How Different Generations View Wealth

Each generation is shaped by its upbringing and the defining events of its time. In this episode of Couchside Conversations, Wealth Advisors Sophie Leahy, Austin Overholt, and Beau Wirick explore how these influences shape financial decisions across generations: Baby Boomers, Gen X, Millennials, and Gen Z (we still need more time to let Gen Alpha cook). Through personal anecdotes and real-life examples, they reveal how family money conversations change over time and why passing down core values, rather than just wealth, creates lasting impact. 

Tune in if you’re interested in…

• How different generations approach money, saving, and retirement
• Why financial values are shaped more by experience than age
• How to have better money conversations within your family
• Teaching kids about money through values
• Balancing spending, saving, and giving across generations
• What each generation can learn from one another

Transcript

SPEAKER_04 0:08

Today, I am joined by two wonderful wealth advisors, Sophie Leahy and Austin Overholt, to talk about how different generations view wealth. And so last year we did this conversation. It's one of my favorite conversations. Last year we did it and we kind of made a caricature of baby boomers and millennials. This year we're going to do something completely opposite. Instead of putting generations in a box, we're going to talk about how every person is an individual within a generational context. And so we're going to try to see things through more of an individual lens. However, you can't talk about generations without generalizing? Generalizing just a little bit. So with that, I would love it if Sophie and Austin, if you would take us through a little bit of a collage of each of the generations that we're talking about.

SPEAKER_02 1:00

Sherbo. And of course, before we do that, I think we need to hear from somebody else that has a little uh insight on these generations.

SPEAKER_00 1:06

Boomers are all about money. Gen X is like, is it all about money? Millennials are like, where is the money? And Gen Z is like, what is money? That's my bad stand-up about it.

SPEAKER_04 1:20

Okay. Sophie, I believe that you are technically, surprisingly, a baby boomer.

SPEAKER_01 1:26

Just technically. Just technically.

SPEAKER_04 1:29

So you have the honor of walking us through the baby boomer generation to start off with.

SPEAKER_01 1:33

So my hi everyone. My bet is that uh today in the room, many of us are baby boomers. Um, so um baby boomers are those uh that are um age 61 to 79, typically retired or approaching retirement. And uh for a bit of nostalgia, have have a look at the uh screen there and recognize maybe the the toys you might have played with uh growing up, um, the music you listened to, and some of the uh movies uh you might have watched for your enjoyment.

SPEAKER_04 2:07

Any baby boomers in the house that are looking at this collage, being like, oh my gosh, that is me.

SPEAKER_01 2:14

So Amy Polar told us that uh baby boomers think that it's all about the money, and it might be because uh they have benefited from the uh economic boom that followed uh World War II. And so they have been able to be good savers, uh, very often have been able to um own their own homes and uh save for retirement, have pensions, and now uh potentially be retired, you know, after uh many years of working hard, you know, in full-time jobs, uh and being able to uh enjoy a life of uh with more leisure uh as part of their lives. So, Austin, tell us about Gen X.

SPEAKER_02 2:56

So I'm not technically Gen X, but I kind of identify as one. Uh I am right on the border between millennials and Gen X. So, Gen X, those are gonna be people that are 45 to 60. And we get a little nostalgia up here. Maybe it might just be the void, we're not sure. Uh there we go. Okay. So when I'm seeing this, there's a lot jumping out. Definitely feeling the acid washed jeans vibe, got the Walkman clipped on, blasting Nirvana, not sure if anybody else is feeling that. Uh, but when we're describing Gen X, we're thinking of you know a group of people that are independent, right? They're resilient, they're uh maybe a little skeptical, uh maybe a lot skeptical, not sure. Uh, but how did they get this way? It really goes back to their childhood, right? Because that's where all things start is in our childhood. They were the latchkey kids, they're the ones that had to take care of themselves, you know, after school. They were waiting for mom and dad to get home to make dinner, you know, gonna be in before the streetlights get on. That's that generation. Let's fast forward a little bit into their early careers. They're hit with a dot-com bubble. So their portfolio takes a hit, but they're resilient. So it's okay. They're gonna claw out of this, they're gonna start building it back up. What happens? The great recession. They get hit again. It's okay. We've had 15 years now, their portfolios are there. Retirement is in sight. It might be years, it might be you know, a decade or two, depending on where you fall in that generation. But retirement's looking different. It's not gonna be the hard stop like it is with the baby boomers. It's gonna be maybe a semi-retetirement or a little bit more flexible, phased-out approach.

