Episode 39: Investing Complexity: How Passive or Active Is Your Investing Style?
Are you like many of the Invested Teacher listeners who are thinking you want to go all in on side hustles, real estate, stock options trading, infinite banking, and more? While it might all seem like roses and butterflies, there is a lot of learning and a ton of ongoing work related to the Invested Teacher Team wealth building journey. In fact, our journey might be a perfect fit for you, or it might feel like shoving a round peg into a square hole.
In this episode, we are going to help you discover how to identify where you stand on the investment complexity continuum and pinpoint the level that aligns best with your financial goals and risk tolerance. We’ll also unveil why, for many, the extra effort that active investing demands is truly “worth it,” while for others, it just might not be a great fit.
Wherever you land on the passive vs. active investing spectrum, we are certain you’re going to learn a ton from this episode!
What you’ll learn:
- The details of how the Invested Teacher Team got started on their wealth building journey including the significant amount of learning that took place in the beginning as well as the ongoing work required to continue on this path;
- Why you should reflect on where you are on the continuum of investment complexity and where you are comfortable (and excited) to go;
- How to realize what level of complexity is the right fit for you as an investor including how active or passive your investing commitment might be; and,
- Why all of the additional work and complexity that active investing brings with it is still “worth it” for some;
- Who Not How [Book] Dan Sullivan
- The Invested Teacher Wealth Building Booklist
- The Real Group Windsor Real Estate Team
- Invested Teacher Ontario Mortgages
- Invested Teacher Wealth Planning
- Download our Wealth Building Blueprint
Interested in Joint Venture Opportunities?
For those interested in being considered for potential Joint Venture (JV) opportunities, reach out to us here.
Contact Matt if you’re Buying or Selling Real Estate in Windsor or Essex County!
Check out the work Jon and Kyle do assisting mathematics educators and district leaders.
00:00:00:11 – 00:00:20:19
If it’s available for me to grab, why can’t I grab that? Why can’t I take a hold of that thing right there? It’s one of those things we’ve said a few times we can never go backwards. We’re already here. And you can’t unlearn things you’ve learned along the way. And that makes me want to learn more. Ten years ago, it’s like I didn’t know these things and I can’t go back to go.
00:00:20:20 – 00:00:45:21
I’m not going to invest in real estate anymore because I already know this. It’s a no brainer to keep going on this instead of saying, I’m just going to stop. You can’t do that to yourself when you’ve learned this. And I think that sparks us on to learn more.
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Welcome to the Invested Teacher podcast with Kyle Pearce. Matt Biggley and Jon Orr.
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Hey folks, get ready to be tired as we share our successes and failures encountered during our real life lessons. Learning how to build generational wealth from the ground Up.
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Welcome investor students to another episode of the Investing Teacher podcast.
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Well, well, our invested student friends. You know what the invested teachers are wrapping up a pretty busy week. I’m sure many people can relate as we record this. It is September 7th, Thursday, September 7th. And if you’re listening from anywhere pretty much in Canada, that means school is back in session. Now, some interesting things. First of all, Matt is not back in the classroom right now.
00:01:34:11 – 00:02:06:00
I am not back in the classroom, but I’m in a different classroom because I’m doing a course that I am painfully trying to work my way through. But John, however, is in the classroom. He’s back at it, working with students, having a blast there. But at the same time, we’re all feeling completely beat up. Sports are back in class, is back in chaos, is back in with three of our spouses, all in the education business.
00:02:06:02 – 00:02:42:18
They are also super busy and we all have children who are back in school. So we are coming off a pretty crazy week. And today, before we hopped on, Matt was dusting off some of his files, which was really, well, call it your financial or family organizer of just all the important things, right? The oh, Hipp card numbers and the license numbers and the life insurance policy numbers and the bank accounts and this property and that property and all of these different things.
00:02:42:18 – 00:03:03:24
And we we started we started thinking to ourselves and it really it was Matt, you were sort of saying like, holy smokes, there’s a lot going on here. First of all, you were like, It’s all over the place. If you died tonight in your sleep, you’re like, Leslie’s going to have no idea what’s happening. She’s going to be calling me probably to say, Kyle, what’s going on?
