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Joel
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Joel
Welcome to how to Money. I'm Joel. I'm Matt and today we're talking from Monk to Money Monster with with Doug Lynam.
Matt
Yeah Joe. So I don't think it's a requirement to have the lived reality of life experience to be able to speak to our particular subject, but I think it can certainly help. Which means our guest today, Doug Lyman, is someone who we are very excited to speak with as his incredibly varied life as well as career, it spans more than I thought was possible in a lifetime. So he's been broke and bankrupt to living a comfortable life. He's taken vows of poverty to helping oversee over $250 million in assets as a money manager. He's, he's graduated at the top of his class as a Marine. To living for 20 years as a Benedictine monk. We've got plenty of questions for him. We're also going to get into his latest book, Taming your money. Nine paths to money mastery with the Enneagram, which comes out next month. Doug. He takes spiritual wisdom, he blends it with some psychological insight, all in an effort to help folks to successfully handle their money to reach their financial goals. Doug Lynem, thank you so much for joining us today on the podcast.
Doug
Thanks, guys. It's an honor to be here.
Joel
We're glad to have you. Doug. First question we got to ask, got to get out of the way. We ask everyone who comes on is what do you like to splurge on? Matt and I are drinking a craft beer and some people are like, you spend how much on a bottle or a can of craft beer?
Matt
A very nice one from Vermont.
Joel
That's right.
Matt
Yeah.
Joel
This is good one here. But what's that for you? Where people might be like, what, what are you thinking over there, man?
Doug
I probably, it would be art. Like, I have a lot of like art in my house and I have a hard time. It was just too much like, you know, I don't, I don't always go like, like, you know, high end original stuff. I'm not like collecting Picassos or anything like that. But, you know, but I do like Picasso and like so, you know, I get reprints mostly, but I try to get really high quality reprints of famous art. And wherever I go, I tend to pick stuff up and you know, my walls are just covered in art.
Matt
Okay.
Doug
There's a guy named Vladimir Kush who's an artist from who. There's a Russian artist who lives in Paris and anytime I come across some of his stuff, I just, I gotta grab it.
Matt
Okay. So when you're grabbing his stuff, are those originals? Since he's not nearly as well known as Picasso.
Joel
Okay.
Matt
Even still.
Joel
See, if you're gonna go for originals like I do, you gotta go with the super cheap folk art variety.
Matt
That's a self trained guy living out in the cabin in the woods.
Joel
Like, you don't have a. I got.
Doug
Plenty of that too. Yeah, I got plenty of original. I Do. I do have lots of originals. They're just not like the. Yeah, but not the, you know, stuff you find. A museum.
Matt
Yeah, got it. All right, Joel, might have to look in, look into some Vladimir Kush.
Joel
I might.
Matt
Doug, in my opinion, considering or in your case, joining the Marines, like you graduated top of your class, that seems like a path that, I don't know, quasi reasonable. Like, there's millions of folks out there who have joined the military who have, who have served our country. But when it comes to joining, I don't even know, like, how do you join? Like, how do you become a monk? And specifically, I'm curious, what caused you to go in that direction after having graduated at the top of your class?
Doug
Well, it's a big question. The simple answer is I think I joined the Marines to kind of impress my, my father. I wanted to prove to him that I was a manly man who could do manly things and didn't really work. He didn't. He didn't bother showing up to my graduation. And I also had a bit of a kind of a spiritual epiphany at the time. And I realized that unresolved anger issues and high explosives were probably a really bad combination, and that maybe might not be the best career choice for me. So I decided to turn down my commission as an officer in the Marines and went. And just right after that joined a Benedictine monastery. And, you know, it was also. I did it for a couple of reasons. One, of course, I was looking for a higher calling and something that would give me all the things I loved about the Marines, like the esprit de corps, the camaraderie says a purpose and structure that I liked without necessarily having to go out there and kill people for a living. So that, that seemed like a trade up way to trade up. And it was also a great way to really annoy my parents. Like, it just absolutely flabbergasted them. Like, I couldn't have picked anything. Being a monk was about as radically different from the way I was raised as you can imagine. And, you know, it did a really good job of pissing my parents off. So that was a bonus.
Matt
So. So there was like a sinful desire. There was some, yeah, like a sense of rebellion, of that rebellious spirit. So that.
Joel
That caused you to do that.
Matt
But yeah, it's one thing to have done it for just like, okay, you end up doing that for a couple of years. Like, you turn down your offer or your post or something like that. Post graduation, it's one thing to do that. And Maybe just do it for like a couple years, but you did it for a long time. Like, this is. This wasn't just sort of like a. I don't know, like a wild hare. This was something. Something that you stuck with for like two decades, is that right?
Doug
That's right. 20 years. And it was a teaching order. So I was, at the same time I was teaching in a private school. I was the head of a math department. And. And yeah, it was, it was a good life. I mean, there were. There were parts about it that I really loved. And then after a while, things kind of got a little stale. And I think the struggle with all monasteries is that most of them are dying. Like, monastic life is just not that popular anymore. And at the time, I was the youngest Monk by almost 30 years, and there were really no new monks coming into the community. And it just got older and older. It was like, well, if at some point this is like you're on a treadmill and people are falling off and there's no one coming up behind me, like, well, how is this going to work? What's my life gonna be like if I stay? And yeah, and it was basically, I eventually just end up being, you know, doing hospice care, essentially, and then I'd be the last one standing. And that just wasn't. And the community kind of got a little rigid and a little, you know, had its other issues. Other issues as well. But eventually I realized that this was not gonna be. This was not the place. It's kinda like a marriage, you know, you kind of. It's good at the beginning and then it's not good at the end, and you stick it out, hoping it's going to get better, and then it doesn't. And eventually you just kind of got to pull the plug. So that's kind of what happened. And then, of course, I went into finance after that. So that's another story.
Joel
What was the. Tell me about, like, the declining monastic life. And you talk about in your first book the financial difficulties that your monastery was facing, and it forced you to kind of have to confront money head on in a way that you. You never had to before. In fact, like, army or, you know, life in the Marines. And then. And then monastic life kind of insulated you in some ways from having to think about money too much. Is that right?
