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It's Not Too Late: Smart Money Moves After 50 | Bill Yount - E105

April 23, 2025 / 58:38

This episode covers personal finance strategies for late starters, featuring guest Bill Y, co-host of Catching Up to Fi. Key discussions include the importance of understanding income versus expenses, the concept of buying the dip, and simple rules for financial success.

Host Jesse Kramer shares a review highlighting the podcast's effectiveness in explaining complex financial topics. He emphasizes the need for late bloomers to grasp basic financial principles and avoid common pitfalls.

Bill Y discusses his journey from financial struggles as a physician to achieving financial independence. He reflects on the emotional challenges faced by late starters and the importance of creating a financial plan.

The conversation addresses practical steps for improving financial health, such as maximizing savings rates and understanding the significance of tracking expenses. Bill shares his personal experiences and insights on overcoming financial mistakes.

Listeners are encouraged to join the Catching Up to Fi community for support and resources tailored to late starters in their financial journeys.

TLDR

Bill Y shares his journey to financial independence and practical tips for late starters in personal finance.

Episode

58:38
00:00:00
Welcome to personal finance for long-term investors, where we believe Benjamin Franklin's advice that an
00:00:06
investment in knowledge pays the best interest both in finances and in your life. Every episode teaches you personal
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finance and long-term investing in simple terms. Now, here's your host, Jesse Kramer. Hello and welcome to
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episode 105 of Personal Finance for Long-Term Investors. My name is Jesse Kramer. Later today, Bill Y will be
00:00:27
joining me. Bill is the co-host of Catching Up to Fi. FI as in financial independence. It's a podcast targeted
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toward late starters who now need to play a little bit of catch-up in their financial lives, but certainly still can
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achieve financial independence if they write the ship in time. And Bill has a lot of interesting lessons to share with
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us, especially targeted towards, you know, late bloomers to personal finance investing and financial independence.
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But before Bill joins us, I have some thoughts to share. And as always, we're
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going to start off with a quick review of the week. This one comes from MXXX. That is a lot of X's. And the
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title of this review, it's a five-star review on Apple Podcasts. The title is,
00:01:04
"Great job explaining retiree issues. I recently spent a fair amount of time
00:01:08
finding and educating myself on Roth conversions. Today, I listened to Jesse's podcast number 99, and it was
00:01:14
all there in a few minutes of discussion." Well, MXXX, I'm glad this was helpful. The podcast has been
00:01:21
helpful for you in your retirement planning. It's certainly a topic that I'd love to talk about and if you shoot
00:01:25
me an email to [email protected], we'll get you hooked up with a supersoft podcast
00:01:30
t-shirt. Okay, before Bill joins us today, I have a couple old articles, interesting thoughts I wanted to share.
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Again, targeted towards maybe some late bloomers or some people who are just discovering the world of personal
00:01:40
finance and investing themselves. And then I'm recording this in in late March. And we've had a pretty tumultuous
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March and and part of February, too, in terms of investing in the stock market. So I want to share some thoughts with
00:01:50
you guys about this concept of buying the dip which is essentially you know holding on to cash to some extent maybe
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hoarding cash waiting for a market to go into a minor correction a bare market an
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outright crash and then boom you pounce and invest once the price crashes. It's
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a concept that on its face makes a lot of sense but I think as you'll hear today there's much more to it than meets
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the eye and more often than not it actually might not be worthwhile. So, we'll get to that article and those
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thoughts eventually, but first a couple articles, some thoughts targeted towards
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again the late bloomer. So, the first one is called the stupidly simple secret sauce of personal finance. Some people
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out there, you'll hear them say, you know, take your income, divide it into five equal buckets, take each bucket,
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multiply it by your age, you know, if Mercury is in retrograde, convert two buckets to Bitcoin, otherwise use 14% of
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your future social security income, calculated Pratta, and buy lottery tickets, something like that. Well, that
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is stupidly complicated. But people understandably, they yearn for hidden knowledge, for secret knowledge, the
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secret sauce, and they hear things like that rambling that I just had, and they go, "Oh, that sounds like secret sauce
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to me. Maybe that's what I need to do." But personal finance does not have to be
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complicated. The real secret sauce of personal finance, in fact, is incredibly simple. So, we're going to talk about
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four stupidly simple rules first off the bat. the following four rules, they aren't highlighted enough in the
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personal finance space. Or or maybe they are, but I think maybe because they're
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so simple, we we overlook them. But these rules provide the easy answer to, for example, how a frugal teacher can
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end up in a better financial scenario than some slick Wall Street banker or than some doctor. As you'll hear later
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today, you know, Bill Bill Ya is a emergency room doctor. And despite spending the first maybe 20 to 25 years
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as a doctor after medical school, he still ended up in a position where, you know what, he was a little bit lost
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financially. And it's because I think you'll hear him attest to this fact. He
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didn't have all these four rules in place. And they are number one, spend less than you earn. Number two, double
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down on the above and spend way less than you earn. Number three, find ways to earn more money, but don't increase
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your spending while you do so. And then number four, invest. Make your money grow on itself. As hopefully we all
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know, but you know, even today, this morning with a client, I had this conversation that there are two equally
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important inputs to the final product of good financial planning. The first input
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is how much money comes in. The second input, or maybe it's an output, but it's
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how much money goes out. It's how much you spend. And we all love to focus on
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money coming in, right? Salary. uh if not for salary, how would I compare myself to another human being? asks many
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of the modern midases around us. But salary alone or income alone, that's an
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incomplete statistic. Much like in a way like batting average was described in Michael Lewis's Moneyball, if you're
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familiar with that, it accounts for some results, but it does not account for all
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results. And that's why savings rate is a much better statistic at least when it
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comes to personal financial health because you know saving 50% of your income is is noticeably better than only
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saving 10% of your income and it doesn't matter whether you're a teacher or a
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banker or someone else. Whereas if we only compare salaries alone and we say well someone's earning 50% more than
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someone else that's not enough to really come to a good conclusion. My second
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stupidly simple rule of personal finance is that the winners are loud but the losers stay silent. Now, what do I mean
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by that? Well, we've all seen a headline that looks something like this. 28-year-old turns $30,000 into 1 million
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with Tesla stock or with Bitcoin or with something like that. We love winners. We
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love the stories of, you know, woman gets rich off of great stock pick. Man shorts a company right before it goes
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bankrupt. Uh, dog digs a hole in the backyard and owner finds gold. We love those stories. Planet Money had a had a
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great episode a couple years ago on people making money off of Hertz, the rental car. They had a bankruptcy and
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then they had this subsequent roller coaster of their stock price and a bunch of people made a bunch of money off of
