Entrepreneur, the buzzword title of the decade found in almost everyone’s Instagram or LinkedIn profile caption.

Owning or starting your own business is one thing but running it successfully and being profitable is another. Contemplating starting a business or a side hustle? Let’s explore entrepreneurship from a practical perspective to see if it’s right for you.

Let’s start with the basics. Here are sayings you’ve likely heard before:

  • Find a need then provide the product or service to serve it.
  • Identify a problem and fix it.
  • Look for a gap and fill it.

Sound familiar?

These statements summarize the core question when deciding whether to start a business: is there a need for what I want to do?


Supply and demand | Policonomics


Without question, you need to make sure that people or businesses will actually buy what you’re selling. If this pandemic has taught us anything, it’s that not all products and services are “essential”. In simple economic terms, is there a demand for your idea?

It’s very sad that many small businesses have been shut down or will not survive much longer due to the economic shut down caused by COVID-19. For many small business owners, their business is their crowning achievement and means a great deal to them. After all, it takes an inordinate amount of time and energy to start and run a business, so who can blame people for feeling devastated.

That said, there are many businesses that have flourished in spite of the pandemic. No one could have predicted the current economic environment; however, it’s possible to discern which businesses are more “essential” and “recession-proof”.


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This is something to consider when deciding what type of business or industry you want to enter. Do you want to cast a wider net of customers and provide a product or service that almost everyone needs? Or, do you want to specialize and zero in on a specific audience? Both have their merits; it all comes down to what you love to do.

Herein lies another fundamental principle of entrepreneurship I believe in. It takes a certain type of personality to be an entrepreneur. I assert that entrepreneurship shouldn’t be the path you choose out of desperation or as a last resort. It should be a chosen path of passion and desire.

Because of the time commitment, and often a financial investment, you need to love what you’re doing. Sure, some people may choose a particular business because of the profitability, but I believe that you’ll be more likely to succeed long-term if you also love what you do.

Regardless of the type of business you’re looking to build, being an entrepreneur takes some non-negotiable personality traits:

  • Self-motivation
  • Strong mindset
  • Work ethic
  • Vision
  • Patience

Oh also, don’t be afraid of sales.


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I’ve spoken to many people over the years that say “oh, I don’t like sales”, or “I’m not a salesperson”.  If this is you, then you may want to consider another path. Like it or not, sales is part of being an entrepreneur. You need to be able to sell whatever service or product you’re providing, but more importantly, you need to be able to sell yourself. End of story.

Whether you’re a veteran entrepreneur or contemplating this path, I recommend you follow some influencers in this space:

  • Gary Vaynerchuk (IG @garyvee),
  • Tony Robbins (IG, YouTube @tonyrobbins),
  • Grant Cardone (IG, YouTube @grantcardone), &
  • Hector LaMarque (Twitter @HectorLaMarque).


Would you prefer some feedback about entrepreneurship from local business owners? I got you covered. I surveyed some of my peers and colleagues from various business networks and I asked them the same two questions:

  1. What is the best part about running your own business?
  2. What is the greatest challenge of being an entrepreneur?

Here is what they said (and their industry + area of operation):

Q1 – Best part of entrepreneurship

Mortgage Broker, Oakville

      The ability to set my own goals and chose the people I want to work with.  

      Also, the ability to time block my schedule. 

Law Firm Owner, Halton

      The freedom to make decisions and the ebb and flow as I want.


Interior Designer, Halton/Peel

     Complete creative control and master of my own universe

Social Media Marketer, Halton

     Talking to other business owners and learning about their business, as well as different ways that I can help and contribute to their business

     It’s amazing how many hats we have to wear or have had to wear, and how we can each relate to that 

Business Coach, Halton/Peel Region

     The best part about running my business is that I can operate it with the filter of my values, and always choose to come from contribution

Financial Advisors (multiple firms), Halton

     The advisors all shared similar beliefs that the best part is the flexibility of schedule and having control over your time.

     Also, the ability to earn passive income and have unlimited earning potential.


Photographer, Halton

     Being able to control everything. I am able to make my own hours, workflow and my own success.

     Knowing that it’s all up to me is both good and bad. The success of my business is solely up to me which can be overwhelming at times but always rewarding in the end.

Q2 – Greatest challenge of entrepreneurship

Mortgage Broker, Oakville

      Keeping focused especially during difficult times.

      Using the time effectively and efficiently to ensure business growth continues and I stay ahead of the curve.    

Law Firm Owner, Halton

     Finding the right people for the different jobs that need to be done, balance, and being responsible for others.

Interior Designer, Halton/Peel

     Wearing too many hats (responsibilities)

Social Media Marketer, Halton

     As someone that has never worked for anyone else but myself or my immediate family, I always look at challenges as opportunities.

