The Dark Side of Entrepreneurship

What is The Dark Side of Entrepreneurship?

The only place we hear about the dark side is – Star Wars! and we love it when they say “May the force be with you!”.

The Force fighting the dark side.

Now life as an entrepreneur would be so easy if we had a force to help us fight the dark side of entrepreneurship.

Wait – I still have not answered the question “entrepreneurship has a dark side. What is meant by this statement or what is the definition of the dark side of entrepreneurship”.

For college books – the simple answer to your question is – the dark side of entrepreneurship is the ugly side of entrepreneurship which includes depression, Struggles and at times, suicides.

This is the side of entrepreneurship no one talks about or hear about because we all like to stay positive and aim for the next billion-dollar exit.

When the media only tells us about Rich entrepreneurs, the millions of dollars of funding, a multi-million dollar exit, etc. Why on the earth would you want to hear about something so depressing?

The truth is Entrepreneur is a lonely guy. A misfit. A maverick or a misunderstood genius who is struggling alone to achieve the unachievable.

The truth is – One of the steps of becoming an entrepreneur involves dealing with failures, pain, depression and a lonely world at the top.

Famous Entrepreneurs who lost to the dark side of entrepreneurship:

Jody Sherman who worked with the Downtown project and Aaron Swartz are two entrepreneurs whose name come first to my mind when I think about entrepreneurs who could not keep up with the pressure of the entrepreneurial world.

In the USA, the Depression among entrepreneurs is more than 7% and the number is only growing every year because of a large number of youngsters joining the startup bandwagon to hit that unicorn startup mark.

How I came face to face with the dark side of entrepreneurship?

One of my close friends convinced me to start my first venture.

I was so intrigued by what is Entrepreneurship that I left a decent paying cushiony job as a programmer to test the waters of Entrepreneurship.

Trust me. All the fuss about Entrepreneurs makes starting your own venture so tempting.

Those were the days when leaving a job was the biggest crime that can be committed by a middle-class family person.dark side of entrepreneurship

The marriage stocks would plummet. Family standing would go down. Everyone would talk behind your back on your foolishness.

How naïve could you be to leave a job in an IT Company?

We leave our jobs out of frustration, salary issues, family issues and many other reasons.

I wasn’t very fond of my job but it was not a reason big enough to leave my job.

For me, the fascination to do something of my own was bigger than any of the issues I mentioned above.

Whenever I spoke to my Entrepreneur friend on the phone, he had his wonderful entrepreneurial experiences to share with me.

The stories ranged from how he does sales despite being from the technical background to the day-to-day challenges he faced.

I was fascinated.

Soon Fascination turned into inspiration.

I started looking up to him.

His tales of conquering the big bad world of business was no joke.

I assessed my current position as a programmer in a company, where I worked on a small module of a big project of a bigger company.

The glass façade of the building was enough to get me a good wife.

No one would know whether I sat next to my boss’s cabin or toilet. Both of which are equally dreadful.

But I didn’t join my company to get a good wife.

And I did get a good wife, even after not working in an MNC.

One fine day, I quit my job.


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The venture I had spoken for months finally took off.

Oh boy! What I read in newspapers and what I heard from my friend was nowhere near to what I was witnessing.

Everyone said, “There is nothing like Entrepreneurship”.

I didn’t realize the meaning in between the lines until the reality hit me.

And it hit me hard.

From small issues like me learning to say No politely in Business to major issues like – Every vendor wanting an advance.

Salary cycle always running ahead of the payment cycle and Unhappy Clients. Life Sucked!

Predictably, we made no money.

And then, there was no time for family.

I was so ill-equipped to handle failures.

Damn! The good friend never spoke about the ugly or dark side of being an Entrepreneur.

All I heard before deciding to take the plunge was “Being an Entrepreneur is so much fun.”

Seriously? Is it fun?

I haven’t seen the fun part in years.

If you call living frugally.

Investing your savings in growing your company.

Begging in front of investors.

Pampering the most spoilt employee for all the wrong reasons as fun.

I beg to differ!

Entrepreneurship’s dark side is not fun.

Let me start with how Employees view the owners of an organization.

“Dude! The guy sitting in the cabin has the best job in the world. He makes money. Spanks us for work and always cribs about client payments. He makes money and we get no hike. Life is so unfair.”

The above lines came from my conversation with college buddies who are employees in some of the best companies.

I am sure, the employees in our company do not have any better views to share.

Most of my friends think “I am the luckiest guy on earth”.

They have their own reasons to believe, how lucky I am.

At times, I wish we could trade places.

How our families suffer with us is another story?

After 2 years of marriage, we took our first vacation.

I barely had any money when we got married to splurge on honeymoon. And the kind Dad, who sponsored my wedding spent all the money on the lavish, extravagant wedding of mine.

We still refer to the trip after 2 years as our honeymoon 🙂

Since then, I am either busy handling projects or finding funds to grow our company further.

