REIG Jessilyn | Money Mindset


Tony Robbins once said that success is 20% strategy and 80% psychology. This has never been more true than in the investing game, where almost everything depends on your money mindset. Taking that to heart in the way she helps women is Jessilyn Persson, a founding member of Legacy Global, a full-time investment banker, real estate investor, speaker, educator, and coach for women. In this episode, she joins Monick Halm to share how to best position our money mindset to invest. She takes us across her career journey as well as her work with joint venture matchmakers and distressed properties. Jessilyn also shares some of the lessons she learned, the mistakes she overcame, and the keys to her success.

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The Money Mindset To Investing Success With Jessilyn Persson

I’m super excited to have with me Jessilyn Persson who has been investing in real estate since 2009. She has fifteen-plus years in the corporate public sector. She left a highly successful career as a project management professional and became one of the founding members of Legacy Global. She works as a full-time investment banker, real estate investor, speaker, educator and a coach for women, especially around money mindset, which is so important. We’re going to definitely talk about that.

As Tony Robbins says, success is 20% strategy, 80% psychology. Eighty percent of our success is what happens in our brains. When you’re doing this investing game, then your money mindset, your ability to receive funds is everything. We’ll talk about that. Also, with Jessilyn and using her strong powers of leadership expertise in financial education and real estate investing, she educates and supports women to create a vision and plan that can transform their lives. She says, “I want women to have a life full of abundance that starts with their relationship to money, wealth and worth.” We both share a heart to help women. I’m super excited to have her with us. Welcome, Jessilyn.

Thank you, Monick. I’m grateful to be here. I thank you for bringing me onto your show.

It is my pleasure. To start at the beginning, how did you get started in real estate investing?

Money Mindset: When you get some of those hard knocks in real estate, you’ll quit if you don’t have the perseverance and don’t know how to deal with them.


In 2009, I was working in the marketing department for a real estate brokerage and a client brought in a condo to sell and she couldn’t sell it. She kept dropping the price to the point where I went to my boyfriend at the time, who is now my husband and said, “We should buy this.” I didn’t even know why I thought it’s a good idea. We went, looked at it and we bought it. From there, after we got the keys, I was so excited. I felt like I own real estate. It’s not like I don’t own my own home, but it was not the same. I knew this was supposed to be long-term wealth and building up assets. I decided at that time in my head that every two years I would buy another property. From there on, we did until probably 2016, where my husband said, “I’m managing too much,” because he’s a property manager. We realized shortly into our real estate careers that I was not meant for that role.

We have two kids. We were both working full-time. He’s like, “Enough,” and I was like, “I have to support this. I don’t like it.” What I did is I did some research when he was gone to look at one of our properties out of our province. I found the largest real estate investment network we have here in Canada. I signed him up, figuring he would meet people who were like-minded and understand maybe the excitement and what it can do for you a little better. It worked. He was in there. Probably by about the sixth month that he was in that network, we turned around and bought two more properties in less than twelve months. It’s the mind shift. Nothing here changed in terms of his workload. It was how he was with dealing it and how he was managing his time. That’s how I got into it and how we progressed to where we did.

I want to rewind a bit because a lot of people, if you had a home and he decided, “We should buy this. I’m going to rent it out,” and a lot of people, especially women, we don’t just come up with that. A lot of people don’t even think to do it. I know I completely fell into real estate by accident. What was it that made you go, “I want to be an investor. I want to buy this and rent it out. Let it make me money?” Where did you learn that? How did you come up with that?

I’ve always had a passion for real estate. As I grew through my career, I was approached to be a realtor, be a mortgage broker, and I was like, “No, thank you. I’m not interested.” I still love the idea of real estate and I couldn’t figure out why. As I became more knowledgeable, I was like, “All the wealthy have real estate in their portfolio somewhere, somehow.” It just went and clicked. If you want to grow your wealth for 20, 30 years down the road, this is a good way, especially when you’re young enough to be able to manage it all on your own and figure out the bumps along the way. That’s how it sunk in for me. Once the first one happened, it was contagious.