     The opportunity that presents itself when running your own business is being able to remove oneself from working in the business, to be able to work on the business. Takes great effort, and a systemized process

Business Coach, Halton/Peel

      The biggest challenge with being an entrepreneur is that you feel like it will give you flexibility in your time when true flexibility comes from structured discipline.

Financial Advisors (multiple firms), Halton

     The advisors all shared the same thought on the greatest challenge in that it’s difficult to have discipline in prospecting and constantly expanding your network.

     In addition, managing your time can be very challenging if you’re on your own.

Photographer, Halton

     The biggest challenge with being an entrepreneur, at least for me, is finding a consistent flow of clients/income.

     Always being on your toes with marketing and social networking can be exciting and exhausting.


Stats Canada reported that 2.9 million people were self-employed in 2018, up from 1.2 million in 1976. Self-employed workers accounted for 15% of total employment, up from 12% decades earlier.

The income numbers are a bit dated, but as of 2004, Stats Canada reported average annual earnings for self-employed people was $55,600 vs $40,900 for employee status workers.

A more recent study from Monster.ca confirmed a similar trend. Over 35% of respondents said they earned at least 25% more, while many others reported they made about the same as employees.

The other factor you need to consider is that the income earned from self-employment is not the same. Unlike employees, self-employed business owners get to deduct expenses against their revenue, which often leads to greater NET profits.

There’s also a load of favourable tax advantages, especially if your business is incorporated, but that is a whole other topic for another day.


MY $0.02.

Let me close with my personal thought process and story on the subject.

My motivation for becoming an entrepreneur was driven completely by having control over my time and income. I’ve held a variety of jobs in different industries. No matter what the job was, after enough time I always ended up unsatisfied with a feeling of not “being where I wanted to be”.

In my late twenties I realized that it had nothing to do with salary, or title, and had everything to do with my drive to compete and constantly advance. Working for someone else simply didn’t provide me with advancement opportunities quick enough, and I had no control over increasing my income to what I felt I deserved based on my work ethic.

So, why finance Ben? What happened to your sports background?




Well, to put it simply, I didn’t see a way forward in the sports industry that would allow me to fulfill my core career philosophies. I had taken finance & economics courses in university and always did well. I enjoyed talking about money and looking at statistics and data. But oddly enough, neither of these were the primary drivers for my choice.

I needed a business that would allow me to have no limit on my earning potential, complete control over my advancement, and most importantly, doing something meaningful that would help people. I always enjoyed sales and building relationships, so these were also important factors.

It also didn’t hurt that according to the Canadian Securities Institute, in 2019 most investment advisors earned $100,000 annually after 3-5 years. Experienced top performers in the industry earned upwards of $500,000 annually. So, the potential for a big income was there if I worked hard. Check.

There was, and still is, an apparent opportunity in the financial service industry in Canada (i.e. loads of demand). I kept reading about the massive opportunity with the biggest generational wealth transfer happening in the next couple of decades (psst…it’s already happening).


Wealth Management Mag Infographic - Wealth Transfer - Kathleen Kowal


I also found that small business (less than 100 employees) was a target market that was underserved and often ignored when it came to financial services. BDC reported that in 2019, there were 1.1 million small businesses in Canada, 55% of which had fewer than 4 employees.

Along the same lines, reports show that less than 40% of Canadians have workplace retirement support. Employer pensions are going by the wayside and mostly only exist in very large companies or government institutions. Stats show that Canadians are not saving enough for retirement on their own, and let’s be blunt, the Canadian Pension Plan (CPP) and Old Age Security (OAS) will basically have you retiring in poverty.

The last trigger point for me was hearing that the debt ratio in Canada is over 170% (i.e. Canadians spend $1.70+ for every $1 they earn…yikes!). Granted, a lot of this is mortgage debt, but still, this means people are over-leveraged and buying more house than they can afford.

I saw all of these issues as problems that needed to be fixed and COULD be solved through education and greater financial literacy. I figured I had the skills and desire to do this, so I took the plunge.

It’s now been 4 years and I’m still feeling like I’m only just getting started.  I’ve been able to help a bunch of people and businesses thus far, but I have a long way to go to have a greater impact. If you’re interested in joining me on the journey, reach out and let’s have a chat to see if finance is right for you.

It’s an awesome feeling to be in control of your time and income. Running a business has its challenges and rewards, but ultimately, I couldn’t see myself going back to working as an employee building someone else’s dream.

If you want to chat about whether starting your own business is right for you, connect with me and let’s have a chat. Entrepreneurship is one of my favourite topics to discuss so I’m always down to have a chat and offer my perspective.

Thanks for reading! Catch you soon.