Where is the time for family?

A wise man once said, “No amount of money or success can take the time spent with your family.”

I wish I could meet “the wise man” and ask him “Sir. Was the quote written from the perspective of an Entrepreneur?”

Few years into the business, I was on the verge of quitting.

All my money was stuck in government projects. Employees had not been paid in months.

The owner of our office would pop out of nowhere and ask “when will you pay your rent?”

Worse. I had no money in my pocket.

The dark side of being an Entrepreneur was starting to show its true colours.

Life was shit.

I had almost decided to close the company when destiny smiled.

Yeah. Destiny does smile after screwing your life upside down.

I sometimes refer to the crooked smile of destiny as “mocking”.

The money I got as payments was duly disbursed further to cover past dues.

I did manage to save a few thousand for myself.

In the end, I got paid enough to survive.

I called one of my other “Entrepreneur friends” to discuss the problems I was facing.

Let me tell you a secret. We entrepreneurs do not have the luxury of confiding in 1000 people we meet.

For us, the only buddy who can understand what we are going through is another Entrepreneur.

We do bitch about our employees, clients, life. And we do it secretly.

I call it the brotherhood of Entrepreneurs.

Everyone is screwed here.

So while speaking to my friend, I shared the issues I am facing in business.

His problems were just worse than mine.

All I could gather was some empathy.

Did it help?

Yes, it did.

Sometimes venting out your frustration through discussions can have a positive effect.

At least for me. It does.

What about loneliness?

As they say “It’s a lonely world at the top”.

One of our new joiners in the company gave us all the fake documents.

When we did the verification check, the reference number of her past company turned out to be the number of the best friend.

Thanks! Whatsapp and truecaller for showing names along with numbers.

The company on resume did not exist in reality.

As per company policy, we asked her to go.

Obviously, there was no payment for the time she wasted with us.

We almost lost a project because of her work and fake experience.

The employee went on one of the consumer court websites and wrote

something very derogatory about me.

When I did more research, I realized there was more praise for me and our company on the internet.

One thing common in all the praise showered on us was the fake names next to the “wise words”.

I was frustrated. I spoke to my lawyer and he advised me to not get into legal troubles.

India’s legal system can give the tortoise a run for the money when it comes to speed.

So where do I go and speak on how employees have royally screwed us over the years.

We have had an employee who forged the experience certificate given by us.

She had the audacity to call our HR and ask her to verify the fake experience.

We had another employee, who left without notice. He expected us to pay us for the days he worked.

When we showed him company policies, he promised revenge.

One of the employees, who had left us abruptly recently came to my office and asked me to prepare an experience letter with fake experience.

When I confronted him for asking me to do something unethical.

He replied, “even you are no angel”.

You worked as a contractor under the name of a different company.

I have no idea what my working as a contractor had to do with him asking for a fake certificate.

But he made a point.

We did see a new comment on one of the stupid consumer websites a few days after I refused him a fake experience certificate.

Now if one of these guilty guys goes on the internet and posts something about me.

Where am I supposed to go?

Nowhere. Right?

I just have to keep up my composure. Take a deep breath and get ready for the next challenge.

Entrepreneurs cannot confide a lot in their employees.

What if the employee leaves tomorrow? He/she takes all your confidentiality along with him.

I have heard stories of friends losing money and reputation when their trusted lieutenant joined the competitor.

The dark side of being Entrepreneurs at times is too dark to see through.

When I see all the hype around youngsters starting startups for all the wrong reasons, I wish I could tell them the dark side of entrepreneurship.

Within years of starting a startup, you might end up without money, friend, family.

I am sure, the wise men didn’t tell you this before you started.

A budding Entrepreneur in our family once told me how inspired he was to see my company grow from nothing to a company with a decent turnover without any funding or help.

I didn’t want to be a party spoiler and dampen his spirits by speaking to him on the “ugly side of being an Entrepreneur”.

The dark side of Entrepreneurship is a secret which unravels itself after you become an Entrepreneur.

We, the entrepreneurs are supposed to encourage. Speak nice stuff about startups and paint a rosy picture of being an entrepreneur.

I always lived up to the expectations and spoke nice things about being an Entrepreneur.

Obviously, I did not want to come across as a cry-baby who cannot handle the pressure.

However, I have changed over the years and now – I handle the pressure strategically by openly speaking about my struggles.

I make it a point to speak about the hardships youngsters can expect while starting a venture and why the world is so lonely at the top.

I have come to accept the fact that Entrepreneurship is like life. Everyday You can not have a good day. To make sure, I do not screw up – I try and not to let the bad days get the worse out of me.

Do I still get depressed over failures and challenges?

Yes – I do but then I take happiness in the small joys of life like thinking on my kid’s smile or coming back home to a beautiful family who despite being a part of my struggle never complain and always, greet me with a smile.

The dark side of entrepreneurship is a reality of being an entrepreneur, face it before it gets the worse out of you.

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