Skip to main content

It was twenty years ago, just after the August Long Weekend that I set off on an entrepreneurial journey that would change my life forever.

I had just resigned from my position at Bell Canada on Tuesday and by Friday, I was set up in a small 8×10 office space, with only a desk, telephone and printer to keep me company. I began making calls from 8 a.m. to 8 p.m. to connect with prospects from the east coast to the west coast.

Let me tell you, each was a new adventure – my emotions ran from nervous excitement to trepidation to mind-numbing fear. Luckily, the business started turning a profit within a few months, and I got the sense that we would make it. There is nothing more exhilarating than starting something from scratch and experiencing all the emotions as you begin to gain traction and break through to success.

It was only through trial and error as well as listening to advice from those who came before me, that I learned what it takes to be a successful entrepreneur. And as we emerge out of the Covid-19 crisis, it’s easy to draw parallels with the economic turmoil in the early 2000’s, when I first began.

What better way to make use of all this knowledge than to pay it forward to future generations of entrepreneurs?

Here are my thoughts on what it takes to be a successful entrepreneur and some of the most important tidbits I’ve learned over the years. To be clear, there is no actual blueprint for success, as everyone’s path is different – I can only gently steer you in the right direction.

What is an entrepreneur?

Simply put, an entrepreneur is someone who launches a business venture, usually in the form of a company, that builds and sells a product or provides a service. They capitalize on an existing problem or new opportunities to create a solution others may have overlooked.

Entrepreneurs serve as stewards of the business, holding down the fort, initially for themselves and later for the members of their team. A successful one generally has a solid mix of industry knowledge, skills and experience – leveraging partnerships can help fill in any gaps.

It all starts with a good business idea

Did you know that up to 75 per cent of startups fail and over 22 per cent of small business fail within one year of launch, half fail within five years and two-thirds are gone in ten?

There’s no sugar-coating things – having your own business is exciting but there is a lot of hard work ahead of you. Just because you’ve decided to start one, there’s no guarantee you’ll build a profitable business.

In the beginning, all you have is your idea, so you should choose something you’re passionate about. Make sure you get your business plan validated before you sink in valuable time, resources and effort. There are many great business ideas out there but not all of them are sustainable.

From there, you’ll need to consider the following:

  1. What is your product or service? What are your priorities?
  2. Who is your target audience? Who are you competing against?
  3. Why should customers purchase what you offer?
  4. When and how will your business operate?
  5. What are your contingencies for unexpected emergencies? (i.e., Covid-19)

Traits that all successful entrepreneurs have

Regardless of what anyone tells you, entrepreneurs are made, not born. That being said, there are specific traits you want to have in your back pocket, to increase your odds of success.

On the surface, successful entrepreneurs have good communication, organizational and time management skills as well as an aptitude for strategic thinking. These are all necessary for day-to-day operations and effectively dealing with customers, vendors and team members.

Digging a little deeper, there are some more nuanced skills that a successful entrepreneur must have to lead a business:

  1. Level-headedness – As an entrepreneur, you’ll constantly face challenges and struggles. The key is to be able to deal with them effectively and not get overwhelmed. When you’re centred, you’re able to tap into your creative juices and solve problems with great ideas.
  2. Trust yourself – While you should always be open to feedback, never doubt your instincts and vision. Don’t apologize for your choices. In the early stages, when you don’t quite have the resources, it’s natural to be worried about what the clients and employees will think. This will only compromise your decision-making. To be a successful entrepreneur, you need to focus less on where you are, and more towards where you’re going with your business.
  3. Listen to complaints – No one enjoys failures or criticism, but they are a necessary part of successful businesses. If you want to succeed as an entrepreneur, especially as a small business owner, you’ll need to keep it all in perspective. It’s a good idea to take classes or seminars and read as much as possible about other entrepreneurial successes to see their thought process.
  4. Passionate – I touched on it before, but to be a successful entrepreneur, you need to love what you are doing because success isn’t always immediate. having this fire inside you will help you overcome those inevitable failures.

It’s unlikely that you possess all these traits, much less at an above average level – I know I didn’t. You’ll need to fill these gaps by finding and delegating duties to ambitious, talented people.

Building a foundation for entrepreneurial success

When you’re in the business for over twenty years, you tend to pick up a few lessons along the way. There are certain foundational items you need to maximize your chances, no matter which industry you are in. These include:

