AAR45 - Is Dollar Cost Averaging Losing You Money?

14 Apr 2026 · 43 min · 17 chapters

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In short

Whether dollar-cost averaging (DCA) is “losing you money” versus investing a lump sum. The episode argues DCA isn’t inherently worse, because missing the market’s biggest up days can erase returns; DCA reduces timing risk and supports automation and emotional comfort. Lump sum can outperform when invested well, since it maximizes time in the market and avoids cash sitting idle.

Guest backgrounds

No traditional guests. Co-host Andrew (described as a “professional stock picker”) joins Evan Ray (host). They also reference author William Green and investor interviews from his book Richer, Wiser, Happier, plus Vanguard’s 2012 study and Jeremy Siegel’s Stocks for the Long Run.

Key claims

Missing best days hurts returns; lump sum beats DCA about two-thirds of the time in studies with good timing; DCA reduces downside risk and fear; risk tolerance and psychology matter more than math for many investors.

Notable examples

“Take 10 worst days and 10 best days” thought experiment; “biggest moves happen in a single day”; Evan’s Value Spotlight $150/month DCA portfolio; Andrew’s weekly automation and “sinking fund” approach.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

The Importance of Timing in the Market

0:00 to 0:31

Learn why missing key market days can significantly affect returns.

“If you take the best days out of the market, so let's say you're a great timer, you took the 10 worst days out of the market and you weren't in there.”

Personal Credit Card Update

4:41 to 6:16

Hear about the new credit card addition and its benefits.

“using dollar cost averaging is actually costing you money and losing you a lot of your gains.”

Dollar Cost Averaging vs. Lump Sum Investing

7:21 to 11:40

Explore the differences between dollar cost averaging and lump sum investing.

“Yeah, let's make a clean up your wallet app that'll siphon through your Apple wallet.”

The Case for Lump Sum Investing

11:40 to 14:01

Discuss the advantages of lump sum investing and market timing.

“So to kind of start off, maybe a bit of the devil's advocate since we discussed dollar cost averaging so much, the case for lump sum, when lump sum would be best for you.”

Understanding Market Timing Risks

14:01 to 15:02

Learn why trying to time the market can lead to underperformance.

“but basically if you take the best days out of the market, so let's say you're a great timer.”

The Case for Dollar Cost Averaging

15:03 to 16:18

Explore how dollar cost averaging can benefit investors, especially beginners.

“And I also just anecdotally notice it with my stocks too, the individual stocks I own, is a lot of just kind of nothing for a while, a little bit up, a little bit down, and then a huge up day.”

Benefits of Automation in Investing

17:30 to 21:36

Understand how automation enhances the investment process through dollar cost averaging.

“We have the inside scoop on something that's absolutely taken over the internet by storm.”

Risk Management in Investments

21:37 to 24:10

Discuss how personal risk tolerance impacts investment strategies.

“do you see it as a good complete substitute for something like lump sum?”

Balancing Risk and Investment Strategies

24:11 to 28:00

Evaluate how different investment strategies can affect emotional and financial risk.

“If you have this mindset where I can't stomach losing $1 ,000,$100 ,000,$1 million, whatever the number is, it's very personal for everybody.”

Risk Tolerance and Investment Strategies

28:00 to 29:15

Understanding how personal risk tolerance affects investment choices.

“that to them would not be life-changing.”
Show all 17 chapters

Personal Approach to Investing

29:15 to 30:29

Hosts share their personal investment strategies regarding lump sums and dollar cost averaging.

“you know, inheritance, a bonus at work, you know, however else you just end up with a lump sum of cash.”

The Importance of Dollar Cost Averaging

30:29 to 31:38

Discussion on why dollar cost averaging is essential for building wealth over time.

“As we mentioned before, we have a free budgeting outline available online at einvestmentforbeginners.com slash budget.”

Managing Emotions in Investing

31:38 to 34:06

How emotional management plays a crucial role in investment decisions.

“We could talk about that till the cows come home.”

The Mechanics of Dollar Cost Averaging

37:19 to 40:02

Exploring the long-term benefits and mechanics of dollar cost averaging.

“I got something for my son who's going to be here soon.”

Compounding and Wealth Growth

40:02 to 42:02

Understanding the power of compounding in wealth accumulation.

“I am somebody that would feel that risk outside of investing.”

The Power of Compounding in Investing

42:02 to 44:02

Learn about the significance of compounding and dollar cost averaging in building wealth.

“One of the sayings that Charlie Munger used to say, Charlie Munger, business partner Warren Buffett, billionaire himself as well.”

