Angel Investor Jay Vasantharajah On Building His Portfolio One Day At A Time
Jay Vasanthararajah is a Toronto-based entrepreneur and investor.
Ara Ehamparam
Business Owner
Toronto, Canada
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I had the pleasure of chatting with Jay Vasantharajah about his business philosophies and more. Check it out below.

A bit about Jay from his website:

After narrowly escaping a brutal civil war in Sri Lanka, the Vasantharajah family was forced to flee the country, seeking refuge in Canada. The Canadian Dream started, with a newly claimed refugee status and no more than $30 to my family’s name.

Throughout my childhood, I carefully watched my father build small businesses from the ground up. From a pizza shop to a mechanic garage to an airport taxi service, I first learned business principles from my father, adopting his work ethic and immigrant hustle.

I decided to enroll in an accounting degree at the University of Guelph, fascinated by the language of business. Numbers came easy to me which allowed me to fast-track through my degree and get hired by the university as a Teacher Assistant (TA) for my own cohort.

While in university, I began developing and selling websites, sealing my first deal with a local accounting firm. Eventually, the student councils noticed my work and hired me to develop websites for them too. As my website business started to grow, it had to be put on hold as I was recruited by Deloitte to work in their downtown Toronto office. I graduated from The University of Guelph with High Distinction and jumped into the corporate world.

At Deloitte, I felt that I just wasn’t challenged enough, constantly dreaming of pursuing entrepreneurship. I would work at Deloitte throughout the week and drive cabs on weekends for my dad, in order to earn more money to fund my future business idea. After watching my father struggle with digital marketing solutions for his small business, I spotted an opportunity. I knew that there had to be a better way to scale digital marketing solutions for small business owners, like my father.

With that I started ClientFlo out of my condo which was the answer for small business owners to acquire new customers through pay-per-click (PPC) marketing. ClientFlo eventually evolved to manage campaigns and build tools for over 300 clients including InMode ($448m IPO in 2019 NASDAQ: INMD) and Cynosure (acquired by Hologic for $1.8bn in 2017). ClientFlo was awarded Top PPC Agency by Clutch in 2017, 2018, and 2019.

I was awarded the Young Entrepreneur of the Year 2018 by the Canadian Tamil Chamber of Commerce for my work at ClientFlo.

I have since gone on to start and invest in other business ventures as well, including PureFilters, a seven-figure eCommerce business with over 25,000 customers.

Today, I continue to grow my portfolio I and am actively looking to invest in/acquire more online businesses. I also invest in multi-family real estate in the Greater Toronto Area and manage a small portfolio.

Outside of entrepreneurship and investing, I also enjoy reading and traveling as much as possible!"


How did you go from working full-time at Deloitte to becoming a full-time investor? 

The short answer is, by reinvesting all my earnings. The long answer is, by jumping into entrepreneurship first, which allowed me to rapidly increase my cashflow (in comparison to my Deloitte salary). From there, I heavily reinvested profits into a diverse portfolio of real estate, stocks and private businesses. After a while, my passive cash flows from my portfolio basically covered my living expenses, which allowed me to focus full time on investing.

Love your break-down of the Wealth Roadmap - how did you come up with this?  

By reflecting on my path. It's not something that I planned in advance, but easy to see in hindsight. I've met a lot of entrepreneurs that jump straight to "Phase 2" and have gotten stuck there, and it inpired me to tweet/write about it. 

What does your typical day look like? 

Looking at various deals and investment opportunities. Working with my partners and team members to grow my portfolio companies, scaling and growing my eCommerce business, and reading/writing as much as I can.

In recent years, there’s been a glamourization in the start-up world around raising money and growth at any costs, how do you feel about this? 

Well, I guess it depends on what you want to do. If you want to build something that's going to change the world, that path makes sense. But if your goal is to build wealth for yourself, I really don't think it's the best way to do it. After I put out the Tweetstorm about the Wealth Roadmap, I had a ton of people reach out to me, thanking me and saying that they've previously been convinced that they needed to start the 'next big' thing in order to generate wealth...only to realize a few years later, that there are other (more effective) paths.

Have there been any investor opportunities that you had an opportunity to invest in and missed out on? 

A ton of missed opporunities, but I don't get hung up on it. Like Charlie Munger once said, "Someone will always be getting richer faster than you. This is not a tragedy." 

You’re an avid reader - what is your favourite book(s) you’ve read recently and why? 

The best book I read so far this year was 'The Man Who Solved The Market'. It's the story of Jim Simons and Renaissance Technologies, an algorithimic-based hedge fund that has the most impressive investing track record anyone has ever seen. It's an amazing story, with great insight into the world of algorithimic trading.

What is a new belief, behaviour or habit that has most improved your life? 

Constantly reminding myself that life is short. It will all be over soon, so I never wait to do something that I feel compelled to do. I draw inspiration from Steve Job's Stanford Speech, when he speaks about his near-encounters with death at the time. As well as Jeff Bezo's regret minization framework, highlighting why he quit his well-paying job to start Amazon.

Anecdotally, I see a lot of entrepreneurial stories like yours in the Tamil community.  Why do you think newcomers to a country turn to entrepreneurship as their chosen occupation? 

Leaving your home country to start a new life in a foreign place is probably one of the hardest and riskiest things anyone can do. Especially if you don't speak the language, have any money, or connections.  The risk of starting a business pales in comparison.  Also, many new comers really have no choice. Entrepreneurship might be the only way to grow wealth for their families.

Did you have any naysayers in your family or friend circle when you initially started down this path by choosing to leave Deloitte? 

Honestly, not really. Most people were supportive. My dad has always ran his own businesses so he understood my desire to do the same.

What is your favourite Tamil food (meal or dessert)? 

Kottu Rotti obviously!

What is your favourite Tamil movie? 

I've probably watched 3 Tamil movies in my life, one of which was Anniyan. I actually watched this in a movie theatre while I was in Sri Lanka. I still listen to the soundtrack today, so I will go with that one!


***If you want to connect with Jay, please reach out to him via his TC profile -***


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Ara Ehamparam
Business Owner |
Toronto,  Canada
Podcast Host: @TheTamilCreator Co-founder: @ContinyouCare Community Builder: @TamilCu...
Podcast Host: @TheTamilCreator Co-founder: @ContinyouCare Community Builder: @TamilCu...
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