The Often Hidden Dark Side of Entrepreneurship


Entrepreneurship is everywhere, celebrated as the quest to solve big problems, come up with innovative solutions, and make the world a better place.

Entrepreneurs and startup founders, are hailed as a unique breed of people that can handle the uncertainty of building a startup, the unbelievable challenge or putting things together while on the move, and the courage to pitch ideas to investors who will rip them apart, make fun of them, and question why they should risk your money and invest!

But entrepreneurs and founders are not unique. Behind the illustrious facade of the “founder” title, and the anecdotes taken from famous entrepreneurial success stories there is a dark side of entrepreneurship.

The Raise Race

Many see founding a company as the antithesis of the “Rat Race” not realizing that life is in many ways still a race to something when you are in business. 

While you may not have a 9-5 job, and an asshole boss telling you what to do, as a founder you are most likely trying to raise funding in one way or another, be it a loan from a bank, or investment from an angel. 

You are desperate and working your ass off to get the next injection to pay your team, execute on your plans, achieve the next milestone, pay rent and even pay for your next meal. 

There is one else to complain to, no one to blame, no one by your side, no one working on this with you, there is no one to take this load off your shoulders even for a minute. 

Meanwhile the pressure is intensified with the constant stories you see in your email and social media feeds about all the founders that just raised millions, the constant rag to riches stories telling you-you too can do it, the mentors and advisors that keep pushing you to move forward, and the investors who will invest but only down the road when you have raised the first round!

As for the government, and all the organizations set to “help” and “support” small business and entrepreneurs, well they are right there waiting for you to succeed and reach the finish line, and only when they are ready to step in and help!

When you were just an employee, you may have been in a rat race, but you had others right by your side in the rat race. In the raise race, the pressure is always on you and you alone.

The Trap of The Start

From “Just do it,” to “Give it a go,” and “Take a chance,” entrepreneurs are tricked by these overused statements, that have nothing to do with entrepreneurship, into believing that all it takes is just starting and universe will line things up in such a way that it will be smooth sailing from that point.

So they “take the plunge” “jump with both feet in” and “follow their passion.” After all YOLO “You Only Live Once,” right?!


Entrepreneurship is akin to climbing Mount Everest, starting is easy, but it’s hardship from the very first moment till the moment you are back at the bottom. With every step, it gets harder and harder, the risk increases, and the summit is the most deadly. (Think about it do you really want to be Mark Zuckerberg of Facebook right now, or Travis Kalanick of Uber, or Jack Dorsey of Twitter!).

And just like climbing Mount Everest, you can’t make it on your own, you need a team, and sherpa (guide). Many are taken over by the mountain, and the 200 frozen bodies that are still on the mountain are proof that it’s the most dangerous and severe endeavour you can ever take on.

So the start is not the most critical and calculated decision you have to make, one that you must take with the utmost seriousness, and one you need to prepare for with every ounce of wit you’ve got.

The Tyranny of Others

While entrepreneurs have a lot to deal with, the others are the worst.

From well-meaning family members who are voice their concern in ways that fluctuate between benign and destructive. Friends who can’t see beyond their limited view of the world and are baffled why would you become an entrepreneur when you could’ve continued to build a thriving career. And community members, fellow entrepreneurs, investors, mentors, and others who mean well but lack the training to indeed help and support entrepreneurs and end up sending you down the wrong path with lousy advice and feedback.

It’s in those moments that you realize you are “fucked” and indeed on your own! 

It’s in those moments that actual weight of what you have taken on lands on you and crushes all the passion, stamina, and energy you’ve mustered to get here. 

You try to voice how hard it is, you try to reach out, you start to share, and immediately you are faced with people who brush off your shy attempt to call for help with “that’s what you signed up for,” “I don’t know why you do this to yourself, just get a job,” or they turn on advice mode and start telling you what you should do, when all you needed is someone to truly listen.

Some even face backlash and anger from people who proclaim that “you have no right to complain,” after all “you are doing what you love,” or “you have money,“ so “you have no real problems!” 

Is it any wonder that most founders suffer in silence from depression, anxiety, and mental illness. And many are afraid to share any of the challenges they are dealing with to avoid the tyranny of others.

What Can Founders Do?