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that fact. And much like a roller coaster, making money creates this wild and exciting curiosity. You know, who
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doesn't like a story about someone making lots of money? It's a big short.
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It's one of my favorite books in movies. Making billions of dollars is is a cool
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story. But people are rarely publicized when they screw up. Mundane failures aren't in vogue. They never really have
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been. You know, man spends $50,000 on silver coins and never really sees a return. A woman neglects free retirement
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accounts and regrets her choice. Some bros buy crypto at the top and they lose their shirts. Oh, those aren't stories
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that stick with us. They aren't stories that are written about, but they should
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be, right? Those should be the stories that we hear and they should be cautionary tales of of what not to do.
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Instead, we hear stories through the filter of survivorship bias, right? The winners make the cut and we hear those
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stories. The losers don't get publicized. For every winner you hear about, you should consider the silent
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losers. Your slow and steady solution, it might seem lame compared to the people who are taking rockets to the
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moon, but a lot of those rockets actually blew up on the pad, and we shouldn't forget that fact. The next
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stupidly simple rule is that boring is best. Picking stocks, it's fun. So is
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picking horses, but unless you're really, really good at it, it's probably
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a losing bet for you. And let's face it, most of us are not really good at that.
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There's some really good breakdowns out there and I've I've written one or two
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I'll share in the show notes about luck versus skill in stock picking. You can't
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just be above average, right? That's not good enough. You've got to be consistently above average, far above
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average for a long period of time. The alternative to such complex stock picking analysis over over long periods
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is to invest in something like a boring index fund. It's what Buffett recommends
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to a lot of people like us. I mean, he does it his own way and he's really really good at doing it his own way. And
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you're right, he he doesn't invest his own money in index funds. Not yet. He
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said that a lot of his estate would go into index funds once he dies. But the idea is that if you know enough to be
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like Warren Buffett, well, go ahead, pick individual stocks, buy whole companies, and make your money that way.
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That's what he does all day every day. And he's been doing that for over 80
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years now, something like that, right? He bought his first stock, I think, before he was 13, and now he's 93 years
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old. For the rest of us, we might want to do something simpler so that we can go out and live our own lives. And
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that's not the only one where there there's a contrast in personal finance
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and investing between something that's exciting versus something that's good.
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Gold and Bitcoin can be exciting. Is saving tax dollars via investing in a 401k. Is that exciting? I don't know. It
00:08:04
sounds pretty boring to me. And yet maximizing your tax advantage investing accounts. It's one of the best methods
00:08:09
for the average American to achieve a healthy retirement. It's like saying, "Hey, eating carrots and jogging every
00:08:14
day, it'll help you lose weight." Great. I bet it would. But isn't there a magic
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weight loss pill out there or some Himalayan calorie burning meditation technique? We yearn for solutions to be
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exciting and exotic. But they don't have to be. Boring and rich or exciting and
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broke. For me, it's an easy choice. My next rule is that you make the economy
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go. At least in part, you and I make the economy go around. It's our purchases
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that keep money flowing. And that flow of money greases the wheels of the economy. There's an enormous vested
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interest in ensuring that average Jane and average Joe spend a significant portion of their incomes. The
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advertising industry is predicated on that interest, right? Drink this beer because you'll be the most interesting
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man in the world. Buy this computer so you're not an Orwellian drone. That's a
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famous Apple ad from 1984. You know, these shoes will make you cool, just like insert your favorite athlete here.
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We're urged to consume until we're fat and broke. And once obese and opulent,
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we're urged to lose that weight and store that stuff. and the cycle continues. To the powers that be, you
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are a consumer. You make the economy go around. Well, something like the fulfillment curve is the antidote to
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that mindset. If you really know what you're spending and how it correlates to
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what makes you happy, you'll most likely spend less. And once you have your personal answer to that question,
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maintaining these stupidly simple rules of personal finance becomes a really easy task. The next one is that
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measurement is the key to management. frequent contributor to the the best interest blog, Peter Ducker, had this
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famous quote from the 60s or 70s when he was kind of at at his peak. And the quote is, "You can't manage what you
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don't measure." So to manage would be to analyze, take care of, and improve. And
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to measure would be to watch, to observe, to take notes, to quantify. Let me present two people to you. One of
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them tracks every single calorie she eats. The other one pays no heed to what she slides down her gullet. All else
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being equal, who do you think is going to end up healthier? Now, the first instinct, it's the woman who measures
00:10:08
all of her food intake. Why? Well, because we know that her abundant self-nowledge is likely going to lead
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her to make smarter food choices. The woman who doesn't care, well, she doesn't care. And that's probably going
00:10:18
to lead to worse food choices. And the same exact principle applies to personal finance. You don't have to track every
00:10:24
single dollar, and you don't have to check your accounts on a daily basis, but you should have a really good idea
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of where your money is going and where your net worth stands. Are you improving? Are you slumping? Are you
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spending thousands of dollars on Nepalese meditation retreats? Measure your money and then improve. Now, what
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happens if you don't follow some of these stupidly simple rules? The secret sauce. The stupidly simple secret sauce.
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Well, you might end up something like Dave. And in uh July 2020, I wrote this article. Do you know Dave? Somewhere in
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middle America, there's a man named Dave. You might know him. Today, for the
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first time ever, Dave is realizing that he's in a financial death spiral. Dave
00:11:00
makes about $60,000 per year. He knows he pays some taxes, but he's not sure
00:11:04
how much. All Dave knows is that his monthly take-home income ends up around $3,000. Right off the top, Dave pays
00:11:10
$1,200 for rent. His apartment is sick, or perhaps on fleek. Pick your parlance of the times. It's a modern, stylish,
00:11:16
could easily fit another person in his apartment, but Dave likes to live alone. Fair enough, Dave. And after driving a a
00:11:22
junky Honda Civic in high school and college, Dave is finally able to afford a nicer car. So, he leases changing cars
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every 2 years. Currently, he's behind the wheel of an Audi A3. It's 320 bucks
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a month, but insurance and gas brings it up to about 500 bucks a month. Dave's
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young, his friends are young. They all like to socialize around town. And a couple drinks and dinner later, the $35
00:11:41
bill comes. And life gets a little slow in middle America. So Dave does this a few times a week. Spends about 250 bucks
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a month on dining out. What about some other stuff? Well, Dave isn't really sure, you know, whether it's Amazon
00:11:53