SPEAKER_04 4:27

It's really amazing thinking about the Gen X generation because, like you said, they kind of had a double whammy with two back-to-back recessions. Whereas the baby boomers were established in their careers in their mid-30s to mid-40s. Gen X was like mid-20s, maybe 30 years old when the dot com bust hit. It's like lose your job once, six years later, lose your job again. Brutal time for Gen X. I'm really sorry, guys. But don't worry, you got Michael Jackson.

SPEAKER_02 4:55

Alrighty. Up next, we have the millennials. The millennials are going to be those 29 to 44 year olds.

SPEAKER_04 4:59

My favorite generation. As a narcissistic millennial, it's all of our favorite generation.

SPEAKER_02 5:05

And unfortunately, our favorite food is what has kept us from buying houses. You see the avocado toast up there, spending$14 for a piece of bread and some smashed avocado. Uh a few more factors, obviously, going into that. Uh, but millennials grew up with computers, they grew up with cell phones, they're very tech savvy. Uh, when they were coming out of high school or maybe coming out of college, they were hit with that great recession. But the hit wasn't to their portfolio, it was actually to the job market. And so they're taking on lots of student debt with the promise that there was going to be this high-paying job out there, and there wasn't. So they were feeling underpaid. To make up this gap between what they were earning and where their living expenses were, we saw a rise in the gig economy. So we see side hustles coming up. We even see the social influencer rise. A lot of people just trying to find some way to, you know, afford to live essentially. Uh right now, retirement's a long ways out for most of us. What we're looking at is really just financial freedom over retirement. So we don't have a hard set date on it, but we just want to know do I have to work? I'm getting to work because I choose to.

SPEAKER_04 6:10

And then Sophie, you have a few kids who are in the Gen Z, this mysterious, this mysterious new generation called Gen Z.

SPEAKER_01 6:18

I have three kids who are in their 20s and fit in uh within the Gen Z category. So these were our age uh 13 to 28. So the teenagers of today and the young adults. Uh it also includes uh most of the NFL, you know, if that's as a fun fact. Um Amy Polar told us, you know, that this generation asks uh what is the money? It's because uh they're very much uh digital natives. Um, you know, they have grown up with social media, the internet uh influencers, uh, and it's also a generation that was very much influenced by the COVID pandemic that has uh influenced the way uh they've been socializing and uh looking for work. So they value uh flexibility, purpose. Uh they're ready to take on non-traditional um jobs. Uh and as far as retirement is concerned, we don't really know.

SPEAKER_04 7:15

Right. I I heard a story, um, I think it was a client of ours who said he challenged his grandson to a ping pong, to ping pong. And he said, I'll bet you$50 I beat you. He gets beat by his grandson, takes out a$50 bill, slams it on the table, and the kid looks at it and he's like, What is that? Can't you just Venmo me? Never seen a$50 bill before. Didn't know what to do with it. So, with that, that's the generalization of the generations. I want to get a little bit more individualized with you guys. And one thing about Sophie and Austin, both of you are definitely uh individuals who are value-based. And that's where I want to take the conversation now to hear about your individual values, how you've passed them down in your own family, have you received them from the generations above you? And so that's where we're gonna take the conversation now. Um, Sophie, I want to start with you with this question is how did your upbringing, I'm gonna say that again, how did your upbringing shape your financial journey?

SPEAKER_01 8:21

So I was uh raised in France by parents who uh were uh born um just you know around the beginning of World War II and uh grew up you know in the years that followed. Uh and I think the values they passed on to me were very much uh you know centered around family um education, spending a lot of time on investing in one's education to uh build a bright future, saving. Um and um generally I think it was very much um compared to the uh upbringing my kids have had, uh there wasn't a lot of impact uh from outside factors. You know, it was very much family-centric, and so it was a time when it was easier probably to save and not overspend because the temptations were not there.

