The Wealthy Barber Podcast - #57 — Daniel Crosby: How to Overcome Your Financial Biases
Episode Date: May 19, 2026Our guest this episode is Dr. Daniel Crosby — psychologist, behavioral finance expert and Chief Behavioral Officer at Orion Advisor Solutions. Daniel is the bestselling author of several books on th...e psychology of money, including "The Behavioral Investor" and "The Soul of Wealth," and is the host of the popular podcast "Standard Deviations." His mission is to help investors and advisors understand how psychology shapes financial decisions and what true wealth really means. In this episode, Dave and Daniel dive into the psychology behind investing and the behavioral biases that quietly sabotage even the smartest investors. They break down the four major investor biases, why overconfidence is the most damaging of the bunch and Daniel's "Three E's" framework for overcoming them. They also explore why money is emotional rather than purely mathematical and the role behavioral fintech design can play in helping people make better long-term decisions. The conversation also explores the rise of the "gamblification" of investing, the impact of social media on young investors and why personal benchmarking tends to serve people far better than chasing the S&P 500. Along the way, Daniel shares his framework of believing, belonging and becoming as the keys to a good life, his perspective on managing anxiety in uncertain times and why so many investors still fall into the trap of buying high and selling low. Whether you're a seasoned investor or just starting to think about your relationship with money, this episode is packed with insights that will help you understand yourself as much as the markets. Show Notes (00:00) Intro & Disclaimer (00:55) Intro to Daniel Crosby (03:02) Daniel's Path From Psychology to Finance (05:21) Statistics on Reading (06:48) The Four Major Investor Biases (13:12) The Three E's to Overcome Biases (18:25) Why Overconfidence Is the Most Damaging Bias in Investing (19:02) Money Is Emotional, Not Just Mathematical (22:50) Daniel's Role at Orion & Behavioral Fintech Design (24:56) Personal Benchmarking vs. Chasing the S&P 500 (25:45) Mental Accounting & The House Money Effect (26:50) The Gamblification of Investing & Young Men (30:36) Social Media's Damage to Young Investors (33:51) Believing, Belonging & Becoming: Keys to a Good Life (38:56) Managing Anxiety in Uncertain Times (42:05) Why We Buy High & Sell Low (44:19) Conclusion
Transcript
Discussion (0)
Hey, it's Dave Chilton, the wealthy barber and former Dragon on Dragon Stand.
Welcome to the Wealthy Barber podcast.
Well, we'll be hosting some of the top minds in the world of personal finance.
Yes, that's to balance me out.
The podcast is about making this subject not just easy to understand, but dare I say,
even fun, honest.
Whether you're trying to fund your retirement, figure out how to build a down payment,
save for your kids' education, manage debts, whatever, will be here to help you.
You do it. Before we jump in, a quick but important note, nothing we discuss here should be taken as
investment advice. We don't know you and your personal financial situation, so we're not here
to tell you we're specifically to put your investment dollars. We're here to educate, get you
thinking, and we hope entertain. But please do your own research and or consult with your
financial advisor before taking any action. Hey, it's Dave Chilton, the Wealthy Barber with the
Wealthy Barber podcast. Thank you, by the way, to all the followers. I know I say this a lot,
the podcast has been booming in terms of popularity. A lot of word of mouth. And we really do appreciate it.
I've mentioned many times we don't monetize it. We're not looking to take advertising or anything
along those lines. We're thrilled that it's helping people and so many are sharing it at work,
sharing it with friends, sharing it with family. That's the way it should be. And hopefully
today's episode will live up to the high expectations we've set. We've got a wonderful guest.
He's American. Do not judge him based solely on the fact that he is American. He's a very fine guy,
a very bright guy who's going to shed a lot of light on some important issues for us today.
Daniel Crosby, welcome to the show.
Dave, it's great to be with you.
And thank you for the preamble.
I needed it.
You've got a tremendous reputation.
Of course, I read the laws of wealth.
And what was that 10 years ago-ish?
Goodness.
I think that's about right.
I think that's about right at this point.
Outstanding book.
One of the first books to really jump on the subject of behavioral finance and you've done a
wonderful job.
You're a clinical psychologist who's come over and really into some extent
studies the mental approaches and weaknesses and mistakes that people make when managing their
money. Is that a fairly good summary of what you do? Okay. And you do it very well. And you use
humor and your delivery and you're very calm. And I've enjoyed watching you throughout the
years, watching you in clips and everything else. But what an unusual job you have. You work for
Ori and advisors. And it's unusual for a firm. They're an AUM firm, assets under management firm.
So by revenue, we're about half fintech and about half half asset management.
Yeah, very interesting.
And then they brought you in to provide that unique value at, truly unique, and that
I haven't seen this before, where you're talking to the company's clients about
behavioral issues and how to manage yourself a little bit better as you tackle money
challenges.