Doug
Well, no. Okay. Yes and no. I mean, that was the hope. I mean, I certainly joined those. I was hoping that those would be lifestyles that would allow me to avoid the world of money, because I was really you know, I hated thinking and dealing with everything to do with finance. I just was kind of allergic to it because of the way my family treated money growing up, which was to weaponize it. My father was a fairly successful executive for an oil company, and in my childhood environment, I assumed that money was the root of all evil or something like that. So that's kind of why I did run away to the Marine, try to get away from money. But unfortunately, about three years into the. The monastic journey, the community went bankrupt. And so, like, somebody had to figure out this. It turns out if you live in a community where everybody hates dealing with money, like, it just doesn't end well. This is not gonna work. And we basically took the vow of poverty a little too seriously. And so it was a real mess. Like. And so here I was, joining a monastery, hoping to get away from money, and I ended up having to deal with it more than I would have if I hadn't joined the monastery, because, you know, it was just. It was just an absolute train wreck. And so it took me a couple of years to figure that problem out, but I did and got the community on solid financial ground. And then because I was the head of a math department at the school, I decided to start offering economics and personal finance courses to the kids, because I thought one of the real problems in our society is we don't teach kids about money. We don't teach them how to the basics of budgeting and, you know, how to earn, save, invest all these things that are just basic skills that everyone needs to have. And so I did that, well for maybe 10, 12 years while I was teaching. And then just then what got interesting as I was doing a class project with the kids, and for fun, I thought, well, let's just open up the school retirement plan and show the kids how retirement plans work. And I did that. And as soon as I opened it up and started looking around, it was a complete train wreck. Like, if for those who are familiar with the world of finance, there was essentially no fiduciary oversight. The fees were very high on the funds, the performance was terrible. There was. Things hadn't been managed. No one had any maintenance on this plan for 20 years. So it was completely adrift. And I'm like, oh, this is a nightmare. And. And so then I went looking around for a company that could do a better job. And then what I realized is that almost every school, every retirement plan, and almost every private and public school in this country is an absolute mess. It's a disaster. And I Couldn't find a company that I really liked that would do a good job to solve this problem. And so I realized, well, that's a pain point and I know how to do. So I had this crazy idea, I'll start my own investment advisory firm while I'm a monk. And so I did. So I started my own firm to solve that problem to build better retirement plans for schools and colleges. And then this just by. And then of course I left the monastery, started this business, and then I actually merged my firm very quickly after that with a larger company in Santa Fe. But what was really just bizarre stroke of luck is right when I was launching this business, the New York Times did a six piece expose on the problem of teacher retirement plans across the country. So every month they were doing this hard hitting article about how awful the school retirement plans were. And then I just reached out to them on Facebook and said, hey, I love what you guys are. I love these articles. Here's me, this crazy monk, starting this business to try to solve this problem. And, and they loved the idea. So they flew. Ron Lieber, who's a, the financial column, the columnist for the financial section of the New York Times, flew out to Santa Fe, did, spent the day with me, did a big piece that went on the COVID of the business section of the Times and that went viral. That just launched my career in finance. So that's kind of how I got to that point in my life.
Matt
So it was almost out of a. I mean it was necessary. Like, like you said, there is a pain point, but it's something that y' all are facing there as a monastery in and of itself. We've got more questions here specifically too about your monastic journey. But just as like a small tangent, like it sounded like the fees were the worst part about the retirement plan there for the, for the monks. Like I almost picture you cracking this thing open and it basically had fees from 20, 30 years ago, like from the 80s, right?
Doug
Exactly.
Matt
And like, would you say that that's one of the best advancements of retirement funds and the ability for individuals to manage their own retirement, to manage their own IRAs, is the fact that yes, we have total control, but just we've seen fees decrease significantly. I'm curious if that's, if that's what you saw when you took a look there.
Doug
Oh yeah, fee compression is great. Like fees are going down funds. But also like in a retirement plan, you don't have infinite choice. Like you have, you have control over your investments as the individual, but the plan Administrator, whoever's running the show gets to pick what funds you get to choose from inside the plan. And so, yeah, so the fees were high, but the funds were terrible. They should have just been, you know, some of those should have been mothballed, you know, decades ago. So it's fees, it's performance. I would say those are the two biggies, but there's lots of other subsets, problems.
Joel
You mentioned taking the vow of poverty too seriously. And when you look at kind of like church history and stuff like that, there are, you know, the Desert Fathers or whatever who took a vow of poverty to the extreme. And there have been many examples, I think, throughout the ages in different religious sects. But now you're like a money manager, which is kind of the exact opposite of how poverty feels like it. They feel like antithesis. Right. So what's your take on that? I was reading a book on spiritual disciplines recently, and the author talked about how, like, hey, actually, money in the hands of Christians, doing good work with that money, that's the best place that money could be. So I'm curious to hear your take on that duality or seeming contradiction there.