SPEAKER_02 9:09

What about you, Austin? So my parents are baby boomers, but they're probably the most millennial baby boomers financially speaking. I like them. And by this I mean that they focused more on experiences than just that wealth accumulation. Uh, you know, if I reflect back when I was a teenager, I wished that we had the bigger house, the house with the pool and the game room and the big screen TV, you know, when there were monstrous things that took up half the living room. That was what I wanted, because that's what I thought was needed for me to have my friends come over and be the cool house to hang out at. And my parents and all their wisdom, you know, were able to talk me through this and just like that that's not what you need. We're not gonna pour tens of thousands of dollars into a pool. Instead, what they did was they took all of that money and they poured it into myself, into my sister, our friends. And feeding a group of teenagers every single week is a very expensive thing. I think that we need to come up with some kind of you know tax-advantaged account just for that. Um, but they made their home welcoming, they made it inviting, and it's so great to see that now. My friends still reach out to my parents or they stop by when they're there. And this really taught me just to be content with what we had. And it wasn't that it was wrong to want something else, uh, you know, but let's save up for it. We don't need to go into debt for it, and we don't need to do something just because that's you know what the next door neighbor's doing.

SPEAKER_04 10:24

Did either one of you resent your parents for how they were raising you with regards to their view on money? Or did either one of you rebel against that worldview that you inherited from them?

SPEAKER_01 10:36

You know, I did not, but my brother did. So same upbringing, but different environment, and I was kind of blind to the uh, you know, what was going on outside and pretty content.

SPEAKER_02 10:47

I I didn't rebel, but I definitely in the moment as a teenager probably felt like, hey, that's great, but let's get a pool.

unknown 10:53

Right.

SPEAKER_04 10:56

I never understood why we didn't have a pool. I didn't get it.

SPEAKER_01 11:00

Now you can say for one, Austin. You know, have you have your kids asked for a pool?

SPEAKER_02 11:05

Uh no, so let's not share that with them.

SPEAKER_04 11:09

Actually, great segue. Um so you both have kids. Austin, your kids are on the younger side, but you still have conversations with them about money that that are age appropriate. What do conversations look like now that you're a father with kids? How do those conversations look?

SPEAKER_02 11:23

Yeah, so my kids are nine and eleven, and when it comes to money, we're not talking about just the pure finance of it, right? We're talking about values, and we're trying to share those values with the next generation. And for me, my biggest thing is my kids, and that's who I want to share the values with. They're always watching, they're always listening, they are very well aware of what your values are because that's where you're putting your time and your energy and your money. Uh, they might not be able to always articulate it, but they know. And so when I'm looking to convey that value, I'm gonna do a couple things. One is I'm gonna talk to them about it, and the other is I'm gonna make sure that my actions match what I'm talking about. So think about what, you know, a trip to the grocery store. We're buying certain foods and we're avoiding other foods, or maybe we're just not buying them right now. Well, if I say, hey, we don't have money for that, that kid could dig that just one little simple phrase of like, oh my gosh, my parents don't have money. We don't have money for food. This is a problem. That's not the case. It's just, hey, we're not buying those cookies this week. You know, we're gonna save that for a celebration or something. Uh, you know, and the same can be true for vacations. Hey, we're gonna go and we're gonna do every activity, or you know what, we're gonna go horseback riding, but we're not gonna go paraselling. And that's okay, but help talk them through. And do we need to go line by line with a nine and eleven-year-old over our expenses? No, absolutely not.

SPEAKER_04 12:36

You think it's silly to act to think about this, but I think the most cutting-edge research shows that your financial mindset gets solidified by age seven. Age, age seven.

SPEAKER_02 12:52

You know, and that's why we want to include them in so many of these types of activities. And that includes giving. So, you know, for my wife and I, we give to our church, we give to local nonprofits. Our kids are a part of that, and that's great because they're getting to build that habit, see the value in that. I don't want to just wait for them to, you know, be adults and hope that they're giving back to society. But that's a lot of actions, right? That's kind of like in the moment. But we also do have intentional sit-down conversations with them. What is money? What is the role of it? What is the value in our family? And so for anything that my kids earn, there's gonna be split up into three buckets, right? So they might be doing chores or working in the vineyard with their grandpa, they can spend it, they can save it, or they can um give it away. And the reality is they have to do all three. So the spending is gonna be the biggest bucket on this. Go buy a treat, buy a toy, have fun. If you're wanting to bring a living creature into the house, that is a family discussion. That is not just a pure financial discussion. No raccoon in uh Austin's house. No. Uh and then, you know, for saving, they're nine and eleven. So we're looking at weeks and months, not years. I'm not expecting them to save up for a car or a down payment on a house, but let's get the bigger toy set or the bigger experience save up for a little bit for that. And then there is a portion that's always going to be going towards giving, and that is not something that I'm directing where it has to go. They need to come up with that, but it does need to go out to somebody else that needs it.

