The MapleMoney Show » How to Invest Your Money » Investing

Here’s Why Anyone Can Start Investing, with Keisha Bailey

Presented by Wealthsimple

Welcome to The MapleMoney Show, the podcast that helps Canadians improve their finances to create lasting financial freedom. I’m your host, Tom Drake, the founder of MapleMoney, where I’ve been writing about all things related to personal finance since 2009.

If you’re not currently investing your money, what’s preventing you from getting started? Are you worried about the risks involved? Do you lack the know-how, or are personal circumstances, including your current financial situation, getting in the way? My guest this week understands the barriers that stop people from learning to invest because she’s been there.

Keisha Bailey is the industry powerhouse behind the Profit Jumpstarter brand and is an experienced Financial Strategist, Investment Educator and Entrepreneur. She spent 17 years making money for wealthy individuals and corporations before shifting her expertise towards serving the up and coming generations of wealth builders. Keisha joins me on the show to explain how actions you take today will impact the kind of lifestyle you will have tomorrow.

Keisha works with people in underserved communities by teaching them about the importance of investing building wealth. And Keisha can relate, having come from humble beginnings herself. Early in our conversation, she shares some of the lessons she learned early on about money.

Keisha believes that wealth is built over generations. You spend your adult life building wealth, then you pass it on to the next generation, giving them the opportunity to pick up where you left off. But before someone can build wealth, they need to know how to start. And that is often the problem for people who lack the know how or have limiting beliefs regarding money.

In Keisha’s experience, many people believe they’re investing when they’re not. They don’t realize that the savings account paying .01% interest is not getting them ahead. The good news is that it’s easy to get started. Wealth is built in increments of $5 and $10 dollars, and every little bit counts.

Regardless of your background, if you know that you need to start investing but you’re not sure where to begin, I highly recommend that you listen to this episode!

Do you prefer to invest in socially responsible companies? If so, our sponsor Wealthsimple will help you build a portfolio that focuses on low carbon, cleantech, human rights, and the environment. To get started with Socially Responsible Investing, head over to Wealthsimple today!

Episode Summary

  • Keisha explains what led her to help others with investing
  • Wealth is built across the generations
  • A lot of people think they’re investing when they’re not
  • Reasons that people put off investing their money
  • Ways that mindset and lack of knowledge lead to inaction
  • How does one overcome a poverty mindset
  • Investing is created $5 or $10 at a time
  • With investing, the most important thing is to just get started
  • The superpower of coming from humble beginnings

Read transcript

If you’re not currently investing your money, what’s preventing you from getting started? Are you worried about the risks involved? Do you lack the “know how” or are personal circumstances, including your current financial situation, getting in the way? My guest this week understands the barriers that stop people from learning to invest because she’s been there. Keisha Bailey is the industry powerhouse behind the Profit Jump Starter brand and is an experienced financial strategist, investment educator and entrepreneur. She spent 17 years making money for wealthy individuals and corporations before shifting her expertise toward serving the up-and-coming generations of wealth builders. Keisha joins me on the show to explain how actions you take today will impact the kind of lifestyle you will have tomorrow. 


Welcome to the Maple Money Show, the podcast that helps Canadians improve their personal finances to create lasting financial freedom. Do you prefer to invest in socially responsible companies? If so, our sponsor, Wealthsimple, will help you build a portfolio that focuses on low carbon, clean tech, human rights and the environment. To get started with socially responsible investing, head over to today. Now, let’s chat with Keisha…


Tom: Hi Keisha. Welcome to the Maple Money Show. 


Keisha: Thanks so much for having me, Tom. I’m excited to be here. 


Tom: The reason I wanted to have you on is you’ve done a lot of work helping people learn the importance of investing, especially anyone in an underserved community that may not fully realize this is something they can do and that it’s maybe not as intimidating as they think it is. I had this problem myself way back in the late ’90s when I probably should have been investing. But back then it just seemed too complicated. There are all these different numbers around stocks and everything. I think it’s fair to say it was a lot harder to get started compared to the options now. Can we go back to the beginning with you? You were originally in Jamaica. How was that for you and how did you get interested in investing and helping others? 


