10 Lessons on Wealth, Happiness, and Family
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This past week, I learned so much about the complexities of wealth, family, purpose, and the pursuit of happiness, and I really want to share all of those learnings with you. And they happened because I got invited to a retreat for high net worth individuals and investors put on by Long Angle. The event, speakers, attendees, they were all so amazing. So today I want to share a recording of one of those talks with you, where I sat down with Tad Fallows, one of the organizers,

To break down our top 10 takeaways from the whole event, from understanding how money can shape your mindset to learning why resilience can be more valuable than chasing perfection, we're going to share insights that you can use to live a happier and wealthier life. I'm Chris Hutchins. If you enjoyed this episode, please share it with a friend. And if you want to keep upgrading your life, money, and travel, click follow or subscribe.

And if you want to check out Long Angle, it is a free community and you can learn more at longangle.com. Now let's get into it right after this.

I love helping you answer all the toughest questions about life, money, and so much more. But sometimes it's helpful to talk to other people in your situation, which actually gets harder as you build your wealth. So I want to introduce you to today's sponsor, Long Angle. Long Angle is a community of high net worth individuals with backgrounds in everything from technology, finance, medicine, to real estate, law, manufacturing, and more.

I'm a member of Long Angle, I've loved being a part of the community, and I've even had one of the founders, Tad Fallows, join me on all the hacks in episode 87 to talk about alternative investments. Now, the majority of Long Angle members are first-generation wealth, young, highly successful individuals who join the community to share knowledge and learn from each other in a confidential, unbiased setting. On top of that, members also get access to some unique private market investment opportunities.

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To kick this off, takeaway one was that wealth can amplify issues, whether they're good or bad, and that it doesn't really necessarily matter how much money you have. If you have problems, both personal with your family, professionally, no matter how much money you have, those problems will seem to actually get harder and not easier. And so one great example of that was into this quote that Morgan Housel used, which was money's a financial asset, but a psychological liability.

And that the biggest issue can often be in your mind. And so as you have more money, there becomes more pressure with the decisions you have to make. And a lot of people struggle with when is enough. And he shared a John Rockefeller quote, how much is enough? Just a little bit more. And that's something that really stuck with me as I think about my journey through financial wealth and what that means and how to make sure it doesn't control me and I can learn to live with it

When he shared that Naval Ravikant was often jealous of other people until he realized, oh, you could be jealous of Warren Buffett. But do you want to have the relationship he had with his family? Do you want to be that old? And if you frame your jealousy or your desire for more against what you might have to give up to get it and to take the place of someone with it, I feel a little bit more content with where I am right now.

Yeah, what I thought was interesting on this one is this same theme came up across multiple sessions. So if we looked at the family office panel or we looked at the estate planning panel, there are different objectives, different things they're talking about. But this same concept came up repeatedly. The way I was taking it was basically money doesn't make you happy or unhappy.

but it really amplifies whatever is going on. And so if you are fundamentally dissatisfied, money is unlikely to change that beyond a basic level of sustenance. But if you're a happy person, you probably will be even happier if you get more money. There was an interesting podcast I was listening to where it was talking about the famous research that happiness basically tops out at something like 75 or 100,000 a year of income. And then some follow-on studies that seem to disprove that, that actually keeps going up beyond that.

And as they dug into it, really, both findings were valid. On average, it tops out there. But if you break it down to people who are

basically unhappy and basically happy. You do see for those who are fundamentally happy as sort of linear with no real endpoint increase in happiness with wealth. And so it really is being more of a tool and an amplifier than a fundamental driver. Yeah. The only other thing I'll add is that there were a lot of people that were really honest talking about their life after accumulating wealth, after selling a company. And one takeaway was that

people felt like they couldn't talk about these issues. When you're struggling and you're out of college and you're just starting to make money, it's really easy to talk about money with your friends because none of you had it. And then you make money and maybe your friends haven't yet, or you have a little bit more and now you feel guilty talking about it. So the more money you have, not only do those problems get amplified, but your ability to discuss them with peers becomes harder. So I will come back to that with another takeaway. But what was your second takeaway? So the second one was really, there's no...

one right way to invest. There's multiple versions of good.

And I thought a great analogy we heard from this was people argue about, hey, I like Mexican food. You like Italian food. Neither of us asserting that we are fundamentally right about which is a better kind of food. And the same thing that there is not a fundamentally right or superior way to invest in general. But that doesn't mean for individual people, there's not a better and worse ways to invest. So I think a lot of it comes down to this is not just

a two-factor analysis of, okay, the more risk I take, the more return I'm going to get, or the more work I put in, the more return I'm going to get. It's probably those things, but it's a lot of others, including things like liquidity came up a lot, scale, access, et cetera. And so maybe an example that came up a lot in the alternative asset panel there was around this idea of a liquidity premium, where if you look over a very long span of time, U.S. public equities returning something like

10% nominally, maybe 7% after inflation. But private equity doesn't go back as far. But over a significant time period, multiple decades, returning more in the mid to high teens. So you're looking at extra, say, 5% of return there. Some of that may come from leverage, but a lot of that is a willingness to accept a liquidity premium or an illiquidity premium.

And so thinking about that, there's not a right answer there. There's some people who really need that liquidity. But if you're saying, hey, this is money I got at 25 and I don't need it till I'm 65, then really, if you don't accept that liquidity premium, you're going to end up with a lot less than you might at the end. And so, again, not one right answer, but multiple ways of approaching it there. I was going to say to tie on the first one.

If I'm remembering correctly, I don't think Morgan Housel mentioned it here, but I believe that he's paid off his mortgage. For him, psychologically, having debt is a problem. Now, you could argue rationally that if you have a really low interest rate, you're better off investing and leaving that money as a loan. But for him, psychologically, that just wasn't comfortable. And it's not to say what he did was wrong and what my choice to keep a mortgage is right. It's that for him, it's right. And for me, my version is right. And

Neither one of us are doing the best thing. If you look only mathematically at the highest expected return, maybe you could make a case that one is better. But when you look at the grand scheme of things, you look at how it affects your psyche. There's no actual mathematically correct answer. No, I agree with that. A couple other things that came up here. One was around the importance of being disciplined. While there may be no one right way to do it.