Yeah, that's exactly right.
Orion understands how important it is to get that right.
And they know that it's central to how we plan, how we invest, how we save, how we
save, how we spend, and even how happy our money can make us. So I think it's very forward
thinking of them. Yeah, I do as well. What got you into the area? What got you so excited about
taking your background and applying it to the money business? Yes, so I am the son of a financial
advisor. So I grew up talking about investing at the dinner table from a very young age and went to
college thinking that I would be a financial advisor, that I would be an investment manager.
But after my first year of college, I dropped out of college and went on a two-year
mission for my church to the Philippines. And so two years of living in a new place, helping people
focusing on a different culture and a different language, I got back with this deep fascination
with human behavior and why we do the things that we do. And so I said, no, I'm not going to do
the investment piece. I'm going to be a psychologist. And about the time I was 23, Dave, when I started
counseling, which I think is an age where you have a lot of wisdom to dispense to other people about how to
their lives. You know, I was 23. I was quite young when I started counseling. I was 27 when I finished
my PhD and I was burnt out candidly. I had poor boundaries. I was working with sort of a very heavy
clientele. Some of them had done really sort of horrible things. And I, you know, I felt very young to be
as burned out as I was. And so I came to my father and I said, look, dad, I love studying human behavior.
I love thinking about why people do the things that they do, but I don't know that I want to do it in a clinical context.
And he goes, I wonder, he said, my job is effectively, I'm effectively a counselor for people's money.
And he said, I wonder if there's something in my world.
Now, my dad is a wirehouse advisor in a mid-sized town in Alabama, the poorest, fattest state in America, right?
He did not know what behavioral economics was or what behavioral finance.
finance was. But that comment from him put me on a path. And what I found, Dave, was there were very
smart people, the Amos Tverskys, the Daniel Kahnemans, the Richard Thalers of the world,
who were publishing papers, but they weren't trickling down from the ivory tower to everyday individuals
or to the advisors who served those people. So that's kind of been my life's work to be the intermediary,
to be the translator between those two worlds. Now, you said all that very well. And it's interesting that
a lot of the research says that most advisors don't read much, period. They're just not a big
reading group. I should, out of fairness, say that's not necessarily true of female advisors. It's
been more than male advisors that have been accused of not reading a lot. So thinking vast and
thinking slow is not a book that's going to have a huge penetration rate in the advisor community
for the most part. So you stepping in and bringing some humor and you bringing some stories and
different ways to get examples across, I think has probably helped a lot of people.
Dave, as the author of four books, I agree that they should definitely read more. I agree that they should buy more of my books. But there was one funny stat that I think you'll like. His book, Conneman's book, Thinking Fast and Slow, which is the behavioral finance magnum. It's incredible. But the year that it came out, Audible can track. They have data on who's reading what and when they put it down. That was the most put down book of the year. That was the book that so many people,
people started and so few finished.
Now, it's shocking in general those stats about how many people buy books,
don't read them at all or read the first X percent and then put it down with,
I think, best intentions to get back to it, but also shows you in this very challenging
world with all of these stimulations out there, how hard it is for authors like us to keep
people's attention, to rise above the noise.
I mean, every chapter has to stay entertaining.
You can no longer be just informative and you have to use stories.
But the good news for you is your end of the.
industry really sets up well for that. That there are a lot of interesting examples that you can
give us about mistakes people have made. To some extent, a lot of what you do comes down to biases.
And the fact that we're all wired to have certain biases, we're all guilty of it, even those
of us who think we're not. Walk me through what the word means in your context and some examples.
Yeah. So there are over 200 now codified biases, 200 ways that you can screw it up, that you can
get it wrong with respect to your money. I think I have 196 of them. I have mastered
196 of them. I'm like Pokemon. I've collected them all. I've done it. I've done it wrong
every possible way. But what I did in my second work, the behavioral investor, is I took that
universe of 200 and I looked at them and I analyzed them and I said, look, there's really some
meta biases that sort of underpin these. There's a handful of bigger problems that account for a lot
of these sort of very small, very particular ones. So if I may, I'll just share those four.
The four ways that people get it wrong. The first is ego. This is the various flavors of
overconfidence. So in particular, we as a human race think we're smarter than average, better than
average, luckier than average, and more knowledgeable about the future. And if you think about
this constellation of overconfidence, right, yeah, we understand that people,
should diversify, but yeah, maybe I'll just go all in on this one stock.
I know that people should diversify, but I'm different, right?
I know that you can't time the market, but I'm a little worried about these tariffs.
That's a great example.
Yeah, it's like thinking that the rules don't apply to us.
This overconfidence makes us a stranger to the rules that candidly most people know.
The fundaments of good investing are relatively simple.
You could put them on a note card.
But overconfidence tells us, yeah, that's other people's problem.