When you realize the flip side of abundance, the money will be everywhere, and some people will want to invest it and partner with you. Share on X

Also going back to your story about your husband having that mindset shift when he went through it, and this might be a question for him, what do you think caused the shift? I have ideas based on your story but I’d love to know what you think caused that shift for him.

There were a couple of things. Part of it was he was supporting my dream. He wasn’t maybe fully on board with the vision I saw of why we should own X amount of properties and what to do. When he was with others, which probably appreciate in this room with several hundred people, it’s dominantly men, so they’re maybe saying it differently than I did. I got him to realize he was thinking small, but like, “This is enough.

When you run the numbers, if you want to leave your job or anything should happen, it’s not. If you want to build wealth, especially if it’s something you want to pass on to your kids, what we had was not. He shifted slightly there. He realized that he needs to think bigger. When he did, he was like, “I’ll just get a process in place.” We’ve lined it up. If we ever need to bring in a property manager, we’re prepared 100%. Here are the files, here’s what it is. We’ve even put it into our budget for rent and stuff.

Our renters pay as if we have a property manager right now because sometimes we know we will step out of that role. That was part of it, for sure. Being surrounded by like-minded people who a lot of them had much bigger portfolios. When you’re sitting with those people, you’re intimidated. “How do they do that? I want to know.” They were very giving of information in those rooms. He got wowed by it as well to the point where we learned enough and stayed in it long enough to give back to the new people in the room.

That is the value of events. That’s the value of network. That’s why I created Real Estate Investor Goddesses in large part because I know the value of network in real estate and having people that are further along than you that can inspire you, show you the way, but also as you are saying, most of those rooms are all men. It’d be nice if there was a room like that with all women. That’s what we created here because it was like, “This is amazing. It’s awesome for women. We’re so good at it.” It’s not like most of the places you go. There’s so much value in that. Tell us a little bit more about what you’re currently working on. Before we started, you were sharing, but share again what are the types of deals that you’re doing now. What are your investments like now?

We do have a mixed portfolio of condos and what we call suite of houses, what you would refer to as a duplex. We’ll buy a home and then we’ll get the basement, suite it and then rent both the up and downstairs. As we grew our portfolio, we realize some of the purchases we weren’t maybe the best, so we are slowly getting out of condos and single-family homes. We sold a couple in 2020. We want to focus. If we’re going to tangibly hold these properties, we want just the duplexes properties or larger units. It makes more sense for us when you run the numbers and when you have to manage it to show up at a property online versus the property of say 4 or 20 units. That is one and then we’re also partners with Legacy Global, which it’s a combination of education on my coaching on money mindset. Also, we offer options in real estate there. We have the Distressed Property Fund and then we have the Joint Venture Matchmaker.

REIG Jessilyn | Money Mindset

Money Mindset: You can find the investors and the renters out there, but finding the properties that are the right deal is the hardest.


Tell us a little bit more about each of those. What’s the Joint Venture Matchmaker and Distressed Property Fund?

The Distressed Property Fund is we go and buy properties that are distressed and it’s a cash offer. For the owner who’s selling it, they don’t have to do anything with realtors, list it or anything. We just make them a cash offer. If they accept it, we take it off their hands right away. We do what we have to do with it. Does it need renos? Sometimes we reno and sell, sometimes we reno and rent. People can invest in it because we don’t buy one. We have a fund so that we have the money when it’s time for a property to come up to be able to buy it straight out. That’s the distressed property one.

The Joint Venture Matchmaker, there are a lot of people we finally run into that either have money and they want to invest but don’t want to do the work or can do the work but don’t have the money to invest. We match them up so they can create the working relationship and the deal to whether they’re doing flips or buy and hold. It’s all depending on the partners that we’re matching up, but it’s a singular place for people to start to go to find what they’re looking for.

I want to switch gears a little bit and ask my favorite question because I believe that we get so much more wisdom and gold out of things when it doesn’t work out than when it does. What was your biggest mistake and what did you learn from it?

Our biggest mistake was a combination of buying condos cheap because they were cheap. It had nothing to do with the location, whether it was rentable, whether it needed renos. When doing that, buying blindly, we had no metrics. Let’s be honest, we didn’t know what we’re doing. We just do it. We’re going to buy it if it looks like a great deal. We did that a couple of times before we started to learn a little bit of our lesson, big condo fees come or assessments come, even things you don’t know.