Understanding Dollar Cost Averaging

44:02 to 45:01

Understand how dollar cost averaging can impact your financial future and alternatives to consider.

“So I hope that was helpful for some people out there.”
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Transcript

Automatic transcript. May contain errors.

0:00Evan Raidt:If you take the best days out of the market, so let's say you're a great timer, you took the 10 worst days out of the market and you weren't in there. If you also took the 10 best days out of the market and you weren't in there, you would actually underperform somebody who had stayed the entire time. Stocks, the biggest moves in the stocks happen in a single day. So if you miss one of those days, you could miss the entire 2026 return. We don't know what day in 2026 is going to be a big one, but if you miss that big one, you'll miss a bunch of that return. This show is sponsored by Liquid IV. With the days getting longer and warmer, I'm spending way more time outside, but lately I was hitting a massive afternoon slump.

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3:27Andrew Sather:good day everyone and welcome back to an any rate my name is evan ray and we're here to help you make sustainable financial changes without breaking a sweat and as you're used to everyone please wish a good late morning to my favorite co-host andrew say there how are you doing

3:42Evan Raidt:what's up dr evan

3:46Andrew Sather:could be causing your cough to get worse. I'm just going to say that. But a medical professional might not say that. Well, hopefully it doesn't bother the listeners.

3:55Evan Raidt:Bro science is... I'm all about bro science. If it sounds good, it probably is right in my mind. The solution is just not to lay down. I think you sleep standing up.

4:07Andrew Sather:You get a coffin that's standing up against the wall or something like that.

4:12Evan Raidt:Okay. I'll do that, doctor.

4:41Andrew Sather:using dollar cost averaging is actually costing you money and losing you a lot of your gains. But to start off first, a little update. I did an episode pretty recently, a few episodes back on the credit cards that I use. I went pretty dang in depth into it of the different credit cards that I have, what I use each of them for, how long I've had them for, blah, blah, blah, a lot of detail. And since then, I've actually had to change. Since I recorded the episode, I actually got the Robinhood gold credit card. This is a credit card that I was on a wait list for quite a while for. And when I got off the wait list, I did a little bit more looking into it and decided to pull the trigger on getting it.

5:17Andrew Sather:So to kind of just give a quick overview on what the card is and why I got it, it's a card, of course, by Robinhood. And it gives you 3 % cash back on every purchase anywhere, unlimited. The only catch is to redeem that cash back for its full value. You transfer it to your Robinhood brokerage account and you can do with it what you want from there. You can invest it. you could withdraw it to cash, whatever you want to do. But for me, it seemed like a really good fit. You also do have to have a Robin Hood Gold membership to get access to the card, but I already had that for the Roth IRA match, so again, kind of a moot point for me.

5:51Andrew Sather:So, so far I've been very happy with it. It seems like it's going to work really, really well, and just to be clear, this isn't sponsored or anything like that. This was a card that I've been on a wait list to get onto for at least a year and a half, maybe two years at this point. I've been on a wait list for a long, long time. and eventually got into it and decided to pull the trigger on it. But I just kind of wanted to give everybody an update on that new credit card that I've added to my pile of credit cards. So I believe that that puts me to five total at this point. So kind of on the upper end of where I would want to be in terms of total credit cards, but definitely not a problem whatsoever.

6:26Andrew Sather:And same as everything else, I'm paying it off weekly. So it's not going to add to my overall balance or anything like that.

6:32Evan Raidt:Do you load them up on the Apple wallet? because my Apple wallet's starting to get really, really long. I don't know. It is. It is.

6:39Andrew Sather:It is starting to get long. And then another problem is that it's a nice feature that the Robinhood card has, but it's also going to be a problem for that is that it has something called virtual cards where you can create a card for like a short term in case you're going to, you know, maybe use it somewhere sketchy or whatever it is. You can put a short hole, get a short term card number that then expires basically and gets invalidated after a set period of time or number of purchases, which is nice. but that means that if I had that card saved Apple Pay and then I canceled that virtual card number, now I need to add another card and remember to go delete the other one.

7:11Andrew Sather:So I am worried my Apple wallet is going to become 13 different Robinhood cards that I need to sift through to figure out which one is the active one. We're going to need an app for that. Just to clean up your wallet. Yeah, let's make a clean up your wallet app that'll siphon through your Apple wallet. Million dollar idea. So today's episode, primary topic for today. Like I mentioned at the top, we're going to be discussing dollar cost averaging specifically versus lump sum method. These are two different methods of how to invest the money that you have. But yeah, so when you're investing into anything, specifically, we usually talk about the stock market.