There do appear to be some wrong ways to do it. So, you know, an interesting discussion I was having with one of the members of the crypto panel. He's been very successful in crypto for a long period of time and continues to be successful in there. And his particular strategy is looking more probably at shorter term trends and saying, hey, when we're in a bull market here,

I look at a broad basket of altcoins, which are the smaller ones, not your Bitcoin and Ethereum, but the things with small market cap that move around a lot more. And for him, he'll put in X dollars and when it's gone up to 5X, sell it off. But then the key thing is puts in a thousand, gets out five. He doesn't put in 5,000 to turn to 25 the next time and then put in 25 to turn it to 125, but has much more disciplined controls there because he knows, hey,

This is a weighted coin. On average, it's going to pay out, but sometimes I'm going to get killed. And if I roll the whole thing over every time, there's going to be one day where I go to zero. And so this idea of, hey, for some people, crypto is a terrible asset class. You don't understand it. You don't believe in it. You're not going to hold it through a downturn. For others, there's a lot of money there. But however you're choosing to invest, you need to do it right and have the sort of discipline to go through long periods of time with that strategy you've set up. Yeah.

Yeah. So lots of ways to invest. What else about investing? I think there is also a point around that markets are efficient, but they are complex. And so

based on your individual needs, you can optimize for yourself and outperform for yourself. So we talked about liquidity as a good example there, but that's not the only example where some people care more and less about liquidity. I think volatility is another good example. I remember this more from my personal life. After I went through my exit, I was talking with an advisor at Goldman Sachs and he said, okay, you know what we can do for you? We will get you half the S&P return for 25% of the volatility.

And I said, all right, well, how about you give me four times the return for twice the volatility? And he looked like I had two heads and I thought this guy has no idea what's going on, but we were both right. But we just had two very different objectives where I said, okay, I don't need this money for 40 years. So I don't really care. I mean, I would rather a perfectly linear line, but it's not that important to me. That's a straight line. I care more about where we're going to be in the end. And that again, to your point around Morgan paying off his mortgage, some people may care much more about how much volatility, but those are different preferences. It

in these efficient markets, if you're willing to recognize the things you want to optimize for and the things that you're not trying to optimize for, you can get for yourself a much more efficient outcome. Another example would be that in this world of alts, if you look, we went very deep recently on oil and gas investing. And, you know, I'm a big believer in climate change and the importance of that. And so a lot of both individuals and institutions have said, hey, you know, we want to totally divest from this sector. But what that does mean is for an investor who doesn't care as much about that,

the return on equity in that sector has become astronomical. Like if you look at the return on equity and drilling, it's something like 70 to 90% of the drill head. So if you're, I'm not at all saying that people should not invest along with their preferences, but it's an example of, hey, there's an efficient market, but it's efficient across 20 or 30 variables, not just simply risk return. Yeah, I think I'd always viewed the transition

trade-off, when someone says, oh, I've got this deal and it's going to make an extra 5%, my Spidey sense has always gone off. And someone pointed out when we were talking about the liquidity, they were like, well, what you're giving up is liquidity. I was like, oh, okay. This seems so obvious, but this moment clicked where

You know, yes, if someone comes to you and says they're going to give you 28%, you can redeem it any day and it's going to happen every year forever guaranteed. Yeah, your Spidey sense should be going off. But if someone says, hey, we have this asset class that usually performs better than the markets, but you can't touch your money for 15 years. Well, that's a trade-off and that's a trade-off that sometimes you might be willing to make. Also, the other kind of interesting market around search funds brought out this idea of, oh, there are small businesses out there.

And someone brought up that one third of businesses in America are not part of the public markets. So I thought, oh, wow, you know, you invested in DTI. I got the total stock market and you do, but you don't have the total market. So there are all these other companies. And they talked about how there's a ton of companies that are run oftentimes by the baby boomer generation that don't have a plan. And it made me realize. So my mother had a travel agency and it was pretty small and she planned conferences kind of like the one we're at right now.

And when she was done, she was like, well, I have these five clients. I really need to make sure that they're serviced well. So she was looking for someone to take over the business. And she came to me one day and she was like, oh, I was able to find someone to take it over. And I was like, oh, how much did they pay? And she was like, no, she took it over. I was so appreciative. I was like, well, you handed her five contracts for like multiple conferences that's worth money. And to her, it didn't even have any value. And so this kind of got me thinking, gosh, if you're willing to look in the right places, if

If you're willing to take a little bit more time, the markets are just open to a lot more than you might see on the surface level and that you might see investing in the total market. No, I agree with that. Maybe just the search funds, that brings to mind another interesting example of a member I was talking to here who's been very successful in the search fund space, which again is this idea of investing in entrepreneurs shortly out of business school who want to buy these truly micro-cap businesses. And his strategy there is basically in writing articles

six figure checks into 40 or 50 of these each year to the idea of efficiency, you know, efficient market hypothesis, you can't beat the average. What's interesting is you can change what the average is or what that benchmark is you're investing into. So I was talking about saying, hey, you're investing in 40 or 50 of these. You've talked to each of these guys maybe for an hour before you write your first check into it. How do you know that you're really beating the benchmark or beating the average? You say, well, no, I don't think I'm beating the average.

but I'm investing in an asset class that has average returns of 30 or 35% each year. So I don't need to be the average. I just need to get exposure to this micro cap. So again, efficient markets, the market is not only the S&P, it's private credit, private equity, it is litigation finance, it's all of the above. And so you can increase your returns without having to beat a given benchmark by changing what your benchmark is.