That’s why I’m not the biggest fan of condos in the first place.

That’s why we’re done. That was our biggest one, but we don’t look at it as a loss by any stretch. We look at it as education. We very likely would not have learned it as well if we were just reading a book, and we still made money. It’s not like we didn’t make money. We held on to them and rented them out. They were just not a good moneymaker. You cover your cost thing and that’s not the idea of real estate. It’s cashflow and pay down.

I always say that you’re going to get your education either at the frontend or you’ll get it at the end, or in the middle. Either way, you’re going to educate yourself. It tends to be less painful if you get the education at the frontend. That’s tuition into the university life and it’s not a wasted opportunity if you learn the lesson. You definitely got the lesson. There might have been other ways in which you can get that lesson but that was good. What are you most proud of?

I am most proud of investing with my spouse. I say that because it’s not easy, especially upfront when you’re both trying to figure it out. I also realized when I started going to those rooms with the investors, that’s the number one question my husband and I always got asked, “How do you get your partner on board? How do you get your partner involved,” especially when you have different personalities enough to take on different components of the deal. I’ve mentioned my husband is in property management, and he does numbers as well. I’m really not the number cruncher, but then I’m the one who loves looking at the real estate. I’ll go look at a deal with the realtor, the lawyer, get the contractors in, more of the business side was me. For us, it worked out to pair together. Upfront, we didn’t know our roles, so when I tried to do property management, we learned our roles. I would just get so emotional when things were like, “What do you mean they didn’t pay the rent?” He says, “Maybe you shouldn’t be involved in this part.”

I work with my husband too. Figuring out those roles is a big part of it. At the beginning, we were both trying to do everything, the same things. Both of us are doing everything, and it’s stepping on each other’s toes, and that we had to figure out, “This is what you do best, that’s your lane. This is what I do best, this is my lane,” or “This is what I might even do best. This is what I prefer. That’s what I’m best at and this is what you’re best at.” We split those lanes. It makes us so much better. It is a joy when you do have your partner on board, and you can work together and you’re building wealth and a legacy for your family together. I think it’s the best. To what do you attribute your success?

It’s a combination of willing to take the risk. To buy something on the blue, it was risky. That’s not the only thing. The partnerships we’ve created were also investments and risky. Perseverance, when you get some of those hard knocks in real estate, you’ll quit. You figure it out, you learn how to deal with it. That’s anything from bad rental to renters who leave you to dealing with the courts. It’s there. If you can learn it and get past it, you’ll come out the other end much more successfully. You’ll appreciate what you have out more because you know what it took to get you there and to get you through it.

You have a great abundance mindset, money mindset. I know you were at work with other women helping them with that piece. What advice do you have for women around that money mindset piece?

I say abundance and I was there. I had the poverty mentality, the survival. I got to work and save. When you realize the flipside of abundance, and money’s everywhere, and there are people who want to invest it, and partner with you, you start to see it. It’s almost you attract it. It comes your way. That would be one thing, shift your mind into abundance, and you’ll start to see it, but also own your worth. A lot of women, I think we struggle with our self-worth, and you can do it. Anyone can do this. It’s really not that hard. You can partner with these people who have millions. If you want to do you work, you can. Trust yourself, step off the ledge, and it becomes available.

That’s definitely something that I realized too. As I was bringing groups of investors together to purchase properties, I thought like, “How do I find the money? Who’s going to want to give me money to invest in properties?” I realized there’s so much there. I used to think the money was the issue. It’s like, “The money is not there.” There is so much money, it’s just finding the appropriate deals that make the most sense. That’s the bigger challenge. I never would have thought that at the beginning. Having recognized that it’s not about you, that’s what shifted things for me. It’s like, “They’re not giving me money.” This is an opportunity they’re investing in, and I’m helping them take advantage of this opportunity and allowing their money to grow. For me, it was about not making it about myself at all. It’s allowing opportunity. You buy a property, you give somebody an opportunity to rent. They have at home or you give somebody an opportunity to invest, but when it’s about others, that was what helped me have the shift.