7:47Andrew Sather:That's what we're most familiar with. That's what we feel is most accessible to the largest number of people, but it's certainly not the only place you can invest. But regardless of where you invest, you're going to have two different options of how to invest. The first is lump sum. So you have, you know, let's say you have 10 grand just sitting around what you got it. However, you got it. You have 10 grand sitting around and you invest that whole thing at once. Maybe, you know, you use whatever money you have to purchase a house all at once, or you purchase $10 ,000 worth of stocks all at once, whatever it is, you take that full sum of cash and lump sum it into an investment all at once.

8:21Andrew Sather:The other option is dollar cost averaging. And that is something where you essentially purchase a small amount of whatever that investment is on a regular basis, the same amount of that investment on the same frequency. So for example, 50 bucks into a stock on the stock market every month, that would be dollar cost averaging. Even if you had$10 ,000 sitting to the side, you still do$50 a month into whatever the investment is. And you kind of slowly chip away at whatever the lump sum was without investing at all at once. And usually dollar cost averaging is the way that I lean as my recommendation of how to invest, obviously not taking anybody's personal finances into account, but just as an overall idea, I tend to lean towards dollar cost averaging.

9:04Andrew Sather:But today we kind of want to explore and discuss and see where we land of whether this is actually the right way to go. But Andrew, could you kind of quickly cover why the difference between these two investment methods even matters?

9:19Evan Raidt:Because people who are geeks about finance need something to talk about and something to debate and something that they can get angry at each other about. Which is funny, they have studies and everything talking about one is better than the other. You can run a compound interest calculator and show differences and things like that. I guess depending on what numbers you're talking about, yes, it can certainly matter. I've always been on the camp of there's behavioral things to consider too especially as an investing for beginners podcast there's more factors than just the numbers so it is actually an interesting and nuanced discussion that especially if you're new it should it should it should take some of your thought process because if you have like 300 grand from an inheritance and you've never even heard about a stock until yesterday, I think it could be something to consider whether you want to go one way or the other.

10:30Evan Raidt:So definitely worth talking about. And yeah, I guess the numbers are one thing and you can make a case either way and maybe we can just talk about what works for us personally and people can use that as a learning tool to their own situations because it is a personal situation in my opinion.

10:49Andrew Sather:The behavioral aspect of it, like you said, is what I definitely find most interesting. There are studies in both directions, you know, what kind of mention, what situations each might numerically, mathematically work out to surpass the other. But the behavioral aspect of it is much more custom and I think has a much larger aspect on the returns that you can generate and the comfort you're going to have with those returns and how you're going to behave with the money you have access to, whatever it is. There's a lot of behavioral aspects that we'll touch on as we go through this that have a much larger impact than just the numbers show.

11:27Andrew Sather:But just kind of to frame the end focus of this is we just want the most people to find the easiest way for them, the most comfortable way for them to maximize their return. That's really the end goal of what we want to help with this. So to kind of start off, maybe a bit of the devil's advocate since we discussed dollar cost averaging so much, the case for lump sum, when lump sum would be best for you. The first reason that lump sum can be better is it just maximizes time in the market. it. When you talk about compound interest, when you talk about a snowball effect, the longer that snowball has to roll down the hill, the better.

12:04Andrew Sather:Overall, ignoring some other factors, the longer that snowball can roll, the bigger it's going to become and the more it's going to grow. Also, you're just avoiding cash that's not growing. The worst case of all of this is that you just have cash sitting in a checking or savings account somewhere or sitting under your bed or whatever, and it's just not growing or earning anything, that's by far the worst case. And so a big upside of lump sum is you never have any cash sitting not growing because whatever money you have access to is instantly being invested somewhere. Also, there was a very interesting Vanguard study done back in 2012 that showed that lump sum can, now there's obviously always going to be some factors that lead into this, but can beat dollar cost averaging around two thirds of the time given solid timing.

12:49Andrew Sather:timing being when is that lump sum invested and how frequently is dollar cost averaging performed and what a dollar amount all that sort of stuff so there's a lot of variables that go into this but there are some studies showing that lump sum from from very reputable organizations that show that lump sum can beat dollar cost averaging when it's done well but Andrew as a professional stock picker since that that is absolutely a title of yours where do you see the difference between lump sum investing in something like an index ETF? Like you mentioned, for beginners, we recommend indexes and ETFs a lot just because they're so easy to invest into.

13:26Andrew Sather:So where do you see lump sum in something like an index or ETF versus something like individual stocks that you focus on a lot?