purchases, groceries, gifts for his mom on Mother's Day. Dave knows that he buys
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these things. It's just that he doesn't really know how much or how often. He's
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unaware that he's spending another $400 a month on all these things. Like most
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his peers, Dave has student loans. He pays 500 bucks a month. And in the 5 years since college, he's paid about
00:12:10
$30,000 towards his loans. That's crazy. Now, his statement says he still owes 90
00:12:15
grand out of the original $100,000 in debt. But by Dave's math, 100 grand minus the 30 grand he's paid. Well, that
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means he only owes 70 left. So, the loan company must be wrong. He thinks, well,
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they're not. Dave's dad annoys him about saving for retirement. You know, get
00:12:30
that compound. Dad suggests that compound. At 27, Dave isn't even halfway to retirement age. He's got more
00:12:36
pertinent things to consider than retirement, he thinks. So, let's add it up. All of Dave's finances, we just laid
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them out. And if you've been keeping track, well, good for you, because Dave
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really hasn't. The first problem is that Dave's total expenses are greater than
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his income. He makes 3,000 a month, but he spends about 3100 a month. Now, it's
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not that big of a difference, right? But for the 5 years since college, that $100
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monthly deficit, it ends up on Dave's credit cards. $100 a month multiplied by
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five years. That's about $6,000 of credit card debt. Dave looks at his Visa bill, he sees a charge for $90 per month
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of interest, and that interest doesn't even affect his $6,000 in debt. What the
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heck is that? When Dave adds up his net worth, he finds that he's about $90,000
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in debt in total. And a lot of people are in lots of debt, he thinks, especially young people, college loans.
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It's normal, Dave thinks. Well, chronic smoking used to be normal, too. And much
00:13:27
like an empisemic, Dave is in trouble. To the outside world, Dave's a reasonable example of a successful young
00:13:33
guy. And I'll give Dave some credit. It seems like he has some nice things going
00:13:36
for him. Education, steady income, nice apartment, nice car. What's not to like?
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Well, Dave's multiple and repeated financial mistakes are catching up to him. And let's call a few of them out.
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After working for 5 years, he's decreased his debts by only 10%. He isn't aware of what he spends per month,
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and therefore, he's in credit card debt. Despite being in debt, he's still
00:13:56
spending a significant amount of his money on luxuries and fun. And our young years, yes, we want to enjoy being
00:14:02
young. They're also some of the best times to invest for retirement, and Dave
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hasn't done anything there yet. These mistakes are easy to avoid, but nobody
00:14:09
ever really taught Dave about them. In fact, I would argue that our economy, much like we just described, it's
00:14:14
actually a funnel designed to trap people like Dave. Even though Dave's in trouble, his path to improvement is
00:14:19
pretty well defined. He should start off by setting some financial goals. Right now, he's foundering. He's got no real
00:14:24
direction. And Dave, much like his dad said, he needs to get that compound, right? Dad is right. Our younger years
00:14:30
are the best time to invest. And Dave really needs a budget or he needs to be tracking his finances somehow, right?
00:14:36
Money in versus money out. I used to use the tool uh you need a budget. I currently use a tool called e-oney.
00:14:42
Whatever tool you use, you've got to track your finances. You've got to track
00:14:46
money coming in and money going out. Of course, Dave could find some pretty easy
00:14:50
ways to spend less. He could get a roommate, drive a cheaper car, spend less at the Fish Fry Friday, whatever it
00:14:55
is. And in my opinion, those are all secondary effects that occur after he sets a goal, after he creates some sort
00:15:01
of budget or tracking system. I mean, maybe Dave really likes his Audi that he's driving. Fine, that's fine. But
00:15:07
something in his budget needs to give. It's up to Dave to make that choice. Now, do you know Dave? Can you relate to
00:15:13
Dave? Maybe you're even named Dave. At the end of the day, odds are we either
00:15:17
know someone or maybe we were at one point this person, much like the first article I read from, it's very easy to
00:15:23
slip into these traps in in personal finance, but at the same time, the way we get ourselves out of them can be
00:15:29
stupidly simple. And now, changing gears, in the light of recent market volatility, and again, I'm recording
00:15:35
this at the end of March where we've had some back and forth volatility. The S&P
00:15:39
500 right now is about 8% off its highs, which okay, first off, we do need to zoom out and say it's not that big a
00:15:46
deal, at least in terms of of market history, right? 8% drops happen probably something like 80 or 90% of years have a
00:15:53
intraear 8% drop. So, it's not something there we need to be worried about. If we
00:15:57
want to be worried about what's going on out in the world, politically, socially,
00:16:00
internationally, those kind of things, totally. I get it. I get it. You know, there's nothing wrong with looking at
00:16:05
the news, looking at world events and saying, "Huh, that that concerns me." I
00:16:09
think there is something different though about tying that into your portfolio and saying, "Ah, because I'm
00:16:14
worried about what's going on, I now need to make drastic changes in in investing for no other reason than just
00:16:20
looking back at at history and realizing that chaos has always kind of been there
00:16:24
in the background, whether we realize it or not. World War I, World War II, Great
00:16:28
Depression, stagflation, oil crisis, nuclear arms race, Cold War. It goes on and on and on and on and on. There's
00:16:36
always been a reason to sell. Did I mention pandemics yet? Anyway, there's always been a reason to sell. And that
00:16:41
leads to some people saying, "Ah, I'm going to buy the dip." And much like
00:16:45
birds chirping at the rising sun, investors talk about buying the dip at the first hint of a of a stock market
00:16:51
pullback, correction, bare market. And yes, buying the dip makes sense at first blush because it suggests that we should
00:16:57
buy assets at at lower or the lowest possible prices. But buying the dip is actually a suboptimal a bad investing
00:17:05
strategy. And we need to talk about why. Now, the basic buy the dip argument is that buying stocks is a risk. The
00:17:11
stocks, their prices, they might go down after you buy them. And holding on to cash, that's a risk, too. Now, the cash
00:17:17
could be invested. It could grow with a rising market. That's the opportunity
00:17:21
cost of not investing is that you miss market growth as it grows away from you. Now either choice to invest or not has
00:17:28
some sort of risk and reward. The risk is that the market moves in the wrong direction. The reward is that the market
00:17:33
moves in your favor. How do we answer whether to buy the dip, whether to wait for the market to drop in price before
00:17:39
we buy? Well, we can't predict what the market will do in the future, but we can
00:17:44
look at previous market data to back test a buy the dip strategy. And that's
00:17:48
what professionals typically do. And and that's what we're going to do today.
00:17:51
Usually what we do is if we have some sort of strategy in mind, we look and see how did it perform in in past
00:17:56
history. Now before I insult too many people today, we do have to baseline ourselves a little bit. There are two
00:18:02
common definitions of buying the dip. Kind of like there are two common definitions of dollar cost averaging. It
00:18:07
is a little bit confusing. The first scenario of buying the dip is that you've been holding on to lots of cash
00:18:12
for many years waiting for some sort of big crash. And then after that big crash, you choose to buy stocks is most
00:18:20
likely. We're going to talk about stocks today. Now, that is certainly a form of
00:18:23
timing the market. But is it the same as buying the dip? I say yes. We'll come
00:18:27
back to this. The second scenario is that you're holding a small amount of cash expecting it to deploy into the
00:18:32
market soon. Maybe you just you did a a quarterly or semiannual review of your financial plan and you realized, you
00:18:38
know what, you've got a few thousand extra in your bank account that you really don't need. You should invest it.
00:18:43
It should go into part of your portfolio. We don't want to find ourselves holding too much cash. So you
00:18:47
have this cash, you want to deploy it, and rather than deploying it today, you say, "I'm going to give myself a month,
00:18:53
and I'm going to wait for the first red day in the stock market, the first day
00:18:57
of like a 1% drop before buying." Because even if the market only drops that 1%, you end up buying that dip. And
00:19:04
then in future situations when you have a little bit of extra cash on hand, that's the way that you choose to
00:19:09
invest. Now, I consider both of these scenarios to be a form of bad negative market timing. I say that both of these
00:19:17
scenarios are a different form of buying the dip. Now, some people disagree with
00:19:21
me. Some people they argue and say that since they're dollar cost averaging anyway since they're investing money on
00:19:28
a monthly basis or on a you know bi-weekly basis anyway through their 401k or Roth IRA or something like that.
00:19:34
Well, why not wait for a red day for a negative day in the market to execute their purchase? Buy low, right? That's
00:19:40
the argument. Wait for a red day, buy low. It makes sense. And in those people's defense, I do see a significant
00:19:48