Yes. And I think the one important takeaway to pair with that, which I guess isn't one of the 10, some of these things might make sense at certain scales. And so I did a lot of venture capital investing. And part of that was angel investing that came after. And you can't just do one deal. Like you said, you need to invest in the basket. So I think diversification is really important in a lot of these things. And so, yes, there are multiple good ways to invest. Yes. If you find places in the market, you might get outsized return, but you're

You need to do it at a scale that makes sense because any asset class has failures. And so the reason why I'm a big fan of investing in the total stock market instead of picking one stock, because we all know there are lots of stocks that go out. And so when you think of all of these other asset classes, you can't think of it as, oh, I want to diversify by doing one search fund deal. And I want to diversify by doing one startup investment. You have to really be able to bring in the asset class.

and have enough funds to do that, which might mean that for many people, if you don't have six figures to invest in an asset class, it might not make sense to be in your portfolio right now. And that might happen down the road. Next takeaway. I had building resilience is more valuable than chasing perfection. And duration came up a lot. It's just the ability to be patient. There was a Charlie Munger quote. The first rule of compounding is to never interrupt it unnecessarily. This stuff works and it works even better when you can just let it run.

and you can sit back and watch things grow and compound over time and being patient, that unlocks alternatives. That just unlocks a little bit of peace of mind. I can't tell you how nice it is to not feel like I need to check the market every day. It doesn't stress me out. I have no idea. The entire time we've been at this conference talking about money and investing, I have no idea if the market's gone up or down. And it kind of feels nice knowing that I'm playing a 30-year game, not a daily game.

Yeah, I was speaking with a real estate sponsor who I've worked with, and I was asking him why he had not started paying distributions because, hey, you're fun here and you're sitting on 100 million of cash. You're in some interest, but not that much interest. You're throwing off positive net operating income. You've got your debt. Why don't you start paying distributions? And he said, well, the first rule of business is to stay in business. These are fundamentally profitable assets. And yeah, I don't think we're about to go into a recession. I don't think the Fed will keep raising rates.

I don't think we're going to have issues with collections, but I'm not sure I need of those. So I want to build enough buffer so that whether that means, hey, our net return ultimately is going to be 13% rather than 15. It could have been said, but I'm confident we're going to get you that teen return because we'll get that over the next six years. If I start paying those distributions and then I have to be sure the Fed's not going to raise interest rates again, I'm introducing a risk of zero in a portfolio that I can have confidence will have a solid return if I don't introduce that risk.

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And this lesson, everyone here and everyone listening probably knows that I'm a fan of travel optimization. It's come up a lot of times inside conversations. And so this lesson of being resilient doesn't just apply to your money. People have asked me constantly, how do I make sure that my Amex points or whatever points you have can get the most value? And I said, well, if you're really flexible, it's pretty easy. But if you're not, and like most of us, we want to go on a trip and we'd prefer to take a nonstop flight and we have dates that we can get off work or kids are out of school.

You probably aren't going to find a great deal every time, but you will probably find an incredible deal. One in five, one in 10 times. And so if you can be patient, let those points hang out. One of those 10 times, you're going to get 10 times the value of them and it will have paid off for waiting. So I think you could be resilient with your points. You could be resilient with your money, your time, but

But having that duration can be really valuable. And maybe just one other anecdote that hit home for me is I was one of the members on the family office panel. He runs a multifamily office. And so he was talking about somebody who was asking, hey, if I hire a family office, am I now actually just introducing

a new single point of failure into my world because, you know, what happens if something happens to you guys? And he was saying, well, yeah, we think about that actively. He and his number two, they never fly in the same airplane. And when they hire new people in the firm, say, okay, we've got a partner born in the 60s, a partner born in the 70s, a partner born in the 80s. And again, none of these things are totally fail safe. Bad stuff can happen. But as you're saying, this concept of resilience is very holistic. Okay. Next takeaway, number five.

Yeah.

had a huge exit, a ton of money. And he said, you know what I want to do here? I want to really get this right. This is a life-changing sum of money. So I'm going to talk with all the right tax advisors, all the right trust advisors and set it up. And so he found, hey, you know, there's this farmland trust thing. It has all these interesting benefits. It's not common, but Bill Gates uses it. And so if I put money in this farmland trust and I structure it so I can skip my kids and go straight to my grandkids, then we're going to miss all these taxes here.

And the crazy thing, I'd never heard this before, but you can depreciate the soil on a farmland, which doesn't make a lot of sense to me, but apparently it's in the tax code. So he ended up buying 80,000 acres of farmland and putting it into this farmland trust. I was talking to him now. He's like, okay, I did that at 24. 20 years later, I've got a four-year-old kid. The first person to take money out of that is his kid. So,

So we're looking at another 25 years before even a beneficiary. So he says, I'm growing coffee in Hawaii. I'm growing oranges in Florida. I've got corn in Iowa, but I'm still driving my Camry because I can't touch that money. So this idea of saying, hey, there's a mathematically right answer and a tax code, optimally efficient answer. And I asked if we could share this anecdote. He said, yeah, I want everybody to be aware of sort of how this stuff works.

but thinking about the flexibility of giving yourself some options in case you want to go a different direction in the future. There was a lot of conversations about AI and what impact it has. And we learned that the Wright brothers had no idea what the commercial use case was for an airplane when they created it. And we were talking about AI right now. What is it going to become? How will it impact our jobs, our money? We really don't know. And in almost every step function change in history and technology, we haven't really been able to predict what would happen.

And so leaving lots of flexibility in every aspect of your business, of your life seems to be really valuable. In a conversation about estate planning, we talked a lot about there are different levels, by the way. It's like, here's the version that everyone should do. Here's the version that people that have $10 million, who have $60 million, who have $100 million, and making sure you don't get too pigeonholed into a specific plan saying, okay,

I've heard a lot of examples of people say, hey, I want my kids, they need to have this much income or this many years of a steady job in order to get money. And then one of them gets disabled and now they can't work, but they've written their trust in a way that now they can't have any income and they can't be supported, which of course wouldn't have been their intentions. And so one of the takeaways I had when it comes to estate planning, which by the way, for almost everyone is worth doing because I like to say that if you don't have an estate plan set up,

then you're just saying that the courts will be my estate plan. Someone told me the same line about prenups. Everyone has a prenup. It's just whatever your state decided. And so being intentional about how you want things to work, but leaving the flexibility that someone you appoint could make decisions for you. And you could say, hey, I want you to consult with my kids. I want you to try to help them. But you don't have to say do this exactly at this age and only under these circumstances. And it's kind of given me a lot to think about.