Doug
Well, I agree with you. The last thing you just said, which is that, so money is power, and it's also morally neutral. Money isn't good or bad. It depends on how you're using it. If you take all the good people in the world, the Christians in the world, and you take the money from them, you take the power from them, then it's all going to people who, you know, maybe I'm not saying they're bad people, but you're. You're essentially. What came to mind. Sorry, is like, you're essentially castrating yourself and your ability to, like, make a real big difference in the world in terms of, you know, having this impact, that money is one of the best tools we have for love and service possible. Now that. Now I don't want to take away from the people who take a vow of poverty either. I think this maybe gets into my new book. My new book is Taming your Money Monster. And there are people who take a vow of poverty for the right reasons, and they take it because they want to live in solidarity with the poor and the oppressed. And I think that's extremely noble. But then there are people like me and the monks in the monastery who took a vow of poverty because of their money issues, because they were avoidant of money. There was unconscious. They were doing it. There's some good, obviously good reasons on the surface, but deep Down. It was like this rebellion against my parents rebellion against society. It was like it wasn't a healthy rejection of money, it was an unhealthy rejection of money. And on the same side, you can have a healthy relationship to money and have a lot of it, and you can have an unhealthy relationship to money and have a lot of it. It's really about what's going on in your conscious and most importantly your unconscious mind. What's driving you here and motivating you. And then what's the outcome? Is it outcome going to be more love and service in the world? Then great if it's more selfishness and more greed or more so. Like for example, we obviously can think of examples like Gordon Gekko on Wall street and all these people who are going after money in a horrible, greedy, avaricious way. And that's one model that we obviously don't want to want to emulate. But then there's people who have a lot of money and now have all this ability to heal our broken world. That's great. But on the flip side, for example, there was a monk in the monastery, I'll call him Brother Pius, he refused to touch money for any reason. He wouldn't use a credit card or a debit card or cash. For years he went without thinking that money, even touching money, would pollute his soul in some weird way. And so the weird thing about that is it made all the other monks around him touch money more often to keep his soul pure and clean. And what it did is actually it didn't diminish his ego, it inflated his ego. It gave him a sense of superiority from the other monks. He was on this sort of pious perch. They could look down on the rest of us who are handling this dirty, dirty money all day to keep him fed and housed. And it was just, it was, it was utter insanity. Right. And so it really isn't the vile poverty or it isn't the having a lot of money. It's like, well, why are you doing this? Is it reducing your ego? Is it making you more loving and kind or not? And it's, you know, it's by the fruits you shall know them. And so that's really. So it's a of a long winded answer to a complicated question. But it isn't a simple black and white issue.
Matt
Sure, yeah. So for a second there, like you touched on selfishness and greed at one point you said like you are trying to encourage folks to become capitalists, not consumers. And it seems like you are pointing folks more towards that selfishness mindset. If we are sort of greedy, how that could lead folks down paths of disaster as opposed to criticizing the overall system of capitalism. It sounds like you're. But you're basically pushing folks towards frugality to a certain extent, which I know that's something that, that we talk about a good bit here on the show, but can you talk to that for a minute?
Doug
So, yes, so. So it's. Frugality is important. You gotta, you gotta save more than you earn if you ever want to have real wealth. And so, yeah, it's the idea that you, you know, as I put in the book, like your capitalists are somebody who invests and saves and invests and has wealth and a consumer, someone who just sort of goes out there and spends everything they have on stuff and then they're broke and sort of, they're feeding into the negative side of the capitalistic system. And so the word capitalist has positive and negative connotations. And maybe the language here is a bit of a barrier. But essentially what you need to be able to do is to have enough money to take care of yourself and, and really live a comfortable life. Now, what that means for me and what that means for you might be very different things. But what I don't want is for people to endure the unnecessary suffering that poverty produces in their lives. Because we know from the science that your socioeconomic status is the best predictor of mortality. So the less money you have, the more poverty. Poor people get hit with more bad things that you don't want in life than you could possibly imagine. So poor people have higher rates of obesity, of drug addiction, of domestic violence, of crime, of workplace injury, cancer. All the things in life that you don't want to get hit with. Poor people get hit with it more than the rest of us because the stress of being poor is unrelenting. It's. It's like walking over a pit of alligators on a tightrope every single day. It's truly something that we should be trying to eliminate from the world. So is it so much like, oh, I want everyone to be billionaires, billionaires. Well, that'd be great. But mostly it's like I see this as a way of preventing suffering, like helping people with their finances. It isn't just about, oh, being super rich and greedy. It's about. No, it's about. It's about being a suffering prevention specialist is what I call myself sometimes. It's like, I'm going to try to help you avoid all the pain that's unnecessary if you can get your finances in order and have a robust and healthy relationship with money. So that's.
Joel
I'm going to update my LinkedIn now, change my title from Suffering Prevention Specialist Co Host to the Suffering Profession Specialist. I love that. I think, I mean, I think that's true. I've never thought, thought about it like that, but that's like a big motivation behind what we do is to help people not suffer with money. And we talk about this even in kind of our, our bios on the how to Money website. It's like, you know, neither of us are aiming for Elon Musk levels of wealth. And in fact, like, not even, not even close to a goal that registers on my radar. But helping other people, like, not mess it up the way I've seen people, including people in my family that are close to me, mess it up, that creates so much hardship. That's certainly a goal. I'm curious too. You mentioned in your book that you had a minister friend of yours who was quite stingy and that left an impact on you too. So part of this goal of inspiring not only good money habits, but also generosity, you've seen the opposite at play. Yeah. What's your take on stinginess in money?
Doug
Stinginess is a real problem for some people, right. And so you need to be frugal, but maybe we need to maybe distinguish between frugal and stingy. And I'm just kind of winging it here a little bit on these definitions. But like, frugal is all right. You need to be prudent about how much you spend because you need to have money to save so you can invest. But then stinginess is this kind of avariciousness that, that is basically a lack of love. It's a lack of, it's like where generosity is a virtue, let's put it that way as well. Like, so, so saving is important, but you need to learn how to be generous with your, with your resources at the same time. So there's a balance between, like, well, why do you have all this money? Well, the point of having it is again, to love and serve God in the world. Like, that's, that's why you've got it. So you, if you aren't giving, it's what I call the four pillars of finance. The four pillars of finance for me are earning, saving, investing and giving. You kind of got to master the first three pillars before you have any money to give. But once you have some wealth, that's the final pillar that is essential that everyone should be giving back. And to the extent that they're able to fix the crack in the world that God put them on this planet to heal.
Matt
So you are segueing very nicely into your new book before and we're going to talk more about the Enneagram right after the break here, Doug. But before that, I guess I got one quick follow up. So you mentioned with your pillars giving being essentially sort of like the final step, what are your thoughts on folks giving money essentially all along the way so as they are first learning how to handle their money well while they are still in debt, perhaps to essentially build that muscle. Because that's something that we've talked about here on the show before and it's something that we both, that Joel and I both have done too, where it's always been a part of, I guess just how it is that we handle our money as opposed to seeing it as like this sort of finish line, like, oh, because once I get to this certain net worth amount or once I get this whatever promotion, then I'll finally be able to be a giver. Can you, can you speak to that?