Only crazy people climb mountains alone. Sane people put a team together and get a sherpa to guide them, and they make sure they have the right, and they are fully ready for the journey.

So as a founder:

  • Assemble a team of supporters and fellow climbers first. DO NOT go it alone.

  • Prepare for the journey, just like every mountain is different, every market is different, know what you are getting yourself into, research the market, learn about the challenges in it, meet and ask the people in the industry.

  • Get the right tools and support systems in place. Usually, some people did it before you, if not in your town, in the city next to you, if not there then in the larger city a little bit further... find them and engage with them.

  • Get the right mentors and advisors. Just because someone is successful doesn’t mean they can be good mentors. So do not be fooled by optics, find those who are genuinely dedicated and capable, and work only with those.

  • Be very skeptical of government efforts to help entrepreneurs, and read the fine print. Due to the Political business cycle, most politicians are interested in quick wins not building for the long run, and most funds will end up going to growth stage companies and getting international companies (who have no loyalty) to open offices in the city, and not towards helping early-stage entrepreneurs. 

  • Remember, real entrepreneurs are not risk takers, they are risk averse, they make every effort to limit risk, they test, they try, they take small steps, they measure, and they apply what they learned. They never make big jumps into the unknown, that’s gambling, not entrepreneurship. 

  • Speak out, reach out, there are many out there that genuinely want to help, are willing to listen, and dealing with similar challenges. YOU ARE NOT ALONE! 

What Can You Do To Help Founders?

Entrepreneurs and founders are the lifeblood of the economy, your economy, they are the reason you a have a job, they are the reason you have income, they are the reason you have all the fantastic innovations you enjoy today. 

So this is not a plea or a request if you want a functional economy that is growing, more jobs, higher GDP, and more wealth and prosperity, it’s your fucking duty to help entrepreneurs, cause your livelihood and the livelihood of your community depend on these trailblazers.

So as a someone who is not a founder:

  • Always look for something of substance or value to say or do. Like, point out what the founder can do to get to the next step faster, point out if there is some opportunity in the market they are missing. Introduce them to someone or something that can help or add value.

  • Empathize and put yourself in their shoes. Do not give personal advice from your own world view. 

  • Always ask, “how can I help?” But only if you really intend to help. If you don’t thank them for taking the time and get out of their life.

  • If you have nothing of value to say or do, shut the fuck up and get out of the way. No really. Founders are fun to hang around, they are inspiring, they usually work at the edge of innovation, so they are interesting. But founders have limited time and a shit load of things to do. Why waste their time if you have no desire to help and add value.

  • Paying your taxes is not enough. Invest 5% of your savings in early-stage venture funds, crowdfunding, and directly in startups. Money isn’t everything, but one of the most significant challenges founders face is funding and in particular early stage. This is not to say give them money, do your due diligence always. However, increasing the pool of investment in that critical stage of building a startup will help early-stage startups in places that do not have a developed ecosystem, like Silicon Valley and other leading startup hubs, to have more access to capital, which leads to more startups, which leads to more growth companies, more jobs and economic prosperity. It’s not that hard a concept to grasp (yes I’m talking to you economic development bodies, government officials, politicians and everyone supposedly working to create more jobs.)

  • Demand that your government, the politicians, and business leaders do real work to help early-stage entrepreneurs and support small business, not just with words, but with real action on the ground and get involved and help.

In case you are still wondering, yes this post is a little bit of a rant and I’m angry. 

I’m angry because I’m surrounded by entrepreneurs and founders and I’m experiencing the total lack of support from investors, the business community, the large enterprises, and the federal and provincial governments.

It sometimes seems like everyone is sitting on the sidelines while entrepreneurs struggle to succeed, and those who are genuinely working to help entrepreneurs are left to their own devices, with no right backing or support.

It’s time to stop this and work together to build a thriving ecosystem that genuinely and effectively supports those who are willing to take on the torturous journey of taking a startup from idea to a growing business.

This post is dedicated to the memory of Kim (Kay) Hansen, who is no longer with us. One of the kindest, smartest, and most hardworking founders, that I had the privilege of knowing, mentoring, and learning a ton from. She was an advocate for the community and was always willing to help. She will truly be missed.