00:03:03:24 – 00:03:27:08
What did he have? Where’s it at? And John, you had done something similar about a year ago, and now you’re saying yours is completely out of date. And I’m ashamed to admit it, but mine is just a bunch of files in folders that would probably take Shawn, tell a good month to go through to try to figure out and map out all of the chaos that’s going on in the background.
00:03:27:08 – 00:03:47:04
And it really got us thinking this is something that I think is super real for those who are listening, especially those who are listening and just want to get into the investment world in a greater way that at the other end of this wonderful tunnel is a whole lot of complexity.
00:03:47:07 – 00:04:11:13
Yet we’ve all got these files somewhere in our house, you know, could be in a safe or a fireproof box or something like that. But it’s been on my project list to get this stuff organized in a format that’s going to be easily shareable and something that can be passed on easily. So what actually spurred me on to this was I was really thinking about opportunity, and it kind of led me to thinking about death at the same time.
00:04:11:15 – 00:04:13:08
So, yeah, morbid.
00:04:13:11 – 00:04:35:18
I was trying to catalog some insurance policies that have got and I went back this spreadsheet that I’d created. I wanted to make a spreadsheet so I could update it in the regular. And actually Kylie shared it with you. In the event that I died, I wanted somebody that beyond maybe Leslie, to have access to it with all my account numbers, all my policies for everything I credit card numbers, all these things, when someone passes away, there’s a mess to clean up with.
00:04:35:18 – 00:04:55:03
As a realtor, I deal with estate sales and people leave a real mess behind. And so I would feel really good that this was well-organized. So this started from an opportunity because we’ve been talking about some different investing in getting some things in order to be able to analyze what those investments might look like. So that’s what spurned me today, to carve out a time block, some time to work on this.
00:04:55:05 – 00:05:11:23
But really, as investors, I think it’s a characteristic of investors to have just a web of things I have bank accounts at, I don’t know, maybe added them up to four or five banks or lines of credit that I’ve maybe never even used. But as an investor, you always want to have that extra line of credit just in case.
00:05:11:24 – 00:05:29:04
Just in case. Just in case. If you’re on plan F and you’re not sure where to pull the cash from. So I’ve got just this web of insurance policies, bank accounts, all this stuff that I wanted to just be able to collate and organize and put together and then have a nice paper copy alongside the wills and all that stuff.
00:05:29:04 – 00:05:52:17
So that I mean, listen, we’re investing to be able to pass a legacy on to our family eventually. I’m not planning on dying anytime soon, but if my family didn’t know how to find where to access these policies, these properties, all these things, then it’s a moot point to even be leaving them a legacy. And it seems so straightforward to have this all together, but it’s mind numbing work.
00:05:52:18 – 00:06:10:21
It’s incredibly boring and it actually pretty frustrating as well because you’ve got different files in different places and you’re emailing people to try to get up to date copies of it. And so it’s really awful work to do and I’m not done it. But man was ever feeling good during and Kylie was messaging you throughout the day, updating you and sharing things with you.
00:06:10:21 – 00:06:14:19
In the john. You said you’ve got something really similar that also needs updating.
00:06:15:00 – 00:06:41:05
Yeah. You just said you felt really good organizing this because you’re thinking about if I did leave the world and my family’s still here, you feeling that sense of security? You’re providing them by saying, Hey, here’s this binder. I think mine’s a binder where we filled it all out with all the dying, where the wills are, who to contact in this situation, where the passwords to all the Google drive accounts that we have, everything is in here.
00:06:41:11 – 00:07:00:21
But you’re right. You feel that sense of security providing your family because you know that it’s the right thing to do. You have to make this work so you do feel good doing it. But you’re right, there is a lot of paperwork involved. There is a lot of collecting documents, thinking about all that complexity of the hillock numbers are over here, and here’s how you access this.
00:07:00:21 – 00:07:19:07
And then we take for granted, I think, what we’ve built along the way to go, like grabbing that, we’re grabbing that, we’re putting this piece here, we’re putting this piece here, we’re moving that piece over here. And we haven’t say shared that all these little pieces that these moves that you take for granted and if you go, the whole house of cards falls down.
