Angel investor Jay Vasantharajah on building his portfolio one day at a time

Jay Vasanthararajah is a Toronto-based entrepreneur and investor.

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 entrepreunership first, which allowed me to rapidly increase my cashflow (in comparison to my Deloitte salary). From there, I heavily reinvested profits into a diverse portoflio 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.

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