Episode 216: The Capital Gains Time Bomb: Why Waiting Could Cost You Millions

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Are your capital gains quietly building into a financial time bomb that could detonate right when you need liquidity the most?

For many high-earning Canadians—especially tech professionals with stock options and RSUs or business owners with most of their wealth tied up in their company—capital gains don’t feel dangerous… until they suddenly are. As positions grow year after year, so does the tax liability, the concentration risk, and the emotional resistance to selling. By the time liquidity, diversification, or retirement planning becomes urgent, the opportunity for elegant, tax-efficient strategies has already closed. This episode digs into why capital gains become such a trap, how optionality slowly disappears, and what both employees and business owners can do before they hit a point of no return.

In this episode, you’ll discover:

• How concentration risk quietly compounds and why waiting makes the tax burden exponentially harder to manage.

• The strategic moves that only work before you need to sell, from trimming positions to pairing gains and losses to building diversified buckets.

• Why business owners face the same capital-gains trap as employees—and what they can do to de-risk while keeping growth potential and flexibility intact.

Press play now to learn how to unwind capital gains strategically—long before the tax bill dictates your decisions. If you’d like, I can tighten the tone further, make it punchier, or create a more SEO-optimized version.

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• Ready to take a deep dive and learn how to generate personal tax free cash flow from your corporation? Enroll in our FREE masterclass here. 
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• Dig into our Ultimate Investment Book List
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Calling All Canadian Incorporated Business Owners & Investors:

Consider reaching out to Kyle if you’ve been…

• …taking a salary with a goal of stuffing RRSPs;
• …investing inside your corporation without a passive income tax minimization strategy;
• …letting a large sum of liquid assets sit in low interest earning savings accounts;
• …investing corporate dollars into GICs, dividend stocks/funds, or other investments attracting cordporate passive income taxes at greater than 50%; or,
• …wondering whether your current corporate wealth management strategy is optimal for your specific situation.

Building long-term wealth in Canada requires more than earning a high income—it demands intentional capital gains planning, smart financial strategy, and a clear financial vision. Whether you’re selling assets, optimizing RRSP room, choosing between salary vs. dividends in Canada, or structuring corporate wealth planning as a business owner, every decision shapes your path toward financial independence. A strong Canadian wealth plan blends tax-efficient investing, real estate investing in Canada, and well-designed financial buckets to balance growth, liquidity, and security. For Canadians pursuing financial freedom, early retirement strategies, or a modest-lifestyle wealth approach, understanding personal vs. corporate tax planning, capital gains strategy, and corporate structure optimization becomes essential. From passive income planning to estate planning in Canada, and from evaluating real estate vs. renting to leveraging retirement planning tools and corporation investment strategies, the goal is simple: create a diversified, resilient system that supports wealth building strategies in Canada today and protects your legacy for tomorrow.

Transcript:

Jon Orr: All right, we’re coming hot off the seventh annual Make Math Moments Virtual Summit, which is our, you can argue this is our biggest online event of the year. And this year, the seventh year in a row that we’ve hosted this free virtual conference for the entire weekend. You we had 19,000 people register, which is, it’s a little lower than last year, but last year we had 22,000 register, but this year we had 19,000, so we had a great weekend.

Kyle Pearce: Mmm.

Jon Orr: Lots of engagement in the, I think we had 48 sessions happening throughout the weekend. It was fantastic. It was great to see the learning. It was great to see the engagement from the participants in the sessions that many were, most of our sessions are live. We have a few recorded sessions, but overall, we can’t be more proud of the Math Moment Maker community to show up on a weekend on a Friday night to engage in math learning professional development.

In this episode, we wanna highlight a session that each of us thought was impactful for us and impactful for the Math Moment Maker community. We wanna share some of the insights we gained from those sessions and that’s what we wanna do here with this next time we wanna spend with you, the listener. All right,

Yvette Lehman: Okay. it’s interesting you were saying how dedicated people were by the end of the Sunday evening. I was asking people in the chat, know, who’s been here since Friday night? Who hasn’t missed a session, you know, and almost everybody.

Jon Orr: Mm-hmm.

What?

Yvette Lehman: It was

like person after person, like, I’ve been here since Friday. I’ve been here since Friday. Yes, I did all day yesterday. Unbelievable. The dedication of the community to commit to their own professional learning. was awesome. Okay. It’s really hard to choose because I attended so many really impactful sessions throughout the weekend, but I’m going to start with Dr. Nikki Newton’s because she surprised me.

Jon Orr: Amazing.

