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Jackie Lamport
There is one thing that pretty much every single founder we have spoken to has said once they have bought it, they could never go back. You see, making money is one thing, and for a lot of people in our community, it's actually kind of the easy part. The hard part or the weird thing is what happens next, which is figuring out what to do with it. From the outside, it seems obvious. Get the car, get the designer clothes, deck out the house, maybe the boat. Or the watches. God, the watches. The problem though is that everything that you buy is another thing that you're responsible for. And everything that you're responsible for is, well, another thing that you're responsible for. And not only that, but the things that cost money, they might not actually make you feel good or like yourself. We had one guy on the show who talked about he. He bought a souped up Tesla and he was driving it around and he just felt like such a tool. So he eventually just got rid of it and bought a regular pickup truck, which felt way better for him. That doesn't mean that there aren't things that are worth spending on. In fact, there are a few things that have consistently come up on the show where everybody has said, yeah, that 100%. But if you're new here and you're wondering who those people are, it might make sense if I explain it a little bit. This is Moneywise, a podcast for High Net with founders over@joinhampton.com and that means it's a podcast, not for people who are trying to break into business or get rich. This is for people who already have and what comes next. And I'm Jackie Lamport, the producer of the show, which gives me a funny perspective because I have outsider objectivity and also insider access in the form of over 150 interviews I've done with founders for the show and also the network of founders of over a thousand people@joinhampton.com which means that I can kind of act as the collective perspective of these things. And in this episode, that collective perspective has decided on five luxury purchases that are actually worth spending your money on, Starting with something that sounds physically impossible to buy time. And yeah, I'm not talking about the watches. You might be able to tell how I feel. What I am talking about is buying back the time that you spend doing things that are tedious or unenjoyable so that you can spend more time doing the things that you do want to do. That means the housekeeper, the private chef, the personal assistant, that kind of stuff. There are obviously a lot of benefits to that, like, you know, personal enjoyment. I would spend all day playing guitar if I could. Or spending more time with your family. That's also probably a good idea. Also maybe just like putting it back into work so that you can really up that financial roi. And there's also the benefit of removing friction in your household. So there's no conversations about, did you do that thing yet? Or you should have done that thing, or why are you doing that, not me, that kind of stuff. And on the chef thing specifically, if you're anything like me and you hate cooking, it means that you get to have three healthy meals a day, which is healthy. I know that it can be a really fun thing for some people and food can be great, but I swear to God, for some of us, it's the most annoying thing in the world because you can never stop thinking about it, which means that you are also buying back some mental space. Now, if you thought that I was going to go through this whole list and not also list the caveats, then you clearly don't know me very well yet, because there are always trade offs. The first one here being for the people who aren't like me and do enjoy cooking, because somehow there are a lot of you. So, yeah, there are two risks here. One is that you accidentally end up getting rid of the meditative time that you didn't realize was meditative or restorative because it doesn't sound like it should be like cooking or honestly for me, cleaning the bathroom. Getting more time back means that you also have the potential opportunity to push yourself maybe a little bit too hard because you still want to make something of that time. Restorative and easy things are important. So if you're buying your time back, just make sure that you're also still making room for that kind of stuff. The other risk is that you make life a little bit too easy. Being a well rounded person does mean being disciplined and doing some things that maybe you don't want to do sometimes. Take it from Tommy Mello, discipline's one
Mike Brown
of those things that just I feel
Travis
like it's a massive, massive dopamine release when you do something hard.
Jackie Lamport
And it's not just about you. It's also about your kids because if they don't see you do hard things, then why should they? And I realize that I just spent maybe more time arguing against this than for it, but I think the pros are just a lot more obvious. The reason that it's on this list is because it is worth it. And so, yeah, but let's move on. You know what else buys time in maybe a little bit more of a real sense? Being healthy so that you can live longer. Which is why the next item on this list is personal trainers and some high end health investments. And by the way, that doesn't mean that you have to be Brian Johnson, because I mean, who can compete with that?