And so, Dave, with respect to bias is one thing that makes them so tricky to navigate
is that they serve us so well in other places.
A lot of the things that account for this constellation of overconfidence are the same things
that buoy us up and get us out of bed in the morning and led me to go talk to the woman in
class who's much too good looking for me and then marry her, right?
Things like this are overconfidence too, but in many cases it serves us well.
But we have to learn when to turn it off and turning it off with your portfolio is for sure the right answer.
So the second of these is emotion.
This is the tendency to confuse how you feel with how you should act.
And with respect to your money, it's about 180 degrees different.
We tend to feel most worried when markets are most advantageous and most secure when
markets are most overpriced. Howard Marks, the great investor, calls this the perversity of risk,
that basically sort of our emotional signals are flipped. And so again, in other places in life,
emotion serves us really well. And it's a useful shortcut and it can give us great insights and
shortcuts into knowing whether we should talk to a person or do business with a person or trust a
person. But in markets, it tends to lead us astray. The next one is conservatism.
conservation or conservatism is the various ways in which we are risk averse, loss averse,
status quo prone and sort of small-minded generally.
You know, I was talking to you before the, before we hit record and told you I spent the best
summer of my life in Alberta.
And one of the things that I found so interesting when I spent that four months in Canada
was that Canadian investors, most of the Canadian investors that I met with, had about a 75 or 80%
allocation to Canadian stocks in their portfolio. Now, you see that around the world. That's not a
dig on Canadians, but it's less of a problem in the U.S. where we're 50% of the world's equity
exposure and Canada's 4 or 5%. So it's interesting, this is that conservatism. We tend to
confuse what we know with what is safe or good. And so because you've heard of these Canadian
companies, you're more comfortable investing in them. When in reality, Americans should be overweight
non-U.S. Stocks. Canadians should be overweight non-Canadian stocks. And we have to kind of get past
this provincial mindset and this small-mindedness. The last of these is attention. We tend to
confuse things that are loud with things that are likely. So if you ask people, are you more
likely to die of a shark attack or diabetes? They'll tell you a shark attack. It's because a shark
attack is very memorable and very loud, whereas eating a little bit too much sugar for a few
decades and becoming diabetic is sort of a slow burn, low salience problem. We see this all over. One
one example I gave was in the U.S. post-9-11, right? So here in the U.S., every September 11th,
we honor, we remember the 3,000 people who lost their lives in that tragedy. But what we saw
was there was a second layer of tragedy in the aftermath of 9-11 because people stopped flying.
Everyone was so scared of flying. So what did they do? Instead of getting on a plane,
they got in their car and drove 8, 10, 12 hours,
getting in a car wreck is not loud, right?
Car wrecks happen all the time,
so it's not on the news every night like 9-11 was,
but it's very likely,
whereas something like a terror attack is very loud,
but very unlikely.
And so we confuse loudness and likelihood
all the time with investing,
and you see people who will remain conservative for a lifetime,
trying to avoid that loud event,
that next big crash, and what they're doing is slowly killing themselves financially by not
taking adequate risk. So those are the four. Now, I think you did a great job there. You know,
I enjoyed when you were talking about emotion. I have a friend named Simon Lewis, and I'm
going to use his name because it's very positive here. March 2009, the markets are bottoming out
in the great credit crisis. I'm with him. We're on a vacation in Costa Rica, and he loves stocks.
He stays fully invested. And he said, I have never been more tempted to get.
out of everything. He said, every emotion, every five of my beings tell me to get out. He said,
so I'm going to get it. I'm going to get Admore because he knew that when it got to the extremes,
emotion tends to be almost the opposite of what you should do. Because again, as you pointed out,
you're more likely to be panicked at a bottom. You've just been through a very painful experience.
And you're more likely to be euphoric at the top. Everything's been roaring along. Emotions, wow, can they be
tough? How do you get around them? Do you believe in automation? Yeah, I do believe in automation. I believe
I believe I have what I call my three E's of behavior change because behavior change is very tough.
There's a reason why every year effectively all of us set intentions and goals and the south of
20% of us see them through. It's really hard to change your behavior, especially around money.
So I think there's three things we need, three E's. The first of these is education.
We need to have just a basic idea of how markets work. We need to tune into the wealthy
barber and get educated on how markets work. Your friend is a great example of that, right? He said,
look, I am terrified and I know enough to know that's a positive thing. That's actually a bullish signal,
right? So we need some education just around the fundamentals of how markets work. You know,
the best example I can give there is over the last 35 years, the average Peketroft entry year
drawdown has been about 15% for the U.S. stock market. You would think every time we have a 10%
dip in the market, if you listen to the media, you would think it was the only time it had ever
happened and that it was the end of the world. It's as regular as your birthday. And once you
know that data point, you can start to contextualize the news, right? So education is that first one.