Keisha: When I was in Jamaica, I did my undergrad in actual science. I always loved the numbers. I was kind of a nerd at heart, but my passion was also teaching people always. I’ve been teaching for as long as I can remember. One of my mentors really taught me about investing and showed me the power of money. I didn’t really understand that because I grew up in very humble beginnings in Jamaica. We didn’t have a lot. And so I didn’t think certain things were available to me like, who am I to be wealthy? I had never seen that before. But once I finished my degree and started working in banking, I really was lucky enough to have a manager that showed me that money is possible. And this is how you create wealth. Once I saw that, it kind of opened up my eyes to a whole new world where I could be wealthy. And me believing that was very inspiring for others who were in a very similar situation, who came from the same type of background. It was an eye-opener for all of us to say, “You can’t be wealthy. Let’s do this. Let’s actually learn investing. Let us put what we’ve learned to the test.” So I did a whole lot of schooling on finance and investing—a whole lot of education. I moved to Canada to get global education and experience. I went to the Ivy Business School and did my MBA there. That was very interesting. I was living in London, Ontario and coming from Kingston, Jamaica, it was quite the change in weather. But it was a really great experience because I was able to get a global, high-quality, education around finance. That was really helpful to kind of propel my understanding of investing and take me to that next level. After that, I worked in banking for a bit. I learned a bit more there and now I’m teaching people all I know. Teaching people they can turn the money they have into the money they want by investing. 


Tom: It’s interesting that you said it wasn’t around you when you were younger? You didn’t realize that this was something you could do? I think there’s a lot to that because you hear someone’s doing well because their parents did well. And, obviously, there could be wealth passed on. But there’s also knowledge passed on. If you don’t see it, where it’s an actual lesson—like seeing your parents investing or saving at least you’re noticing it and there’s something to mimic. 


Keisha: Yeah, so we didn’t have that at all. Growing up I didn’t even know that you had things to pass on. People would just die and that was it—end of story. Maybe passing on some clothes, but never any form of assets or anything like that. It was when I actually met my mentor and he really showed me that there are ways that you can pass on assets to future generations, that’s really how you want wealth to be built. You build, pass on to the next generation and then they build on top of that. But growing up, that was not an option for me. We didn’t talk about money a lot. We were very happy, but not with regard to being wealthy and having money and the wherewithal to just go out and spend. We did a lot with the little that we had. But me being here today, I’m living proof that it doesn’t matter where you started. No matter where you start in life, you can,  through learning the value of the skill of investing, you can make your life better. You can be wealthy. I believe everybody can be wealthy. I’ve helped so many people to achieve wealth also. My personal story is a living testament to that. Learn investing. Apply the knowledge, and it will change your life forever. 


Tom: You mentioned having a mentor. Can you tell me a bit about that? How did how did that come about? Did you seek someone out or did you just fall into something where you had someone to help you? 


Keisha: Well, I fell into it. I literally fell into it. It was my boss at the time. He was very interested in passing on more than just on-the-job knowledge. I started working with him when I was in my early 20s, right out of college. I was just really happy to have a job. I was on the desk there and he saw some of the habits I had and he would speak to me and say, “Well, you know, you may want to think about doing things this way…” He told me about the CFA exam, for example, and said, “You know, you may want to consider that as you’re building onto a career.” So, I started doing that, and going along that path I learned a lot about investing. He also taught me things like, instead of going out on a shopping spree, buy some stocks for yourself. Invest in your future “wealthy self.” That’s one of the main lessons he taught me. Actually, today impacts the kind of lifestyle you’ll have tomorrow. 


Tom: The people you’ve been working with, how do they look at finances at that point? When they first come in to see you, what’s their situation like? Is it a lot of people that feel they can’t invest or don’t even really understand what investing is? 