difference between the two scenarios I outlined above. It's not just my opinion. The difference that I perceive
00:19:52
in these two scenarios, it is backed up by convincing analytical data, which we'll talk about. holding on to cash for
00:19:59
years, you know, stockpiling this cash, waiting for a big dip to then deploy that cash. That is a humongous losing
00:20:06
scenario. It could literally cost an investor millions of dollars over the course of a 30-year investing timeline.
00:20:12
It underperforms basic dollar cost averaging by as much as 800% in total returns in historical back tests. Now,
00:20:20
the other scenario where you're only holding on to cash for a few days or a few weeks or a month, that's a little
00:20:26
bit better. Well, I shouldn't say that. It's actually much better than the first
00:20:28
scenario, but it's still a losing scenario. Over most historical 30-year investing periods when we back test this
00:20:35
kind of wait and see, buy the dip. Let's wait a few weeks. Attempting to buy that
00:20:40
dip, attempting to wait for that dip would drag your overall portfolio down by about 1% over a 30-year period. And
00:20:47
for someone retiring with $1 million, holding on to cash to buy the dip would have cost them something like $10,000
00:20:53
over 30 years. It's not a huge price to pay, but it's certainly not good, and
00:20:57
it's not something that you just want to opt into. Why would you opt into losing
00:21:01
out on $10,000 on a million-doll portfolio? Now, some people would argue, well, you have to wait for a little
00:21:07
bigger dip. Wait for the market to crash by 2% before you invest or or wait for the market to crash by 5% before you
00:21:13
invest. But the data is clear. The bigger a dip that you're waiting for, the bigger a dip you need to trigger you
00:21:20
to turn your cash into stocks, the more painful, the more damage you're doing to
00:21:24
your own portfolio. So, no matter how big of a dip you wait for, it'll impact
00:21:28
your portfolio negatively. And the bigger the dip that you're waiting for, the worse it'll be. The best thing to do
00:21:33
is to not buy the dip at all. Some of you might be asking right now, but why? Cuz I mean, we already talked about it.
00:21:38
Buying the dip on its surface makes sense because we want to purchase stocks. We want to invest at lower
00:21:43
prices. The best way to explain it is with this simple example. Let's say Adam
00:21:48
has money to invest. And it's uh based on when I wrote this article, it's April
00:21:52
2021. And this is using real data, by the way. So on April 1st, the S&P 500 was valued at 4,020 on April 1st, 2021.
00:22:01
And Adam decided to wait before buying. He wanted the market to drop so that he could buy the dip. Unfortunately for
00:22:06
Adam, the S&P 500 increased by 4.1% in the first two weeks of April 2021 from
00:22:12
4020 to 41.85. 85. Only then after a 4% increase did the S&P dip. It dipped by
00:22:19
about 1.2% in in midappril back down to 4135. So should Adam buy that dip at 4135 even though 4135 is much higher
00:22:31
than where he was previously sitting at the very beginning of April? It was 4020. 4135 versus 4020. Or should he
00:22:38
hold out for an even bigger dip? And what if that bigger dip never comes? Right? the market is unpredictable. I
00:22:44
bet Adam or these hypothetical Adams feel pretty conflicted, full of regret when those things happened. Now, April
00:22:50
2021 was a very typical uh month in the stock market. On the whole, the market increased about 4% that month, but there
00:22:56
were a couple times with a a 1 or 1.5% dip. For most months, just like April 2021, the best day to invest is the
00:23:04
first day of the month. And for most years, the best day to invest is January 1st. Early is better most of the time,
00:23:10
right? the market in general goes up and to the right. And if you know that, if you zoom out on that fact, you'll
00:23:17
realize, sure, I mean, the market might go down tomorrow or next week or next month or next year. It's possible. But
00:23:24
on average, if you just ask yourself this question over any month in market history, you will have realized that
00:23:30
investing sooner is better than investing later. Waiting for a dip is a losing proposition. A future dip might
00:23:37
come, but it usually gets swamped out by the larger gains in the meantime. That's
00:23:41
the other thing, right? There's always going to be another 2% down day or 4%
00:23:46
down day or even more, a six or an 8% down day. A really scary day in the market. Those days are going to come. I
00:23:53
guarantee it. That's the way the market works. But they usually get swamped out
00:23:57
by all the gains that occur between now and then. So, waiting for lower prices, yeah, it makes logical sense. But we
00:24:04
have to ask ourselves, what if lower never comes? The problem isn't buying the dip. The problem is waiting for the
00:24:11
dip. Here's a quick ad and then we'll get back to the show. Every week I send
00:24:15
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00:24:37
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least once a month. They're enjoying it, and maybe you will, too. You can subscribe for free on the homepage at
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bestinterest.blog. Again, that's a free, no strings attached subscription at
00:25:00
bestinterinterest.blog. blog. And with that, we're going to welcome Bill G onto
00:25:04
the podcast. Bill is a 57-year-old practicing emergency physician, happily married, family man, but he's got an
00:25:11
interesting backstory that's led him to now being the co-host of of one of the
00:25:15
biggest upand cominging podcasts out there, Catching Up to Fi. While Bill has spent much of his life caring for other
00:25:21
people's health, he never learned or didn't until recently learn how to care
00:25:25
for his own money and his own financial well-being. He spent first and saved second. didn't know much about investing
00:25:31
in personal finance. Seems that he made most of the mistakes in in the financial
00:25:35
books and Bill will attest that waking up from that reality was painful, full of whatif regrets about his past and
00:25:42
even some shame. And and we dive into that today. But the recovery has been hard but incredibly rewarding for him.
00:25:49
And now Bill's mission is to help other late starters start now, right? And get
00:25:53
others to start as early as possible on their individual journeys to financial independence. So without further ado,
00:25:59
let's welcome Bill Y to Personal Finance for long-term investors. [Music] Bill, thank you for joining us today.
00:26:10
And as the listeners are now aware of and and especially those who listen to Catching Up Defi, your story is so
00:26:17
resonant with so many people who feel like they're coming to personal finance,
00:26:22
they're coming to investing a little bit later in their life. So, what was the
00:26:25
moment for you that kind of flipped the switch inside your head? And then what were some of the first major steps you
00:26:31
took to turn your boat around as it were from whatever financial path you were on
00:26:35
before to this better financial path now? Oh, it's funny you mentioned boat because we had a boat named Yolo. That
00:26:42
was kind of the mentality. You know, as as you may have mentioned, I'm a physician. I came out of residency with
00:26:47
delayed gratification. I thought I deserved a lot of things like the new house, the new car, lived paycheck to
00:26:53
paycheck uh with my wife for the better part of 20 years. Uh we made every mistake in the book. We bought whole
00:27:01
life insurance. We had a so-called private investment advisor that was with now out them Northwest Mutual.
00:27:09
Unfortunately, bought a disability policy from them. Uh eventually we were in the private bank at JP Morgan and
00:27:16
paid them exorbitant fees to really do us nothing and they didn't even talk us
00:27:20
out of selling. Uh they tried to maybe but they didn't really try hard selling
00:27:25
at the bottom of the market in the great financial crisis and de-risking our portfolio. So we did that. We were house
00:27:31
poor because we'd renovated a house in 2007 that was underwater in 2008. Uh so
00:27:38
we were house poor. We had bottomed out in the market and sold and then we kind of missed because we weren't
00:27:45
aggressively saving a lot of the bull market in the 2000s. And so we made what I call the trifecta mistakes and we came
00:27:54
out the other side of that. I woke up at age 50, let's say. And that's late. How
00:28:00
did I wake up at 50? I turned 50 and I realized nobody was going to take care of me but me. And that was a shock. I
00:28:09
was ashamed. I had my head in the sand. I didn't know how to pull it out. There
00:28:14
began the journey of the late starter. Can we dive into some of those emotions, Bill? I know it it can maybe be a
00:28:19
challenging thing to talk about, but it's one thing to get someone to understand the numbers. We do plenty of
00:28:25
conversations here on this podcast talking about the numbers, but at the end of the day, a lot of these decisions
00:28:30
are emotional in some form or fashion. And you just used a word there, shame. Can you talk us through just some of the
00:28:37
some of the challenging feelings when you realize like, oh, I'm not exactly where I want to be, but I've got to do
00:28:42
something about this. There's kind of a universal path for late starters. And
00:28:48
there's always a shock to the system, whatever it be, like divorce, loss of a
00:28:53
job, there's always a financial shock. And you go, "Oh my god, I'm not where I
00:28:57
want to be. I can't, you know, escape this lack of emergency funds or FU money
00:29:03
that protects me from this shock. And so it was shock, it was awe, it was shame,
00:29:09
it was regret. You would realize that, as I said, you had your head in the sand. I I got lost, as I referred to it,
00:29:16
is in the funnel of life. We grew our family. We were focused on our kids. We had a child with developmental
00:29:23
challenges that took a lot of focus and money. Life just passed by so quickly in
00:29:28
this paycheck-top paycheck lifestyle. We unfortunately spent first and saved last
00:29:35
around tax time. We did exactly the reverse of what people should do. It's I
00:29:40
mean it's not complicated what you should do. But nobody took me aside and said plastics like in the graduate.
00:29:47
Nobody told me that save in your 401k, max it out. That's all somebody needed
00:29:52
to tell me. And you know, I'd been saving here and there, but we were singledigit savers. It was what was left
00:29:58
over at tax time when we go, okay, there was no dollar cost averaging. I didn't
00:30:01