The second one is environment. This is where we would attend to things like automation, which is
so powerful, right? It is so much easier for you to set and forget a process of withdrawing
and allocating funds rather than trying to make the good decision every two weeks when you get paid
from now until eternity. It is so much easier. And the thing that I love about it, Dave,
is you're taking a human tendency, which is this tendency to be forgetful and status quo
prone and lazy and fearful and you're making it work for you. The same mechanism that has led me to
forget about my HBO account for two years and then I like, you know, I remember it and I'm,
God, I'm paying for this. You can do that with your retirement savings and it's so powerful.
Environment also includes things like your media diet. A lot of people, we all have the same goals.
We want to be patient. We want to be long term. We want to be thoughtful. But we
execute on those goals with varying levels of success, and a lot of it has to do with what we're
putting in our mind and our body. If you have an intention to be a patient long-term investor,
but every night as you eat your dinner, you're tuned into the news and watching the cable
financial news tick by tick, it's going to be very hard for you. So the way you allocate your
portfolio, right, allocating for anxiety-adjusted returns and not just
trying to hit home runs, right? The news you put in your head, the way you automate,
all of that is your environment. And that, if you just had one, that's the best predictor of your
success. And then the third one is encouragement. Getting a coach, getting an advisor,
getting someone in your corner who in March of 2009 can be that encouraging voice,
be that voice of calm and wisdom that will just keep you on course. So educate yourself,
set up your environment so you're poised to win. And then,
surround yourself by people who can support you on that journey.
Okay. I'm going to be on. I love your stuff.
Steal it. Seriously, I love that answer. I think it's bang on and matches up perfectly to all
the experiences I have seeing people manage their money. And I've talked a lot in the wealthy
barber on the podcast on the page about how the best investors I know pay almost no attention
to the stock market. They're not pulled in by emotions because they're oblivious in many
instances to what's happening. And you said that so well when you said if you're watching every night
to see what markets have done, what forecasters are saying, it's almost impossible not to get
pulled into efforts to market time, almost impossible. I do it relatively well because I find all that
interesting, but I stayed attached. I don't let it affect my portfolio decisions at all. But most people
again can't do that. That was a great example. My father is the master. He's had index funds forever.
never even looks at them.
Doesn't even know they're doing well.
He just stays completely detached.
So that's such good stuff.
So when you go beyond this, where do you see the biggest mistakes being made?
You talked about the different biases and grouped them in sets of four.
What's the one or two that haunt more people than any other?
The biggest one is ego or overconfidence because that's the one that tells you don't have a problem.
Right.
It's like a 12-step program.
Admitting you have a problem is the first step.
I think most people never get to the point where they say, hey, I'm not great at this or I need help.
I need an advisor.
I need to automate this.
They just kind of winging it.
So I think overconfidence is the granddaddy of them all for sure.
But you know, the other thing that I would say in my second book, The Behavioral Investor,
there's one study that I cite in there that has always stuck with me.
And I think it's so important for people to know this.
They did an fMRI study.
So this is like a brain scan.
Yeah, love them.
Yeah, they hook people up to brain scans and they show them different excitatory stimuli.
So think about Dave, if we were to go to a cocktail party tonight, all the stuff that would get you slapped or talked to by HR, right?
Sex, death, politics, religion, money, like all the taboo topics, they prime them with these stimuli and they measure the level of excitatory power in the brain.
Would you believe that money had more excitatory power than sex, death, religion, politics, any of these?
We are more emotional about our money than anything else.
And I think a lot of people think it's a math problem and it's not.
And they think, oh, I'm not going to get involved or I'm not going to learn because it's a math problem and nobody likes math, right?
Like it's a math thing and I don't do math.
So I think people fundamentally conceptualize it wrong.
In addition to the overconfidence, which is so big, I think people fundamentally misunderstand
how emotional and how human money is.
And so they continue to get rocked by it because they don't get the bottom most turtle
of what it is all about.
You're 100% right on that.
And you're right.
Ego and overconfidence plays such a role.
Going back to your arguments about automation, one of the beauties of the 401 case, of course,
the group RSPs in Canada, the money comes right off the top of the paycheck.
You don't have an opportunity to blow it.
And because it's money focusing long term thinking retirement, people pay less attention to the balance or at least the portfolio construction and are less likely to go in and do something silly in most instances.
All of the evidence says people manage their 401k's better on average than they do their non-registered money.
So much of that, all of that is behavioral.
To your point, that's nothing to do with arithmetic, nothing to do with math.
I literally forgot I had a 401k until the other day.
We're moving.
And so I'm going through some paperwork and things.
And I was on my own for about a decade and I worked for Orion for about the last five years.
And yeah, I have this 401k through Orion.
I literally had forgotten I was contributing to it.
And it's like finding money in your pocket times a few.
And it was just so wonderful.
And it is so much better run.
