THE GOOD, THE BAD, and THE UGLY of working at a small business

Over six and half years ago, I left corporate America to start my own business.  I now own five different businesses and consider myself to be unemployable.   I worked for a Fortune 100 company with more than 50,000 employees worldwide and now handle building and executing visionary plans for the future of my industry.   If you are at the crossroads of still working for a large company or potentially making the move to work for a small business in your neck of the woods, here are some the of the good, the bad, and the ugly that may influence your future decision.


  • You Can See A Direct Immediate Impact From Your Work– You can usually come up with a new idea, an implementation plan, and begin to see immediate results on customers and the organization from your hard work.  In larger organization, it can take a year (or more) just to get an idea through the red tape.
  • You Can Learn Many Different Skill Sets– Since the company won’t have 27 different departments, the opportunity to cross train between different types of work can be invigorating.  You may learn operations, sales, marketing, and more because of the limits of human capital in the company.
  • You May Get A Chance To Cash Out Big– I don’t care what people say, getting some stock options isn’t ‘equity’ in a company.  If you truly add to the bottom line or get on the ground floor from day one, you can have the opportunity to earn or buy into stock in the company for a potential exit down the road.


  • You May Have Limited Upside Opportunity– If the small business you work for doesn’t grow fast or the owner gets complacent, the “director of …….” may be as far as you go with your career.  Small businesses have very thin infrastructure, so you’ll have to help grow top line revenue to create more layers of management.
  • You Will Have A Lack Of Resources– Unless the small business is venture capital or private equity backed, your resources will be limited to your owner’s cash, line of credit, or their (ummm how shall i say) kahunas.   You want a bang up holiday party?  It might end up being sliders and keg.   You want to run a huge marketing campaign.  It might be you and a sandwich board.  You need to be prepared that resources are finite and most owners are concerned some months about making payroll.
  • You Probably Won’t Get Much Training– Training? LOL.  If you are lucky enough to catch the owner between making sales calls to generate revenue, a half hour pow-wow once a week may be all the training you get.  If you aren’t somewhat independent, working for a small business can be a very lonely, lonely world.


  • There is a 100% Chance Of Rain–  Small business owners must weather storms that larger companies worry about less.   Any fire (small or large) can quickly become a company fire.  If the owner is moody at all, you better be able to predict the weather because some days can go from euphoria to sadness in a heartbeat.
  • Job Security: Tied To Profits Or Personality?– The only ugly truth about small businesses is that they are small- it’s just that simple.  Your owner will generally make decisions (barring that there aren’t family members galore in the business) based upon the mood of personality or profits.  If they don’t like you, there is nowhere to run and nowhere to hide.  In larger organizations, you can turn to HR or try a different division, but that is a much harder path to go in a small company.   Your job security will be tied to whether your boss likes you or whether or not you really move the needle for the bottom line of the business.

Loyalty is an interesting word.   Some people suggest large corporations have no loyalty anymore to their employees which is one reason I believe that many executives are flocking to own their own business or go to work for a smaller business owner.   In my experience, many hard working small business owners will be loyal to those that get in the trenches and help them fight the battle to the line of success.   Either way, strap in for a thrill ride.   What are your good, bad, and ugly for working at a small business?

Written by: Ted Jenkin
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About the author  ⁄ Ted Jenkin @ Your Smart Money Moves

Ted Jenkin @ Your Smart Money Moves


My friends and family all think I’m a workaholic, but I say I’m just a guy that loves to help people do better in life.

My mother is still the only one that calls me by my real name Theodore Michael, my wife calls me Teddy, but for the rest of you it is just plain old Ted.

Ever since I was a little kid, I always loved money and being an entrepreneur. In fact, I still have cassette tapes of me talking to my grandmother at the age of five and my mother tells me all the time how much I played with money as a kid...

Read More About Ted Here

Ted Jenkin is a frequent guest columnist for the Wall Street Journal and Headline News Weekend Express. He is the co-CEO of oXYGen Financial. You can follow him on LinkedIn @ www.linkedin.com/in/theceoadvisor or on Twitter @tedjenkin.

Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. oXYGen Financial is not affiliated with Kestra IS or Kestra AS. Kestra IS and Kestra AS do not provide tax or legal advice.

The opinions expressed in this commentary are those of the author and may not necessarily reflect those held by Kestra Investment Services, LLC or Kestra Advisory Services, LLC. This is for general information only and is not intended to provide specific investment advice or recommendations for any individual. It is suggested that you consult your financial professional, attorney, or tax advisor regarding your individual situation. 

Background and qualification information is available at FINRA's BrokerCheck website.

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