  1. Develop a business plan. Make sure it’s clearly outlined with objectives and strategies for reaching them. This is a crucial step for getting investors on board and monitoring your progress in the early goings. It will also help you manage your risks, so you don’t overspend and stretch yourself thin.
  2. Build a great team. As much as it pleases your ego, you can’t do everything on your own. Getting the best people around you to help your reach your goals is essential. Delegate tasks based on their personal strengths – the more they can take on their plate at once, the better. This way you focus on the areas of the business where you can bring the most value. After this pandemic, people will be more mindful of their company benefits, so if you’re an established company, you’ll need to offer better sick leave policies, more comprehensive health coverage and so on to entice talent.
  3. Evolving with the times. Successful entrepreneurs know that it is important to have open and ongoing conversations about new ideas and processes as well as maintaining an agile operational structure that can respond to crises. One thing you can do is have an open-door policy. Keep your senior leadership upfront and transparent with lower-level employees, sharing details and updates about the company on a regular basis. It may not always be obvious, but this sort of connectivity is greatly appreciated. You also need to be aware of changing circumstances in the business sector. The future of the workplace is hybrid. According to Emergent Research, 15 to 18% of the workforce is likely to remain home-based, with most workers operating on a hybrid model, splitting time between the office and home. As a business owner, you need to prioritize the employee experience and remain flexible. If your business does continue to operate out of an office, be mindful of its layout. Ideally, it should look less like a workspace, with rows and rows of cubicles, and more like a place of community. It will make it a more exciting place in which to spend time.
  4. Start with a minimum viable product (MVP) & promote it. With any business venture, you’re going to need to convince consumers that whatever you’re selling is the best option for them on the market. To do this, you’ll need to hone in on your unique selling proposition and business model. Once you have that, you’ll want to use it as the centrepiece of your promotions – Google My Business and social media are two free tools you should be using. Facebook peer groups are also beneficial.
  5. Avoid hiring mistakes. Making additions to your team is a big investment in time and money. To avoid disruptions to the status quo, I often tell business owners to hire people based on cultural fit and personal motivations, not just on revenue potential. Trust me, you don’t want to deal with the headaches. Whatever skills your new employees may be lacking, you can always train them.
  6. Figure out your funding. Without some financial backing, it’s difficult to get your venture off the ground. Depending on the type of business, you’ll need a source of funding to purchase equipment and materials, develop your product or service, iterate upon your offerings and refine your processes. My advice for entrepreneurs is to always aim to do more with less. You have two different financing avenues you can take: self-funding or raise capital from investors. If you go with the former route, you’ll need to take out personal loans or have your family or friends invest. If you go the latter route, there is a lot of money and interest among venture capitalists right now, with stock markets near record highs and numerous multibillion dollar IPOs in the news. There are also many government programs in the U.S. and Canada pushing economic growth, which is driving investment. If you are an entrepreneur with a tech company, even better, as investors are always looking for emerging technologies.Take the path that makes the most sense. Whatever you do choose, however, I’d strongly advise allocating part of your revenue into an emergency fund for those unexpected crises. You can also opt for insurance to protect yourself and your business.

Guiding a successful business through murky waters

If I’m being completely honest, the best teacher over the last twenty years for me has been adversity. Heck, when I first started my journey as an entrepreneur in the early 2000s, we were knee-deep in an economic recession.

But if you have the right structure in place and focus in on your decision-making, you can make it out of any sticky situation. Here are some of my best practices for established and newly-minted entrepreneurs:

  1. Be financially diligent. This starts with being prepared even before a crisis hits. Set some money aside and save it for that rainy day. Being consistently disciplined with your business’s finances will ensure that you’re able to do this, as you will already have costs under control and be operating within your means. When the difficult times do come, you will have to adjust, but won’t have to undertake wholesale changes, a welcome relief for your employees.
  2. Maintain a positive mindset. In business, as with life, you’ll face challenges. Any crisis is manageable, regardless of the triggers, if you maintain a healthy frame of mind. How do you do this? Successful entrepreneurs know that it’s about what you allow into your brain. Limiting engagement with negative people, build a strong support network, reading inspirational books as well as consuming less news and social media are a good start. I’d also recommend focusing on what you can impact right now, such as responding quicker or communicating and strategizing with your team.
  3. Control expenses and cash flow. Even though you’re feeling optimistic that we are finally, truly rounding that corner toward a better economy, if there’s currently more money going out the door than coming in, you risk not making it across the finish line. We can’t predict just how long the full recovery will really take. As an entrepreneur, being optimistic is in your blood. But too much optimism can sink you, especially if it’s a new business. This is a marathon not a sprint.
  4. Prioritize your health. Without you, there is no business. Take an introspective look at your personal life. As an entrepreneur, it can be pretty lonely carrying the weight of a business on your shoulders – it exacts a toll on you physically and emotionally. Many entrepreneurs have 10 to 12-hour days and are constantly dealing with the anxiety of paying bills and waiting on cheques. Get regular exercise, don’t skimp out on sleep and consider taking up yoga or meditation to help you filter out the stress. It’s also a good idea to limit your caffeine intake!
  5. Keep your business health in perspective. Analyze the year that just passed and review any aspirational budgets – that lofty number you wanted to achieve. Continue to focus on key client relationships and add value wherever you can, so they continue to appreciate what you bring.
  6. Embrace technological trends. Staying ahead of the game can help your company deal with any crisis. Here at the Wish Group, we actively hunt for technological trends, whether or not we’re in a pandemic. Obviously, without a crystal ball handy, we can never know for sure what is coming but we pay attention to the indicators. As an entrepreneur, you’ll want to do the same.

It takes more than luck

There’s nothing like having your own company, being your own boss and making your own money.

However, becoming a successful entrepreneur is difficult and not for everyone. There is a steep learning curve, and most entrepreneurs don’t end up realizing all their ambitions. Beyond a good idea or opportunity, you have to possess the necessary skills and qualities, including taking risks and managing uncertainty, to see long-term success.

If you take only one thing away, it should be this – success in the entrepreneurial world doesn’t happen by accident.

Need more? If you’re an entrepreneur with questions about getting started, managing your business through difficult periods or any other topic for that matter, I want to hear from you. Get in touch with me at


This blog was first published on LinkedIn.






Leave a Reply