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Top 5 Entrepreneurs of the Modern Era

Innovative. Visionary.  Courageous. Passionate. Dedicated.

Five words always found to be associated amongst the top tier of entrepreneurs.

Welcome to the Canada Startups weekly blog.

We write to you today, May 26th of 2018, with our top 5 Entrepreneurs of the Modern Era (accounting for their actions from 1978 onwards).

These are entrepreneurs who redefined what ‘challenging the status quo’ means, a group who together, have advanced society like never before (some of whom, you can count on, will continue to do so for years to come).



The Top 5:

5. Elon Musk (PayPal, SpaceX, Tesla)


I’m going to be straight forward. If all goes as planned with Tesla and SpaceX, I believe Elon Musk slides up to the number 1 spot on this list when it is all said and done, solely based on social and economical impact. If Tesla is able to replace all natural gas vehicles currently on the road with electric vehicles, the impact in terms of sustainability on the world is going to be game changing.

Elon Musk is comparable to Superman in terms of his quest to save the planet. At the current rate of carbon dioxide in the earth’s atmosphere, we are no where near being in a sustainable position by the end of the 21st century. However, if you replace all current natural gas vehicles on the road with electric ones, as Elon plans to, the long term impact will save future generations from this serious issue of completely destroying the earth. Electric cars will save the world. Talk about solving a real problem.

If SpaceX goes as planned in coming years, Elon will have successfully laid the groundwork (and may even get us their in his lifetime) to have humans living in space…on different planets.

Im just going to let that sink in. If all goes as planned with SpaceX, we will have humans living in space! On different planets other than earth. Wow!

It’s going to be very interesting to see, so keep an eye on Elon Musk, Tesla, and SpaceX in coming years. We sure are in for an adventure, and potentially a future existence similar to the Jetsons.


4: Mark Zuckerberg (Facebook)


Before there was Instagram, Twitter, and Snapchat, there was Facebook.

Mark Zuckerberg, founder and CEO of Facebook was a millionaire by 22… and, a billionaire by 23. The youngest self-made billionaire in history has forever changed the landscape of things as they are today, ushering in the phenomenon that we now know as Social Media. Most of us spend the majority of our time on social media in one way or another, and what any entrepreneur will tell you is, attention is where all of the value is – and Facebook has a whole lot of it.

With over 2 billion users in 2018, Facebook remains the top dog amongst all social media websites. Behind the social media giant is 34 year old tech entrepreneur and Harvard dropout, Mark Zuckerberg. It takes a special kind of entrepreneur to build and sustain something so popular and so game-changing . Facebook is a masterpiece to analyze for human behaviour; humans love to ‘snoop around’ and see what other people are doing, and the 2 billion users (and counting) of Facebook are a practical illustration of that.

The fact that Mark Zuckerberg was able to pick up on this at the tender age of 19 years old and build ‘’ (back then only available to Harvard students) is an extraordinary display of the entrepreneurs deep understanding of consumer behaviour and simply ‘what people want’.

What made Mark so great to be able to pull off such a feat? He started early (started programming at 10 years old), and had a uncanny interest in people. In high school, Zuckerberg created an AI media player ’Synapse’ designed for mp3 playlists that studied the preferences of a user and would generate playlists ‘guessing’ which songs a user wanted to hear. Both Microsoft and AOL attempted to acquire it from Zuck; but the talented young high schooler refused the offer from the two IT giants. Imagine that? You have to know you have something special in store for the future, to actually turn down hundreds of thousands of dollars and/or the opportunity to work with two of the top IT corporations, as a high school student.

One defining trait about Zuck was that he was never put off by his existing competition. Upon Facebook’s launch, MySpace had 5 million users, and Friendster had already raised $13 million from investors. Despite the others being far ahead of him in terms of positioning and experience, Zuck knew he had something special, and something better than the others. By the end of 2004, Facebook had over one million users. In following years, Mark Zuckerberg would go on to become the young man who went on to successfully connect everyone in the world through Facebook.

Time and time again, Mark Zuckerberg has continuously pushed out a flow of innovative changes to the  Facebook platform. Most recently, Mark has had an emphasis on getting developers in better position to create apps for the community through Facebook and most of all, provide a user experience that stays ahead of the competition.