Oh, I think now to be, let me give some backstory info here. I think out of all the speakers we had this year, Dr. Nicky is the only one who has been at all seven Make Math Moments virtual summits. Only one, I’m pretty sure. I’m gonna go on a limb there and say only one. Okay, okay, go.

Kyle Pearce: Ooh, what surprised you?

Yvette Lehman: Wow, that’s awesome.

Kyle Pearce: That’s fantastic.

Yvette Lehman: Oh, I mean,

Kyle Pearce: And yet, and

Yvette Lehman: I think.

Kyle Pearce: yet somehow all seven are like always different, like offering more and more value, right? So you have to also just factor that into the equation here.

Yvette Lehman: Exactly. Yes. Yes.

Jon Orr: because she was talking about AI

this year,

Yvette Lehman: Yeah, and you know what, I actually, when I looked through an overview of our sessions, I thought AI was a topic. You know, if you were to put like a bucket of some of the themes throughout the session, yeah, AI was one of them. And you know, John, we’ve had conversations about my relationship with AI. Like I struggle, right? Just, I struggle morally with like AI.

Jon Orr: There’s a few, yep. Three, three or four, yep.

Kyle Pearce: Mm-hmm.

Jon Orr: Yeah.

I was gonna say, don’t struggle

with the actual typing on the keyboard. You struggle with how much processing power is eating up in the world.

Yvette Lehman: No, ethically it is. Yes,

and so I really appreciated that Dr. Nicky started acknowledging that AI is problematic, like putting that right on the table because people like me, who are already are starting to feel like, but my gosh, global warming and even just like the bias that exists within the platform and…

Kyle Pearce: Yeah.

Yvette Lehman: There’s a lot of concern about AI for me and ethically I question when I should use it and how I should use it. that’s right. It’s like, when am I using it as a tool or where am I using it in a wasteful way? You know, so I really appreciated that the session started by putting some of those ways that is problematic upfront. Like we’re not ignoring them. being transparent that they exist. But man, did she take…

Jon Orr: You don’t wanna just ask it what you should have for dinner tonight.

Yvette Lehman: my understanding of AI use to a whole other level. This is what was amazing about it. So she talked a lot about, and we know this from our use of AI, like how specific you need to be with your prompts. And so what she provided with to the people attending was, you know, some documents and some guiding recommendations for how you write a really good prompt so that AI generates something that’s meaningful for you and it matches what you’re looking for. But this is was amazing about her.

Kyle Pearce: guys.

Yvette Lehman: She took all of the best pedagogy that she knows, you know, and she brought that into her prompt to create lesson plans. And so when she was designing the lesson plans, she would talk about concreteness fading. She would talk about supports for multi-language learners and she used a six level scale. We’re in Ontario here, right? It would be our steps document. So it’s like incorporate considerations for students at different steps of language acquisition. She was like, give me an if then.

Jon Orr: Hmm.

Yvette Lehman: document for students that have potential misconceptions or gaps in understanding. Like she had all of these ways where she was like not unlike she was like, I’m to be teaching the distributive property. I want to make sure that in this lesson, I’m being responsive to neurodivergent students. And so like she loaded the prompt with so much best practice that to me that was that was more the learning in some ways than the actual use of the tool.

Jon Orr: All right.

Kyle Pearce: Hmm.

Jon Orr: Right, so it’s like you have to have the knowledge of that prompt. This is the important part of why you need to think specifically about what you’re looking for, but what knowledge you bring to the table so that you can get what you need because in order for you to prompt that, you have to know that I do need to make sure I think about this group, I need to think about this, and I need to think about this in my lesson planning. Think about how proficient in lesson planning you need to be.

Yvette Lehman: Exactly.

Jon Orr: even

before you sit down at the computer to help it like what speed up this process a little bit for you find the right resources or our resource that helps you do all of these things at once, which may not even exist.

Kyle Pearce: Right.

Right, which makes me kind of think about it’s almost like forcing you to be explicitly reflective by creating these prompts, right? So when we’re reviewing, for example, I didn’t see Nikki’s session this past weekend, but I have watched her in a presentation talking about AI. And in that session, I’m assuming some of these things align. She was talking about utilizing AI to actually help you determine

what the next step might be for students. And I don’t know if she did that in your session, but ultimately at the end of the day, it’s like if we aren’t being reflective and being able to at least recognize what’s missing and what it is that we don’t know, AI is gonna probably not know how to help you, right? And so to me, I think it really helps us sharpen our…

We’ll call it our observational skills when we’re in the moment and we’re working with students to recognize what are the things that are working here? And then what are some of the things that are not working here? And then I can be more specific if I’m going to, let’s say, student work, an image of student work to AI to try to determine where, what’s falling apart here for the student and what might I do next?

