failure.
  4. The time just isn’t right for you right now.  Too much myth has been created about the 20-year-old college dropout who goes on to build a huge business.  The reason we all talk about Bill Gates and Mark Zuckerberg so much is because the outcome each achieved is incredibly rare. Forbes asks “Does Age Matter For Entrepreneurial Success?”  and the answer is no; there is no correlation between age and entrepreneurial success (or education, background. Or, well anything).  Make sure the time is really right for you before you take the plunge.  Experience, support, network and professional skills are developed over time – sometimes it makes sense to wait to make sure you can develop these before starting off on your own.
  5. You expect to have more free time and work less.  When I was staring out some of my peers would comment about how nice it must be for me to “be my own boss” or “not have anyone to tell me what to do.”  Yeah right!  I had more stress, less sleep and worked longer hours – and the job was on my mind seven days a week.  No boss?  I had investors, customers, employees and vendors that all demanded more from me than any boss ever could.  Just make sure you fully understand what entrepreneurship does – and does not – mean in terms of lifestyle before you commit to the journey. 

I am not trying to discourage aspiring entrepreneurs from raising their hands and getting into the arena.  Nothing inspires me more and goodness knows we need it more than ever.  However, I am exhausted with “hacks”, “four-hour work weeks” or other content that glorify entrepreneurship as fun and easy.  

Rewarding, potentially life changing and magical – yes, entrepreneurship has the potential for all of this and more.  But it is critical to understand the mental part of the game and take full consideration of the risk and challenges that lay ahead.  Not now doesn’t have to mean no forever.  

Like the warning sign above the black diamond ski run – make sure you fully understand what you are getting into – and If and when you are ready for it – jump in, give it your all and make it happen!

Curious if you have what it takes to make it happen? Take the Entrepreneur Survival Test to find out. 

Monkey Masters: Jason Dorsey

Monkey Masters: Jason Dorsey

For my third interview of Monkey Masters, I am thrilled to interview Jason Dorsey.  Jason is one of the most interesting entrepreneurs I have ever met and his insights, experience and background are truly exceptional.  The list of Jason’s accomplishments is too long...

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