Doug
Yeah, I mean you want to be generous along the way. It's just a matter of, it's the giving needs to be in proportion to your income and savings. So as long as you're not harming yourself in some significant way, then of course you need to be giving again. All four pillars have to be in place at all times. And so as your financial health improves, then all four pillars are sort of rising together. Let's put it that way.
Joel
Yeah. All right, we're going to get to more on the Enneagram. Talk about Doug's new book and if you don't know what the Enneagram is, is we'll talk about, we'll inform that it's, it's actually a really beautiful way of understanding yourself and how you're created and then how that impacts how you think about and handle money. We'll talk more about that with Doug right after this. It's an interesting time for business. Tariff and trade policies are dynamic, supply chains squeezed and cash flow tighter than ever. If your business can't adapt in real time, you're in a world of hurt. You need total visibility from global shipments to tariff impacts to real time cash flow. That's NetSuite by Oracle, your AI powered business management suite. Trusted by over 41,000 businesses.
Matt
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Matt
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Matt
Nice.
Joel
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Matt
We are back from the break, talking with Doug Lynam, how he got from being a monk to a money monster. And Doug, let's talk about the Enneagram. I think before the break, you mentioned Brother Pius.
Doug
Yes.
Matt
If I remember correctly, I think that was avoidant behavior of an Enneagram. Number one, you can correct me if I'm wrong here, but you got it.
Doug
Okay.
Matt
Awesome. Awesome. We have seen just a rise in the popularity of the Enneagram. I feel like I read a book on it. I don't know, maybe like several years ago. I'm still not totally sure what number I am. But can you explain to listeners maybe who aren't as familiar with it, what it is and why you yourself have gravitated towards using it?
Doug
Sure. So your personality has two components to it. There's a nature component, which is your DNA in your genes, that has a very deep and profound impact on how your personality is going to be shaped. But then there's also a nurture part to your personality. And the Enneagram explains that side of who you are. How your childhood environment shaped your personality and shaped the ego defenses that you had to have and had to develop in order to survive in this world. And what's interesting about the Enneagram is what, as you think about a color wheel, if you're thinking of a color wheel, a circle. And then if you were to divide that up into nine slices, like nine pie slices, then where each of those pie slices are, that's a Kind of an archetypal pattern of personality that you can develop in your childhood. So there's nine archetypes of personality in the Enneagram, but there's also an infinite variety inside each one of them. So it's got lots of flexibility and room for all of our unique individuality. But there's only so many ways you can design a human ego. Think of it like this. And I like to use car metaphors because I think it helps. So you can think of it like a car. The car you drive has a unique year, make and model. And your car is completely unique from every other car on the road. And yet it still has a structure. We could put it in kind of a category of a type of car. So we can have SUVs, we can have compact cars, we can have family sedans, you can have Hummers. Or there's all these different ways. So there's a kind of a model of car, style of car that you're driving. And that style of car determines how you're going to experience the road of the highway. But same thing with the Enneagram. Your ego is the thing you're driving around in. And the style of ego that you have determines how you perceive and see and interact with everything, life. And so it's a really robust and really important tool to help you understand who you are. And one of the things I've done with this book is try to really ground it in both the latest research in neurobiology and childhood developmental psychology. So it's got really robust scientific validation these days. It used to be a little woo woo, but it's not that anymore.
Joel
Yeah, well, one of the things, too, I guess if someone is really first beginning with their personal finances, they might say, I got to start tracking my spending. Right. That's an important part. I got to make sure I save up that initial emergency fund. I should probably look into kind of my credit score and the importance of that and how that impacts, like, the whole rest of my financial life. And you, you basically say, actually understanding your Enneagram type ranks up there, at least with some of those things. Why do you think it's so powerful for people who want to handle money better? Why do they need to dig into kind of some of that personal personality stuff?
Doug
Yeah, because what the Enneagram will tell you is what your deepest unconscious fear is. Like, what's the thing that you're really most terrified of in life?
Joel
Because that was not like sharks or anything like that, right?
Doug
Well, it could be sharks. Yeah, it could Be. I mean, that. But there's. There's something deeper down down below the sharks. If you, if you get. If you really get into it, it's. That's.
Matt
Keep peeling back the layers, keep pulling back the layers.
Doug
So, so each. Each of these archetypes of personality in the Enneagram is running off of, well, here's a way of thinking about it. If I could go a little deeper into it with you. So you have to imagine what it was like in the womb when your consciousness first flickered on. And my hypothesis with the Enneagram is that you are probably in a state of unconscious unity, meaning you were one with your environment, but you were unconscious. You didn't have a clear sense of what's me and what's not me. You're just kind of floating in this oceanic bliss of oneness in your mother's womb. And then eventually you get born and you get popped out, and it's like, surprise. There's more to reality than just you suddenly. And then there's a physical umbilical cord that gets cut, obviously, and you're physically separated from your mother. But instantly, there's a psychological umbilical cord that forms between you and your caregivers because you develop this egoic co dependence on your caregivers immediately at birth, because they have to do almost all of the driving of life for you for the first several years of your existence. So they're essentially driving you around in reality, keeping you safe and protecting you and telling you what to do and what not to do. Right? Because you don't have reality. You're still trying to figure out what this reality thing is. But over time, that psychological umbilical cord has to be cut in order for you to have an individuated sense of self, in order for you to have a unique, distinct identity from your caregivers, from your siblings, from all of the rest of reality. And so that psychological umbilical cord has to get cut over time, and it has to be cut with sharp negative emotions, because positive emotions will just reinforce your connection to your caregivers. And so what the Enneagram tells us is that there' swe know from the neurobiology that in all mammals there's really three core negative emotions, and they reside in the mid limbic region of the brain for all mammals. And all other negative emotions are some combination of these big three negative emotions. And the big three are anger, sadness, and fear. So anger, sadness and fear are the sharpest emotional lives. And your Enneagram type is determined by which of those three emotions you experienced more of in your childhood did you experience more anger or sadness? And sometimes shame is another term we use for sadness in the Enneagram, and that's fine. Or was it fear? And so which of those emotional labs did the cutting of that psychological umbilical cord? And that gives us what we call the three triads of the Enneagram. So this color wheel we've got, you break it into three sections or three quadrants. And then each of those three triads, those quadrants can now be broken down into three subsets. That's what gives the nine types, because there's three core negative emotions that anger, sadness, or fear. And then there's three ways you could process that negative emotion. You could externalize it. Let's say we're dealing with anger. You could take that anger and you could externalize it. And that's like having a food fight with the world. And that would call what we call that the type 8, which is the challenger. And they hate being harmed or controlled. And so that's. I call them the Hummer of egos. Or you can take that anger and you can internalize it, and you get a Type one. I call them the Improver or the BMW of egos. And their greatest fear is being bad or defective. So they're always trying to improve themselves or improve the world around them. And they're very good at that. And they can also be. All of us have our quirks that can be annoying when we get too deep into our unhealthy parts of our type. But then there's a third option here is which you can have both. You can both internalize that anger and externalize that anger. And that gives us a type 9, which is called a peacemaker, or I call them the RV of egos, meaning their greatest fear is a loss of wholeness from conflict. So type 9s are sitting on so much repressed anger. They've got this internalized anger directed at themselves for not being able to meet their needs as a child. And they've got this externalized anger at the world for not meeting their needs well either. And so they want everything around them as peaceful as possible because they're terrified of a loss of wholeness, of anger ever came roaring out. And so that just. That's just a quick I'll stop there. But it kind of gives you a sense of how the Enneagram works, how it forms and what your greatest fear is. And then we can relate to money here in just a second.