Well, I think another great example of that that we heard was talking about a lot of people will say, okay, I want you to distribute 30% of the estate at age 25, 30% at age 30, 30% at age 35, whatever it is. But if you make that too rigid...

your child could be about to go through a divorce at age 36. And so if you force the distribution at age 35, then they're going to lose half that money in the divorce. And again, that's not something that anybody intended, but the more it's often called trying to control beyond the grave. And so the more you're saying this is exactly how it's going to be. And I have this clairvoyance of what's going to be best. I'm going to know better than everyone else 50 years after I'm dead, how it's going to work. That might work out well, but it could end up backfiring in ways that was clearly no one's intent.

And for the sake of people listening on audio in the podcast right now, this isn't just a thing about money, right? Some of these decisions are who is the guardian of your children. And if you don't decide, well, then the courts get to decide. What do you want to happen with your assets? Whether they're a ton or a few in some states, I learned California, very, very strict rules, kind of messy in New York, a little bit less messy in terms of probate courts, but having these documents. So it's clear who's going to decide who's

what happens to your health. And one example that was shared was, you know, a lot of people say, well, I don't know how to pick between my kids. So I'm going to let both of my kids mutually decide what happens to my health. And they're like, well, one of two things happens. They both agree, in which case it would have been good to just pick one. It would have been the same outcome or they disagree. And then it's really messy. And then you have to get courts involved and nothing works. But you can say when it comes to flexibility,

I want this child to be involved and make this decision, but I require them to consult with their sister or their brother. And so you can add a little bit of flexibility while preventing complication when you do all of these things. And I think one more, you know, beyond health, we don't like to think about it, but sort of end of life decisions. When there's a talk about helping aging successfully and caring for aging parents, there's this question of certain people get to a point with their illness where they would prefer to choose to end their own life.

And some states will permit that, but they will only permit that if you make that decision while you are still totally mentally sound. So at the point at which you have Alzheimer's or some other disease that's impairing your judgment, then you've lost that ability to make that decision. So everyone, basically, if you have kids or you care what happens to you, if you are incapacitated, you probably should set up these documents and it's not that expensive. And as life gets more complicated, you're

There are lawyers that will find infinite ways to charge you money to set up more complicated structures, which may not be necessary, but I think everyone needs to take a look at this.

Next takeaway, everyone can benefit from advice. And this is an interesting one. We did hear one anecdote about the most successful investor of all time, who I believe had something like 60% returns year over year, still had a financial advisor and how doctors oftentimes have doctors. And when we go back to the first takeaway about how money is a psychological liability, the same thing can be true when you're having to make financial decisions, you can get caught up in your own mind. Now,

My distinction, which I think we talked about and I know you agree, is that that doesn't mean everyone needs to go hire a paid financial advisor. That means everyone needs some place that they can discuss ideas. Maybe that's your spouse. Maybe that's your friend. Maybe that's a group like Long Angle where you can find people in a similar financial situation. Maybe that's going to events. But I think everyone needs some way to get advice and the degree to which that advice is helpful

sound and researched really depends on the magnitude of the decision, right? If you're going through an extremely tough medical situation, go get a real doctor's advice and don't rely on chat GPT. You share an example with me about a lawyer who tried to do this himself. Yeah. I mean, first he was a successful attorney, partnered a big name law firm, then went on to a subsequent non-legal career where he made literally many hundreds of millions of dollars.

And then got to a point saying, okay, I want to set my estate plan. I said, I'm a lawyer. How hard can this be? I'll need to pay this bozo 25 grand to set this up for me. So he set up his own estate plan. Inadvertently, he wrote one of his grandchildren out of his will.

And so then what happened when he passed away, he had seven grandchildren. This guy gets a hundred million. This guy gets a hundred million. This guy gets a hundred million. This guy doesn't get anything. And it led to destruction of his legacy because did he really care about them getting the money or did he want his family to go on, be happy, be successful, be loving and totally destroy that because you have this one kid written out of it. Everyone comes to all the meetings with their attorneys. The other kids don't want to share. So to your point around the more important decision, the

the more you should be willing to pay for that advice. That's a place where he should have spent the 20 grand to make sure he got that right. Now, another example actually came up in terms of in the discussion about how to stay out of trouble with the IRS, which just to be clear, that is not, hey, here's what you can get away with. But here's the things to make sure you stay away from if you don't want to, you know, be getting into legal disputes with the IRS. And one of the key things there was in terms of advice,

If some promoter is bringing you a tax scheme and they're bringing you not just, hey, here's the tax strategy where you put in a thousand, then you've deducted four thousand, which on its face should definitely put up your spidey sense. But if they also say, don't worry, here is an appraiser who's appraised it. Here's a tax lawyer who signed off on it. Here's a CPA who signed off on it. If all that advice is coming packaged for you, you're not really getting advice. You are getting a bunch of people selling you the same product.

So there it's worth spending a thousand dollars, talk with your own tax lawyer and say, hey, does this seem kosher? I'm being told this is very much in the tax code. Is it really? Or is this more of a gray area or, you know, appraising this asset? Again, if you're going to put a million dollars into some sort of conservation easement, you should make sure you're not just blindly taking some appraiser on it, but really talking with your own advice. I should probably rephrase it. Not everyone can benefit from advice. Everyone can benefit from seeking out advice, not letting advice seek them out.

Okay, so number seven. Yeah, so number seven, I love this quote that you're not at the end of history, which it really makes a lot of sense once you're told, but it's not intuitive, I guess, from human nature. So any of us, if we look at what we wanted 10 years ago and what we wanted 20 years ago, what our priorities were, what our values were, it's very easy to identify ways that you have become more mature, that you've just changed your thinking on things.

But it is much harder to recognize that you are very likely to continue to evolve in what your preferences are and what your priorities are going forward. A good example of this would be the one that I shared earlier about, OK, it's made sense to put your 80,000 acres into farmland now, but maybe my preferences are going to evolve in 20 years. So I don't want to totally lock them in there. But I think just this humility to recognize that you are likely to continue to change. And I think one of the things there is you can't know exactly how you'll change.