Keisha: A lot of people think they’re investing when they’re not. Many people think if their money is in an account, or invested at a bank, that they’re good. It’s only when they realize that their money is not growing and they’ve only added a dollar in the last year or so… They started with a $100 and they’re at $100.01, they think, what’s going on? Then they start getting a bit antsy because they start worrying about retirement—will I have enough because my money isn’t growing? What should I do? My clients typically are searching for me before they find because they are not happy with the performance they’re getting with their existing money. They know they need to be doing something better but they just have no idea what to do. That’s where I come in to help them with that education. How do we reallocate what you are doing? How do we make it better? They become more empowered. Through education, they feel liberated. They feel, “Yes, I can do this. I understand my money. I understand what to do. I can take control and have that talk with my advisor. I can ask them for what works for me, what is more suitable for me.” That empowerment now brings activation where they say, “I’m going to do this. I’m going to take action to make my money situation better!” 


Tom: Maybe it’s not the people that come to you directly, because at this point, they’ve probably gotten over a hump already if they’re coming to see you, but with other people you’ve talked with, what is the holdup in investing? Is it all about education or is it a mindset thing? Where’s that roadblock that’s stopping people from getting started? 


Keisha: I’d say it’s a little bit of both. When we think about the mindset it is, “Can I be wealthy? Should I be wealthy? Money is the root of all evil. Should I have it? I see people being happy with money, but I also see people who are sad because of money. What should I do?” That quandary right there creates inaction. Another thing I see with mindset is, “Do I really want to shake things up? I’m okay now, I’m comfortable. I can pay my bills. But if anything happens unexpected, then I have a problem. But outside of that I’m okay so I’ll just not let anything unexpected happen,” and that creates a little problem of inaction. And then there is the know-how where they say, “I don’t know how to open an account. What should I do? They say, go on the website, but where’s the website? What buttons do I click? I have no idea. Should I have a TFSA or RRSP? Do I need a mutual fund? Should I be buying stocks? I have no clue…” Because of that, we have a ton of information out there. People feel there’s a lot (of information). How do I navigate to all this information so I can make the right decision for me? My advisors saying, “Buy this mutual fund, but do I need it? Is this the one I should have?” They don’t know. And because of that, people tend to just play it safe, “My advisor works at a bank. He knows what to do more than I do so I’m just going to go with whatever he says.” Or they check out what’s on YouTube or what their friends are saying about the latest investment. There is lots of trial and error going on. Lots of, “Should I be wealthy? Can I be wealthy? Do I deserve to be wealthy?” Especially within the underserved community where they say, “I’ve come from so little. I’m used to having a little. I can’t even think about life, having a lot. What does that look like for me? Will I still have the same friends? Are people going to end with me because I’m doing better now? Maybe, to keep my little circle and little posse of friends, let me just stick to what I’m doing now because we’re all broke, but we’re happy together being broke.”  


Tom: How does someone get out of a situation like? If someone’s broke and everyone around them is broke, it’s probably more than just investing. I assume you need to come up with some extra income somehow before you can even invest. Or do you just do as little as you can do because it’s got to be hard to convince someone to invest if they’re still trying to meet the minimum of rent, food and everything? 


Keisha: It’s hard for them to even think that there is a better way to life than what they’re doing right now because they’re doing the best they can with what they have. I don’t necessarily come in and say, “Hey, you need to invest right now.” I say, “Let’s see what minor changes we can start making.” Maybe it’s just putting away an extra five or ten dollars a month for that rainy day? Maybe it starts there because what we want to do is cultivate the right type of money habits. We want to develop consistency. We want to develop that habit of building something. And so we start small. We start with what you have and turn it into what you want. Put away some money each week. Put that money into a bank account, a savings account to get in the habit of regular saving. Then we slowly work our way up to, “Okay, let’s take that money that’s been saved and put it into some form of investment.” It may be a mutual fund at first or an index fund. We do that and then work our way up to stock picking and creating that portfolio. But there’s no money made on the sidelines. You’re always better starting than kind of just watching how things will play out. You’re better taking action. That’s the route I always encourage persons to take. Start with what you have, regardless of how large it is or how small it is. It’s what you have, that’s what you’ve got so you’ve got to make the most of it. Interestingly, one of the unique things about underserved communities is that when you start thriving, there is a great chance that you build animosity among your peers. People start hating on you, saying, “Oh, but she’s thriving. What’s she doing? Why is she not telling all of us what she’s doing?” And especially in some communities, you can become a target. You can become a target of robbery, a target of murder and other crimes because you’re living your best life. Another person is suffering and struggling, and they become envious. They want to take you out. So the risks are real. It’s very nuanced. It’s totally a different situation when working with underserved communities and helping persons to build. You really do have to understand the intricacies. We do a lot of, your money is your money. What we’re doing doesn’t need to concern anyone else. Let’s work together, individually, to turn the money you have into the money you want. We don’t need to broadcast what we’re doing to anyone. We’re making your life better. If you choose to pay it forward, which I encourage persons to do, be that example. Let’s try and find a positive spin on your wealth creation so it can inspire someone else. 