00:07:19:07 – 00:07:44:08
And we don’t want that to happen for our families. So making this makes it feel like you’re doing a really great thing. But when you told me that you were doing this and I thought about what I did, I did mine a year ago, and it’s like thinking about all the moves we’ve made over the last year in terms of different real estate deals, different policies from insurance that we started and thinking about the businesses that have changed over the course of the year.
00:07:44:10 – 00:08:07:18
Mine’s out of date. I have to go back and update it. So what I think about this specifically, if I’m a new investor, right, if I’m a new entrepreneur, dipping my toes in the water or you’re thinking about going down this route, you hear someone talk about all of this crap that we have to collate and put together or just make sure you have available or like what’s going on out there.
00:08:07:18 – 00:08:28:14
Not to mention if you’re going the real estate investing side of things, of like dealing with the property managers, dealing with making sure the all of these different property taxes are paid and what mortgage are we going to get here? There’s so many little things that we’ve built along the way and it’s scary, I think, right, for someone to say, I don’t want to do any of that.
00:08:28:14 – 00:08:45:10
I don’t want to add more stress to my plate. And it’s a huge barrier. I think all of this, even though we’re talking about it here, it’s like if someone’s thinking about having to organize that part of their life, it’s a huge barrier to ever going down this route of real estate investing.
00:08:45:14 – 00:09:12:16
Well, I’m thinking about some of the friends out there who are listening and who haven’t actually taken an active role in diving into this world that we’ve been talking about on these episodes up until now. We’re on what, episode 39 here as we’re chatting about this, and there’s probably a lot of people who are still sort of like, I’ve got my little investment account over here that the bank takes care of or whatever, and they’re probably getting stressed thinking about how they haven’t organized those pieces that they’ve already got.
00:09:12:16 – 00:09:43:09
Right. They might have maybe term insurance policy. They might have maybe this investment account over here and RSP for their kids if they have kids and they’re probably thinking to themself, holy smokes, I haven’t done that yet. So if you haven’t, we’re going to recommend that you do, especially while things aren’t as complex. But really, I think one of the biggest pieces is really thinking about this journey and starting to think about how I guess badly you want this thing right.
00:09:43:09 – 00:10:09:18
And we’ve talked about clarity on previous episodes. We talked about trying to figure out what is it that you’re trying to do this for? Why are you on this wealth building journey? Can we all know it’s so that we have more money and so that we maybe don’t have to work as long? Those parts are easy, but at the end of the day, the path that you choose to take to get there I think is one of the biggest things that we’d like you to be thinking about throughout this episode.
00:10:09:20 – 00:10:31:17
For myself and Matt, when we opened up our real estate holding Corporation, that was a big step. As soon as we did that, there was this well, let me back up. Even before then, when I bought my first investment property in the United States, I had opened the door to now having to file U.S. taxes, which was not scary.
00:10:31:18 – 00:10:52:20
Fun, scary. Yeah. And to be honest, I knew that was going to be I’m the type of person I’m a fact finder. As I’ve learned through the Kolbe test. We’ll talk a lot about that in future episodes, but I eat that up. So I would do my own U.S. taxes for a number of years. And then we opened our Real Estate Corp. And then as soon as that came in, it was like I would do the bookkeeping there.
00:10:52:20 – 00:11:09:19
And then I started to realize This is hard and maybe I’m doing it wrong. So you start to bring in someone to do some of that work, and now you’re paying an accountant to try to do your taxes to handle that. Now you’re talking to the lawyer about buy sell agreements to go. What happens if Kyle dies? Who gets the company?
00:11:09:19 – 00:11:30:18
Is it Kyle’s wife? Now has a say in the real estate holding corp and all of these different things, and that complexity continues to grow. So it’s really interesting because in some ways you sort of go, Well, isn’t that a good thing? Right? The more complex things are getting, then obviously the bigger things are getting in. Yes, I would say for sure we love that aspect.
