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Joe Carter, left, and Chris Samdeo, seen in 2013, teamed up to make the Joe Carter Classic Golf Tournament a success.

George Pimentel Photography

Entrepreneur Christopher Samdeo is used to taking risks.

The Trinidad native, who immigrated to Canada as a young teen, lived a hardscrabble life in Toronto's Jane and Finch neighbourhood after moving out of the house at age 15. At 18, he moved to the South of France to help a friend run a marketing company that promoted nightlife events. With some cash in his pocket, Mr. Samdeo returned to Toronto a year later to pursue a career in marketing and consulting.

After a brief internship at a boutique marketing firm, Mr. Samdeo started his own consulting business at age 22, where he lined up an all-star client, former Toronto Blue Jays player Joe Carter. Together, they teamed up to create the Joe Carter Classic Golf Tournament, one of the largest golf charity events in North America.

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Today, through his company Port of Spain Holdings Inc., the 29-year-old has a financial interest in a few marketing ventures including a 50-per-cent stake in The Power of Success, which promotes inspirational speakers such as Tony Robbins.

The Globe recently spoke with Mr. Samdeo about his investing style, which includes taking big risks on single stocks.

What was your first investment?

I was around 20 years old and a friend I was playing basketball with told me about Research In Motion and the BlackBerry. It was starting to gain traction so it was something I invested it, around 2006 [when the stock was around $25]. I sold most of it two years later [when the stock was around $120].

I remember at the time I went to sell and the bank said 'you've made a decent amount of money on this. Why do you want to sell? Imagine how much more you can make?" I said 'Listen, I remember being 15 years old and having no place to live. This is more than enough money. I'm fine with what I have.'

I thought it was the right time to get out. It turned out to be a good move.

What stocks do you own now?

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Tesla is my main holding, because I believe in what they're doing.

Coming from my background, not having a lot of capital, I believe that if you're going to commit to something, commit. Some people say you have to diversify. I believe that's for people with wealth that's inherited or are in a different position than someone who started really from the bottom and is working their way up. That's what makes us unique, to be able to build something from nothing. When you make a decision, you have to be all-in.

When I listen to people like [Tesla founder] Elon Musk, I see that being an entrepreneur is having the ability to take risks. Some of my friends who come from different circumstances don't understand that.

My background – coming from an environment of not always knowing where you're going to sleep or eat – those things make you into the person who you are and allow you to take more risk. I don't want to be conservative. I want to take risks.

What other investments are you involved in?

We are working on launching a new food and beverage company, but I can't disclose the details just yet. It's a chain of franchise restaurants. We [including Joe Carter] are looking at partnering with a grocery retail giant in the industry. That is something we're investing a lot in as well. It comes from my philosophy of betting the entire house.

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Do you have TFSAs or RRSPs?

No, I don't. It comes down to where I'm at in life. I'm more about going all-in on something, which is why I think I am able to work on the projects that I am.

What's the best investment decision you've made to date?

Investing in BlackBerry when I did. And it wasn't because an analyst told me it was a good investment. Sometimes, the most obvious investments are in our face. I figured if I was using it [the BlackBerry], why shouldn't everyone else?

What is your worst investment?

I invested into a friend's real estate deal when I was 23 years old. He needed some cash to close a project. It didn't happen. I lost $75,000 on that which, at the time, was a decent amount of money to lose. It was really stupid on my part, but a great learning experience.

This interview has been edited and condensed.

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