Joel
So the Goal of recognizing that. Right. Is it essentially shining a light on ourselves, how we tick, how we function, that maybe we go through life more unaware of, typically. And because we haven't done the introspection, we don't really know why we do some of the things that we do. And once we dig a little deeper into the why behind how we work, that's going to reveal some stuff to us that's going to help us get better with our finances.
Doug
Absolutely. What I've done with the Enneagram is I've taken the Enneagram and I've layered on top of it what I call the attachment theory of money. Now, the attachment theory of money is very similar to the attachment theory of relationships. It's almost identical to it, just applied to money for those of you, your listeners who might be familiar with it. But what the attachment theory of money says is that there's two unhealthy ways that we can relate to money, which is we can be anxiously attached to it, which is like the Ebenezer Scrooge or the Gordon Geckos of the world. Or we can be avoidant of money. We can push it away like I did when I was younger. People who are fearful of it, who hate opening their bills or doing their budget or just the world of finance scares them too much. And so you can be either anxious or avoidant. And then that gives us two money monsters for each of the nine Enneagram types. And then also going back, if we could, just to those four pillars of finance which we talked about earlier in the show, which was earning, saving, investing and giving. Now you can be anxious or avoidant in different areas of your financial life. You might be an anxious earner and saver investor, but an avoidant giver. Or you could be an anxious earner, but a terrible saver if you spend savings. So the system of the Enneagram combined with the attachment theory of money really dives deep into where you're likely to be struggling in your financial life. Why? And then offering people the tools to overcome those problems.
Matt
Is there something that determines whether or not someone takes a more anxious approach or more avoidant approach? Because as I was reading your book, like there was, I saw myself in both of those behaviors at different points in my life. And sometimes, like, almost simultaneously regarding the same task. Right, so like you're talking about here, going back to the four pillars, even when it comes to. Let's just like, choose one. Like saving, like I have seen at different points in my life, a more anxious approach, while Simultaneously somewhat being avoidant when it comes to. I'm just thinking of, like, certain bills or something like that. There have been times where I am very on top of it. And this isn't to, like, turn this. It's not like Matt Enneagram time.
Joel
Oh, come on. Let's do some dissecting here.
Matt
But I guess I'm curious to hear your thoughts there, Doug. What is it that causes someone to take a more anxious turn versus a more avoidant turn where they're just ignoring it altogether?
Doug
Yeah, that's a hard question to answer. I can only guess. And I would just say it probably has to do with childhood. Most of the stuff goes back to childhood issues, like, you know, what kind of childhood traumas you might have had as a kid around money. The emotions, the positive or negative emotions that come up for you around it. If you grew up in a. Really. Some people who grew up in a lot of scarcity and. Or poverty or tend to be more anxious about money. That's an oversimplifying. It's a really complicated question. There's no right answer. But the simple answer is it probably just goes back to your childhood. And for whatever reason, it's triggering either an anxious or avoidant emotion around the money. Depending on the context, we could be jumbled in our style. Right. Most of us are not all anxious or all avoidant. We tend to be jumbled. We're anxious in one area and avoidant another. And we can flip back and forth depending on the time of day or our mood.
Matt
Okay, so you're not necessarily locked into one type of process. Okay. Yeah. Doug's pattern.
Doug
Right, but you're going to have a pattern. You will see a pattern. Tend to see a pattern, though.
Matt
Okay.
Joel
Okay. So it's interesting. My wife's been studying the Enneagram much longer and more in depth than I have. I have, like, peripherally scanned some of the materials, including your book, Doug. But I pretty instinctively knew. Oh, I'm a seven. Like that, to me, resonated really quickly when I read about that personality type in the Enneagram. And one of the lines, let's maybe we'll turn the.
Matt
Is it Joel's turn?
Joel
So one of the lines in your book in that section, Doug, you say money. Anxious sevens treat budgets as fun sucking vampires and will often work to have enough money so they don't need to worry about a detailed budget. And I was like, I feel seen right now. Doug knows me.
Matt
No, Joel, a budget is a permission slip. It gives you.
Joel
I know.
Matt
It's a hall pass to allow you to spend.
Joel
And you're, you're right. Like I, I see the wisdom in that, but I also see my own intuitive response, which is I don't like the details. I like to fly by the seat of my pants. And so what allows me to do that is to have enough savings to where when stuff flies at me in the face, like, I don't get nearly as anxious or fearful if I have done that, or even just about an expense or I'm just excited about. And I'm like, this is more than I assumed I would spend. But I've got the money in savings to back me up, so it's okay. So I guess, I don't know, what would your suggestion be for someone like me who tends to use savings as a way to maybe avoid some of that money hygiene? I should be practicing.