00:11:30:20 – 00:11:53:01
But on the other hand, the question that Matt had mentioned after he was looking at this massive spreadsheet of chaos, Matt, you were Sadik wondering to yourself, you’re like, If we could do it all again, would we do it this way? Would we make the same choices or would we change anything? And I almost immediately said, I think I know the answer for me, and I would do that.
00:11:53:01 – 00:12:13:17
I enjoy that chaos. But I think what we want for you friends, as you’re thinking about this, is thinking about the difference between being and there’s never a full passive investment out there, but how passive do you want to be and how active do you want to be? Think back to John. You talk about your parents, for example.
00:12:13:17 – 00:12:30:15
Their investments are probably all. They just log into one account and I’m going to guess that they could price see them all stacked up. Right? If they’re with one of the big banks, they got their checking account, They might have a savings account. They’re older now. They might have a riff here in Canada where your retirement funds eventually go over there.
00:12:30:15 – 00:13:05:11
But it’s all stacked there. Here’s the one log in and password, and they’re losing something by doing that. That passivity means that the returns are going to come down. Potentially expenses are going to go up because someone else is kind of doing the work for you. However, they are saving a massive amount of complexity, whereas you go all the way to the other end where I would say that we’re ultra active and we have other costs associated with it, which is that time and effort to learn and understand and do and manage and organize, as Matt was doing today.
00:13:05:13 – 00:13:16:09
So I’m wondering what else should our invested students be thinking about here as we kind of explore this continuum from passive to active investor?
00:13:16:13 – 00:13:38:17
I think what people would really say, what popped into my mind right there when you said my parents were set up really easy, there’s no complexity. They don’t even think about it, right? That’s a lot of people. And they’re choosing that. Whereas when you said we slide down to our side and we have all these complexity because we’ve built that up and we’re okay with that, I think a lot of people are saying that might come down to a time aspect.
00:13:38:17 – 00:14:00:23
I don’t want to spend time on that. I don’t have time to spend on that. I will pay someone else to do that versus when we’re over here, we’re spending a bunch of time. There’s arguments to say we’re spending some time here. Now some time is offloaded to somebody else to deal with some of these issues. But we are spending some time to manage that side of things.
00:14:01:00 – 00:14:19:07
And I guess that whole time aspect is related to money, too, because it’s like, well, what do we value? Do we value our time or do we value our money? You’re going to spend the one that you value the least first. And so when you think of my parents who were doing that, they’ve got their time that they’re really cradling this chunk of time.
00:14:19:07 – 00:14:33:16
I don’t want to have to think about anything else. I’m okay with not getting the gains for that over for us. We’re like, you know what? For us, is it time? I don’t think for us it’s time. I think for us it’s like a lot more than that. I think we’ve got a lot more drive. I think we’ve got a lot more curiosity.
00:14:33:21 – 00:14:54:03
If it’s available for me to grab, why can’t I grab that? Why can’t I take a hold of that thing right there? It’s one of those things we’ve said a few times We can never go backwards. We’re already here. And you can’t unlearn things you’ve learned along the way. And that makes me want to learn more. Ten years ago, it’s like I didn’t know these things and I can’t go back to go.
00:14:54:04 – 00:15:17:05
I’m not going to invest in real estate anymore because I already know this. It’s a no brainer to keep going on this instead of saying, I’m just going to stop. You can’t do that to yourself when you learn this. And I think that sparks us on to learn more. But the one thing I think I want to share with the audience is that even though there’s a lot of complexity, Matt, you’re saying there’s so much complexity with all these moving pieces.
00:15:17:07 – 00:15:42:15
I think what’s really important to know is that everyone’s somewhere on their investment journey. You might be at the beginning and there is maybe no complexity at the time, but then when you take that first step, you’re not going to go from point A all the way to point Q Maybe where we are, you’re going to go from point A to point B, and then that adds one tiny little piece of complexity to your overall puzzle.
00:15:42:17 – 00:15:55:13
And you’ve got to like, okay, well, I can manage that, right? And that’s where we did. That’s exactly how all of us would have done this. It would be like, okay, we can handle that piece. And then once you’ve got a handle on that piece, you’re like, okay, well, we’re going to take another step. We handle that step.