know what that was. I didn't know what a net worth statement was. I didn't know
00:30:05
what an expense report was. I just knew if I had money left at the end of the month in my checking account to make
00:30:11
sure I could pay off these big credit card bills was, you know, literally handtomouth.
00:30:17
I hate to say and I'm a physician remember I was highly trained, highly educated in how to help people with
00:30:24
their health but I could not help myself with my wealth. So yeah, there's a lot
00:30:30
of emotions associated with this and then it migrates. You know, you wake up and you go, okay, let's give myself
00:30:36
grace. Let's pause, try and figure out what happened. Where do I stand? What is
00:30:42
my net worth? What are my assets? What are my liabilities? What are my expenses? What am I spending every
00:30:48
month? Just figure out where you stand. And then so you plan at that point. You write your investor policy statement.
00:30:55
You don't jump in and start working the numbers. You got to work the emotions,
00:30:59
which is 80% of the battle, and you get to the numbers, but that's the last step. Investing is really the last step.
00:31:07
So, you pause, you plan, and then you pivot. You change what you you've learned from your mistakes hopefully,
00:31:13
and then you ask for help. You know, you go down the rabbit hole. You whether it's books, podcast, vlogs, your
00:31:19
podcast, my podcast that catching up to five. I I call it me search because I get to learn from experts like yourself
00:31:27
that we have as guests on the show. New nuances to investing every time we record. So you just need to open your
00:31:35
ears, open your eyes, ask for help, do your own research, and then with your investor policy statement, which is
00:31:41
comprehensive. It isn't just what investments am I going to invest in? you know, it's kind of my estate planning,
00:31:48
it's my insurance, it's all these other facets of a financial plan, my giving
00:31:52
plan. There's a comprehensive look at this and people need like yourselves, financial advisors sometimes to work
00:31:59
through these things and put together this plan and then you invest. I took back my money from JP Morgan. I took it
00:32:08
back, put it in vanguard and I had read things like the simple path to wealth, set for life, you know, I will make you
00:32:15
rich by Sethi. I read these things. Actually, if you can see behind me, I've
00:32:19
got two or three shelves of books. Yeah. The thing that happened to me as a physician was I was in analysis
00:32:25
paralysis, which is kind of the next emotion. You're like, what do I do? It's
00:32:29
overwhelming. and know how do I but then you got to learn how do I take a bite out of this elephant one small bite at a
00:32:35
time to get where I need to go that hopefully that answers your question. Oh it totally does. It totally does. You
00:32:41
hit on a few things there that that kind of got my brain spinning. One being you're right. So even in this world of
00:32:47
professional financial planning which certainly can get into some complexities where do we almost always start the
00:32:53
conversation? Well there's that emotional part of it or just trying to understand the person we're sitting
00:32:57
across from. But when it gets into the numbers, you mentioned four things in your response there, Bill. You said I
00:33:03
needed to understand my income against my expenses and I needed to understand my assets versus my debts. I call those
00:33:09
the big four and they really are the foundation numerically speaking at least of any financial plan. And it's not
00:33:16
rocket science. It is something that everybody out there listening can start to do themselves and and can get to
00:33:22
completion themselves if they want to, right? It's just this idea of if you don't understand those numbers and and
00:33:27
how they interact with your life, you will find yourself in a position where you just say to yourself, I'm
00:33:32
uncomfortable with my money situation because I don't understand it. Often you
00:33:36
start with your debts if you have debt and you work those out and then you work towards you have your emergency fund,
00:33:43
your debts, then your savings plan. You follow a cash flow waterfall that I'm
00:33:47
sure you've talked about on your show with buckets that you put your money in
00:33:52
as you flow down that cash flow waterfall. And that's where the boring middle start. That's really the second
00:33:57
phase of being a late starter. You go down the rabbit hole. You learn all these things. You get advice. You get
00:34:02
help. You've overcome your regret, shame, and awe. You've given yourself
00:34:06
grace. And then you got to work the plan. You know it. There's no magic buttons here. You've got to follow, as I
00:34:13
didn't actually, the KISS principle of keep it simple, stupid. I went complex.
00:34:18
I went all in on the Paul Marman 10 Funds for Life portfolio. You know, the first book I'd ever read was by Bill
00:34:24
Bernstein, the intelligent asset allocator, where I had to learn how to use a financial calculator in order to
00:34:31
figure out some of the things he said. It's not that complex. Start with, say,
00:34:35
the simple path to wealth. That may give you enough knowledge to really get started. That's one thing that we always
00:34:41
come back to as kind of the gospel of simple index investing. It can get a little more complex later, but you just
00:34:48
got to get started because you don't necessarily have the time of an early starter. You know, 35 year olds, as we
00:34:55
said, can feel late. 45 year olds can feel late. 50 year olds, 55 year olds, but it's never too late. You know, when
00:35:01
was the best time to plant a tree? 20 years ago. When's the second best time?
00:35:05
Today. Mhm. Late starters got to learn is, you know, you you may be working a little longer, but actually it's not
00:35:12
necessarily the case. The boring middle can be 10 to 12 years. If you get it right and read the shockingly simple
00:35:19
math of early retirement by Mr. Money Mustache, you know what you need to save and invest in order to find financial
00:35:25
freedom and independence within 10 to 12 years. Can you talk about your journey a
00:35:31
little bit more? And specifically, I'm thinking about what your rabbit hole period looked like and how long it was
00:35:37
from that moment you you kind of woke up at 50. You spent some time just deep diving into the Paul Maryman's and the
00:35:43
Bill Burn scenes of the world, the JL Collins as well. But now, is it fair to say you're in the boring middle? And
00:35:49
since you have an understanding of your future financial plan, how long do you foresee that boring middle period being
00:35:56
for you? Well, the analysis paralysis probably lasted a year. It's scary. I mean, it's scary to take over your money
00:36:04
and do it yourself. I mean, maybe 20% of the people do it and 80% of the people still have a financial advisor and that
00:36:10
is okay, but you need to find the right one. So, the boring middle for me is looking like because we didn't save
00:36:17
nothing. I don't know what our net worth was when I woke up at 50. I could probably figure it out, but it'd be
00:36:23
pretty complicated. I know where it stands now, and we're about 80% of the way to financial freedom. And so I've
00:36:30
gone from 50 to 59. I've got three or four years left in my 12 to 14 year journey. The problem we have is we
00:36:38
downsized our life, but we didn't necessarily downsize all our expenses. And we're needing to pursue a fat fire
00:36:45
lifestyle. Lean Fi, as you may have talked about, is one thing. Coastf is another. Standard FI is 25 times your
00:36:54
expenses. And then fat FI may be 30 times your expenses. So, you know, that's where we're kind of at. And I
00:37:01
plan on, you know, retiring essentially on time as most people do at 62 or 63. And what does that mean? You know, I've
00:37:09
got to have a plan for what happens after that. It isn't margaritas, my ties, the beach, and golf. It's going to
00:37:15
be this podcast. It's going to be educating people on these issues to try and create generational financial
00:37:21
literacy where our kids are better off than we were. Because my generation, I refer to it as the average American. The
00:37:30
average American is a late starter. I'm in the silent generation. We don't talk
00:37:34
about it because of the shame. We are also the lost generation because we went from defined benefit plans to defined
00:37:41
contribution plans. And nobody told me the difference. My dad had a pension and all of a sudden in Gen X, I wasn't going
00:37:48
to have one and I had to do it myself and nobody told me really what a 401k was. So, we need to wake up this
00:37:55
generation. so that our kids generation doesn't fall into the same traps we did.
00:38:00
So when you wake up someone in this generation, what are the most effective levers that you've seen either for
00:38:05
yourself, Bill, or I'm just thinking of of so many experiences you have from
00:38:08
your listeners? The most effective levers that a late starter can pull on to start making up for lost ground? Is
00:38:14
it simply about earning more? Simply about just saving first, saving more aggressively? Looking at their budget
00:38:21
and really starting to trim the fat? What helps the most? Well, you've got to
00:38:25
maximize your savings rate and create the gap, which means earning more. And that's one of the levers that late
00:38:31
starters have to pull. They're in their high income years. Take advantage of
00:38:34
that. We went from a say 10% savings rate to a 35 40% savings rate within a year. And guess what? We didn't really
00:38:44
feel a difference in our lifestyle. And I was like, "Oh my goodness, where did
00:38:50
all that money go? It just trickled through the civ of life. And as soon as we harnessed the holes, took our house
00:38:58
from 4,500 ft² to 2,800 square feet. We paid cash for cars where we hadn't done
00:39:03
that before and and bought used. You know, we got control of our food budget and well, we haven't gotten control of
00:39:09
our travel budget, but you got to let something go there. I mean, you've got
00:39:12
to look at a balanced life. Personally, I think the live on one income and the two-income family or live on half,
00:39:20
meaning 40 to 50% is a great rule of thumb and you need to start that early because as soon as you let lifestyle
00:39:27
inflation run away from you, it is hard to unwind that. So, you know, downsizing
00:39:32
is a lever. Increasing your income, increasing your savings rate, decreasing your expenses, those are all levers. But
00:39:38
you can't forget that late starters have social security. That is a backs stop
00:39:43