And I'm supposed to be an expert on these things.
And yet we know, to your point, we know it's been studied in 19 different countries now.
We know there is a monotonic relationship.
So monotonic meaning stepwise, right?
There's a stepwise relationship between how much you look at and mess with your portfolio and how well you do.
Absolutely.
The more you look, the more you look, the more you touch it, the worst you do.
That's true in every developed country that's been looked at.
No, I push that hard in the wealthy barber.
And I often tell people, I spend 20 times more effort on my hockey pool than I do my investment portfolio.
That's where my passion sits.
and I think I can actually make positive differences.
I can't with my investment portfolio.
I tend to leave it alone.
You mentioned that you've been alone for years.
I thought you meant that your wife, who was too attractive for you, had left you.
No, no, she should.
You meant you're out on your own workwise.
Okay, I just want to clarify that.
She's still there.
She should.
If she wise up, she'd be out.
But here, I'm still fooling her so far.
What biases have left her to stay?
What things have kind of screwed with her mind and caused her to make this poor judgment call?
For her, this is great.
She's not one. She's not one to rock the boat. If she tested the market, she could do much better in every regard. She's very conservative, though, and I thank God that she is. As you go out and coach clients, are you doing this one-on-one on behalf of their advisors? Or are you on a stage normally? And the advisors are inviting people out and you're talking about all the different things you're mentioning today. Yeah. So I do a couple of things. One is I design technology. So Orion is, again, by revenue about a 15.
percent financial technology for financial advisors. So we're very thoughtful about even how we position
the colors we use, the order in which a technology is presented, the aesthetics of it, the way we bucket
funds. A good example, we have a bucketing system called protect live dream. You and I know that money
is fungible, of course, a dollar is a dollar, but yet people don't treat it that way. We know from
the research that the way that you label your money has a material impact on the way that you
spin, save, or invest it. People are dramatically more likely to save if it's labeled Dave's
retire to Whistler Fund versus Chilton Fund ABC 123, right? Being able to visualize that. So we're
thoughtful about even the pictures we put next to a fund, what we call it. And so a big
part of my job is designing technology to help people make good choices. A big part of it is
educating advisors, usually from a stage, so that they can educate their clients. And then I have
a podcast and I write and create a bunch of content as well.
The technology that your firm is creating, is it going into the investor's hands or is
only the advisor seeing it? Is this also being used by the consumer and they're being nudged
in some way by some of what you're doing? Most of it is the advisor facing. Some of it
through the investor portal they would see. Most of it.
Most of what I do is advisor facing, but some of it is investor facing.
You can tell I'm quite fascinated by your job.
I think it's a great idea that your firm has done that.
And I think more firms should look into something along that line because I think it can make a big difference.
And most consumers need to hear these messages over and over and over again before they sink in.
They realize they have to make some behavior changes.
Yeah, I gave a whole speech recently about what I call personal benchmarking.
And the need to use a personal benchmark and a personal measure of what you need and what you want out of life rather than, you know, the S&P 500 or whatever, right?
And as soon as I finished my one hour remarks, you know, someone raises their hand and goes, shouldn't I be beating the S&P 500?
And you're just like, oh my gosh.
These things, these things are so contrary to our nature, Dave.
Every single thing that you are asking people to do to be paid.
to be long term, to take on risk, to deal with uncertainty.
Every single thing that you are advocating on your show is psychologically complex and
difficult.
It is.
And so people need to hear these things again and again.
Okay.
Let me ask you a weird one.
Somebody wins $1,000.
They're on a cruise and they win it playing poker.
Why do they view that as found money?
And they're much more likely to be reckless with that money.
They call it the house's money.
But of course, it's not.
it's in your pocket. Now it's your money. You're much more likely to be reckless with that. What does that
come from? The technical term for that is called mental accounting. And it says, look, the way that we
receive the money and the way that we account for it mentally has everything to do with how we spend it.
So that's why we have these protect, live and dream buckets because this protect fund, what you can tell
people is, look, if you've got two years of cash or 18 months or whatever the number is, two
years of safety assets here, when the market's bad, you can point to that and say, hey, look,
the average bear market's two years. You've got two years of cash here. You're not going to eat
cat food. You're fine. That is no different literally than a 60-40 portfolio with a little bit of
cash in there. Right. But the experience of it is very different. One of the questions I was
most excited to ask you was, what do you think about all this crazy gamblification we're seeing
of the investing arena right now, particularly by men 35 and under according to the data?
It was a problem five years ago. Now it's beyond a problem. How does this tie into a lot of what
you've come to learn? I won't mince words. It's a cancer on young men in particular that has the
semblance of investing, but none of the benefits. And I think people have become so cynical
I'm sure you've had the same experience when you sit down on a plane and someone asks you what, you know, you do and you say you work in finance and they go, well, I don't gamble with my money.