00:15:55:13 – 00:16:18:18
There’s another piece of complexity here. Can we handle it? Yeah, and it’s built up over time, so it doesn’t feel as when you look at it as a whole, it’s very complex. But right now, when you look at your, say, portfolio and all the things you’re managing and Matt, when you look at, say, your portfolio and all the things you’re managing, it probably doesn’t seem that complex just because you built up your understanding of the systems that go into making this work.
00:16:18:18 – 00:16:35:21
So if you’re early on your journey, you’re not thinking, Oh my gosh, just because I’m going to be a real estate investor and I really want to be in real estate investing, I think it’s the right move. But I have to deal with all this complexity. Just remember that it’s not going to be all of it because it’s going to be baby steps, going to do one thing at a time.
00:16:35:23 – 00:16:52:17
John And I think something I’ve been reflecting on a lot in the last week is a conversation I had with my real estate coach, and I think you guys made me think of it tonight with your comments, with your sharing. I was asking you about some ideas on how to grow my real estate business and I’m such a doer and hands on, I probably a little bit too much of a control freak.
00:16:52:17 – 00:17:11:01
I like to do things myself or possible. I have a hard time letting go of that. And then we call it leverage when we can use other people to do things. So I have a new assistant in my real estate team and she says, Matt, you don’t let me do enough for you. And I think that’s just sort of symptomatic to I am and my coach is really pushing me to consider who and not how.
00:17:11:01 – 00:17:25:11
And there’s a great book out there on it. I’ve got to finish reading it. And she was urging me to think about who I could bring into my team that could do some of the things I was talking about rather than me thinking about how to do them myself. And I think it really that lesson applies here as well.
00:17:25:11 – 00:17:51:10
I think for listeners it’s about identifying the expertise out there and utilizing that, learning from that because that reduces your intimidation and it allows you to skip a bunch of steps. It allows you to learn from, say, our failures or your coaches failures. And I was a history teacher. And so history is full of lessons of people not learning from history and insisting on experiencing ketones screwing up for themselves and experiencing that.
00:17:51:14 – 00:18:07:01
And I think real estate investing is kind of full of that as well. There’s so much expertise out there. Certainly I’d consider the three of us to be experts and I’m obsessed with expertise. That’s why I hired the top real estate coach in the country. That’s why I have so much respect for the two of you. I consider you guys to be experts in so many things.
00:18:07:03 – 00:18:23:15
So I think there’s a lot of amateurs out there, but there’s a lot of experts as well. And so it really just encourage our listeners to think about who can help you accelerate your investing journey wherever you’re out in that continuum and not be so worried about how you have reflected a lot about this in this past week.
00:18:23:15 – 00:18:43:02
And I think back to as I got started as a realtor, I was obsessed with learning about how to do stuff. And really it was the who was it connecting with a coach, connecting with great mentor realtors that had allowed me to accelerate my real estate to the point from being something I thought was going to be a side hustle to what has become a new and very successful, lucrative career for me.
00:18:43:02 – 00:18:44:10
So that’s my big takeaway.
00:18:44:14 – 00:19:03:11
I love that. Matt And I got to ask you before I have a few thoughts on that as well, but have you answered your question? Is it all worth it? Is that complexity, that chaos that you were looking at when you were probably up to your ears in documents and files open and wondering what the heck, whether you’re coming or going?
00:19:03:13 – 00:19:14:09
What do you think now that we’ve had the chance to sort of chat this out, is that complexity worth it? And here’s the key question for you, because again, it might be different for people listening.
00:19:14:10 – 00:19:32:08
100% going through these policies. Actually, I got to see shredding things today, looking back on these old insurance policies. And it helped me reflect on how much we’ve learned and evolved over time. But I would never take out those insurance policies today that I had ten years ago that I’m shredding the documents with today. And I think that I’m proud of our learning journey.
00:19:32:09 – 00:19:49:08
There’s not much I would actually change because everything that has happened has brought us to this point. All the failures and the challenges and the stresses it truly has brought us here. And we’re in a beautiful place. We’re at a place where we’re curious, where we’re learning, where we’re inquisitive, we’re passionate, we’re every day is truly an opportunity, and I really value that.