SPEAKER_04 14:12

Oh, have a financial advisor as a father. That's great. These kids. Wow, that's amazing. So if your kids are a little bit more, they're adults now. And so how have conversations looked like in the past? What do they look like now with your kids?

SPEAKER_01 14:26

Well, I'm glad we're still having conversations. That's the main point. Because, you know, to Austin's point, I mean, the way um, you know, uh the kids are watching, I mean, is there and is it remains there. But it's so great to be able to see them uh growing up on their own and making their own decisions. You know, you kind of uh keep your mouth shut and hope for the best. Um, but as they were growing up, as teenagers, conversations we had were around careers, you know, how much do you want to um you know decide the type of career you really want to do? And does it matter whether you make a lot of money or not? We've had these conversations, discuss what my husband and my choices have been, including the fact that I took a long career break to be at home with the kids, which you know had financial implications, but was you know one of our family decisions. We've discussed that, and I have two daughters, so that's very relevant uh to them, uh, and to my son too. Um we've talked about um college, college choices, you know, has been a big decision in our house because we both both my husband and I came from a background where education was highly valued. Um, and so we saved a lot of money so that our kids could have choices for college. But we told them uh, you know, we can finance uh, you know, uh your undergraduate education, but if you go to an expensive college, uh we will not help you out financially for graduate school. So they had a little bit of a choice. I think they realized they were extremely lucky that we paid for their uh college education. Uh my daughters chose uh expensive options, uh, but they found ways to pay for their graduate education. So one got a scholarship for to go to law school, and another one also got uh funding for research while she was doing uh a graduate degree uh in the sciences. So it was pretty we're pretty proud about that. But we've always you know discussed these choices and these options that they could have.

SPEAKER_04 16:22

Same question for you that I asked before of did you ever rebel against the advice that your parents gave you? Have you seen with your own kids now that they're adults that they've flown the coop, are they adopting the the value set that you gave them? And if so, what does that look like?

SPEAKER_01 16:40

I don't think they're rebelling, but I see them as being bigger spenders than I was. Uh so maybe some of you in the audience will relate to that. And that's you know, as I said earlier, I think it's it's largely a function of the different world they've grown in. I mean, you know, advertising, uh social pressures, and so on. And also what Austin was talking about, you know, this um desire to have experiences and uh live in the now uh rather than necessarily say for the future, especially when you see that it might be hard, you know, to own your own home in the future. So why bother? And uh why not you know enjoy yourself and do some traveling and uh go to concerts and so on, even if you can't always uh afford it. So not true a billion, but a different spanning pattern for sure.

SPEAKER_04 17:28

Final question for both of you What's something that you admire from a generation that is not your own? Above you, below you. Austin, you can go first.

SPEAKER_02 17:37

Yeah, so I'm gonna I'll I'll pick the baby boomers here. I I appreciate so much just their long-term mindset, right? That consistent putting money away for retirement, knowing that that will be the safer play for them.

SPEAKER_01 17:50

So and I think the uh you and my the fact that the younger generations willing to take risks, uh, don't have clarity about their future necessarily, but are willing to uh find their own way and find that balance between spending and uh thinking about their future.

SPEAKER_04 18:07

I I really hope the theme that we're trying to get across in this is that every family is a multi-generation multi-generational unit with in and of itself. And our hope is that you're gonna be able to have better conversations with the people within your family, grow connections, weaving those stories together after you after you've listened to this. Um I think we have like qu like maybe a minute worth of questions. If anybody has a question for Austin or Sophie, yes. I guess that's I mean your kids are Gen Alpha, right?

SPEAKER_02 18:44

Yeah, so we were focusing more on the generations that are still in the workforce, definitely. Gen Alpha is so new that there's the data is just not consistent right now of trying to identify them. I remember as a millennial, it took them a long time to try to pen us down. And some of that is just because you're going through so many different growth phases there. Um my kids are awesome though, so it looks good.

SPEAKER_04 19:05

And my son is four months old and he's Gen Beta. Uh I don't not a good financial investment so far.

SPEAKER_01 19:50

And I wish I had, you know, invested earlier outside of retirement plans, uh, you know, where the kids were growing up, but we put a lot of money in five to nine plans that we've used you know in that way. But you know, that's that's always something that gives flexibility to uh invest outside of uh you know deferred uh deferred plans.

SPEAKER_04 20:09

Great question. I I think we I think we're at time. Um, but thank you so much for joining us. If you have any other one on one questions for either Austin or Sophie, please come up and talk to them. They're very friendly. Bye.