13:34Evan Raidt:In my mind, it's kind of one and the same. And there's another study that I'm going to add on to the great study you mentioned. And if you look at the returns of how stocks get returns, there's an example. I don't remember the timeframe, but it's quite easy to look up. One book I would recommend if you're curious about this is Stocks for the Long Run by Jeremy Segal. Old book, classic. but basically if you take the best days out of the market, so let's say you're a great timer. You took the 10 worst days out of the market. You weren't in there. But if you also took the 10 best days out of the market and you weren't in there, you would actually underperform somebody who had stayed the entire time.

14:25Evan Raidt:So stop like the, the way to visualize that is stocks, stocks, the biggest moves in the stocks happen in a single day. So if you miss one of those days, you could miss the entire 2026 return. We don't know what day in 2026 is going to be a big one, but if you miss that big one, you'll miss a bunch of that return. And so that is a big reason why you don't try to time the market because missing one or two or 10 of the best days of the year can completely negate what, over the long term, is the returns from the stock market. And that is something you see for the index. And I also just anecdotally notice it with my stocks too, the individual stocks I own, is a lot of just kind of nothing for a while, a little bit up, a little bit down, and then a huge up day.

15:19Evan Raidt:And yeah, you get some big down days too, like an earnings call and a growth stock becomes of value stock and now it's 25 % down or 40 % down. But a lot of times also on the way up, you get these little step change higher moves in the day. And I'm still trying to figure out why that's the case. I don't know if there'll ever be a good answer for that. But it's just one of the realities you have to face. And that is why you mentioned two thirds of the time beating timing. So the time in the market, you want to get in there as soon as possible because you don't know if that big day is coming.

16:03Andrew Sather:Yeah, so that's actually really interesting. So that could lean towards lump sum or dollar cost averaging being a good way to go as long as it gives you time in the market, only leaning away from lump sum when you're trying to time the market with that lump sum. So if you had 10 grand sitting around doing anything but waiting with that 10 grand, hoping to put it in right at the perfect time.

16:29Evan Raidt:Now that springtime is here, it is time to update and reset my wardrobe. Last month, I talked to you guys about how I was getting my shipment from Quince in the mail. I got myself a three-pack of Lima Cotton shirts, and they are quite easily my favorite shirts to wear right now. The material is soft but still airy, so I feel cool while I'm wearing it but comfy at the same time. Looks great, looks premium, and the price was not what I expect to pay for that type of quality. What's cool about Quince is they make high-quality everyday essentials with premium materials at great prices. How do they do that?

17:00Evan Raidt:Quince works directly with ethical factories and cuts out the middlemen. So you're paying for quality, not brand markup. Everything is designed to last and make getting dressed easy. And with my new tees, it's not just easy, but looks great and feels great too. Refresh your wardrobe with Quince. Go to quince.com slash beginners for free shipping and 365 day returns. Now available in Canada too. Go to quince.com slash beginners for free shipping and 365 day returns. Quince.com slash beginners. We have the inside scoop on something that's absolutely taken over the internet by storm. Live shopping on Whatnot is exploding.

17:38Evan Raidt:I've seen the shows firsthand. The amount of product that sells through is just amazing to see. Really a breakneck pace. Whatnot has climbed to the top of the app store and sellers are earning. Small, medium, and multi-million dollar businesses are all growing. That's because Whatnot is not just about listing products. People selling on Whatnot are building real connections with their buyers. That's resulting in them selling 10 times more than on other major marketplaces. In fact, Whatnot is the largest dedicated live shopping platform with categories like electronics, luxury fashion, beauty collectibles, even cookies.

18:13Evan Raidt:With Whatnot, sellers are building real and thriving businesses. The buyers on the app spend more than an hour a day, and they're not just browsing. They're bidding, buying, and coming back. If you are selling online or looking to sell online, you absolutely should be on Whatnot. And for a limited time, Whatnot will match your first$150 sold in the first month. Visit whatnot.com slash sell to start selling. That's W-H-A-T-N-O-T dot com slash sell. Whatnot.com slash sell. I finally had a lightbulb moment about a stock we've all heard about, growing 18 % a year out of 15 PE. I share this insight in a special deep dive report to subscribers of my research service, Value Spotlight.