But if you look at people who are further along in the journey, you certainly see common patterns on how people tend to evolve. And so try to learn from those. One thing that I think was for me very uplifting, again, this talk about successful aging, as Jacqueline was saying, she's actually really looking forward to getting older. And I was saying, well, that's surprising because conventionally you wouldn't think about something. I'm looking forward to being 80. And certainly there's downsides to it.

But she says one of the things you look at, if you look at people's happiness, it starts very high in their 20s. It sort of hits bottom in the 30s and 40s as you have a combination of family stress and marriage stress and career stress and all that sort of thing. But after that point, it goes up and it doesn't stop going up. So people in their 50s are happier in their 40s. They're happier than in the 60s and 50s and the 70s and 60s. And it just keeps going up through the end.

So that's a very positive example of you're not at the end of history and some things will continue to evolve for the better from there. Yeah, it's actually a good segue to the next takeaway. But one of the pieces of this that I'll touch on was that it also made me think you're not at the end of history. Things are changing, but it might be worth not thinking of this defining moment of death as this point in time where lots of things change. So.

You don't want to wait till the end to give all your money away to charity because you might get a lot more value giving it away while you're alive and watching the impact it can have. You might not want to wait to give your children money until you die because you might want to see the impact it can have on their lives. And so not thinking of here's this moment that I'm planning for. This is when it all happens. And by the way, you might want to spend it along the way. Maybe you don't want to give it away at all. We've heard references to die with zero a lot.

But thinking about all of these things happening along a spectrum, being able to change your decisions and not think of let's all plan for one moment, which by the way, is the one moment we never know when it's coming. Okay, so the next one that actually connects perfectly, number eight.

Yeah. So number eight is that the key to happiness is a purpose beyond just accumulating wealth. And again, that may seem self-evident, but it's something that's important to remind ourselves on. So again, thinking about successful aging as one example of this, keys there being to have a plan, to have a purpose and to keep physical movement. And maybe to tie it back to maybe more of the people who are in your listener base who are probably not in their 80s, but, you know, maybe in their 30s and 40s and building actively.

that as we talked about in this life after the exit panel, when you're in this process of whether you're an entrepreneur building your own business or whether you're trying to make partner at a law firm or any point in your career, you may tell yourself, I'm just doing this to get to this financial success. You know, I want to sell this company for $10 million. I want to become a partner. I want to do whatever it is there. But it can then be sort of deflating when you actually get to that moment and you're

you become suddenly less happy and you realize, hey, it wasn't actually I have more money than I had before, but actually that sense of purpose, that sense of drive, whether it's, you know, I'm passionate about the people I'm working with, whether it's I'm passionate about the customers I'm serving, I just really enjoy the activity of building and growing. That was really giving you purpose. It wasn't the money was more of a scoreboard, but not actually the drive. Yeah, we learned that most of the people that pursue the financial independence, retire early movement,

often go back to work because they realize they didn't have a purpose yet. They didn't know what it was and they need to go find it because I just don't think most people, some probably, but want to just sit at home and do nothing all day. And so if you tie your identity and your purpose up with your work, but not intentionally, not because you said, I want to build this thing, I'm a builder, but just because you thought it was the path to wealth,

You can have some really struggling problems after you've hit that milestone. And I was surprised at how many people who'd accumulated wealth and gone from, I've sold my company to, I'm not sure what I'm going to do, that openly talked about going to therapy, trying to figure out their life because they felt like they lost their identity. You know, when they introduced themselves to people, it was all about wealth.

What do you do? What's your career? What's your job? What's your company? And it wasn't about what are you passionate about? And so people actually said one way to fight this is they shared the prompts they use when meeting people at parties, at dinners, and none of them are about work. They're like, what are you excited about? What do you care about? What's a crazy thing you've done recently? And by shifting that attitude, they were kind of able to transition their identity to things they cared about, which was way easier to understand.

find your purpose when it's not just tied up in accumulating wealth, because at some point you'll realize that's not the end goal.

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Yeah.

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I just want to thank you, Quick, for listening to and supporting the show. Your support is what keeps this show going. To get all of the URLs, codes, deals, and discounts from our partners, you can go to allthehacks.com slash deals. So please consider supporting those who support us. I think tying back this idea of in a number of ways, there's no one right answer. I think there's no one right answer to that purpose. It is not a legitimate decision.

to say that building stuff and being an entrepreneur does give me a sense of purpose. So if you look at one of the people on the post exit panel, one of their next steps was to buy back the company from the person who bought it because they just enjoy doing that, building businesses or starting a new business. That's purpose. But it doesn't have to be something financially remunerative. You know, another good example is talking about philanthropy. That for a lot of people can drive a huge amount of purpose. And so then saying, hey, I'm in the fortunate position of

having this $100 million. I actually don't want the lifestyle of just blowing it all on yachts and houses. Fine if you do, but maybe you don't. But you get a whole lot of satisfaction out of deciding the impact that you want to see, whether it's on your local community or the arts or whatever it is. And that's a new set of purpose. We can look at a lot of people like Bill Gates or others who they've made that their purpose. And I would imagine find a great deal of validation in it.

I did an interview back in episode 47 with Arthur Brooks, who's written a lot of books and studied happiness extensively. One of the interesting things was this idea that there's these two curves of happiness based on intelligence. So you have your fluid intelligence and crystallized intelligence. And so when you're younger and you're grinding those 20s and 30s years of your life, you get a lot of your intelligence from hard work. And then...

You've built up a lot of knowledge and you have this crystallized intelligence and people who don't professionally jump from one curve to the other end up in this place where they're like just trying to brute force their way in an environment of other people who are younger, have more energy, have more time, and they die very miserable. And so a classic example was Charles Darwin, who just tried to be a scientist and like do the research and died very unhappy versus Phelps.

I believe it was Mozart who decided he really loved classical music. And instead of trying to learn all the newest, coolest musics, was like, I'm just going to teach this music that I love and died wildly happy. And so figuring out the thing you love and not trying to brute force your way into some ambition, I think is a noble goal for all of us to have.