And I've heard people refer to Wall Street as a casino so many times, but the setup is just so different.
And I feel like the lower middle class in North America feels so behind after years of relentless inflation.
I think young men in particular feel like the only way that they can get ahead is to take a big swing.
The other thing is, I talked earlier about the power of environment and I said of the three E's, it's by far the most powerful.
Yeah, I agree with that.
These things are made to mislead you.
They are gamified to just nickel and dime you into poverty.
They're the investing equivalent of a Big Mac, right?
perfectly engineered in a lab to hit every button to get you to over consume. It's perfectly
primed to exploit the lonely, the forgotten, and the left behind. And it's going to do so much
bad in the world. I have nothing good to save it. I agree. And again, it's a problem that you
and I and everybody else in the industry was very worried about three years ago, but it's gotten
even worse. And you're looking at the online platforms, the brokerages, have become so adept
at advertising to this weak spot among that constituency they know is most likely to give in
and start option trading and meme trading and everything else.
And the leverage that I'm seeing used by some young people on speculative investments,
even if they get the call right because of the volatility that's involved,
they'll be wiped out long before that ends up helping them.
It's frightening.
It really is.
Yeah, people don't understand probability, right?
So if you're on a prediction market, which, by the way, in and of itself is a disgusting
euphemism, right? Like that the fact that betting on what someone's going to say in a press
conference or something like that is any more dignified than anything else, it's not a
prediction market. It's gambling, right? If you get it right, you make a few cents on the dollar.
If you get it wrong, you lose the whole dollar. And so people don't understand that asymmetry
and how it works against them and it can just slowly erode them. And then you get to the larger sort
of moral perverseness of betting on things like young people going to war and things like that
and betting on whether people live or die and whether or not nations go to war. It's morally
ugly in addition, I think, to being bad for your pocketbook. All well said, I look at the
prediction markets and I'm asked about them by the media and they'll say, what are they? And I'll say,
well, when you go to a casino, you're betting against the house and you're going to lose.
when you go to the prediction markets, you're betting against insiders and you're going to lose.
So they're very similar on that front.
The question, what's the difference between gambling and investing?
Investing, you think, and I think rightly so, that if you handle yourself well, the odds favor
long-term success with gambling, no matter how well you handle yourself, it's giving.
The odds favor long-term failure.
And the fact that, as you said, they're being made synonymous and they're being used interchangeably
in some instances is frightening.
Now, along that same line, you must see what social media is.
is doing to some younger people and how it's pulling them in and giving them misinformation and
drawing them to these not so good things, conflicting with some of the messages that you and I try
to deliver. What are your thoughts there?
Yeah, the Jonathan Haidt book, I think the age of anxiety has done a better job of anything
than breaking this down. I have a teenage daughter and we just let her have a phone for the
first time when she turned 16 and she's still not allowed to have social media. This is absolutely
cancerous to young people in particular, actually to all of us. You know, people who quit social media
see about a 10% increase in their happiness almost immediately. And Dave, if you think about that
is commensurate with the rise in happiness you see when you start taking psychotropic medication.
I mean, it's basically a Prozac level intervention on your happiness to just stop looking at
Instagram. There's that level. But for young people in particular, what it does is for
millennia, we grew up and the average person knew about 100 people. You could know about 100 to 150 people. And frankly, their lives looked a lot like yours, right? Absolutely. Yeah, like they were in your same village. They were in your same town. They all had similar work to you and you didn't have much basis to book down on yourself. The most followed people. I talk about this in my most reason book. If you look at the most followed people on Instagram, their average wealth is in the
hundreds of millions. They've got great hair, great abs, tons of money, great cars. And so what
happens is young people compare the ups, downs, pimples, warts, nightmares of their own lives to this
highly curated stylized highlight reel of everyone else's lives and especially the best and brightest.
And you just make yourself very, very sad. So we are very strict with our own. I mean, all I can do is
is tell you how I operate in my own home. And I can tell you we don't allow social media and we're very, very strict with phones.
No, it makes perfect sense. And I think you're right. It sets the bar so high that people are inevitably disappointed, at least subconsciously. I mean, I think you and I right now are guilty of that with our amazing hair.
Yeah. You know, we both have great hair. People are watching this podcast. Inevitably, they're disappointed in their own hair. So we're part of that problem. But there's nothing we can do about it. It's a gift.
Yeah. You can't benchmark to the two DCs. We got a little gray at the temples.
but we're hanging in there.
Absolutely.
Yeah, absolutely.
No, I agree with everything you just said and it's actually scary.
Did you see that report that came out a few years ago that said, interestingly,
the group that seems to be most adversely affected happiness-wise by social media,
women 20 to 35.
I thought it was going to be teenagers.
I thought, and the reason is interesting.
They said because they have more to compare than younger women.