18:53Evan Raidt:The report is called A Generational Moment, Reigniting Human Connections Through a Tangible Network of Intangible Assets. For a limited time, you can access this research at a discount at einvestingforbeginners.com slash reignite. That's einvestingforbeginners.com slash reignite. yeah but like if you just throw it in all at once do you increase your chances of that big day being just around the corner so it makes the case further for lump sum actually gotcha gotcha

19:23Andrew Sather:okay so now that we've kind of covered lump sum in the case for that the case for for our favorite or resident favorite dollar cost averaging so a great thing about dollar cost averaging for the average person and like andrew was emphasizing for the beginner somebody who's just learning about stocks, doesn't know what the heck they are, doesn't trust them, blah, blah, blah, is that dollar cost averaging does a lot to reduce overall risk and time input that you have to do and effort input that you have to do to invest. The reason that it reduces overall risk so much is like Andrew was mentioning, if you try to lump some and time something and there was a big rise just around the corner or a big fall right around the corner, you are betting the entire farm, quote unquote, that entire 10 grand number that we keep keep calling back to taking that entire 10 grand and betting that what's going to happen in the short term is going to be good for you and you're going to take a lot of risk because it could be very very bad for you in the short term whereas something like dollar cost averaging if you're just constantly putting in money regardless of what's happening you're always going to be risking a smaller amount of money at any given point and then when it does drop you still have funds left over to continue investing now at that lower price and that's where the name dollar cost averaging actually comes from is as the price fluctuates over time, you're always averaging out your cost.

20:38Andrew Sather:So you're never going to be able to get the craziest high gains that you could get with lump sum, but you're also not going to be able to lose nearly as much as you could with lump sum. So it just reduces your risk overall. So you do lose your ability to outperform anybody who makes perfect decisions, you know, luck, timing, skill, whatever it is, you're never going to be able to outperform those people. But you're also going to be very, very confident that you're going to outperform anybody who makes bad choices or has bad luck or you know does bad analysis whatever it is you're going to be able to outperform those people very consistently and then the last and my favorite point is automation you know i freaking love automation it makes everything so so much easier and for beginners it is by far the best step that you can take for yourself financially at least when it comes to investing in the stock market the best thing you could possibly do for yourself to make things easier make your returns much more consistent and just make everything much more comfortable for you.

Read the full transcript

21:31Andrew Sather:And dollar cost averaging is a perfect vehicle for automation like that. But Andrew, do you think that dollar cost averaging is a good, do you see it as a good complete substitute for something like lump sum? Or do you, as a professional stock picker who has a really in-depth understanding of the stock market, do you just see it as kind of the easy way out that's good for beginners because it's easy to do, but something like a professional doesn't really need to touch something like that.

21:59Evan Raidt:Oh man, you're asking the tough ones. You are asking the tough ones. I don't want to make it easy.

22:07Evan Raidt:Yeah. I mean, for beginners, for sure, the dollar cost averaging. It's practical. It feels good. I love one of the things I do, a little bad boy here, but I like to put my, what do you call a sinking fund. So I have a car sinking fund that I've got. I love to just dollar cost average that into the market. I've got my Plink brokerage account and it's automatically every month buys a stock that was a recommendation of Value Spotlight last year. And I'm just like, every month we're buying that stock and it goes up or down. I don't care. One day I will buy a car with that sinking fund. And it's, I don't know, there's something about that that's just really cool.

22:53Evan Raidt:And if you haven't tried automation with dollar cost averaging, whether that's in your regular brokerage account like Plink or a Roth IRA account, you need to do it. It's magical. And for a beginner, that's definitely the case. Now, I've had times in my life where I had a lump sum that was like half my net worth. And at that time, I was not comfortable because it was like a rollover. So at that time, I was not comfortable just lump summing it because it felt like a lot to me at the time. But you asked me 10 years later, is 50 % of your net worth in the lump sum, is that going to feel risky? I might have a completely different situation for you.

23:39Evan Raidt:So it's so dependent. When we start talking about percentages, you look like a billionaire's wealth, his 50 % and our 50 % is not trying to say it's not the same, but does your life change if 50 % of your net worth is knocked out? Probably. If we're talking about bigger amounts, maybe not, depending on your lifestyle. I don't know. Lifestyle comes into play. Your expenses come into play. Your psychology comes into play. If you have this mindset where I can't stomach losing $1 ,000,$100 ,000,$1 million, whatever the number is, it's very personal for everybody. There's a book called Richer, Wiser, Happier by William Green.

24:27Evan Raidt:And we've had him on the show years ago. And he talked about the book. It's a great book. I recommend picking it up. He did an interview with one of these investors. And he said, how do you manage your risk? And the investor said, I listen to my body. He says, when my body starts breaking down and basically my immune system or my back, I think he used his back was the example. When my back starts screaming at me and telling me like, hey, we have a problem. It's actually related to his risk management. And he's looked back over time and been like, wow, my back was actually really good at telling me when I was taking on too much risk.