Doug
Well, the first thing is just to be aware of it now. Now you know. So what are you going to do about it? Like, it's up to you to figure out, you know, how you want to be able to, you know, if it's working for you, then it's working for you. Like, you know, you don't need to become a different person or other than you are. But if that's how you want to roll, if it's working, then great. I think that's fantastic. If you want to, if you think you could do better, and if you think that there's a more robust way forward for you to have a healthier financial life, then okay, well then maybe just try baby steps. Like, what's one thing you could do each week that would sort of resolve that issue for you? But again, you don't have to be someone when you're not. You just need to be able to work around the, the own your weaknesses and own your strengths and, and try to minimize the weaknesses and maximize the strengths.
Matt
Nice. Awesome. Doug, we've got more to get to. We're gonna. I've got another enneagram question for you. We've got more to get to here with you right after this.
Joel
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Matt
All right, we're back.
Joel
Still talking with Doug Lyneham, who former monk, now manages money and really helps other people, especially with this new book, figure out, hey, what's going on? Who are you? How do you handle money? What are the ways that your personality is biased towards handling money so then you can shine a light on it and make some changes to improve your finances over time? I'm curious too, Doug, especially coming from the monk perspective. You talk about the mindful practice of managing money and you kind of seem to link money habits to religious practice. Do you think there's overlap there? And is there something we can maybe learn from some of the tenets of classic religious practice that can help us with our finances?
Doug
That's a big question. My brain just sort of short circuited on that question. Such a big one. Well, you know, traditional religious practices are, what they're doing is they're giving you a structure that allows you to live a healthier and happier and more loving and compassionate life. And so when you bring that in alignment with your financial life, when you bring those two things in harmony now you have, as we talked about at the beginning of the show, you have money is like your superhero utility belt. If you use it right, that allows you to do an awful lot of good in the world. And so it has to be wedded to a spiritual practice or else it's going to be used in the most, it's just inevitably going to be used in abusive and harmful and selfish and self centered and greedy and narcissistic and, you know, jerky ways. You know. And so with without a spiritual practice, everything in your life is probably going to be very, very challenging. But especially how you're relating to money and how you're using it and how you're earning it. And how are you living an ethical life? You really can't live a deeply ethical life, I don't think if you aren't bringing your spirituality into how you earn, how you save, how you invest, and how you give. So is there a particular, like, rule that from a particular religion. I don't think I could come up with that in my head on the spot. But I do think it's essential that you have a spiritual practice.
Joel
Yeah, I'm sure there are some people listening right now and they're like. I mean, they think it's interesting. They're curious about your story, but they're also like, either I went to church and I was burned, or I haven't been to church, I'm not interested. And they've also seen, of course, some hypocrisy or injustice done by the church. And so they're saying, well, religious practice. And I think I can keep those separately and do pretty fine with my finances. What would you say to someone like that? Like, hey, do you actually need a spiritual life? Or are there things that you can glean from spiritual practice without practicing anything spiritual yourself?
Doug
Well, I mean, I want to respect people who have been burned by traditional religions and suggestion that everyone needs to go out and join the church on the street corner up the street. But I know lots of people who are very spiritual, people who fall into the spiritual but not religious category. People who have a spiritual practice but maybe aren't doing it in a traditional way. I think that's wonderful as well. But obviously you can do just fine in your finances without a spiritual practice. You don't have to have it. But I think if you want to be happy in life, it's about being connected to community. It's about being connected to your sense of the divine and God in whatever faith, tradition, whatever that looks like for you. But essentially, I think it's really about how do you have community and how do you have. How do you find love and service in the world? What does that look like for you? And I just would suggest that that's something that we all want and long for. I think we fully happy and complete as human beings.
Matt
Yeah, I believe it. Yeah. Okay. Going back to, I guess, the enneagram for a second, I'm wondering if you think that there are different types of enneagrams that we tend to see more in the world. Like you, you Mentioned it almost as, like a color wheel. And I like, you think about colors in the world and, like, if you zoom out enough, like, the earth is blue.
Joel
Right.
Matt
Like. Like the blue marble, like out there, floating out in space.
Doug
Sure.
Matt
Is there a type of Enneagram number that you tend to see over and over in your life? Maybe. I don't know. That might be helpful for folks to hear you. Maybe quickly summarize.
Doug
I mean, there are some types that are less common. Like, type fives are maybe one of the least common types, but other than that, it's kind of. I don't know the exact statistics on it, but it's pretty evenly spread. There isn't one type that's more common than other types. I think statistically it's around 7 to 12% of the population is one type or the other. I think that's the rough.
Matt
Yeah.
Joel
So for someone who's listening and they're like, oh, I took the Myers Briggs back in the day, maybe that shed a little bit of light on how I think about myself and how I understand the personality that I have, what would you tell them? Like, is there a good place to get started to figure out what their Enneagram number is? Because especially if it's so revelatory and it's going to help us understand how we tick so that we can then understand why we're using money in the way that we are. Where's a good place to figure out, well, what. What enneagram number we are and find out some more. Some more details. Obviously, your book would be a place to kind of do some digging on that. Anything else?
Doug
Yeah. So I have a licensing deal with a company called. It's called IEQ9, and they have an excellent Enneagram test. And I can send you a. I have a promo code and link, and it's a great test. The reason I partnered with them is because it's got the. It's the most scientifically rigorous and accurate enneagram test out there. There's lots of free ones, and they're just not great. The free ones are maybe 50% accurate, which is great.
Matt
Says accurate as a coin flip.
Doug
And this one is closer to like, over 95% accurate and much more detailed. So I think it's worth it to spend a few bucks and do it right.
Joel
The free one told me I'm a type 13 and. Wait a second. How'd that happen?
Matt
Oh, man. Doug, we appreciate you taking the time to chat with us and we'll definitely link to your site. I know you've got that test linked as well. And we'll make sure to include any sort of promo codes that might help listeners get a discount. But can you share your URL with folks who may not navigate over to our show notes where they can find all that? Sure.
Doug
Just my name. Go to douglynam.com, that's L Y N A M dot com, and you can find all kinds of cool resources on my website.
Joel
Awesome. Doug, thanks for joining us today. We really appreciate it.