and a lever that you have to plan on and pull in your investment plan. It's going
00:39:47
to be there in some form or another. Whether it's 80% of what it is now, but
00:39:52
don't forget about that. It is also a powerful lever. Diving into that social
00:39:57
security, any recommendations or in general for the late starters, does it make sense for them to wait as long as
00:40:04
possible? Is it really just a case- by case basis as to when they elect to start collecting social security? Well,
00:40:10
if personal finance is personal, social security is very personal. I have to recommend in making this decision, you
00:40:16
go to open sec opensocial securitycurity.com. It's a website founded by Mike Piper. And generally in
00:40:24
a married couple, the high-income professional, the higher income professional should try and wait till
00:40:30
70. The advantages are tantamount. They're huge. And then with regards to the other spouse that's the lower
00:40:37
earning spouse, especially if it's a female who has a longer lifespan, you can take it earlier. You can take I mean
00:40:43
your full retirement age these days is 67, but you could potentially take it at 63, four or five and as long as you have
00:40:50
longevity on your side. The crossover point tends to be in your early 80s. That's exactly align with my
00:40:57
understanding of the question too. Going back though to your previous answer, Bill, and the interesting changes that
00:41:03
you made in your lifestyle and how it seems like to some extent you barely even notice the changes. I would think
00:41:10
that's more common for the average listener than they suspect it is. And I guess the other way of putting it is we
00:41:15
spend all this money in our life currently and there's sometimes we don't
00:41:20
quite notice that the marginal benefit for having spent that money. Do you have any specific stories? I mean, you did
00:41:25
share some specifics already, but whether it's a a listener story or something from Jackie's story or from
00:41:30
your your own story where it's just like, wow, I can't believe I was spending X per month on this thing and I
00:41:36
cut it off and I barely even noticed it. I want to tell you who Jackie is first.
00:41:40
Jackie, my partner, my co-host on the podcast Catching Up to Five, her story is incredibly inspirational. She woke up
00:41:48
at 38 with a net worth under say $100,000 and by 49 she was retired with a net worth of 1.3 million just by
00:41:57
making the right decisions. And inspirationally she never made more than five figures. She came from poverty. She
00:42:06
knew the value of money and setting her free. She knew the value of an education
00:42:10
in increasing her income. And she's a single mom that did it with a daughter.
00:42:15
It's just incredible. And another incredible story was my previous co-host Becky Heptig. I mean she and her husband
00:42:22
had a net worth of zero zero at 50. And by 63 they were retired with 1.3 1.4 million just because of making the right
00:42:32
decisions with their money. That that speaks to the path of 12 to 13 years. Both of them kind of followed that path
00:42:40
and everybody has that available to them should they wake up make a few right decisions and just follow the path. We
00:42:49
had bought luxury cars and actually we didn't buy them, we leased them. And that's a huge difference. You know, buy
00:42:55
a three to five year old car for cash. Let somebody else take the depreciation hit. It makes a huge difference. I mean,
00:43:02
Rob Burgerer, who was on our show, said cars are kind of a retirement buster. Think about cars over your lifetime. And
00:43:09
if you and just like Rammit Sethi says, who cares about the lattes? Make the $30,000 decisions right. and you know,
00:43:18
keep your car expenses lower. For example, we were buying luxury cars for $50,000 when we could have been buying a
00:43:24
Honda or a Toyota for $25,000. And guess what happens to the difference? You invest it and there's opportunity costs
00:43:32
there that you give up if you buy the expensive car and it can mean a million dollars, right, over 20 years in
00:43:38
portfolio, literally. I mean, do the math, right? Yeah. Yeah. I mean, especially, you know, one of the other
00:43:43
big costs is housing. And someone might listen to this and say like, well, should I stretch for housing? And well,
00:43:48
the answer there is at the very least if you go a little bit beyond your means to
00:43:53
buy a house. It is expensive. Mortgage costs can be quite expensive, the interest costs you pay. I will say
00:43:58
though, at the end of the day, you have an asset that is most likely appreciating even if in a small way.
00:44:04
Now, personally, I don't view residential like my personal home as an investment. But I am comforted by the
00:44:10
fact that it's most likely going to retain its value in the long run. Well, it's a store of equity. It's a store of
00:44:15
equity, but it's a let's say it's a savings vehicle, but I don't view it as
00:44:20
an investment either. Correct. I view it as a liability because the cash flows out. No inward cash flow. So, I think
00:44:27
very strongly that a house is a liability. Renting is not a bad thing. You know, you don't have those all those
00:44:34
ancillary maintenance costs, all the big surprises. You don't have the headaches.
00:44:39
And so these days with the cost of housing and the interest rates, I think there's going to be a generation of
00:44:44
longerterm renters. Quite possibly. Quite possibly. But I think if you compare that to going back to the car
00:44:50
example, right? Whether you're buying new or buying used or leasing, at the end of the day, call it 10, 12, 15 years
00:44:58
from now, you are going to have a rusty car that no longer works and has no appreciable value. I mean, one way or
00:45:03
the other, it's we all know it's a depreciating asset. And to your point, I
00:45:08
think what you're saying is you just want to minimize the pain of that depreciation asset as best you can,
00:45:14
however that the math works out for you. That's correct. I mean, minimize the
00:45:18
holes in the bucket. You know, make it leak proof and then, you know, it'll fill up and flow into your next bucket.
00:45:24
Money is potential energy. You create a dam and then you you fill up the lake behind it and then you release the
00:45:32
energy as you need it. I mean, it it flows. It's infinite, but it's really in
00:45:36
in the end of the day is not something we own beyond our death and it transfers to other people, but you want to try and
00:45:42
make a perpetual store of energy that lasts for generations, not just yours. Here's a quick ad and then we'll get
00:45:49
back to the show. I still remember it was 2019 and a guy from Fidelity came in to speak to my then employer about
00:45:56
personal finance in general and about our 401k plan in particular. There were 60 or so of us who attended, mostly 50
00:46:02
plus years old, clearly with retirement on their minds. And nothing against this
00:46:07
individual from Fidelity, but unfortunately the guy just didn't really know what he was talking about. It ended
00:46:11
up being a major disappointment. And a bunch of my colleagues afterwards said, in short, you know, man, we're really
00:46:17
thirsty for good financial retirement information. Where do we go find it? Now, does that sound true, listeners,
00:46:23
for you and your colleagues? Last year, either in person or via Zoom, I spoke to
00:46:28
about 800 employees at 11 different organizations. Sometimes about personal finance in general, sometimes about
00:46:34
specifics of their retirement plans, sometimes about the the nitty-gritty details of social security and
00:46:39
withdrawal planning and retirement math. The point being, if you're interested in
00:46:43
inviting me to come talk money to you, to your colleagues where you work, that is absolutely something I'm interested
00:46:49
in talking to you about. Simply drop me an email to [email protected] blog
00:46:53
and let's start a conversation. Something on on catching up to FI. I mean, have you found anybody who
00:46:59
started, you know, was very much a late starter, but now has gone not only to the point of their own retirement
00:47:05
planning, but is starting to think about that next generation and and all the assets they're going to be able to leave
00:47:10
behind or the the long-term impact that they're going to be able to leave behind, whether it's charity or their
00:47:15
children or or some other long-term cause. There's a Bill Perkins book that says, you know, die with zero. Sure.
00:47:21
that there's that option where you don't create generational wealth and then you
00:47:25
maximize your quality of life during life. That's not part of our investor policy statement. I think we do want to
00:47:33
live something for the next generation. It would be nice to have a perpetual money machine that helps them, their
00:47:39
kids, their grandkids. You can look at 529s that way. Build up an educational fund that passes down to generations so
00:47:47
they don't have to worry about educational costs. build up a donor adise fund where you can have perpetual
00:47:54
giving and they learn about giving as part of their portfolio. Generational wealth is to us important and you have
00:48:01
to plan for that because that means that your number that you need to save maybe
00:48:06
need to be a little bit more. I'm thinking about the late starters who are tuning in right now or even I mean I can
00:48:12
think of some people Bill who are my age and I know they listen to this podcast and they're probably considering
00:48:16
themselves a late starter. So, it's not just the 50 and 55 year olds. We're
00:48:19
going down into the 30s, too. But either way, there's always going to be that
00:48:23
roadblock in their minds of I'm a little late to this game. And therefore, they
00:48:28
might be susceptible to some of the I'll call them the biggest myths out there
00:48:33
when it comes to financial planning in general, or more specifically latestage financial planning. What are some of the
00:48:38
more interesting myths that you and Jackie have heard through your Facebook group, say, Catching Up to Fire, or just
00:48:44
your work over there? And and how have you helped people overcome those mythological false mindsets? Well, one
00:48:51
myth is that risk is to your advantage. You know, there's no magic buttons and
00:48:55
to take on too much risk as a late starter is probably unwise. You know, you really need a 10-year runway for
00:49:02
equities and you could be potentially 100% equities for 10 years, but you need to wind that down as you get closer to
00:49:08
retirement. Within five years of retirement, that should be wound down. But then you got to be able to sleep at