25:06Evan Raidt:So that sounds super woo-woo and whatever, but consider it that your risk management matters a lot and your risk tolerance matters a lot. And that is whether you're talking about just regular personal finances or if you are a stock picker and you're managing millions of dollars and you have a big portfolio, the risk management and how you feel about it matters a lot. because if your back breaks, so to say, and you start getting really stressed out and you make a decision out of fear that would have actually, if you would have just stuck with it, would have been the big great unlock for your gains down the line.

25:48Evan Raidt:It's huge. It's huge. So don't discount the importance of your feelings about risk and how that affects investing returns because it does. It affects them a lot. And we've seen it from lots of people. you look at there's another study about most individual investors underperform the market because they're just bad market timers or they sell out when things are uncertain we've seen that with lots of people just try to learn from those mistakes and I think dollar cost averaging is a great substitute unless you have a good sense of your lump sum is is like a good feeling. You're not stressed about it.

26:34Evan Raidt:But what about you? I know you have good frameworks for lots of different situations that people can attach to. So how do you think about dollar cost averaging and lump sum?

26:44Andrew Sather:Yeah, I think that fear that you brought up, that's the biggest thing that I think everybody needs to stay away from. In a lot of places in your life, maybe your career or relationships, it's good to push your boundaries and push for sort of the unexpected or the unusual to grow as a person or grow in your career, grow your skill set, whatever it is. But when it comes to your finances, your finances are something that needs to be solid and needs to be there for you and be there to support you in your life or else you're not going to be able to pursue any of those kinds of things. And you're not going to be able to afford to take any emotional or career risk if you don't have a financial backbone to support you.

27:24Andrew Sather:And people make the worst decisions when they're in fight or flight mode. So if your finances are putting you in fight or flight mode and you're afraid of your finances, you're afraid of looking at it, you're afraid of the action you're about to take with your finances, that's when you're going to make the worst decisions. So for me, it's all about minimizing fear. Now that's going to change, like you said, drastically person to person. There are a lot of people out there that are comfortable taking big financial risks or somebody like a billionaire who has a ton of financial foundation beneath them that they know they can take a big risk on what to us is a massive amount of money that to them would not be life-changing.

28:02Andrew Sather:It would suck. They'd be very, very upset, but it would not be life-changing. It would not affect their ability to live or have a roof over their head or travel. It wouldn't change any of that. And so if the amount of money you're looking at investing doesn't have that large of a life impact on you and you don't feel a ton of fear with the idea of not entirely losing that money because realistically it's not going to go to zero but that amount of money turning into less than it is now if that scares the heck out of you then it's probably not worth taking on something higher risk like lump sum and it's probably better to do something like dollar cost averaging where you're going to take on a lot less risk you're going to you're going to have less ability to turn that money into a crazy amount of money than if you invested all at once but you're going to take on a lot less risk and feel a lot less fear.

28:49Andrew Sather:If you're somebody, however, that that doesn't really scare you that much, you know, for you, life is about a lot more than money and you know, you're going to have enough in the bank to support yourself afterwards. Then, you know, taking on that, that amount of risk could be okay. Cause you won't feel a ton of fear from it. You're, you know, your back isn't going to be throbbing because of it. You're not going to panic attacks because of it. Then you could be okay to, to be transparent about how I handle things, how I handle this personally. For me, any windfall or surprise amount of money, you know, inheritance, a bonus at work, you know, however else you just end up with a lump sum of cash.

29:24Andrew Sather:I am okay with lump sum investing that all at once. Not because I am a very, you know, risk tolerant person, but because I know that what I'm investing in, because I invest in the overall market, I talked about a ton, I use VOO, just an overall index fund stock for the stock market, I'm okay with putting a bunch of money into the overall stock market at once. Even though the overall stock market can fluctuate, absolutely, it's not going to fluctuate as crazily as a single stock would or a much smaller fund or something like that. So I know that I'm not taking on nearly as much risk as I would be in those situations, and I would rather just have that money in the market instead of letting a bunch of it sit and take, I don't know, maybe a year or whatever to get it all invested.

30:08Andrew Sather:I would rather just put it all in at once. Yes, I'm taking on some more risk, but I know I'm putting it into something that doesn't have a ton of risk inherently. Then anything else is always going to be dollar cost average. So if it's income, if it's, I don't know, smaller bonus or whatever it is, any smaller amount of money that comes in on a regular basis, I'm going to dollar cost average that. And I've always got that built into my budget. As we mentioned before, we have a free budgeting outline available online at einvestmentforbeginners.com slash budget. And that's a great starter tool for you to do.