One takeaway, number nine, that we didn't talk about yet, but I know is kind of very relevant to both of us, people listening, many people here, is around kids and money. And the takeaway, which is probably the least exciting takeaway I have, is that even for the experts, people who professionally speak about kids and money, people who've written books about psychology of money,

Kids and money is hard and there is no perfect answer. And I know that's unfortunate. And we got a lot of great anecdotes of what people are doing. But we heard an example where someone who'd inherited a large amount of wealth and had turned out very, very reasonable, still ambitious. And it was kind of impressive that despite all this wealth that hadn't affected them said, well, you know what? My parents taught me these lessons. And at the dinner table, they talked about this. And this is how we acted.

And he was like, wow, so it worked. You turned out great. And what about your sister? And he was like, oh, she was ruined by money. And then we learned this story about how no matter how much money you have, your experience might be different even with the same set of parents. And so my takeaway was that you need to model your behavior because you're

kids are often learning more from what they see than what you necessarily say and that the lesson they might pick up might not be the lesson that you're intending. And so this lesson that I thought was great was about a grandfather trying to teach his children a lesson by saying, I'll buy you a lift ticket at the slopes. You just have to hike up once. And, you know, the goal of teaching them hard work. And later the children were asked, you remember that? What did you learn? It's like, well,

we learned that grandpa's an asshole. Like, we didn't learn that grandpa was teaching us a lesson of hard work. And so it made me think with two young children that,

Even though they might not be seeing and hearing all the lessons, they're still synthesizing it. And that if I can just model the values and behaviors that are important, that might get appreciated in ways I don't even know until the future comes. And that really teaching them just to appreciate money was kind of one of the biggest takeaways for me was you can spend money on things. You can fly in business class with your kids if you want.

but teaching them to appreciate what it took to get there, the fact that not everyone has it, the things that you are thrifty on can have a lot of impact. What did you take away? Well, I totally agree on there's no right answers there. I did get through several conversations, one consistent thread, which is the wrong thing to do is to try and hide it or a lack of transparency. That tends not to work out well. An example that I heard was

One kid found out that their father was extremely wealthy because they read about the newspaper. And so, you know, what's your takeaway there? Your takeaway is best case, oh, money's something to be embarrassed about. Worst case, my dad's a liar and, you know, didn't tell me anything on this. And so in reality, your kids are smart. They're going to pick up things. They're going to understand how they stand. And so by not having a pretty significant degree of transparency and age appropriate open communication, it

It really just means that you're taking this topic that you probably think is important and just abdicating the ability to teach them about it or the responsibility to teach them about it because you're sort of pretending it doesn't exist, which may be the best case in air quotes of what that looks like is when you pass away, they suddenly found out that they inherited hundreds of millions of dollars they didn't know existed. That's not really a best case, but that's if you sort of managed to keep the secret the whole time.

then otherwise you're keeping secrets and you're not teaching. So I don't have a right answer on how to do it. That seems to be a consistent theme on probably something to avoid doing, which is a natural inclination because people don't want to, in general, talk openly about, hey, here's how much money I make, how much I spend, how much I have, but that it's harder, but probably the right way to go. You don't have to have a hundred million dollars or a billion dollars to be thinking about how your money is going to impact your children's lives. And we talked

a lot about how social media is having a pretty negative impact. I think some of the people that were here that were fortunate to grow up in a childhood without social media are, gosh, I just, I'm so lucky that I didn't have this place where as a kid or a teen or a young adult, I could just see what looks like everyone out there doing better than me, making me feel uncomfortable about money or the opposite. People are ripping on people who have money and it can be really stressful, but it's

A few takeaways were just, like you said, being more honest, talking about it, talking about not just your family and your financial situation, but, oh, what have you seen on social media about money and having a dialogue with your children about that?

showing them what success looks like. So someone pointed out that their child was very, very excited about Taylor Swift and she has all this money. She's flying jets around the world. I want to be Taylor Swift. And their lesson was, well, great. Let's go look into how hard Taylor Swift worked for the success. How much practice did she put in? Are you to the

to their child willing to put in four hours of practice every single day because sometimes success comes from a lot of hard work and teaching them those lessons in kind of relevant ways is something I want to try to find more ways to incorporate. And I think there's also in this idea of being transparent, doesn't just have to be a set of numbers. Okay, this is what exactly our balance sheet looks like. But you are every day, you know, along with your spouse, making these decisions about where you want to spend money. And for almost all of us where we don't want to spend money,

So like an example in our case is that cars are not something we value. We drive two Hyundais. I remember that's probably unusual for our neighborhood. And at one point, our daughter is asking, hey, why don't we have a nicer car? Is it that we can't afford it? You know, which, yeah, seems like a reasonable question to ask and say, no, it's because we don't value it and not there's anything wrong with value. But here's why we do spend money on travel, for example, but we don't spend money on cars.

Not saying that we have the right balance, but that's at least a way that then you're having that conversation with them. And so to the degree you're hoping to impart values, it's in a natural conversation. It doesn't have to be a set, you know, once a week, we're going to sit down and go through the budget. And my kids are young enough that we're not really having a lot of these conversations, but I'm still trying to teach them

The value of money is a thing that lets you do things and we don't have unlimited amounts. So our new thing is we collect all of the glasses and cans and bottles in the house. And then the kids get to take them to the recycling place and they get the money. Unfortunately, it's such a small amount of money that we ended up going to Goodwill. They can each pick a book for a dollar. I try to time it so that our recycling budget will get us about $2. And they're like, oh, if I want a book, I have to do this thing that sucks, which is wait in line to go dump off these cans.