00:49:14
night and you got to know your risk tolerance. You know, your ability and your need to take risk. Those are two
00:49:20
different things. And late starters do need to take some risk. You can't be too
00:49:25
conservative because you need growth and but their ability may not be commensurate with their need. And trying
00:49:31
to assess that may take somebody as a coach or an adviser to help you figure that out. It may be hard to figure out
00:49:38
on your own because, you know, you make a mistake like recent days where you went all in and now we're in a 10%
00:49:44
correction and who knows how far that's going to go because of what's happening
00:49:49
sort of as a manufactured crisis in the economy that we might have expected and some people did, but you know, not
00:49:56
getting too political. You got to stay the course. That's another really important thing for late starters is
00:50:03
don't like I did let your fear dictate what you do next. And don't time the
00:50:09
market. Don't, you know, try and go all out on January 20th and then figure out
00:50:15
when you need to go back in. You know, they call it the whipssaw. You have to be right twice to take advantage of
00:50:21
timing the market. Don't do it. That's a myth, too. What other myths are there?
00:50:26
There's no magic button. You've got to stay the course and, you know, do what
00:50:31
you would do if you were 35. Do it the same thing at 55. The path doesn't change except for the fact that the
00:50:39
older you are, the more aggressive you need to be with savings and having a big gap. And just as a time capsule,
00:50:45
listeners, Bill and I, we're chatting here on March 11th. This episode probably won't come out for a few weeks,
00:50:50
but the the S&P 500 right now live is 5573, as Bill alluded to, down about 10%
00:50:58
from its highs. We'll see by the time this episode comes out where the market
00:51:01
is at. You you never quite know. It's a fun uh this is one of the fun side effects of podcasting, I think, is you
00:51:06
get to have conversations at a point in time and then see what happens from there. I said, "Yahoo, let's buy." And I
00:51:13
also said, "Yahoo, let's tax Lost Harvest." And I'm sure you explained
00:51:17
those uh things and I mentioned it in my community today was, you know, this is your opportunity. Don't forget to tax
00:51:22
lost harvest in your taxable accounts. Take the losses now. Let the government help you stomach those losses and then
00:51:29
uh lower your basis and, you know, let it ride. It's only going to go up and to
00:51:33
the right. Don't let shortterm swings dictate your long-term vision. Did you
00:51:38
chat about the wash sale rule at all in your in your group when talking about the tax loss harvesting bill? Yeah, you
00:51:43
got to be careful with 30 31 days, but as long as you buy a different index, for example, if you trade total market
00:51:50
US for S&P 500, you've avoided the wash sale and you can do it on the same day.
00:51:55
If you try and buy the same thing on the same day or within 30 days prior to and
00:52:00
after, you're going to get into a little bit of trouble and you won't gain all
00:52:04
those losses. Yeah. Yeah. It's interesting. I've maybe what we'll do is
00:52:07
we'll throw an article in the show notes that I wrote about tax loss harvesting
00:52:10
cuz on net there definitely is a benefit there but as you alluded to you are lowering the basis of your portfolio and
00:52:19
essentially it kicks the tax can down the road right eventually that those capital gains will be realized or
00:52:27
eventually you'll die and then pass the assets along to your heirs at a stepped
00:52:31
up basis and so I guess what I'm saying is most likely for most people The taxes
00:52:36
will come due eventually. It's just a matter of, you know what, maybe you're
00:52:39
in a really high tax year this year and it makes sense to tax lost harvest to your to your advantage because when you
00:52:44
kick that can down the road, you'll have some more control over realizing them in
00:52:48
a in a lower tax year. Something like that. You asked about inspirational stories and it doesn't have to be all
00:52:53
paper assets. We had a guest on our show, Monica Scodieri. The name of the show was Mama Are We Poor? and she had
00:53:01
come from poverty but used real estate to her advantage to get where she needed to go again in 10 to 12 years and that
00:53:08
was her vehicle. You don't have to use stocks, bonds and alternatives in paper
00:53:13
assets to get where you want to go. You can start a business. All these things are maybe a little bit more risky and
00:53:18
the more work because it's a job. Yeah, I personally choose to be passive. Well,
00:53:23
let's end on thinking about some of the traditional investment advice or traditional just personal finance,
00:53:30
financial planning advice that either needs to be drastically modified or tweaked for the late starter. Does
00:53:37
anything come to mind as something that you say to yourself, Bill, like, yeah, that that really does work if you're 25
00:53:42
or 30 and just getting going, but if you're coming to this situation at age 50, we have to rethink what's going on
00:53:48
here. Compound growth works great if you're young. It works better. It works
00:53:54
a little bit better. Not better, but as you age, you have less time for doubling. Remember the the rule of 72.
00:54:01
Generally, 7 to 10 years, uh, you'll double your money and you're losing
00:54:05
doubling time. So, you have to save more aggressively. That's a big difference.
00:54:10
You have to downsize your life so you have a a bigger gap. That's, you know,
00:54:14
people need to live within their means, not have too much house as we talked about, not have too much car, you know,
00:54:22
and but then again, remember, you're investing for the long run. It isn't
00:54:26
just a 10 or 15 year runway to your retirement. You've got 30 years ahead of
00:54:30
you if all things go well. So, it is a long time long-term investment and you will more than likely have more than you
00:54:39
started with when you retire. So, you have to make a plan for that. Yeah. You just hit on something there. Speaking of
00:54:45
myths or m misconceptions, that runway or that timeline that we're talking about,
00:54:50
right? Let's say I'm I'm 55. I'm listening to this podcast right now.
00:54:53
You're right. Some of your dollars might have this five or sevenyear timeline
00:54:57
until you hopefully retire and start spending them. But a lot of your dollars have a a runway until you're 70 or 80.
00:55:04
They have a 15 or a 25 or a 30 plus year timeline ahead of them. And it's each
00:55:09
dollar has its own unique timeline and it kind of all comprises a total portfolio. So a misconception that I
00:55:16
hear is someone says, "Oh, I'm 58. I'd like to retire by 60 and that's why I've
00:55:20
moved my entire portfolio to bonds because it's only two years away." And I
00:55:24
kind of hear that and say, "Whoa, so much of your timeline is still a decade
00:55:28
plus away." Well, you need you need to beat inflation. You know, you can't
00:55:32
forget. Absolutely. And bonds won't necessarily get you there. You got to have a have a gap there. you know, keep
00:55:38
your cost of your investments low so that the gap works for you. But remember, inflation is a huge cost.
00:55:45
Taxes are a huge cost, and unless you have growth assets, you could be in real trouble later on as your money loses
00:55:51
value over 30 years. Oh, exactly right. I feel like we've covered a lot of interesting, you know, little little uh
00:55:57
little pockets of information that apply to the late starter today, Bill. And if
00:56:01
anyone wants to join your community, cuz that's really it's more than just tuning
00:56:05
in to the Catching Up to Thai podcast. It really is a community that you've built. How can someone get in touch with
00:56:11
you, get in touch with Jackie, and join the conversations that you guys are having? The first thing I'd recommend a
00:56:17
new late starter to do is listen to episode 100. That is the odyssey of the late starter. We tell you exactly as
00:56:23
we've talked about today, the things you need to do. But as far as joining the
00:56:27
community of Catching Up to Fi, we have a Facebook community of over 17,000 members. We have great moderators. It's
00:56:34
a great place to be vulnerable. It's a great place to crowdsource some of your
00:56:38
questions. It's a great place to meet people, to take things offline. We have
00:56:42
a lot of like yourself, we have a lot of really intelligent people in that community that are ready, willing, and
00:56:47
able to help you with your journey and your questions. And a lot of people will tell their stories. And what you realize
00:56:53
is there's commonalities to all of them. And the best part about it is you're not
00:56:58
alone. You know, in the podcast, we're trying to have a dialogue. In the community, we're having a dialogue.
00:57:03
We're going to start a newsletter that will also allow for a dialogue. So, join
00:57:07
us at Catching Up Defy. We've had people binge on all 120 some odd podcasts and
00:57:13
leave us a review and it just warms our hearts. As a physician, I've been taking
00:57:18
care of people for better part of 30 years. And I've received more gratitude
00:57:23
for what we were created at Catching Up Defy in the last two years than all those 30 years. So, it's an incredible
00:57:30
thing. It's a great thing to be a part of this creative community and it's a
00:57:34
great legacy for me to leave this behind. Awesome. Well, thank you so much, Bill, for for all the work you do,
00:57:40
and I I can't recommend catching up to VI highly enough. What else can I say
00:57:45
other than than thank you and extend my gratitude? And so once again, thank you,
00:57:48
Bill Y, for stopping by Personal Finance for Long-Term Investors. Well, thank you
00:57:53
for having me. Thanks for tuning in to this episode of Personal Finance for Long-Term Investors. If you have a
00:57:59
question for Jesse to answer on a future episode, send him an email over at his blog, The Best Interest. His email
00:58:05
address is jessevestinterest.blog. Again, that's jessevestinterest.blog. Did you enjoy the show? Subscribe, rate,
00:58:14
and review the podcast wherever you listen. This helps others find the show and invest in knowledge themselves, and
00:58:21
we really appreciate it. We'll catch you on the next episode of Personal Finance
00:58:25
for long-term investors. Personal Finance for Long-Term Investors is a personal podcast meant for education and
00:58:32
entertainment. It should not be taken as financial advice and it's not prescriptive of your financial
00:58:37
situation.