30:39Andrew Sather:If you're looking to get into dollar cost averaging or investing in general, that's a great outline to do. But one thing that that's not going to help you with is lump sum. Lump sum is going to, is going to be a one-off situation. Maybe, you know, tracking something like your net worth will give you a good idea. Like Andrew was mentioning, if you know, okay, my net worth is a hundred grand and I just inherited 50 grand. Okay. That's, that's a large amount of money for you. And, and it may be a lot more risk and a lot more stressful for you to take on. If your net worth is 500 grand and you just inherited 10 grand, then maybe taking on more risk with that 10 grand isn't going to scare the heck out of you because it's, it's a smaller percentage of your, of your overall net worth and it's not going to scare you as much.

31:19Andrew Sather:But that's how I personally handle Andrew. How do you personally handle when, and if you lump sum versus dollar cost average?

31:26Evan Raidt:I'm, I'm in your camp, man. Like I like, I like that idea.

31:33Evan Raidt:if we're talking about massive lump sum I'll let you know if my thoughts change kind of a thing you just never know right but definitely having the dollar cost averaging should be an essential pillar in your budget and it will be we're talking about you know if I had 50 grand tomorrow how would that change my life you know lump sum dollar cost average, blah, blah. We could talk about that till the cows come home. I would argue that even that single decision, a big windfall for somebody, even like a 50 % net worth or something, would not have as big of an impact as the simple habit of dollar cost averaging and doing that over a long time period.

32:19Evan Raidt:Because what we're talking about is a sustainable habit that's going to change your life versus something that, yeah, might make an impact, but might not have the same... There is a power, and we could probably talk about it for days, but just the power of that habit of dollar cost averaging. And it really starts to level up if you increase that dollar cost averaging as you become more and more wealthy, as your income increases and you're ratcheting up that dollar cost averaging. Maybe that's a kind of compound calculator we could make. Like that's, someone should make an app for that. You know, how big does the snowball get if you're increasing it by 10 % a year, like how much you're putting in?

33:05Evan Raidt:That could be really nice too. So I'm all about the dollar cost averaging 100 % do that with your income. And I was less on the lump sum when I was first starting in my journey. I'm all about it now. Like I'm down, like let's go. But to your point, I have that foundation now that I've been dollar cost averaging for 12 years. So that allows you other options. So I highly recommend dollar cost averaging as soon as possible.

33:36Andrew Sather:Yeah, maybe a compound interest calculator that could also manage your credit cards and your Apple Walls.

33:41Evan Raidt:Yeah, there you go.

33:42Andrew Sather:Massive app idea. Oh, credit card rewards, right? Yeah, also rewards feed into your Apple. Yes, absolutely. I think that's actually a really, really good point that the short-term effect that something like starting dollar cost averaging is going to have is always going to be smaller than something like a lump sum. And so, yeah, especially when you're getting started and you don't understand as much about the market, you don't have as much experience opening an app and seeing a red chart pop up up front to say, hey, your money's gone down today. You've lost money today until you get used to that.

34:19Andrew Sather:And you're comfortable seeing that and understand that that's not the end all be all. That's not the long-term return. That's not any of those kinds of things until you're comfortable with that. When you get started, something like dollar cost averaging is, is easily the best place to go. And, and it's always great to manage those, those emotions up front. Um, because I would also argue that even if you are the person that now at this current moment is comfortable lump sum investing, like you, Andrew, you're, you're comfortable with that. because you understand how the market works. You've had experience, blah, blah, blah.

34:48Andrew Sather:Like you said, 12 years ago, and whoever else is out there that's listening, who's currently comfortable with that, I guarantee upfront when you were first learning about the stock market or made your first investment, the idea of lump sum investing was scary as crap and you would never want to do it. And you probably thought you would never want to do it at any point in the future because that's a crazy amount of risk to put into something that you think is just, you know, a bunch of meaningless, ethereal BS. and until you understand it and you've lived it and you've earned money from it over the long run, you're not going to be comfortable doing any of those kinds of things.

35:23Andrew Sather:So I guess I got one last question for you. You called out Value Spotlight earlier as an investment portfolio that you manage. How do you handle inside Value Spotlight lump sum versus dollar cost averaging investing?

35:35Evan Raidt:All of you small business owners are familiar with the same challenges we all face. You're wearing so many hats. There's always so much to do, you feel like you never have enough time to get it all done. And you discover time spent on the wrong things just keeps setting you back. Too much headspace focused on accounting, bookkeeping, taxes, and admin work steals energy and creativity from the things that really drive your business forward, really drive revenue, and meaningfully affect the ultimate results of your business. This is why we have a found account, and we believe you should too. Found is reimagining what business banking should be by putting the time-consuming things like bookkeeping, invoicing, and tax tools directly into your business checking account.

