From growing up in August Town, Jamaica with a single mother to managing over CAD$100 billion at one of Canada’s largest banks to running her own business, Keshia Bailey has always been on a mission to help people build wealth.

Speaking on Taking Stock with Kalilah Reynolds, Bailey, the Founder and CEO of Profit Jumpstarter, said her mother instilled in her early the importance of education.

“Her main thing was education because she worked with the University. She always used to tell us to study, study, study,” she said.

She said that growing up managing money and creating generational wealth was never a topic of conversation amongst her family.

“I didnt grow with money. We didn’t talk about money because we didn’t have any money to talk about,” she revealed.

However, after she received her degree in Actuarial Science from the University of the West Indies, Bailey went to work in the investment banking sector, where she absorbed as much information and lessons as possible.

“But it was when I started working in the investment space is when I realised there is a way to build wealth,” she said. She spent the next several years managing pension funds for large institutions and honing her skills in investments.

Some lessons, Bailey said, she had to learn the hard way. The Profit Jumpstarter CEO said she was one of the investors who lost money during the infamous Olint scandal in 2010.

“That was a painful lesson for me about doing your due diligence and knowing where your money is going,” she revealed.

She later achieved her Master’s in Business Administration at the Ivy School of Business in Canada.

“I saw that money creates possibilities and I wanted those opportunities. So, I decided to study as hard as I could and applied myself so that I would learn everything I need to,” she said.

After graduating with distinction from the Ivy School of Business, Bailey began working in a Canadian bank, managing 258 global clients with portfolios totalling CAD$100 billion. 

She admitted that she was plagued with self-doubt, often wondering if a black woman from a tiny island belonged in this majority male-dominated industry.

However, she excelled, growing her clients’ portfolios by at least 10% annually.

She decided to leap into entrepreneurship after losing the zeal for working for large institutional investors.

“I wasn’t feeling the impact anymore because it just felt like I was making rich people richer. And there wasn’t anyone around me that looked like me and I said to myself that there will never be unless I did something to help,” she said.

“What about the young Keisha, who is gonna show her what to do and say look there are opportunities for you,” she said.

She started her Profit Jumpstarter business in 2021, teaching and coaching individuals about the stock market and different types of investments and giving them the tools to make the best decision for themselves and their money.

“My goal is to make wealth building easy, so people feel like they can do it and feel like they can be empowered to take action,” she said.

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