Badges

This episode stands out for the following:

  • 60
    Most inspiring
  • 60
    Best concept / idea

Episode Highlights

  • The Stupidly Simple Secret Sauce of Personal Finance
    Jesse discusses the importance of simple rules in personal finance, debunking complex strategies.
    “Personal finance does not have to be complicated.”
    @ 02m 58s
    April 23, 2025
  • Dave's Financial Death Spiral
    A cautionary tale of a young man named Dave who struggles with financial management.
    “Chronic smoking used to be normal, too.”
    @ 13m 25s
    April 23, 2025
  • The Dangers of Buying the Dip
    Buying the dip may seem logical, but it can lead to significant losses over time.
    “Buying the dip is actually a suboptimal strategy.”
    @ 17m 02s
    April 23, 2025
  • Bill's Financial Awakening
    At 50, Bill realized he needed to take control of his finances after years of mistakes.
    “I woke up at age 50 and realized nobody was going to take care of me but me.”
    @ 28m 05s
    April 23, 2025
  • The Boring Middle
    Navigating the financial journey as a late starter can be daunting, but it’s essential to embrace the boring middle phase.
    “The boring middle can be 10 to 12 years.”
    @ 35m 14s
    April 23, 2025
  • Generational Financial Literacy
    Creating financial literacy for the next generation is crucial to avoid the traps of the past.
    “We need to wake up this generation so that our kids' generation doesn't fall into the same traps we did.”
    @ 37m 57s
    April 23, 2025
  • Jackie's Inspirational Journey
    Jackie transformed her financial situation from under $100,000 to $1.3 million by making smart decisions.
    “She woke up at 38 with a net worth under $100,000 and by 49 she was retired.”
    @ 41m 46s
    April 23, 2025
  • Tax Loss Harvesting Benefits
    Tax loss harvesting can lower your basis and help manage capital gains taxes.
    “Take the losses now. Let the government help you stomach those losses.”
    @ 51m 24s
    April 23, 2025
  • Community Support for Late Starters
    Join a supportive community of over 17,000 members to share your financial journey.
    “You're not alone. We’re having a dialogue.”
    @ 56m 58s
    April 23, 2025

Episode Quotes

  • Personal finance does not have to be complicated.
    It's Not Too Late: Smart Money Moves After 50 | Bill Yount - E105
  • Chronic smoking used to be normal, too.
    It's Not Too Late: Smart Money Moves After 50 | Bill Yount - E105
  • Waiting for a dip is a losing proposition.
    It's Not Too Late: Smart Money Moves After 50 | Bill Yount - E105
  • It's never too late. You know, when was the best time to plant a tree?
    It's Not Too Late: Smart Money Moves After 50 | Bill Yount - E105
  • Don't let short-term swings dictate your long-term vision.
    It's Not Too Late: Smart Money Moves After 50 | Bill Yount - E105
  • You're not alone. We’re having a dialogue.
    It's Not Too Late: Smart Money Moves After 50 | Bill Yount - E105

Key Moments

  • Review Time00:58
  • Financial Rules02:58
  • Dave's Story10:48
  • Market Anxiety16:36
  • Generational Wealth47:59
  • Long-Term Planning54:30
  • Financial Misconceptions54:45
  • Community Building56:04

Tension Over Time

Words per Minute Over Time

Vibes Breakdown