So we're trying to teach some of these lessons, not in ways that they remember the two takeaways from dad's trip to Goodwill, but that they just kind of are starting to synthesize this in our lives. No, I do agree that giving them at a much smaller scale, that sense of agency early on, I think is super powerful. One member was talking about he's got four kids and then thinking about, you know, when they asked to buy this stuff, he's not particularly interested in giving them. He says he errs on the side of giving them a much more significant allowance. So it's really a material amount of money.

but then almost everything they want needs to come out of that allowance, which I think is twofold. One, just selfishly as a parent, you're not fighting this rear guard action of, no, that comic book is dumb. No, that game is dumb. You can do whatever you want, but if you also want that shirt or you also want this other thing, you know, it's all in that same budget and you're giving them that gift of small failure they talk about. If they mess up and they lose $100, that's going to feel catastrophic to an eight-year-old.

But then they've learned that in a way that's not actually affecting their financial future in any way. So giving them that sense of control is huge there. And I would say, just speaking personally, the same thing from an investing perspective is we, for every birthday, every winter holiday, give them one share of stock, and then they have the option of investing their allowance in stocks. And so, you know, when my sons say, hey, I got 92 cents in dividends from Microsoft this month. And you know what else? Three months from now, they're going to pay me another 92 cents and another 92 cents.

And I don't have to do anything to work for it. If you got 92 cents, you'd be annoyed over him. Yeah, this is huge. By making it real, even at this tiny scale, suddenly makes it much more alive than just sort of us droning on about trying to teach them more theoretically. The only last takeaway I had on kids and money was I heard multiple people say that having a

minimum wage job at some point in their life. It came up in a talk and it came up in conversations, was really formative in teaching the value of work. And that it doesn't mean someone has to do it forever, but just doing it once in your life to understand that there is hard work. This can be what someone does forever. Understand this. Go work a summer busing tables. Go do something is something that I want

I want to carry on and, you know, not asking a toddler to go work a minimum wage job yet. But I hope that that's a lesson I can impart at some point. The only other thing that came up about kids and money, and maybe this is more in that category of flexibility, but it was really interesting talking with a state planner around, hey, how do you think about helping people think about their grandkids or great grandkids if they're older? And he said it is such a consistent pattern he sees where people are passionate about thinking about, OK, here's what I want to do for my kids. And

you know, how I want to teach them, how I want to nurture them. If they have grandkids, maybe thinking about that. But then beyond that sort of, all right, what will happen will happen. I don't feel that strongly about it. But then the day that first, you know, grandchild is born or the day that first great grandchild is born, they meet them. All of a sudden they become real people have that same level of passion around helping them develop and helping them realize their full potential that you have for the living ones. So in that idea of humility and realizing things will change, just that

that that is a change that you consistently see when that next generation arrives, they suddenly become much more real. Yeah. Okay. Last takeaway.

This is near and dear to my heart, which is that optimizing is not necessarily a binary game and that you can play as much or as little of it as you want. And so this spans almost every topic that we talked about. Everyone is here because they want to improve themselves, their lives, their relationship, their family, their money. And you can do that on every vertical, but you can also spend an infinite amount of time trying to better any aspect of your life.

Sometimes the rewards are worth it and sometimes they aren't. And learning how to think about that and learning how to make sure you don't go too far down that rabbit hole or go down a rabbit hole you don't need to go. You went to a family office session and you were like, there are people there that are like, oh, this sounds interesting. I would love to have a family office. But if you don't have...

what was like half a billion dollars, you shouldn't start a family office. You could try to optimize setting something up, but it just doesn't make sense. And I know that's not the most relatable example because I would guess that I could count on my hand the number of people who are listening to this right now in this room or later that have half a billion dollars. But there are things that sound fun and exciting to have to do to optimize that cost money that might actually give you no significant impact.

But again, as you said, it's not binary. That doesn't mean that therefore, if I can't have my own family office, I shouldn't do anything. You know, if you go one step down, you say, OK, maybe you have $100 million. You're a great client for a multifamily office. And maybe if you have $10 million, you certainly need good estate planning advice and good legal advice and tax advice. And if you have $100,000, you should be self-educating these things. So as you said, it's not binary. It's a spectrum. And there's kind of a different answer for the right level there.

I think another example of this different levels of complexity, depending on where you are, is in the estate planning one where he was saying, every person who walks in my office, they want to talk about Dynasty Trust.

everyone who walks out of the office none of them ever have dynasty trust because when you start to break down okay well you're gonna need to set up this entity in nevada you're gonna need to set up this one here and you your local council then who's your trustee managing and say all right you know what that's not for me but i am going to set up a state plan it's just not going to go to your billionaire and level yeah it's like everyone needs a power of attorney for property power of attorney for health care and a will and probably a revocable trust to give a little bit more

direction to what happens. Beyond that, we went through like a million four letter acronyms of different things you can set up that can get more complicated. Don't let those things scare you away from getting the basic thing in place, which I've seen people say, gosh, I don't know if I should do a GRAT or an ISLET. I don't know which one's better for me. So I'm not going to do a will until I figure out this decision. And so I encourage people to separate the decision to make one step towards something from the decision to like perfectly dial everything in.

And now you did a talk around points, and I know that's one that's near and dear to your heart, and you probably are in the 99th percentile on points optimization, but I think even you don't go all the way. Can you talk a little bit about how you think about that? Yeah, so I don't think the points game optimizing credit cards is very binary, but often it seems like I either have to play it or not. And it's not that you have to play it or not. It's do I want to

get the most value, okay, you could do that. But do I have to do all the work? There are services that you could pay $100 a person and they will take your points and optimize them for you for your trip. So like you could learn to do it all yourself and find all the sites and stuff. Or you could pay for one tool that makes the searching easier. Or you could pay for someone to use the tool for you. Or you could just get cash back. And it was kind of crazy to think about in the last year, we went from

2% cash back cards being kind of the best out there. Maybe if you parked a six figure amount, you could get a little bit under 3%. And now you can get three. And as of recording this in a month, supposedly U.S. Bank is going to give you 4%. And so this idea that as points are getting devalued and cash back is a better opportunity, what's the right answer? And for some people who have a ton of money,

trying to get that one free vacation might not matter. For other people, it might be the difference between taking a vacation. And I talked a little bit about, you know, yes, do you want 4%? Do you want two points? Or open up a new card and the ROI might be 15% back. And so like, how many cards do you want to open a year is a game that some people are like, I want to open 20 cards with my partner and we're going to do this. People might want to open 99 cards. There are all these paths.

but you could also just do one and that could be your free vacation. Yeah. I mean, I think your example of the panel, you talked about somebody who opened 396 cards and I sort of started breaking out hives and, you know, feel, oh my God, I don't want to do that. But I think there's a bit of you, this feeling of FOMO or like, Hey, I'm being profligate if I'm not going to Costco to buy gold bars and selling them to this broker so I can get 2% interchange here. But then if you

And if you're going all the way there, you are just making that your job. It can be a reasonably well-paid job, but you're deciding that this is what you want to do for your career is just look for every little loophole that every fortune 500 company offers and rip open that loophole and dive into it. And so that's fine. If you want to do that.