Jay Berard
I have the best biomarkers of anybody on planet earth. I'm the healthiest person out of 8 billion people.
Jackie Lamport
Brian's mission is in a whole other league though, so we're not going to worry about that. But there are actually a lot of biohacks and money grabs that are advertised as cheat codes that you gotta watch out for. Good health requires physical effort. So maybe a good rule of thumb is if you don't have to put effort in, it's probably not worth it. But something that not a single person on the show has said wasn't worth the money is a personal trainer. Somebody who can set up your workouts, know what's actually needed for you and your body, and more importantly, hold you accountable. And on home gyms, there are, yes, some people who maybe spend a little bit too much money on the big fancy machines and don't know how the big fancy machines work. But, but it actually supposedly is pretty much always worth it to invest in a gym at home. And that's something that even some of our most modest spenders have said so.
Guest Spouse
We do have a home gym. My husband loves to buy, like, the most weird, random workout equip. Like, he gets into these little. He'll be doing this program and he's like, I have to buy this thing to, like, work my ankle. Like, he had this special thing where you move your foot up and down with like a weight on. I'm like, what is this? It's like the most single use equipment I've ever seen in my life.
Jackie Lamport
So.
Guest Spouse
So we're like, okay, yeah, any kind of workout thing, health thing, we'll spend unlimited on.
Jackie Lamport
I spoke to Anthony over at Daily Body Coach, which is a fitness service for busy founders and also a frequent sponsor of the show, though he doesn't know that I'm plugging him right now. So. Hi, Anthony. I asked him about the home gyms, and he said that the people who invested in home gyms were actually the people who were more consistent and committed because they were creating less friction for them to actually do their workouts. So, yeah, worth it. And as much as muscles and mobility are awesome, the physical health isn't the only thing. Mental health also matters. And there has not been a single founder on the show who has spoken against therapy. It's a no brainer. That's a. There's a pun there. I'm sorry.
Mitch
All right, money wise listeners, here's the deal. On this podcast, we talk about money, and that's great. But the one thing that's even more important than money is your health. And a few years ago, I made a change. So I made a change to get fit. I wanted to get fit for vanity reasons. I wanted to look good, but I also wanted to feel awesome and hopefully live a long time. And the way that I made this change after years of struggling was I hired a coach and it changed my life. I went from being like 25% body fat to 13, sometimes 12% body fat. It changed my life. And that's why today's sponsor is Daily Body Coach. It's a premium online coaching service for ambitious entrepreneurs and executives looking to achieve their dream body and perform their best. Daily Body Coach is run by an exited software entrepreneur and Hampton member. And in fact, a bunch of other Hampton members are using Daily Body Coach. And they hook you up with a super personalized exercise and nutritional roadmap to help you achieve your goals. Their expert coaches are available seven days a week, so you can rest assured knowing that you have someone to hold you accountable every single day and to keep you on track. You can have it all they offer a 100% money back guarantee within 30 days, no questions asked. Make a change. Check them out. Daily body coach.com/moneywise. Again, that's daily body coach.com/moneywatch.
Jackie Lamport
And then there's preventative health care. Nick Huber might be one of the most frugal guests that we've had on the show relative to his net worth. And he has absolutely no problem spending a lot of money on high end health care for both him and his family.
Mike Brown
I spend three grand a month on health insurance for my family.
Sponsor Representative
Yeah.
Mike Brown
But I've probably spent 100 grand on concierge health for me, my wife, my mom, my dad, my wife's mom, my wife's dad. And I'm going to keep spending that money on additional family members because preventative health and things like that are just not a focus in the United States or anywhere in the world. So if you're serious about that, you know, there's a lot of options and things you can do.
Jackie Lamport
And J. Burard goes even further than just premium regular care.
Jay Berard
We get certain, you know, health tests that cost a couple thousand a year that we think is really valuable to us.