Zuckerberg has rightfully earned his spot on our top 5 and will continue to do so for years to come through his cunning business acumen and understanding of consumer behaviour.


3: Jeff Bezos (Amazon)


Introducing the newly crowned, richest man in the world. In 1994 Jeff Bezos founded Amazon, the e-commerce ’everything store’ that has now blossomed into the world’s second most valuable company, with a stock market value of $768 billion.

Amazon continues to grow at such a rapid rate it is wonderful for any entrepreneur to watch. Jeff Bezos continues to challenge the status quo and develop one innovative idea after another; from Amazon Alexa (a smart device virtual assistant and home automation system), to Amazon Go (the world’s most advanced shopping technology, eliminating lines and checkout), and countless others.

“Even when they don’t know it, customers want something better, and your desire to delight your customers will drive you to invent on their behalf. No customer ever asked Amazon to create the Prime membership program, but it sure turns out that they wanted it.” – Jeff Bezos

What exactly is it that has turned Amazon into the fastest growing company ever? For founder Jeff Bezos, the driving force is his obsession with always finding new ways to provide more value to his customers. It all boils down to value, and Jeff has figured out how to provide more value than other e-commerce stores time and time again.

How does Amazon manage to be so innovative? Jeff Bezos has made a consistent commitment to always finding a way to be pro-active for his customers. When you are running a business as large as Amazon, it is so easy to be caught up in being more reactive than proactive and simply meeting the status quo for current operations. However, Jeff proves that working smart and hard always trumps simply working hard or simply working smart. Jeff takes a solo retreat at the end of each business quarter to do exactly that. By removing all distractions, all contact, and simply being in isolation with his own thoughts for two to three days, Jeff has found the formula for developing innovative ideas. During the solo retreat, Jeff will spend time surfing the web and analyzing the current trends that are ‘cutting edge’, and will conclude his retreat by drafting a two to three page memo to himself and/or his executive team.

It is going to be exciting to see where Amazon and Jeff Bezos take us in the future. Keep an eye on this one; Jeff is another entrepreneur with sky high potential to be a fast riser on this list in coming years.


2: Bill Gates (Microsoft)


By the age of 31 years old Bill Gates become the youngest billionaire ever (at the time). By 39, he became the richest man on earth. Having played an essential role in ushering in the personal computer revolution that we are now all comfortably enjoying, Bill Gates is one of the best to ever do it from the modern age.

How does one get to that point? Well from the age of 8 years old Bill Gates was learning to program – an endowment only a few people had at that time in history. This early start combined with an undying passion and commitment to perseverance had gotten Bill Gates to allocate over 10,000 hours towards programming and computers before even graduating high school. That is a large allocation of time. In addition to his commitment to computers and programming, Gates would read one book a week; unveiling his real commitment to learning and always improving himself. Bill Gates teaches us that there are no shortcuts in life, but there are definitely head starts. So get in early, and learn as much as you can. It is this learning, and this love for computers that would ultimately become the foundation for Microsoft.

Now that we know where the founder of Microsoft started, what exactly got him to number two on our list of the greatest entrepreneurs of the modern age? Well, Bill Gates put all of his knowledge, understanding, and technical prowess together of computers and software, and alongside his long time friend Paul Allen, co-founded Microsoft in 1975. Microsoft would go on to become one of the most successful tech companies of all time largely due to Gates’ ability to respond to changing technologies, market demands, and business opportunities.

However, what skill or ability was it that allowed Bill Gates himself to achieve such great long term success with Microsoft, decade over decade? When asked about it, Gates without hesitation boiled it down to his ability to pick the right people. Upon realizing that, it makes sense why Bill Gates and Microsoft were able to completely dominate the PC industry for such a long time. Businesses are vehicles made up of individuals whose execution and actions will together, determine their success. Bill Gates time and time again, selected the right people, for the right position, at the right time, and in turn, reaped the benefits and crushed his competitors. Except Apple … More on that later though.

