Characteristics of an Entrepreneur Boss – Recognize Your Boss? (Friday Fun)

Characteristics and traits of an entrepreneur boss

Know 'em when you see 'em. Then run for cover. (Invasion of the Body Snatchers 1978)

Corporate America is filled with good bosses and bad bosses. Entrepreneurial startups are filled with quirky bosses. For a little Friday brain break, I give you this list of entrepreneur characteristics to watch out for.

If your boss fits any of the profiles, never fear. I know a place offering two for one straitjackets; one for your entrepreneur boss, and one for you.

OCD Entrepreneur Boss

(Example – Jeff Lewis of Bravo TV’s Flipping Out)
Also known as Overly Controlling Dude (or Diva). Not to belittle Mr. Lewis; I’m a he-ewge fan. I mean, who wouldn’t demand desire their coffee be exactly 140 degrees? Really. What’s the point of coffee if it’s only a tepid 137 degrees? Other examples: Howard Hughes

(Why the ad first? Me=goody two shoes. Afraid of Bravo video clip police.  It’s worth the 15 second wait!)

Your Lucky Day Entrepreneur Boss

(Example – Donald Trump)
You must have been born under a lucky star, tripped on a four leaf clover, or used one of your magic genie wishes to get to work for this Wonka. Regardless of what you may (or may never) get to do, it’s your good fortune simply to be around them. This entrepreneur has the largest ego in the land, which also means the most baggage for the villagers to carry.

Who’s Your Daddy Entrepreneur Boss

(Example: Kelly Cutrone of Bravo TV’s Kell on Earth)
Self-described “mama wolf” Cutrone adopts a parent like management style, getting disturbingly involved in her employee’s personal lives. In the process, she grays the line between boss and friend, making it confusing for her litter when she decides to feed on the weakest of the pack.

The Candy Man Entrepreneur Boss

(Example – Willy Wonka)
In Charlie and the Chocolate Factory, Wonka claims to have rescued the Oompa-Loompahs from the monstrous whangdoodles that inhabited Loompaland. “Come and live with me in peace and safety,” he told the Oompa-Loompas. In process, he created a labor force that worked day and night and was paid only in cocoa beans. A saved people, or indentured servants? The Candy Man entrepreneur creates an atmosphere that’s too good to leave, and often too good to be true. Other examples: Bill Gates

Can Always Make a Buck Entrepreneur Boss

(Example- Pope Sixtus IV)
Can’t imagine a priest as an entrepreneur? Hold on to your communion wafers. This fifteenth century business man-of-the-cloth weaved a heavenly deal for Catholics. For a small fee, parishioners could shorten the length of time their deceased loved ones spent in purgatory. A steal of a deal, no?

Bleepin’ Expletive Entrepreneur Boss

(Example – Gordon Ramsey)
“Fat Cow” may be a compliment in 4H, but it’s utterly (sorry) unacceptable anywhere else. These impetuous Wonkas can’t control what comes out of their mouths. Especially when it comes to insults. Tip: Try reciting “I’m rubber you’re glue” to yourself while squeezing a bit of the sticky stuff in his Chapstick tube. For a less legally ambiguous route, respond indignantly with “what the french, toast?” and share some Orbit dirty mouth gum. It works in the ad.

Working for Wonka? Know this: I have bad news for you. Not every enterprise is lead by a Captain Kirk. Then again, not every enterprise requires you to wear futuristics-but-still-looks-like-70’s, polyster jumpers. So there’s always a bright side.

Work for a quirky boss? Who would you compare your boss to? Michael Scott of The Office, Mr. Burns from the Simpson’s? Tell me!


  • Kevin

    Reply Reply July 22, 2011

    and then there’s the mpd entrepeneur – a bit of a combination of all…. good read!!! want more!!!

    • Kathy Ver Eecke

      Reply Reply July 22, 2011

      Memphis Police Department? Oh, Multiple Personality Disorder.

      Wow Kevin, you got it rough. We’ll call your entrepreneur Sybill Disorder Entrepreneur.

      Thanks for adding to the list!

  • Jason

    Reply Reply July 22, 2011

    Hmmm…I’ve got a bit of all the above, but mostly I just suck at managing people, cause no one can get it right. Maybe call me the “You’re Doin’ It Wrong” entrepreneur.

    • Kathy Ver Eecke

      Reply Reply July 22, 2011

      Just the fact that you are aware of any issues, probably means “Your’e Doin’ it All RIGHT.” Assuming you don’t require the polyster jumpsuits.

  • MikeC

    Reply Reply July 22, 2011

    You can learn a lot working for an entrepreneur. But if you find your boss’s behavior unacceptable, then you should definitely quit. Nothing ruins the morale of a workplace more than some loser who is always complaining about the boss. If you really think you can do a better job than your boss, don’t just sit around whining like a little bitch, open your own business

    • Kathy Ver Eecke

      Reply Reply July 22, 2011

      Mike C:
      Great perspective Mike, and I agree. One person’s bad attitude can kill morale. Although that does put into question the wise words of Mr. Jackson that “one bad apple DON’T spoil the whole bunch, girl.” (Now I have to wonder whether Billy Jean really was his lover.)
      Thanks *I think* for the comment.

  • Corinne Edwards

    Reply Reply July 24, 2011

    Dear MikeC and Kathy –

    I did quit.

    I had a boss who would fire me at least once a month on a Friday night.

    Once he even called the police when I told him I was too busy working on a deal to be fired that day. Then, as they arrived, he ducked out the back door.

    One Saturday, when he called to say “Get your little ass in here. You have clients.”

    I didn’t.

    By that time I had achieved my own brokers license. I opened my own real estate office.

    His parting words were “You’ll come crawling back.You know NOTHING!”

    Never did.

    I had picked his brains clean.

    • Kathy Ver Eecke

      Reply Reply July 24, 2011

      Corinne: You worked for a doozie. Yikes, sounds like a gem.

      I think we’ll call him The Apprentice Boss. He likes to fire people, but for some reason people keep coming back for more. Sounds like you had a planned escape! And that you made the most of it.


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