Doug
Thanks, man. Joel. Appreciate it, guys.
Matt
All right, so, Joel, do you think that you need to join a Benedictine monastery in order to find a sense of purpose? So do you feel like you've already got it?
Joel
I'm going to inform my wife this evening.
Matt
Take a vow of celibacy.
Joel
I was going to say she'll be devastated, but she might not be. Who knows? If she's not devastated, then I'll be really sad. Really?
Matt
Oh, dang it. I thought you'd be bummed out, babe.
Joel
Thought you were gonna try to get me to stay. No. Okay. Okay. Let's talk about big takeaways.
Doug
Yes.
Joel
Yes. Mine was when he said part of his goal is to help people avoid the unnecessary suffering of not having enough money.
Matt
That's the suffering prevention specialist phrase that he put out there.
Joel
And that was so good. I love that. I mean, I think of that. Never really boiled it down to that before, but I really do think of that as one of the major goals that drives what we do. And it makes me think of somebody who doesn't know what a balanced diet looks like and how that informs a healthy body. Right. And so they might assume that, oh, it's just about the amount of calories I intake over a given day. And then they eat McDonald's.
Matt
That used to actually be a plan. Weight Watchers. It doesn't matter. It's where the calories come from. But come on, we all knew that that was a whole lot of a whole load of bunk.
Joel
Right. Clearly, you're not getting some of the really important things that your body needs, and so you're probably not going to feel nearly as good. You might try to go for a run and peter out pretty quickly because you're just not providing your body the nutrients and resources it needs to thrive. And I think the same thing is true with money. You might assume some things, but then you don't know what you don't know. And so I want to see people avoid unnecessary suffering on the money front. And so much of that is kind of just getting that Baseline education and even beyond that kind of a greater understanding of yourself, like Doug talked about on this episode. But man, I love that framework.
Matt
There's not enough introspection to just to even understand yourself. So I guess kind of piggybacking off what you said, a big part of preventing that suffering is it's an others sort of focused approach to the world. And so my big takeaway is going to be how he was talking about. And I'm putting within our framework, which is you can be frugal, which he described as being prudent, or you can be cheap, which is a focus on avarice. And there's greed at the heart of that. And what is that but a lack of love. Towards whom? Towards others, towards other people. And so that just helps me to think through because oftentimes we talk about something that's either frugal or cheap here on the show. And I think when you are thinking about yourself, it can be easy to maybe justify something, a purchase or an action. But when you start thinking about others and how you treat the other people and the overall benefit that you're able to provide those, whether you're helping them when it comes to knowledge and preventing them from suffering in a financial way or just the countless different actions that we can take in our lives, I think that that can help act as guardrails in a sense to guide some of our actions and to ensure that we have this sense of unity and harmony within our lives. Which I feel like was just like kind of a running theme throughout everything he was saying. Like that's why he's talking about the Enneagram, is because he wants us to have harmony, like internal harmony with our. When it comes to our actions and how it is that we handle our money and how that aligns even with something as kind of high level as just our spiritual walks.
Joel
Yeah, I think too, being cheap or being greedy is often that sort of attitude of like, I got to secure my bag, I got to look out for number one.
Matt
Yeah.
Joel
Which is potentially an American quality, more so than most places. But that is something certainly to be pushed back against, I think because that's not a healthy habit. And ultimately it's not going to lead to. Yeah, while it might lead to more money in the bank account, it also might not like because you're not playing the long game. But at the same time, it certainly won't lead to, we don't think, greater levels of happiness.
Matt
Totally. Our beer, Joel, that you and I enjoyed today was called an elaborate metaphor. This is A New England pale ale. Oh, it's a pale. I didn't realize that it had very New England hazy ipa. It did sort of vibes going on.
Joel
It's funny, I didn't.
Matt
This is by Burlington Beer Company.
Joel
I didn't realize it was a pale either. I was gonna say it tastes like a session IPA to me. Tastes very like light and it had this soft mouth feel. And so, yeah, I thought if you put it in that session IPA category, it's fantastic. Same with the pale ale, I think. And I don't, to be honest. What's the difference between a session IP and a pale? They're pretty. Pretty much the same.
Matt
Fairly synonymous.
Joel
Yeah.
Doug
Yeah.
Joel
But this, I thought this was not like a mind blowingly good beer, but especially given kind of the.
Matt
Well, now that I know it's a.
Joel
Pale, it's really, really tasty.
Matt
It kind of like jumped like leapfrogged a little bit because it's like, oh, this is a pretty good ipa. But actually, no, this is not an ipa. This is a fantastic pale ale in my opinion because it's got all the complexities and the nuance and the flavor profile and the hops that you expect with a hazy, but just a lighter, easier to drink version of that. So I'm like in the moment changing my rating of this beer from a 375 to like a four and a quarter.
Joel
There you go.
Matt
If I were to rate this on.
Joel
Tap, if you're rating it against other pale ales, it stands out.
Matt
Yeah, absolutely.
Joel
All right, that's gonna do it for this episode. We'll link to some of the resources we mentioned up in the show notes on our website@howtomoney.com until next time, best friends out.
Matt
Best friends.
E
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Doug Lynam
Are there any pictures of you online? Then you could already be in a massive police database without even knowing it.
Doug
Clearview scrapes together images From Facebook, from LinkedIn, from Venmo Accounts.
Doug Lynam
I'm Dexter Thomas, host of Killswitch, a podcast about how living in the future is affecting us right now.
Doug
Police, they are trusting the software with this magical ability to lead them to the right suspect.
Doug Lynam
In this episode, we dive into how cops are using AI and facial recognition and sometimes getting it wrong and putting innocent people behind bars.
Doug
So if your accuser is this algorithm, but you're not even being told that it was used, let alone given any of the details about how it works.
Doug Lynam
Listen to Kill Switch on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Matt
Did it occur to you that he.
Doug
Charmed you in any way? Yes, it did. But he was a charming man. It looks like the ingredients of a really grand spy story. Because this ties together the Cold War.
Matt
With the new one, I often ask myself now, did I know the true Jan at all?