00:19:49:08 – 00:20:12:06
So what we don’t want to do is assume that my wife would want to take that complexity over or something to happen to me. So actually I felt really good about the work today because one of my big whys is to leave a legacy for my kids. And I was joking before the podcast, It’s been a long week and the kids are tired not having slept enough and they’re cranky and we’re not getting along so well today.
00:20:12:06 – 00:20:37:07
I said, I don’t know if today they deserve this legacy tomorrow and definitely yesterday. But that’s one of my big whys is I want to pass this on to them, not necessarily the ownership, but the benefits of what we’ve done. So I did feel good about that today. And Kyle is going to allow you and I to have a really good conversation in the coming days and weeks about another investment opportunity that you’ve been sharing with me.
00:20:37:07 – 00:20:39:03
So I’m excited about that as well.
00:20:39:04 – 00:21:09:21
I love it. I had a funny feeling I knew your answer was going to be yes. But as you’re mentioning here, Matt, I’m thinking to myself one of the hardest parts of this invested teacher journey that we’ve been on in helping some of our listeners so people who are reaching out to us and of course we have friends and family and other contacts that we have, be it just from those who we know, but also people who are reaching out to us and trying to get started on their journey again.
00:21:09:21 – 00:21:27:21
I think the big takeaway and I know that we’ve talked a lot about this on previous episodes for me is getting yourself to really think about what sort of journey you want to have. Do you want it to be more set and forget, right? And there’s a path there for people who want set and forget. It doesn’t make it a bad path.
00:21:27:21 – 00:21:49:20
That’s the one thing that I think is really important. Again, people who are listening to this podcast, I’m going to guess that they’re probably open to a little more complexity. They’re listening to the podcast and they’re furthering their understanding of investing and I think it’s just worth noting, and I wanted to make sure that on this episode we had an opportunity to share that it’s not just about finding the investment, right?
00:21:49:20 – 00:22:11:19
It’s not just about signing the documents at the lawyer. There’s a lot of complexity, a lot of learning, but a lot of reward that comes along with it as well. So ultimately, at the end of the day, I’m hoping that the big takeaway folks get is thinking about who you are, thinking about, who you are as an investor now, and how do you feel when you hear that chaos we just discussed?
00:22:11:19 – 00:22:37:20
Does it make you feel excited? You can’t wait to dive in, Learn more about that. Does it make you fearful or scared, whatever that thought, we can help you through that. So definitely don’t hesitate to reach out to us because there are investment paths and strategies for everyone regardless of the complexity that they want or the simplicity that they want in order to get to the end of their own wealth journey.
00:22:37:23 – 00:22:57:06
Hey, folks, we want to thank you for listening today and being here with us. And if this the first time you’ve listened, then please subscribe button hit it so that you get notified when we have our new episodes that go out every Wednesday morning. If you’ve been here with us before, then please. Five star rating and review on your podcast platform.
00:22:57:06 – 00:23:13:21
Leave us one there, please. We don’t ask a ton of things. We’d love for you to leave that five star rating and review. We are on all social media platforms. Kyle was saying, Hey, if you want to reach out to us, you can reach out to us on any of those platforms at investor, teacher, YouTube, Twitter, Instagram, Facebook, all those things.
00:23:13:21 – 00:23:19:05
So reach out to us and we’d love to talk to you about your buying in. What’s worth it to you?
00:23:19:10 – 00:23:31:19
The links, resources and transcripts from this episode can be found over on our website that’s invested Teacher dot com Forward slash Episode 39. Again, that’s invest in teacher dot com forward slash episode 39.
00:23:31:23 – 00:23:55:08
Also, folks, we have our VIP club which we run contests every single month and you can join the VIP club by heading over to investor teacher account board slash VIP club. All one word there and you can enter into our contest each month. You can win a $50 gift card. You can win bigger prizes as well. So join us over at in teacher dot com for tonight’s VIP club.
00:23:55:08 – 00:24:13:15
All right invested students class dismissed.
00:24:13:17 – 00:24:27:21
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