Keisha Bailey on Carry On Friends

Keisha Bailey: Making Wealth Building Accessible

Born and raised in Jamaica, Keisha now runs a boutique investment education firm. She discusses the importance of wealth management, how we can let our money work for us, and her work through Profit Jumpstarter

First, we dive into a bit of Keisha’s story. We learn how she went from managing over $100 billion dollars as a portfolio manager, to now running Profit Jumpstarter. She also talks about growing up poor with a single mother who was big on education. It was Keisha’s passion for learning that led her to pursue her MBA in Canada, and eventually settle there. 

Profit Jumpstarter is a company that helps people to turn the money they have into the money they want. Keisha is big on financial empowerment around education, and getting people to realize that access to wealth is possible. Her goal is to make wealth management readily accessible to her community.

She explains the different services they offer to meet clients’ needs depending on their current financial situation. Keisha shares a bit of the process they go through to ensure that the right strategies are in place to make clients wealthy. 

In this episode we address the cultural nuances around money management. She points out that one of the biggest challenges people face when they first come to her is a scarcity mindset. However, through working with her team, clients are able to move past this. 

Throughout this chat, Keisha provides us with some helpful tips and tricks to improve our own money management. She teaches us how to apply the 50/30/20 rule to ensure that we set aside money for saving and investing. Additionally, she gives guidance on how to begin investing. Keisha emphasizes that wealth creation is not a race, but instead we must focus on consistency. 

As we wrap up, Keisha encourages us to challenge ourselves now. She believes that what got us to where we are, won’t get us to the next level.

To grow your money to $50,000 check out the Money Blueprint Course, and to become a VIP private client send an email to

Key Points

  • Keisha Bailey discusses the importance of wealth management and how we can let our money work for us.
  • Profit Jumpstarter is Keisha’s company that helps people to turn the money they have into the money they want.
  • We address cultural nuances and challenges around money management.
  • Keisha shares tips such as the 50/30/20 rule and how to begin investing.
  • The first habit to develop in wealth creation is consistency.

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Kerry-Ann Reid-Brown is Founder & host of Carry On Friends one of the first podcasts dedicated to the Caribbean American Experience. She is leading the way for Caribbean Podcast as the founder of Breadfruit Media, the first Caribbean podcast production company; and founder of the Caribbean Podcast Directory a place to discover podcasts by people of Caribbean Heritage.