Tom: I’ve got to admit I never even thought of if you’re in the wrong neighborhood that you start doing well and it starts becoming obvious that there’s a real risk to that. I never thought of that. People who are doing best are actually the people that don’t really flaunt it anyways. They’re not spending their money on expensive cars and everything. You can certainly build wealth without showing it because as long as someone can’t see your investment portfolio, they don’t need to really know. 


Keisha: Right, yes. 


Tom: It’s interesting, though. In one way it would be nice if someone’s doing well in a certain community that they could share some of that information and encourage others. But at the same time, it seems like it could also be worth keeping it to yourself and not really tell anyone. Where’s the line there? Maybe just a small circle of friends and family? Just try to encourage them and bring others up with you? 


Keisha: Well, it’s a bit more than that. I like saying to my clients and generally just everyone “Money talks, wealth whispers,” right? We don’t want to be alone with our wealth and we don’t want to be flashy. We don’t want to be bragging on someone. But at the same time, you’re changing lifestyles. Your changing mindset (that comes from you gradually building wealth) should be inspirational to the next person. They should see you moving differently and not flaunting on them and showing off. You are making changes in your habits. They see that. They see that the results are paying off for you and then you become an inspiration to them. You can show them what you’re doing, right? Paying it forward. That’s a more constructive way. So we never, ever brag. We want to encourage persons. We’re building wealth and inspiring others around us to do the same. 


Tom: I like that because if it’s done the right way, it’s definitely an encouraging thing. It’s not bragging. It’s trying to convince others, whoever this person is, to pick up on it as well. If you see something working, you kind of want to share it with people you know and help everyone out. 


Keisha: Exactly. 


Tom: Another thing you touched on earlier that I just want to ask about was the idea of fear. When someone starts investing, you said sometimes they just don’t want to change what they’re doing, which is one side of it. But is it also just the unrealistic risk tolerance? Are they thinking they could lose all their money in the stock market? Is that kind of what you’re seeing?


Keisha: A lot of it is, “I don’t want to be poor. I’m already poor. I can’t afford to be poorer.” 


Tom: Yeah, you don’t want to lose the money you have. 


Keisha: Yeah, “The little money I have, I’m not putting it in the stock market. I’ve heard about so many people that lost all their money in the stock market. It’s a scary place to be. I don’t want to be there.” What I say in that instance is, what did they invest in? What did they buy? Did they tell you? But they don’t really know. They just know they lost their money. Ask them—what did you buy? Because most times you’ll find that they bought the latest craze, the latest meme stock, the latest penny stock, and that’s why they lost their money. If you are following a disciplined investment blueprint, which is what is needed to create wealth, you are increasing your chances of success. If you’re kind of here and there and everywhere, of course, you’re going to lose money because you don’t know what you’re doing. Take the time to educate yourself on this investing blueprint. Learn what you need to do and then start implementing it. But for sure, you’re losing money—and you should because you don’t know what you’re doing. 