So now they can compare careers, homes, spouses.
And the more you get to compare because to your point, you're comparing.
against people up here, always with the best, or at least showing the best, the more you inevitably
are going to be disappointed. That's where some real separation starts to happen, right? People get married
or they don't. They have kids or they don't. Their career takes off or a dozen. And so, yeah,
that makes some sense to me. Yeah. If you were dealing with a group of say 25 to 35 year old and you only
had three minutes and you had to deliver one message from all of your learnings, what would it be?
My last book was called The Soul of Wealth. And this was all lessons on money and meaning and happiness.
Because like you, I'm proximal to a lot of really wealthy people by virtue of the work that I do.
And about half of them are really happy and thriving and about half of them aren't doing great, despite their immense wealth.
And I looked back and when the U.S. will turn 250 years old this year, when this country was founded, 89% of the world lived in poverty, 250 years ago, $2 or less a day, 250 years ago.
Today, that number is under 10%.
It's this incredible explosion of wealth.
And yet, we're sadder, we're more depressed, we're more isolated, more suicidal.
And so the question I tried to answer was, how is it that we've had this explosion of material
prosperity and it hasn't translated to anything that matters in life?
And the three things that I walked away with, you're going to notice I like, you know,
alliterative threes.
But the three things I walked away with that are the whole.
marks of a good life are believing, belonging, and becoming. Okay. So people who have a good life,
they believe in something. They have a philosophy. They have a moral framework. They have some map
for making sense of the world, some sort of personal credo that tells them what right and wrong
looks like. That's important, right? You need to believe in something. Belonging is the most important.
You need a tribe.
You need to give love and you need to receive love
and you need to prioritize relationships.
And then becoming, you need a bright sense of who you could be one day.
And this is true for retirees as well, right?
You need something to aspire to.
It could be, you know, running a faster mile time,
getting better at guitar, making more money,
leveling up at work, being a better spouse,
a million things, right?
but we need a tribe, we need a personal belief system, and we need to be on a path to somewhere better.
And that's what I would tell them. I would say, get those three things in your set.
I love your stuff. I really do. And I think what you're very good at is taking a lot of this.
And as you say, breaking it down into here's three things. And here's why I think that and bring it
across succinctly in a way people can grab a hold of. And I completely agree with all that.
My father naturally did all this very well.
He was fortunate.
He grew up just kind of wired to get all of this.
And boy, does he hit the fact you have to be improving.
You've got to always be growing and trying new things, et cetera, et cetera.
That's where joy comes from.
It's one of the reasons he's always pushed people, take up hobbies because it not only fills your time, but naturally you improve in the early stages, especially of taking on a hobby.
It's just a part of what that process looks like.
Such a believer in that.
I got to tell you a very quick, funny story.
My dad had to quit golf in his late 70s.
He's 94 now.
When he was about 85, 87, he says to me, I'm going to take a chipping lesson.
I said, you don't golf.
You haven't golfed in years.
You can't golf.
You don't have the mobility.
He goes, I know, but I was always a horrible chipper.
And I saw Jason Day chip.
I like the way he chips.
I'm going to learn a chip like that because I don't want to die a bad chipper.
So he takes a couple golf lessons on how to chip when he doesn't even golf anymore.
But he wanted to improve his chipping because it bothered them.
And again, those are the happy people.
They're always trying to get better at a few things.
And I noticed that you mentioned retirement.
A lot of people stop doing that in retirement, and that is why they head down the wrong path.
First of all, what a great story.
And it would be so easy to say, look, this doesn't serve any purpose because I'm no longer mobile enough to golf, but that's not the attitude that your dad took.
It was continuous improvement even in this small sort of isolated way.
So if you think about those three bees, many of them are met at work, right?
Especially for men who tend to have weaker social networks outside of work than women.
So, you know, belonging, right?
We have friends at work.
We talk.
We check in.
We talk around the water cooler with people at work.
We get that belonging.
That becoming work rewards your progress with money, with plaques, with titles, with all kinds
of things, right?
With paths on the back.
So a lot of people underestimate.
A lot of people are so focused on trying to exit the workforce and enter retirement and getting
that number right that they forget to plan for the non-furtain.
financial elements of retirement. And it's no wonder why recent retirees are some of the sad
people on earth, which is such a sad statistic. They should be thrilled. And often they're not because
they prepared for the number, but not the life. You know what's interesting lately is I've had
a few groups of friends. They're planning on how they're going to retire together. And that makes a
lot of sense because then they're all freeing up time simultaneously for golf, bridge, travel, where they've
got that built in group and they're all going to go through it together. And there's a certain
comfort to that. So everything you're saying there makes a lot of sense. Look, I know you've
already touched on anxiety, but I'm really worried now everywhere you go with the war taking place and
AI coming on so quickly with the threat of job loss and all of the normal fears out there. People
seem anxious, more anxious than ever. And that, of course, seeps into the way they look at their
money. You've mentioned a couple things. But any other tips you can give people on kind of ways to
frame all of these things and stay a little bit more positive and not be as anxious?