Jon Orr: Mm-hmm.

Kyle Pearce: If I’m not doing those things, it’ll probably be way too general and I’ll actually go off probably on the wrong path, right, with the next steps for those students. So I think that’s incredibly valuable to have that sort of insight on the fly.

Yvette Lehman: I was also introduced to new tools. You know, like I use ChatTPT predominantly. Gemini was one of the ones that was highlighted in the tool. And then she talked about a platform called Max.ai, where essentially you can house all of your different AI tools in one system so that you can toggle between them.

Jon Orr: do share, do share.

Hmm, tell me about

Kyle Pearce: Hmm.

Jon Orr: like, cause I’m a, I must be like a one pony show here with like, it’s chat cheap ET, right? So it’s like, no, so like Gemini, fill me in on the details, treat me like a noob.

Yvette Lehman: I think we are, yes.

Kyle Pearce: No tricks

for John though, like it’s not a trick pony.

Yvette Lehman: Well, and this is where I feel like I can’t speak to this yet. We’re going to have to all go back and watch the replay because she was definitely showing how depending on the type of product she was looking for, she would navigate between these different platforms because some were better at this than this, you know? And so I don’t think I’m ready yet to speak to any of them or how they’re different, but I certainly got the impression that Dr. Nikki was saying, you know, when I want to generate this type of

Kyle Pearce: Mm. Mm.

Jon Orr: Mmm.

Yvette Lehman: You know, if it’s a graphic or if it’s a graphic organizers, like that was one of the ones that we were talking about, or we were using diff it, for example, which is an AI tool to generate lessons in response to a particular problem. It’s like, want extra practice. We want a graphic organizer. We want sentence frames. Maybe we go to diff it for that. So she was definitely in the presentation showing us how these different tools do different things really well. And so she uses max AI to keep them all toggled in one place.

Kyle Pearce: Well, I wasn’t planning on bringing this session up, but based on your big takeaways here with Nicky Newton, should say Dr. Christopher Child’s session was also very AI focused. I don’t know if you had a chance to check it out, but based on what you’re saying, Yvette, I think you’d really find his valuable as well, because he did kind of take you through all kinds of different tools. And actually, on his website, which I was like mind blown by, is like he has his own

essentially like chat bot that is beta mode. So full disclosure, you did say beta mode. So it’s not perfect by any means, but you could actually have a conversation with this chat bot and it’s like built around him and how he would respond to certain things, which I thought was like incredibly interesting. And he went around just talking about these different AI tools and how they can help you in different ways.

specifically around the planning of lessons and assessment and so forth. Again, not speaking to, and I know Nicky feels this way as well, it’s like AI is going, he called it like your co-teacher, right? So it’s like your teaching partner that you’re gonna use, but you’re gonna be the teacher. This is gonna be a tool that you can utilize in order to, just like I know Yvette, you had so much experience team teaching for so many years and how valuable you felt that to be.

Jon Orr: Hmm.

Kyle Pearce: so many other educators out there did not have that opportunity to actually teach alongside another human being so that you could, you know, sort of throw ideas off of each other. And he was sort of framing it in that way that like AI can be that, you know, other teacher, that other perspective, you know, for you to be able to maybe think outside your own mind a little bit. And so I think that’d be a good follow-up session based on what you’re saying about Nicky Newton’s session.

Dr. Christopher Child’s session is definitely one to add to your list.

Jon Orr: Awesome, awesome. Okay, I’m gonna jump in. I had the pleasure of hosting Sean Nank and his session was on teacher trauma. So this feels like in a different world than what we were just talking about. And his subtitle here is Seven Steps to Rekindle Joy in Teaching Mathematics. I think it was almost like we said this at the end of the session and it was also later in the evening on Saturday night. So it was like paired with like.

Kyle Pearce: Hmm.

Jon Orr: People might be tired, but it was definitely, we had this like, hey, we just sat through a therapy session. And Sean had, you know, seven P’s, he called it, seven steps to rekindle joy. And some of the P’s just like spoke to us. Like it just made us rethink about, you know, why we do what we do, who do we do what we do with, and how do we get through the day sometimes? And what are some tips to help us do that? And what should we keep remembering so that we keep doing this job? Like he had mentioned that he almost quit.

Kyle Pearce: Hmm.