Tom: Another thing you mentioned was when it comes to getting people started, is to just get started even if it’s just a few dollars a month just to build up that habit. I really like that because it’s not something you should look at saying, “Oh, I’m only putting $10 a month away. That’s not going to add up.” In a way, it’s not going to. Sure, it’s going to compound but it’s not going to be that impressive. But it’s the habit that you’re building up. It’s moving money from this account to this account and at least building that up to the point that they can start to see what they’re doing. It becomes something they’re used to doing. Maybe they get a raise where they can put a little bit more in. I really like the habit I do. 


Keisha: Yeah, and it comes with many things in life. Like going to the gym—you go in, maybe you’re just doing the treadmill for a month or two because it’s really new to you. Then you move from the treadmill, go on the elliptical. And one day we decide to pick up some five pound weights. Slowly, getting in there until we’re at the point where we’re rich. That consistency, where we kind of keep leveling up along the way, it’s got to pay off. This is true for everything we do in life. Consistency is what pays. And getting started, for sure. 


Tom: I also like that at an early stage, you’re not too concerned what they’re doing with it, if it’s a savings account or a mutual fund. I’ve mentioned in the past that my first real regular investment was a mutual fund that had a high management expense ratio. I was paying a lot of extra fees. I’ve kind of beat up on that fund a few times for not being a great investment. But ultimately, I had more money there than I would have if I had hadn’t done anything. If I instead said I was just going to maybe keep that money in my account or maybe spend it, it would have been different. But this money was locked in an RRSP. It wasn’t a great investment, but at least it was a regular contribution that kept building up over a few years. 


Keisha: You can always beat zero. That’s also a very low bar but you can always beat zero. Doing nothing, sitting on the sidelines, keeping your money under a mattress, nothing’s  happening. You will always be where you are. Even putting the money into a savings account, yes, interest rates are low. Yes, you’re earning at smaller amount in a savings account but you’re earning something you didn’t have to work for. 


Tom: Even if you look at inflation nowadays, you’re probably technically losing some money. But at least your contributions are doing something as opposed to having no contributions and spending all that money. I also think that no matter where someone is financially, if you the pay-yourself-first thing where you’re putting something away, you’ll figure out the rest. Maybe you skip one of the more expensive things at the grocery store because you’ve already put some money aside for investments, but it tends to work out. 


Keisha: It always does. You find a way to make ends meet. The thing with coming from really humble beginnings is that one of your most valuable skill sets is making ends meet, right? You have a master’s degree in getting by each month. So switching it around a bit and paying yourself first, you will make do with what’s remaining. We just need to make that little shift—pay ourselves first. Whatever is left, you will find a way to make it work because you’ve always done it. That’s what you know how to do. It’s not a big move, it’s not a big step. It’s not a big change. We’re just starting to make these tiny moves, create these positive money habits and it’s going to reward us in the future, for sure. 


Tom: I like how you look at that, too. It really is a skill. If you’re figuring out how to always get by, people should give themselves more credit for that. That is the skill that’s going to help them in how they do in the future. 


Keisha: Yes, one thing for sure, instinct is all the way up. Being creative and able to see the positive, exciting things (because you don’t really have much positivity around you), are benefits. These are things that we can look to, things that we can hold onto as we build wealth. 


Tom: So you came from Jamaica to Canada. What was that like for you? I’ve sometimes looked at going to other countries thinking, do I want to live here or are there? Do I want to some warmer weather—where Jamaica would be great. But I always think it’s maybe too much of a culture shock. But even in a money sense, I feel very comfortable in Canada knowing what RRSPs and TFSAs are. You’re more into the financial field so I assume it wasn’t so bad for you, but just in general— 


Keisha: It was still hard. It was hard.


Tom: It a shock to try to line things up and figure out how things work here, right? 