Jackie Lamport
I know that those last two things were in the boring, want to responsible, optimize your life kind of categories, but they're not exactly the things that you might think of when you hear the words luxury purchases. So let's talk about some of the luxury purchases. Though I will say that the list has kind of worked out the way that it has because those boring things are the things that are consistently worth the money. And you would be hard pressed to find, as many people argue, that a Ferrari was part three Dream homes On the dream home. I'll let some of our guests take the lead on this one, starting with Mike Brown.
Mike Brown
Building my dream house was one of the greatest experiences of my life. And by no means was this the best investment of my life from an ROI perspective. But how I try to frame investments now is return on happiness and investing in building my dream home. It's become a gathering place for we have monthly founder dinners. I host retreats here. And that has brought me a tremendous amount of joy. So, you know, what I try to think about now is aligning our wealth with our values and creating that life that we actually want to create. And to me, this is the pinnacle of that.
Jackie Lamport
And I say dream home, but in Travis's case, it was a dream cottage. Travis and I are both Canadian, so I can describe it as a cottage, though for everybody else, maybe I'LL say lake house.
Travis
I should be able to sleep easily 45, 50 people at this property.
Mitch
Does that change your happiness?
Jay Berard
Yes.
Travis
You could tell I smile when I say that.
Mitch
Or that's why I'm asking.
Travis
Yeah, 100%. I mean, I never wanted wealth for things. I wanted wealth for memories for.
Mitch
And that creates them.
Jackie Lamport
Yeah.
Travis
And it's a way to share, you know, my cousins, my friends, my, you know, I want this place used. If we're not there, it's not going to be locked up and like, no, you can't go. Like, I want people to go down there. Use it. It's a way for other people to be able to experience or get some joy out of the money we've been able to make. Right. And share that. So that was kind of our dream.
Jackie Lamport
You can hear it when he talks about it. It's not just a flex. It's something that genuinely brings a lot of joy to his life. Because it's not about checking off a box big house because I got the big monies. It's about what it enables, which is qual your family and your friends and maybe creating memories for your kids or having founders over for dinner parties and stuff like they do@joinhampton.com it's maybe not the best financial ROI, but emotionally it is. You knew this was coming. There are caveats because a dream home can very quickly fall into a the house owns you now kind of situation. Especially if you go too big, which you don't have to. Affording a big house is more than just the upfront price tag. There's also insurance and maintenance and property taxes and furnishing and on and on and on. We spoke to a guy named Hank who has a 24,000 square foot home
Sponsor Representative 2
and he said that that actually kind
Jackie Lamport
of turned into a part time job.
Mitch
How much time per week are you spending or per month making sure everything's taken care of?
Jackie Lamport
I mean, it depends. It's whether it's hiring contractors, evaluating their proposals and trying to oversee what they're doing. I probably spend 10 hours a week doing it. Maybe five to 10 hours a week. For him, it was worth it to provide a space for his kids and his grandkids to come over and make memories. But he did say that if he wasn't already retired, he wouldn't do it because even if you pay somebody to take care of things, it's a lot of time taking care of things. And kids. That's another caveat here because you don't necessarily want them to grow up Thinking that a home that sleeps 45 people and has a private chef and basketball courts, that would be awesome is normal. In fact, if I did an episode about the top anxieties that all of our founders have expressed, not raising spoiled kids would probably be at the top. Or at least the top two. For the next part, I'm going to move back to cop outs. Sort of don't blame me for reality. It's not my fault that expensive items don't really move the needle. Now we're going to talk about experiences. Not only do we hear time and time again that this is the best way to spend money, we also have the data to back this one up because we did a wealth report and we asked a lot of founders how much money they're worth and what they spend it on, and the majority of people reported their number one personal spend item to be travel and experiences. For this list entry, I'm actually gonna start with the caveats, because doing experiences just for the sake of them, things that don't actually line up with your personal values or what you want from life that isn't worth the money. Brian Johnson learned by doing just that.