Yeah, I think you've got to control the inputs and the outputs.
And we talked a little bit earlier about controlling the inputs.
I tell a little story about I was promoting one of my books.
I was on, I don't want to narc on people, but I was on a large cable financial news channel.
There is only one.
There's a couple.
But yeah, there's a big one.
And I'm on this channel and I have the little earpiece in and the producer is counting
5,4, 321, counting me down.
And I'm wearing, Dave, I'm like resplendent in my.
my tortoise shell glasses and my tweed.
I'm very much looking the part of a psychologist.
And she's counting me down and she says,
five, four, three, two, give me something good.
Don't be a nerd.
One, you're.
And I'm like, oh, was it that obvious?
But it's fascinating to see how the sausage gets made.
She didn't say, please give me evidence-backed,
sensible investment advice.
She said, she looked at it.
me, she saw a nerd, fair enough, tough but fair. She looked at me, saw, saw a nerd and was like,
we got to spice this guy up a little bit. And so that's how the sausage gets made. So you've got
to control the inputs because the news is not designed for you to make good financial choices.
It's designed to inflame you necessarily. Right. So control those inputs. In terms of controlling
the outputs, you have to control the controllable, right? This is where I tell people to take the power
back. You mentioned my book, The Laws of Wealth. The first chapter in that book, and I was very
intentional about which chapter I put first, was you control what matters most. When people meet
someone like us who works in the business, they ask us, what's Trump going to do? What's the Fed going to do?
What's the president going to do? What's the prime minister going to do? You don't know that.
You don't control that, right? But what you do control is all the best predictors of whether or not you
meet your financial goals, saving, staying long-term, focusing on bridge and Majong and all your
fun stuff that's much better for you than worrying about this, right? So control the controllable
in terms of the outputs, control the controllable in terms of the inputs and what you put in your
head. That's sort of the best you can do, I think, in this time of anxiety. No, it's funny. You keep
coming back to controlling the inputs and being careful, whether it's social media or just taking in
too much news. I mean, you know Jim Moshanisi, and he's a huge news,
and he's backed off a lot.
He has said to me, he's taking in less news than he is to because it is overwhelming.
It is distressing.
Plus, there's so much information coming at all of us now.
I don't think our minds can process at all.
It's almost too much.
I try to follow the AI space.
There's an announcement every hour right now.
And it's absolutely crazy.
Okay, last question.
I have a friend who's a big fan of yours, has enjoyed your work over the years.
And he wanted me to ask you, why when we know that you shouldn't buy high and sell low,
why do we have so much trouble with that very basic tenant? Even smart people will see an asset class
like Canadian real estate five years ago roaring along and say, I've got to get in. I've got to get in.
Even though it's at valuations we've never seen before, what about our minds draws us in at the
wrong time? So there's a few things, right? So first of all, high and low are subjective. And the means by which
we make that appraisal is not by looking at a price to free cash flow ratio or a price to earnings ratio. And
it's by looking at what it's done recently and the human mind is wired to look at what's happened
recently and to project that into the future indefinitely right okay i meet dave chilton he's smart
he's amiable he's friendly right i meet him the first time that's my appraisal of him when i meet you
a second time i will not go into that meeting going what's dave chilton going to be like this time
I will just assume the way you were is the way you are.
And that's what we assume about markets.
It's true of people.
It's not true of markets.
Markets mean revert.
We have just a poor intuitive sense of where things are.
It's back to that perversity of risk.
Again, we are 180 degrees miswired to determine what high and low are.
And we tend to just do the wrong thing at the wrong time and violate the very first
law of investing. No, you said that, well, it's interesting. I think that when, especially on the
selling low front, it's not fun to see your portfolio falling dramatically in value day after day.
And sometimes people sell low, even when they know they shouldn't, to stop the bleeding, to stop the
mental anguish. And then it's so funny how many of them say, I'll get back in later when the markets
recover. Have you ever heard a crazier statement said, I'm going to wait until they go back up. And then I'm
going to get in, but they actually publicly announce to your point, all of this is very difficult.
we're not naturally wired. That's why we have to read books like yours, learn from people like
you because it makes you more aware and therefore less likely to make the same mistakes.
I'm a big fan. I thought you did a wonderful job today. You're an outstanding communicator.
You can see that you're a writer. And I think what your firm is doing, putting you out there,
helping the advisors to help their clients is very interesting. So nothing but good luck in the future.
Please come back on. I welcome the chance to be back. You're a great interviewer. And it's evident to me why
you've been as successful as you have. So congratulations and thank you for hosting.
Yeah, thanks again. We'll talk soon.