Keisha: Right, because a lot of these types of accounts don’t exist in Jamaica. So it was not only translating, it was finding out what this account does. What’s the purpose of this? How do I do this? And opening the account online where I don’t have to go into a branch somewhere. Which one do I do, a TFSA, RRSP, contribution limits, CRA website, mail in the letter—what is all of that? So figuring that out took a little bit of time because with everything, there’s a little nugget in it. There’s a little secret sauce of, “Hey, you’ve got to do this type of way,” and everybody does it differently. Everybody has their own way of doing it. But uniquely, when you’re an immigrant, one of the main things you have to factor in is, I need to take care of my family back home. So yeah, TFSA and RRSP but family back home as well. How do I navigate all of these? I may have some money back home. I may have some money here. How do I look at them in their entirety? And a lot of us, as immigrants, also think, “Do I retire back home because I want to be back there to spend my time? I’ve worked so hard. I want to just retire back in my whole country. How do I set myself up to do that because I already made one transition coming to Canada so how do I transition back?” There is a lot of thinking, lots going on. But I think I’ve figured it out fairly well. A lot of my friends are from Diaspora. There are a lot of immigrants who’ve come here as well, and what really resonates with them when they work with me is that I understand both worlds. We can figure out what’s the right mix, the optimal mix, and I educate them along that way. 


Tom: I often have people contact me through the blog where they’ve either immigrated to Canada or they’re looking at it, and often it’s very basic questions because it’s brand new to them. And possibly, depending on where they’re immigrant from, just the idea of even having money to care about things like investing and stuff might be new to them now that they’re in Canada. It’s very complicated. It’s interesting that you brought up the idea of helping out family back home. 


Keisha: Yes, they must. 


Tom: Yeah, yeah. Yeah, I’ve heard that and I never really fully thought of it as being a big part of the financial plan. But yeah, you’re not necessarily looking to lock up all your money in a RRSP if you’re also trying to help out others. 


Keisha: Yeah. And how do they access it if anything happens to you? There is lots going on there. And they think about wills, “Do I need a will back home? Do I need a will in Canada? How do I do all of that? Can my family travel here?” There are lots of nuances, lots of things to kind of figure out. So yeah, it’s very different. 


Tom: Personally, I was able to do things in stages over a decade or two. I’m focusing on a career and now I’m going to start investing and now I’m going to look at retirement. But if someone enters this country as an adult, everything’s day one. You have to kind of figure it all out at once. 


Keisha: Yeah, it’s like, “ Alright, you’re here, living accounts—heloc accounts, credit cards, debit cards, RRSP, TFSA. But I hear 401Ks are not here, they’re in the US. 


Tom: Yes. Is there anything else you’d like to share, if someone’s trying to figure this all out? If they’re considering investing and they just haven’t made the leap into it yet, what would you want to say to them? 


Keisha: For anyone like that, you definitely can do it. I am living proof it can be done. Education is key, so arm yourself with knowledge. Find the right set of people to also give you advice. Someone to give you tips and tricks that are relevant to you. Depending on the country you come from, each group of immigrants is somewhat unique so paying attention to that and being in the right type of networks and circles to get that information is critical. But once you really find that sort of thing where you educate yourself, you are fine. Migrating opens up a lot of doors for you, lots of opportunities, so take advantage of that. Not everyone can be an immigrant. Not everyone who applies to come to our country is just automatically granted residency so take advantage of this opportunity and use it to build wealth for you and for your family back home, and for the future generations to come. 


Tom: Great. Well, thanks for being on the show. Can you let people know where they can find you online? 


Keisha: My website is We’re on AIG, Profit Jump Starter. You can email me also at [email protected] I’m on Twitter, Profit Jump Starter. And on Facebook, Profit Jump Starter.  


Tom: Great. Thanks for being on the show. 


Keisha: It was amazing being here. Thanks for having me. 


Thank you, Keisha, for sharing your personal story and showing us how through investing, you can make your life better. You can find the show notes for this episode at As usual, if you have a moment, head over to our YouTube channel and subscribe there. We’ll be getting back to releasing never-before-seen content soon. Either search for Maple Money or go to and subscribe today. I look forward to seeing back here next week when Jessi Fearon joins us to share her story about turning her financial situation around, from struggling to pay the bills to debt-free. See you next week! 

No matter where you start in life you can, through learning the value and the skill of investing, you can make your life better, you can be wealthy. I believe everyone can be wealthy - Keisha Bailey Click to Tweet