Jay Berard
I did a few adventure trips like I drove a dog sled across the Arctic I did in Sweden. I went to an active volcano in Iceland. But outside of a few adventure things I'd always wanted to do, it was entirely focusing on the 21st century. It just. It didn't appeal to me to do other stuff.
Jackie Lamport
That's because what Brian Johnson values most is pushing human boundaries and more important, being remembered for it. Which you can't do in Iceland. Although maybe Jules Fern AI search is
Sponsor Representative 2
quickly becoming one of the easiest ways for companies to get in front of customers right now. And the best way to take advantage of it is with mentions. So it was built by a Hampton member and it gives you one simple dashboard that shows you exactly how your company ranks inside LLMs like ChatGPT and more importantly, what you need to do to get ChatGPT to recommend your product or service to potential customers. Every 10 years or so, a new growth channel is born. And for a small window of time, companies are able to get attention for cheap and drive massive growth. Imagine being able to go back in time and buy Facebook ads in 2007 with all the knowledge that you have now. Or even being able to go back and create TikTok content in 2017. The companies who took advantage of these growth channels in their early stages experienced insane growth.
Jackie Lamport
And guess what?
Sponsor Representative 2
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Jackie Lamport
The obvious thing here that makes experiences worth it is creating memorable ones for your family and your loved ones. And in a particularly emotional example of that, Mitch told me told us about how this has become his sole spending priority following his wife's illness and recovery.
Mitch
Our style as a family since the cancer has been pretty much two big values that we live by. The first is we believe in experiences over comfort, which means that, like, how many times would you do something really amazing but you sit on the couch and do Netflix, or you say, I'm tired or life is too busy, but like, experiences are everything. And I told her, Listen, 2024, we are going nuts on trips and things. And I bet you by the end of this year it'll be close to half a million on experiences.
Jackie Lamport
Post exit, one of our earliest guests, Ryan, he made a huge splurge that included his extended family.
Ryan
Also, we went to Antarctica last year, looking at Kenya this year, so we're able to, like, create these experiences. We hosted our whole family. There was like 30 or so people. We had people set up tables and brought in food and, like, had all these activities, rented out a pickleball court. We took everybody for surf lessons. Those memories and those pictures, I look at them every time and I think, wow, it's crazy that we can create situations like this to happen.
Jackie Lamport
But experiences don't always have to include your family. In fact, sometimes they're better not to. Jay Berard talked about how he values connecting with other people and learning about the world. And therefore his experiences looked a lot different, but they were also super worth it.
Jay Berard
Culturally, you're present, you're in the moment. You can take these experiences, these stories, these memories, right? And I've also done the party trips where we're at a club till six in the morning and. And having like, an amazing time. And like, that memory is amazing to take forward as you do more and more of those experiences. I'm not a car guy. I'm not looking to, like, acquire a bunch of stuff. So for me, it's experiences.
Jackie Lamport
Oh, and there's another caveat. Sometimes the big experiences aren't worth it, especially when you're considering your family as well, which is something that Chuck learned.
Chuck
So we decided to take our kids to Europe for a month. So we have kids from 6 to 14. Okay, so we take them out of school. We're going to Europe. And everyone, you know, if I told you right now and say, we're going to Europe, you're thinking like, oh, man, that's so cool. Like, that's great. You're rich. You're rich kids. Like, I know people are like, all the rich kids get to go live in Europe. Here's what I learned in that four months or four weeks in Europe. One, you know what kids really, really
Mike Brown
want just to, I don't know, hang
Mitch
out with their buddies.
Chuck
They want friends in Fortnite. That's my joke. They wanted their friends. They didn't care we were in Paris. They didn't care we were in London. They didn't care we were in Prague. Like, they have glimpses of fund memories that they just wanted to be with their buddies running around the neighborhood. So frankly, we didn't even make it a month.