The majority of Microsoft’s significant ‘wins’ were not from game-changing products, but actually from sharp business practises. Knowing who to recruit, how to build the right team, what ideas to steal, and how to draft and execute a strategic business plan can all be attributed to the cleverness of Bill Gates and the ultimate success of Microsoft.


1: Steve Jobs (Apple)


If you’re reading this blog on your Macbook, iPhone, or iPad: it is because of Steve Jobs.

Steve Jobs is the greatest entrepreneur of the modern age. It is mind-boggling to realize how heavily Steve Jobs relied on his natural intuition, and how little he used market research when developing extraordinary products like the iPhone, Macbook, and iPad. When questioned on how much market research he did for the development of the iPad, he replied ‘None. It isn’t the consumers’ job to know what they want. It’s hard for [consumers] to tell you what they want when they’ve never seen anything remotely like it.’


You have to have a very high level of consumer behaviour understanding, technological understanding, and intuition to be able to say something like that, and actually pull it off. Steve Jobs was absolutely correct when he said it though and he did indeed pull it off. Steve Jobs and Apple have redefined the term, innovation. In doing so, Steve’s impact will forever carry us in to the future and inspire all entrepreneurs for years to come and never let them forget ‘People don’t know what they want, until you show it to them’.

Steve Jobs undoubtedly has turned the iPhone into what the Television was to the radio; completely shifting the attention of people everywhere. The Macbook has long established itself as the top laptop in the industry, and the iPad is the go-to choice for tablets. In terms of impact (that has been realized, sorry Elon), Steve Jobs tops the list.

However, we cannot go without mentioning the long running rivalry between Microsoft and Apple (Bill Gates and Steve Jobs). This rivalry undoubtedly elevated both of these entrepreneurs to their highest extents. After having the chance to work alongside Steve Jobs, Bill Gates was ultimately inspired to create Windows. I believe if the timing was even slightly off, and they didn’t have each other to compete with, neither would have been as great as they were – lucky for us, they did compete, they did push each other, and they both advanced society to the fullest extent in their runs as entrepreneurs.

I give Bill Gates the edge as a business man, but I must give Steve Jobs the edge as the greater visionary, and the greater ‘product’ guy. From his eye for simplicity, sharp attention to detail, dedication to a seamless user experience, all the way to his extraordinary intuition. Steve Jobs is the top dog of the modern age of entrepreneurs.

Steve’s impact is still felt to this day through the continuously evolving iPhone, Macbook Computer, iPad, and countless other Apple products that seem to get significantly better each year.


On that note, I will conclude our top 5 with a quote from the greatest entrepreneur of our age.

“Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it.” – Steve Jobs


Honourable Mention/Watch List: a High Potential, Fast Riser

Gary Vaynerchuk (WineLibrary, VaynerMedia) 

Never before have we seen an entrepreneur be able to cultivate a following as Gary Vaynerchuk has. Combining grade A salesmanship, a competitive work ethic, with selflessness and brute honesty; Gary Vaynerchuk has pioneered a new brand of entrepreneurship – the Social Media Influencer – Entrepreneur hybrid . Having been one of the first entrepreneurs to recognize the enormous potential of platforms like Facebook, Twitter, Uber, and Snapchat, Gary V has leveraged his sharp acumen of trends to buy into these platforms early on.

Not to mention, Gary V has built two massively successful companies in Wine Library and VaynerMedia. Wine Library was one of the first e-commerce businesses on the market in the late 90s and early 2000s. Having assumed control over the business from his father in 1998, Gary managed to turn the business from $3 million a year into a  $60 million a year business. By 2009 Gary had co-founded the social media focused digital agency, VaynerMedia (alongside brother AJ Vaynerchuk). VaynerMedia now works heavily with Fortune 500 companies.

With the cult-like following that Gary V currently has, and the pace that it grows each day, Gary Vaynerchuk is an entrepreneur of extremely high potential. Gary is an uberly passionate, competitive, and driven visionary who lives and breathes entrepreneurship.

With VaynerSports, VaynerRSE, and BraVe Ventures on the rise, do not be surprised if he slides up in to the top 5 in coming years.

Thanks for reading now go out and get it!

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