entrepreneur boss I’m talking about isn’t someone who
takes over a family business, or works as a one-man shop and hires
consultants. In fact, most entrepreneurs would not consider either
of those two business examples to be “true” entrepreneurs.
Entrepreneurs wear their title like a badge of honour, and to earn
the title of Entrepreneur, you have to have started a business.
You have to have sweated making payroll, or been terrified in a
meeting with a buyer or investor because their decision could mean
the difference in you making a mortgage payment. You have to understand
the nuances, the overwhelming amounts of stress and the crushing
workload that comes with starting a business to be called an entrepreneur.
firemen who run into burning buildings while the rest of us
retreat, a true entrepreneur runs toward these challenges,
excited at the prospect.
Like firemen who run into burning buildings while the rest of us
retreat, a true entrepreneur runs toward these challenges, excited
at the prospect. So yes, true entrepreneur bosses are found in a
start-up environment, or in a few cases, at the helm of a grown-up
stuff of legends
Working for entrepreneur bosses isn’t always pleasant. There
are many reasons people choose to work for entrepreneurs. Some employees
at the executive level are lured in by the prospect of riches. Not
in the form of salary; typically you’ll make far more in the
way of salary and perks in the corporate world. These people are
drawn in by the offer of company equity and the hopes of a quick
The stories of the money made when companies were sold is legendary.
(In some cases, it is only legend). You see it a lot in the beverage
business where companies like VitaminWater and Snapple sold for
billions of dollars. Early employees with equity stakes made millions.
People hold on to these stories like lottery tickets and think that
if they can just get in the right start-up they’ll be set
for life. I’ll admit that I’ve done it. I’ve joined
several companies that had plans to grow and sell quick, hoping
to get my golden payday. Sometimes it worked, more often it did
More junior hires usually join start-up environments because of
the atmosphere. They think a less structured office will be more
fun. And it probably will be. The environment is also appealing
to them because in a start-up it’s all hands on deck, every
day. Most junior employees will get to work way above their skill
level, and pay grade. If they succeed, their resume will look fabulous.
The only caveat is that as a first job, it’s easy to learn
bad habits that won’t translate well if the employee ever
decides to make the switch to corporate America.
On the positive side
There are lots of positives to working for an entrepreneur
boss. I think the biggest plus is the ability to get involved in
the business outside of your area of expertise. As I mentioned,
most start-ups work on a shoestring budget, so employees have to
work in many areas. You may be a product development person when
you start with the company, but you may leave with more advertising
experience, or financial knowledge, or operational savvy than you
ever dreamed you have. This can be a great career booster, or can
even help you find a new passion or strength you didn’t know
There is also nothing like knowing that what you do each day affects
the business. I mean actually makes a difference in the success,
or failure, of your company. In the corporate world very few people,
outside of upper management, can say that their job affects the
The bottom line is that if you’re a business person at heart,
if you are interested in understanding and building a business,
then a start-up company and an entrepreneur boss might be perfect
for you. Just keep in mind who you will be working for, buckle up,
and enjoy the ride.
Do entrepreneur bosses usually hire HR
or do one of the leaders typically take on the function
and run with it?
Kathy : This question made me
laugh out loud. In a word, no; entrepreneurs typically
do not hire HR. In fact, if you see an entrepreneur run
screaming from a cocktail party, it’s probably because
they were just introduced to an HR executive.
What I have found is that entrepreneurs are focused on
moving forward, as fast as possible, to reach whatever
end they’re working towards. They fear anything
that they perceive will slow them down or box them in.
Unfortunately, they feel that HR is about rules and restrictions.
They believe that once HR is in place, they will have
to watch what they do and what they say.
I think most entrepreneur bosses want their employees
to be happy and satisfied with their jobs. But they don’t
want someone else monitoring that, or telling them how
to accomplish it. A perfect example is an interview I
watched between an old entrepreneur boss and a potential
new hire. Not only did my boss ask the applicant’s
age, he also asked their religion and if they were married.
When he was told that the applicant was single, my boss
asked, “are you gay?”
I can tell you that this boss is not homophobic; he was
simply curious. The answer to the question would not have
affected his hiring decision in any way. However when
I mentioned to him, after the fact, that he had just opened
the company up to a lawsuit, I was told to “stop
with the human resources B.S.”
This boss believed that all new hires should know what
he was like, and what they could expect from him, before
joining the company. And yes, by the end of the interview
this applicant understood fully that this boss had no
boundaries. Sadly, I think that most entrepreneurs, especially
those who haven’t worked for other companies, don’t
understand the true role of HR and the value that the
department brings to the table.
If any of your readers are interviewing for a job with
an entrepreneur, it will most likely be because the entrepreneur’s
company has grown to a size that they don’t have
a choice but to bring in an HR executive. They may be
forced to, by investors or their own Board. During the
interview your readers should keep in mind that the last
thing the entrepreneur wants is a boss.
Ver Eecke is a seasoned marketing executive with twenty
years of experience launching companies, products and brands
around the globe.
She has launched everything from an English-language magazine
in Japan to DVDs designed to entertain dogs.
She writes and speaks on topics ranging from how to write a
compelling marketing plan to how to survive the quirky entrepreneur
You can follow Kathy on her blog,
or on Facebook.