You're saying you don't have to feel bad if that's not how you choose to spend 40 hours a week. If instead you want to spend it, you know, with your family or building your business, that's perfectly fine. As you said, it doesn't mean it has to be zero. You shouldn't have a half a percent cashback card. You may as well open one card that gives you that two or three or 4% cashback. And it's fine if you want to call it a day at that point. Or earn a lot of Amex points and on the vacation that you find the great deal. Great. Otherwise don't use them. Just don't cash them out for gift cards. You know, don't throw the points away, but.

It would be crazy to drive 30 minutes to go get gas that's two cents cheaper, right? And for some reason, when it comes to time that is spent outside of our house, it makes so much sense. But when you're at home and you're like, well, I could go spend 30 minutes researching this thing on the internet, that time feels a lot cheaper than the time to drive 30 minutes to go get something.

And so I just encourage people to think, okay, is this where I want to spend my time? And if you've dialed in everything in your life, you have all the free time, you found your purpose. There's a lot of gains you can get from playing the travel hacking game, but you can get a good part of those by just picking one or two things and making those correct decisions without having to do everything. And then even if we go beyond just sort of the financial or money aspects of this travel and points, thinking about

optimizing the experience that you want. You're going to Japan, you're going to Iceland. I want to have a great experience there and how not to get too into your head about curating the optimal experience. Can you kind of share your thoughts there? Yeah. So I did this interview recently with Lee Rowan who runs Savanti. So I won't go too far down planning the perfect trip, but one really big takeaway I had, and it kind of came to me while I was preparing for this talk was that

Everyone wants to have the authentic, amazing local experience, do the best trip ever. And I get why, because I also want to do that. But at the end of the day, we're all going to a country that we're not natively from and we're all tourists. And

And sometimes you could just let yourself do the touristy thing. And like, it might be a great experience. And so do you need to find the absolute best croissant in Paris? No, because any bakery in Paris is going to have a croissant 10 times better, whatever you're getting back in the States. You can have a great experience without having to have the best experience. You don't need to try to find the cooking class that the Slovenian grandmother has that nobody else knows about. You probably pick a cooking class on Airbnb Experiences.

probably going to be really great. And you can get lost trying to have this experience no one else has had. And it can really add a lot of stress to the planning. There's this great book called Happy Money. And they go through like the five ways you can spend money to increase your happiness. And one of them is like plan the trip in advance so you can look forward to it. And I think if you're

constantly tweaking and evolving your itinerary and your plan right until the last minute to try to make it the best. You never get to just relax and say, hey, next week we're going on a trip and we're going to do this awesome cooking class and we're just going to relax on the beach one day. And now we can just soak in the fact that that's about to happen versus trying to go search Reddit and, you know, talk to ChatGPT and figure it all out. So I think

letting go a little bit is really interesting. And I told a few people here how we went on a trip to Iceland last week and we took 15 people from the podcast. And I'm sure I'll cover this in more detail, but almost everyone that went

by nature of being a listener to a podcast about optimizing your life, we're used to dialing everything in. And so they showed up and we were like, we've already dialed it all in. You don't have to think about it. And in the first like half hour, people were really uncomfortable. And by the end, they were like, oh my gosh, this is a vacation. Like I didn't have to think about anything. You did it all for me. And they left thinking, I really should stop dialing in everything and optimizing everything and just letting things go because then I can live in the moment a little bit more and

And life is just a little bit better. And I think because we touched on money, because we touched on family and all of these aspects, it's important to get them right. But there's not always a right answer. And sometimes overthinking them is the wrong answer.

Those are the 10 takeaways we had. Yeah, that's what I had. I really enjoyed this. Yeah, the unfortunate answer to all of this, Tad and I had this one takeaway, and it was that all decisions are personal and there's not a right answer to almost any question. We kind of hit that on all 10, so we didn't include it, but we were talking about it and you said something really interesting, which is,

Yes, there is not a right answer. So we can't give you the right answer, but having more information and getting advice can actually help you get to the right answer for you. Yeah, I think it's exactly that. There's not a globally right answer, but yes, there's a right answer for Chris. And that is different from the right answer for Ted. And also maybe giving ourselves a grace. We won't get you a hundred percent the right answer, but if we just think about these things and think about those trade-offs and you'll get the advice from others, we can get closer to our individual right answers.

And surrounding yourself with people that are in the right kind of situation as you and talking through your situation with them and not your friend that has 10 times as much money or one-tenth as much money can be a lot more helpful. And so finding a group, finding a community, finding an advisor so that you can find your right answer is really helpful. And if that right answer can help you lead to your purpose, I think you could be a lot happier and hopefully a lot wealthier.

I really hope you enjoyed this episode. It was a lot of fun to put together. And for whatever reason, October seems to be conference season for me. And I have three more events I'm heading to this month. So if you like this style of episode, please let me know. And maybe I'll do something similar anytime I'm at an event and I learn a ton like I did at the Long Angle Retreat.

And if you're interested in joining Long Angle, it is a free community that I've really enjoyed being a part of. But they do have a requirement that all members need to have $2.2 million in investable assets because there are some regulatory requirements around the private deals that get shared in the community. But if you meet that requirement, you can join for free at longangle.com.

please feel free to let them know I sent you. And that's it for this week. Email is podcast at allthehacks.com. I will see you next week.