Jon Orr: you know, this many times and I think we all think about that sometimes. it was a very, it was an important message for us in the room to hear that night and I think it helps us to kind of think about what we’re doing. So for example, the first P was purpose. Like what is the why? Like how do we think about why we got into teaching and why we do what we do? And it reminded me, Kyle, when we were, you know, talking about our framework for math.

math teaching and also the six big areas of an effective mathematics classroom, we talk about the pillars of math class. And oftentimes we talk about our why there. Like why are we teaching through problem solving? Why are we presenting material this way? Or why are we grouping this way? Just the why of what we do is so important to help us kind of bring us back into focus about our choices with our lessons, our choices with student and behavior management, our choices with how we deal with our

Kyle Pearce: Mm-hmm.

Jon Orr: peers in our schools, he forced us to kind of say, why are we doing what we’re doing? So that P hit home for me for sure.

Kyle Pearce: Awesome, awesome. I love it. love it. And Sean’s a great, great guy. And I can only imagine that it was probably a great conversation. And based on that, you, you actually, it’s a great segue. I didn’t know you were going to talk about Sean’s session, but knowing him, I can see him presenting and more or less facilitating the session much like these two individuals. The first one I wanted to talk about was Nat Banting, his session.

Yvette Lehman: reminds me.

Jon Orr: Mm-hmm.

Kyle Pearce: Although he was, you know, a little distracted, it was Grey Cup Sunday and, you know, big fan being from Saskatchewan. I actually don’t know what happened in the Grey Cup. And I admitted to him that I didn’t realize it was the Grey Cup because we’re from Windsor, Ontario, which is basically, you know, the Detroit. So either way, his session was all about, you know, teaching moves and the actual title was teaching moves that move teaching and

Jon Orr: Hahaha.

Me either.

Kyle Pearce: The way he, like, I really want to comment just on the way he facilitated the session was an excellent demonstration of exactly what he was trying to teach, because he was engaged in the chat the entire time as if it was a conversation, as if it was a bunch of students. And I know he’s a high school teacher, but you can imagine this from K through 12 or even through 16 into university where, you know, if he’s in kindergarten, you can picture the kids all around the carpet.

and him having the conversation with the kids. As he moves up into high school where, you know, he’s there and he’s putting them through an activity and he’s feeding off of the discussion and the dialogue and the mathematical discourse that was taking place through a very non-intimate sort of setting, right? Being online and, you know, it being text and him commenting on these things. And, you know, why I really loved that session was again, he was demonstrating what he was presenting on.

as he was presenting, which I thought was great. that was, you know, again, John, you said, I don’t know if you can chat about one. I also wanted to highlight Jim Strachan’s session, which is all about mentoring. And I don’t know if it was called Mentoring Moments. It was called Mentoring Essentials is the name of the session. you know, Jim is also a master facilitator of discussion. And while Jim doesn’t necessarily always

hyper-focus on mathematics, he focuses on mentorship in general. He did an excellent job of, again, bringing that chat together and really engaging the group in a great discussion where, again, you sort of felt like it was a little bit of a therapy session. And I don’t know if you’ve ever had the opportunity, if you’ve listened on the podcast to when we’ve had Jim on, or if you’ve had an opportunity to see Jim present or just a conversation.

Jon Orr: Mm-hmm.

Kyle Pearce: He’s very, very nice to listen to. He’s got that perfect sort of voice. So those were two sessions that I really, they had an impact on me based on actually the facilitation style that I think is really important because there was amazing content within it, but it was like you were engaging in what they were trying to demonstrate through the actual session. two to add to the list for sure.

Jon Orr: Nice, nice.

Yvette Lehman: When you were describing

Sean’s session, was going to jump in. I felt like I left Vanessa’s session feeling like I had been to therapy as well. And I was excited about the session because the title was How to Make Students Care with O-Bribes or BS. And I was like, I need this for my child. How do I make my child care without bribes? Because bribes is my go-to move right now. But 100%.

Kyle Pearce: Hmm.

Mmm.

Yeah. You wanna eat dinner tonight?

Jon Orr: Ha

Yvette Lehman: Exactly. So she was saying, and this really resonated with me and I think it will for you as well, that we are the just do it generation. Like it’s like, we all just did it. And it’s like, you just did it because there would be consequences. You just did it because you wanted a good job. You just did it because you needed good grades. And we didn’t really question it. We just did it because we had to. And she was saying, students now aren’t just doing it, but neither are adults. And so it’s an entire,

Jon Orr: Hmm.

Yvette Lehman: societal

change. It’s not just students who are not just doing it. There’s a lot of adults as well who are saying, I’m not just going to do that job anymore. I don’t want this for myself. I don’t want this for my life. I’m not just going to keep going through the motions. Like I need another motivator. need, so I really liked that connection to that. It’s not about kids just basically saying, I’m no longer just going to do this because you said so, because I have to. And she talked about, you know,

Kyle Pearce: Hmm.