Doug
Listen to Hot agent of chaos on the iHeartRadio app, Apple Podcasts, or wherever.
Matt
You get your podcasts.
Joel
This is an iHeart podcast.
Podcast Summary: "From Monk to Money Manager w/ Doug Lynam #998" on How to Money
Release Date: June 18, 2025
Introduction of the Episode and Guest
In episode #998 of How to Money, hosts Joel and Matt welcome Doug Lynam, a former Benedictine monk who transitioned into managing over $250 million in assets as a money manager. Doug's unique journey from a life of vows and spiritual discipline to the high-stakes world of finance provides a wealth of insights into personal money management, financial resilience, and the intersection of spirituality and finance.
Doug’s Journey: From Marine to Monk to Money Manager
Doug begins by sharing his early motivations and pivotal decisions that shaped his unconventional career path. After graduating at the top of his Marine Corps class, Doug sought to prove himself to his absentee father, joining the Marines as a means of demonstrating masculinity and strength. However, a spiritual epiphany led him to question the suitability of a career involving high explosives and violence. Consequently, Doug made the bold decision to turn down his commission and join a Benedictine monastery.
Notable Quote:
“I decided to turn down my commission as an officer in the Marines and joined a Benedictine monastery… it just… it did a really good job of pissing my parents off.” ([05:31])
Monastic Life and Financial Challenges
Doug spent two decades in a monastic community, where he assumed roles such as heading a math department at a private school. Initially, the monastic life provided structure, purpose, and camaraderie similar to his military experience but without the violence. However, over time, the community faced significant challenges, including financial instability. Three years into his monastic journey, the monastery went bankrupt, compelling Doug to confront financial management—a realm he had previously avoided due to childhood associations of money with negativity.
Notable Quote:
“About three years into the monastic journey, the community went bankrupt… I joined a monastery, hoping to get away from money, and I ended up having to deal with it more than I would have if I hadn't joined the monastery.” ([09:10])
Transition to Finance and Addressing Retirement Plan Issues
The financial turmoil within the monastery inspired Doug to delve deeper into personal finance. While teaching, he introduced economics and personal finance courses, highlighting the societal need for financial literacy. A pivotal moment occurred when Doug examined the school’s retirement plan, discovering exorbitant fees, poor performance, and lack of fiduciary oversight. Frustrated by the systemic issues, Doug launched his own investment advisory firm aimed at creating better retirement plans for educational institutions.
His efforts gained significant traction when the New York Times featured his story, catalyzing his entry into the finance industry.
Notable Quote:
“The New York Times did a six-piece expose on the problem of teacher retirement plans… Ron Lieber flew out and did a big piece that went viral. That just launched my career in finance.” ([13:18])
The Enneagram and Personal Finance
Doug introduces the Enneagram as a powerful tool for understanding personal financial behaviors. He explains that the Enneagram categorizes personality into nine types based on core emotions—anger, sadness, and fear—shaped by childhood experiences. By identifying one's Enneagram type, individuals can uncover unconscious fears and motivations that influence their financial decisions.
Notable Quote:
“Your Enneagram type is determined by which of those three emotions you experienced more of in your childhood—anger, sadness, or fear.” ([29:55])
Doug further integrates the Enneagram with the attachment theory of money, distinguishing between anxious and avoidant relationships with money. This combination helps individuals identify their "money monsters" and develop strategies to overcome financial struggles aligned with their personality types.
Spirituality and Money Management
Doug emphasizes the synergy between spiritual practices and ethical financial management. He argues that money, when managed with a sense of purpose and community, becomes a tool for positive impact rather than a source of greed and selfishness. Drawing from his monastic background, Doug believes that integrating spirituality with financial practices fosters a more harmonious and ethical approach to managing wealth.
Notable Quote:
“Money is like your superhero utility belt. If you use it right, that allows you to do an awful lot of good in the world.” ([49:15])
He acknowledges that while a spiritual practice can enhance financial well-being, it is not a prerequisite. Instead, he advocates for personal connections and ethical living as foundational elements that complement financial management.
Final Takeaways and Conclusion
Throughout the conversation, Doug highlights the importance of financial literacy, self-awareness, and ethical considerations in money management. Joel and Matt resonate with Doug’s mission to prevent financial suffering, aligning with their own philosophy of providing practical, empathetic financial guidance. They discuss the balance between frugality and generosity, emphasizing the need to use money as a means to support and uplift others rather than for selfish gains.
Notable Quotes:
Matt: “A big part of preventing that suffering is its an others sort of focused approach to the world.” ([58:22])
Joel: “Money is not just about securing your bag; it's about creating harmony and serving others.” ([58:54])
Doug concludes by encouraging listeners to explore their Enneagram types to gain deeper insights into their financial behaviors and motivations, paving the way for more informed and intentional money management.
Notable Quote:
“All four pillars have to be in place at all times. And as your financial health improves, then all four pillars are sort of rising together.” ([25:30])
Key Insights and Recommendations:
Understanding Personal Motivations: Leveraging tools like the Enneagram can uncover deep-seated motivations and fears that influence financial decisions, enabling more tailored and effective money management strategies.
Integrating Ethics and Finance: Aligning financial practices with ethical and spiritual values fosters a more balanced and impactful approach to managing wealth.
Addressing Systemic Issues: Recognizing and addressing systemic problems in financial structures, such as high fees and poor oversight in retirement plans, is crucial for creating more equitable and efficient financial systems.
Preventing Financial Suffering: Adopting a proactive approach to financial management can prevent the unnecessary suffering associated with poverty and financial instability, aligning with the broader goal of enhancing overall well-being.
For Further Exploration:
Doug Lynam’s Book: Taming Your Money Monster: Nine Paths to Money Mastery with the Enneagram – Available now, this book delves deeper into how the Enneagram can transform your relationship with money.
Enneagram Resources: Doug recommends taking a scientifically rigorous Enneagram test through douglynam.com to accurately determine your personality type and its impact on your financial behaviors.
This episode offers a unique blend of personal narrative, practical financial advice, and psychological insights, making it a must-listen for anyone seeking to deepen their understanding of money management through the lens of personal growth and ethical living.