Jackie Lamport
So how do you make experiences worth it instead of just hollow situations that you put yourself in? In speaking with founders, there have been two rec patterns. One is that you design it around connection and curiosity as opposed to status or being flashy. And two, there's intention behind why this place, why these people, why this time? All that stuff matters. And now for the final item on our list, the thing that I teased at the beginning where I said, once you start buying it, it's very hard to stop. So if you can't always afford it, maybe don't start it's business class or a more elevated version of that private travel. Ali Abdallah was actually a pretty frugal spender. But listen to what he said when we asked him about his spending.
Jay Berard
I really like flying business class. Whenever I do, I try not to take it for granted. I try and, like, do the whole gratitude stuff because I'm like, this would have been like. I wouldn't even have even entertained the possibility. I'd be like, how Fucking dumb. Do you have to be to fly business class? Like economy takes you in the same direction, everyone's getting the same destination.
Jackie Lamport
Totally.
Jay Berard
I just absolutely love flying business class
Jackie Lamport
in the let's go back to our buddy Jay Berard again.
Jay Berard
I can and will fly business class any time I want to. I still don't care if it's like a short flight, if it's an overseas flight, I'm always going to fly business class. That's probably the highest level of the feeling of wealth for a lot of
Jackie Lamport
people in this community. This is the ultimate I made it. It's not the big house, it's not the nice fancy car. It's being able to get on a plane, lay down on that plane, then get off said plane without any back or knee pain. That is the ultimate luxury. There are only two downsides really. One, the thing that I already explained, which is that if you start, make sure you can afford not to stop. And two, the kid thing. Because, yeah, raising spoiled kids. We had a parenting expert on named Dr. Becky and she told a story about why it's important not to forget that part. I've told this story before, but to me it's so compelling because these are the loveliest, most well meaning parents and the dad had become very successful and 16 year old had a full blown temper tantrum in an airport when he found out he wasn't flying first class. So there you have it. That's the list, the five luxury purchases that according to the people who can afford them are actually worth it. We have buying back your time, investing in your health, making that dream home a reality, meaningful experiences and then yeah, of course, just flying in a way that doesn't destroy your body. The pattern here is that the things that are worth it are the things that give you time and make you healthier and make your life feel more memorable, memorable and calm. And the things that aren't worth it are consistently the things that you just bought because you could the items, the things that actually just over complicate your life instead of adding anything to it. I'm Jackie Lamport and this is money wise. And again, this podcast is made for the founders over at the community of founders over@joinhampton.com so if you're a founder doing at least 3 million in revenue, go check it out. Totally worth your while again, joinhampton. Com and if you're interested in a podcast like this, you want to work with me, with my team, then check us out at lowerstreet. Co because yeah, that's what we do. We make podcasts. Thanks for listening.
Moneywise – Episode Summary
Episode Title: 5 Luxury Purchases That Are Actually Worth It
Date: December 9, 2025
Duration: Approximately 19 minutes (excluding ads)
Host: Jackie Lamport (Producer, standing in for regulars Sam Parr & Harry Morton)
Guests & Contributors: Mike Brown, Travis, Jay Berard, Mitch, Anthony (Daily Body Coach), Chuck, others from the Hampton community
In this episode, Jackie Lamport distills insights from over 150 interviews with founders and the wider Hampton founder community to answer a nuanced question: "What luxury purchases are actually worth it when you're no longer focused on making money, but on making the most of what you've already earned?"
The episode is a synthesis of collective wisdom from high-net-worth founders, presenting the five luxury investments unanimously agreed to have real, enduring value—moving beyond watch collections and flashy cars to things that enrich your time, health, relationships, and memory-making potential.
Summary by Theme:
On Moneywise’s “5 Luxury Purchases That Are Actually Worth It,” the consensus among founder community veterans is clear: spend big on buying back your time, investing in your (and your family’s) health, building the home that brings people together, designing experiences to remember, and traveling in a way that reduces stress. Each comes with caveats, but all add lasting value when aligned with core values and relationships—far outweighing the fleeting allure of “stuff.”
For Founders & High Achievers:
If you’re asking yourself, “What’s really worth it?” turn to the things that make life calmer, healthier, more joyful, and deeply human.