Hmm.

Yvette Lehman: Like, do we want kids just doing math because they’re scared? You know, out of fear, out of like, that’s not, we want them to truly be motivated to do it. And so we talked about different types of motivation and how to motivate people. And she talked about one routine about like naming your superpower and how it’s like all kids have superpowers and those superpowers can relate to being a good mathematician. And like, it’s like, we need to find it and we need to lean into it. And so of course I was like,

asking my family during the session, like, what’s your superpower? And she basically said, your superpower is something you love and you’re good at, right? Can like everybody identify something that you love and that you’re good at and how can we leverage that to help you see the mathematics and what you’re doing?

Jon Orr: Hmm.

Kyle Pearce: That’s such an interesting message. I’ve seen Vanessa, you know, again, I was in other sessions while Vanessa was on doing the hosting as you know, we do where we split up all the sessions amongst each other here. And with Vanessa and her saying that it really makes, it’s really interesting. And I think this is probably why it’s affecting kids and adults is that there’s so many other distractors out there that it’s like so easy to just kind of like,

Jon Orr: Mmm.

Kyle Pearce: not do things that are important or not do things that are meaningful, you know, and like, I’m, I’m kind of struggling with my, my own son with that. Like he, he, his superpower is racing, but like, man, when that YouTube gets going, it’s like, you could be doing something productive over here. And in order to make yourself a better, you know, a better go-kart racer or whatever it is that you want to do, whatever that superpower is. And I just think it’s getting harder and harder for us to help, especially students who are young.

informative in order to help them understand like all of these outside factors that are kind of pulling on them and to help, you at some points you just think like, just do it. Like you just want them to do it because that’s the easy route. But at the same time, we know that’s not actually like the end result we want. So that’s a really interesting one that I’m going to definitely dig into myself just to kind of, you know, get a little deeper look into what you shared there about Vanessa’s session.

Yvette Lehman: watch it

with your kids because Leto was next to me during the session and you’ll love it Kyle because she brings a lot of the analogies back to the Blue Jays and getting on the bandwagon and rallying around something even though you had nothing to do with it but all of a sudden you’re super motivated and you’re super invested and you’re super excited about something that really has nothing to do with you and she talked about what were all of the motivators so it was great it was it was

Kyle Pearce: Right.

Yvette Lehman: very relevant, very culturally relevant, very relevant to today’s society. So I definitely walked away feeling reflective about myself, not only as an educator, but just a person and then a mother.

Kyle Pearce: Hmm.

Jon Orr: Excellent.

Kyle Pearce: Love it.

Jon Orr: Awesome, awesome. Well, I hope we shed some light and gave some insights on some of the big takeaways we’ve had in the summit. know that we’ve got a lot of those coming in right now by email and by the forums that we’ve asked our participants to fill out about their big takeaways. So we’ll be sharing those on our website at summit.makemathmoments.com. The summit replays, they’re still up for watching. We’ve got access.

People are accessing for a month or for a year and they also are housed inside the Make Math Moments Academy. They’ll be there forever because there are six other summits sitting there as well. So if you are interested in digging into some of the sessions that we have, then head on over to makemathmoments.com forward slash academy and you can subscribe and you can also start engaging in this summit that we just passed or previous summits. Before we go,

I do wanna, we did share, like, cause you talked about Jim Strachan, Kyle, we talked about Dr. Christopher Childs. I wanted to call to attention that this summit, even though it happened in November, was for us in our, think of our teaching lives, in our teaching roles. But we also have a summit coming up in February. It’s a one day event, and it is for our leadership teams. It is for,

curriculum consultants, coordinators, math coaches, administrators. It’s a one day event and it’s not a pick and choose. It’s not like a hey, you’re gonna, you know, can, because we had 48 sessions running over the course of a weekend and it was impossible to go to all sessions. It’s a conference style that we had just this weekend past. And so you picked and chose where you wanted to go. Just like we didn’t hit all of these. We shared the ones that we were at.

But this one day event is almost like a, in a way like a course. We are going to teach you specifically how to design your math improvement flywheel so that you can gain traction and alignment in terms of math improvement and math professional development. So we’ve hand selected a number of speakers to speak on four big areas that we believe will speak and help all of the math leaders develop math improvement that is traction and aligned to their goals.

That’s a one day event. is also, like this summit, completely free. You can register right now, because registration opened this past weekend, at leadership.makemathmoments.com. Register there. Join our one day event in February, and we’ll start to shift math improvement and the professional development around that this year and going into future years, because that flywheel will keep.

turning year after year. So thanks and hope to see you there and hope to see you in the next episode.

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