It puts pressure on you because you have to perform. You’re providing a home and you’re providing an investment. You want to keep to that integrity, honoring what you can do, but then it also feels good when you’re helping them build their investment and you’re providing a home for these people. You’re supporting other people in their adventures in life and their goals, and you’re helping fulfill what may not have happened if you hadn’t stepped into the role of finding the properties, putting people in homes and just digging. As you said, “The hardest thing is finding the properties.” You can find the investors, you can find the renters. They are out there. It’s finding the properties that are the right deal.

Real estate mistakes aren't cheap. Invest in a mentor who will guide you through. Share on X

You need to learn all of it. That becomes the more challenging part. One last question before we go into our famed end of show trinity, which is a brag of gratitude and desire. What do you wish you’d known at the beginning that you now know?

I wish I’d known to seek a mentor who had been there first, like 100%. I find it interesting I didn’t because I’ve found mentors in other parts of my career. When I started project management, I found a mentor who was a senior mentor to help me understand the whole lingo, what it means, what you do, and I excelled in that part of my career. I don’t know why I didn’t do it with real estate. Maybe I ought to say I didn’t know anyone in my world who did it either. I didn’t think to go Google networking for real estate back at the time when we first invested.

To help with that education on the frontend.

Even if you pay for it. I was fortunate to have a lot of mentors who just mentored me because they wanted to, but then there are the coaches that you pay. Whatever you’re paying them is saving you thousands on the other side from the mistakes. Real estate mistakes aren’t cheap. If you invest in a mentor who will guide you through why you should or should not do, the things you’re considering, they are worth their weight in gold.

Before we get into the trinity, Jessilyn, if people want to find out more about you what you do, how can they do that?

They can go to my website. It’s

Time for our trinity. First is the brag. What is one thing you’re celebrating right now? What’s your brag?

I’m celebrating the flexibility that my husband and I now have because our goal was to be able to work anywhere in the world. Back then, it seemed it was never going to happen. In mid-2020, my husband left his day job. I always almost been mobile because I was always contracting, but neither of us are tied to offices, bosses or locations. That was our goal and we achieved it.

What’s one thing you’re grateful for?

I’m grateful for my husband for doing the hard work. Let’s be honest, when you got to run out to a call from a renter at random times, I’m not sure I would have been too happy about that. He fields the calls, he takes the late nights, he runs the numbers. I say I got the fun job, the pretty job. I’m grateful that he took it on because it’s not like it was necessarily a skillset he had upfront. He was a web designer, by trade, by day. It’s not like he suddenly knew how to manage people and houses. I’m super grateful he not only took it on, but he learned it very well. He went and he actually studied the laws, the books, what to do, what you can’t do. He found a system where renters, we look at them as our clients. We take really good care of them and we thank them when we give them gifts because, without them, we wouldn’t be able to do what we do. He’s good at that kind of relationship as well.

What’s one thing you desire?

I desire to have an impact on as many women as I can reach for as long as I can reach them to help them understand whether it be the money mindset or real estate. I’ll help them get that next level up from where they are and help them realize they too can have it all.

So shall your desire be so much better than you can imagine. Thank you so much, Jessilyn. This was a great conversation. I loved it. You can connect with Jessilyn at You can connect with me at There you can find out our Investor Club where we have passive investing opportunities. You can join our community of Real Estate Investor Goddesses from all over the world, join our all-women events where you will also be inspired and motivated and will meet incredible people. Of course, you can find out too about our education mentorship program. Definitely like and subscribe to this show, share it with your friends and leave a review, five stars is awesome. We love having you. Join us next time for another interview.

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About Jessilyn Persson

REIG Jessilyn | Money MindsetAfter 15+ years in the corporate and public sector, this visionary woman decided to leave her highly successful career as a Project Management Professional and became one of the founding members of Legacy Global, as well as a full-time investment banker, real estate investor, speaker and educator.

By using her strong prowess of leadership, expertise in financial education and real estate investing, she educates and supports women to create a vision and a plan that can transform their life.

“I want women to have a life full of abundance, and that starts with their relationship to money, wealth, and worth”.


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