36:16Evan Raidt:You log in and everything is right there in the dashboard. It's clean, saves time, saves energy, and helps you do the things that matter. Take back control of your business today. Open a Found account for free at found.com. That's F-O-U-N-D dot com. Found is a financial technology company, not a bank. Banking services are provided by LeadBank, member FDIC. Join the hundreds of thousands who've already streamlined their finances with Found. Mom, can you tell me a story? Sure. Once upon a time, a mom needed a new car. Was she brave? She was tired, mostly. But she went to Carvana.com and found a great car at a great price.

36:53Evan Raidt:No secret treasure map required. Did you have to find a dragon? Nope. She bought it 100 % online. From her bed, actually. Was it scary? Honey, it was as unscary as car buying could be. Did the car have a sunroof? It did, actually. Okay, good story. Car buying you'll want to tell stories about. Buy your car today on... Carvana. Delivery fees may apply. Yeah, dollar cost averaging. See, I can't help myself, but those words just like spill out of my mouth. Like, I just can't say them enough. First words. Google got dollar cost averaging. That's funny. I got something for my son who's going to be here soon.

37:30Evan Raidt:All right. I'll work on that. I'll report to you guys.

37:33Andrew Sather:Yeah. First words. That would be huge. The biggest investor brag in the world.

37:41Evan Raidt:Okay. So value spotlight. 12 years ago, I started this newsletter and the whole idea was I want to show that you can do a lot with a little. So it's a real money portfolio. It's a Roth IRA account. I have split into two, but I consolidate into one. That's another story for another day. But$150 a month to prove it could make it$2 million. And the compound interest calculator says 11 % returns gets it$2 million. So probably the longest journey, because it's like watching paint dry of this portfolio just slowly compounding. And so because of the nature of that, I don't lump some into it because the whole mission is$150 a month to make it to a million.

38:32Evan Raidt:So that journey is still in progress. You can follow along if you want. It is like watching paint dry, but it's crazy how you're tracking it, you're tracking it, you're tracking it. I don't know if you've seen this similarly with your own net worth, but you're putting in the numbers every month. that you kind of just do it on autopilot, and then just one day randomly three years later, you're like, oh, wow. This thing is bigger than it was. And how did that happen? I don't know. I wasn't even paying attention. I don't know if that's something that you've seen with your net worth or not, but that's something I've observed with Value Spotlight.

39:14Andrew Sather:Yeah, it starts to get to a point. I mean, you were kind of going on before about how beautiful dollar cost averaging to be in the long run. But yeah, it reaches a point where you're like that it's bigger than it should be. And I'm not talking about it's double, you know, what it should be at this point. Eventually, of course it will be, but at this point, it's not like I'm looking at it and it's like, Oh, I'm twice as rich as I thought it was. That's not what's happening, but it is just, it's larger numbers than it should be. It's increasing at a faster rate than it feels like it should be just because all of the returns that you generated last year are now helping you generate even more returns this year and will help you generate even more returns next year.

39:51Andrew Sather:And that long-term magic of that paint drying into money or whatever the process is, is, is absolutely fantastic and beautiful to see and very, very supportive of your financial future. Um, and a great thing about it for me, because I am somebody that if I were to take on a ton of financial risk, like say I invested a lump sum that I inherited or whatever, all into an individual stock or, you know, into swing trading or some, something that's a lot riskier. I am somebody that would feel that risk outside of investing. I am somebody that, you know, my back would start to hurt. I would have panic attacks.

40:26Andrew Sather:I wouldn't be hungry. You know, I would emotionally be a wreck from taking on that level of risk. But I just don't feel that way from dollar cost averaging. I invest every single week at this point. I've done that for many years and I just don't feel any stress from it whatsoever. Even when I open the app and see red because I've opened the app and seen green many times. And I've looked at the long-term numbers. And like we're talking about, I've just seen myself grow more money than I should have. And all it takes is just taking the time and effort to set that up and do it and build that habit.

40:59Andrew Sather:And that is a beautiful, beautiful habit to build that just doesn't cause me any stress. And that was one of my favorite things about doing it.

41:07Evan Raidt:I love that. Yeah. And it's cool to hear it too in your voice. you're walking it and it's a great example and very motivating for me personally to hear and I hope it's motivating for others out there. Can I leave us with like a math thing or is that just completely Do I need a pen and paper? No, no. And a TI-84?

41:33Evan Raidt:My daughter's school is asking people to donate their TI-84s. I don't even know why. Everybody wants them, man. I don't know.

41:41Andrew Sather:I mean, I guess... You want one? You don't have one. I've got one. Are you kidding me? I've got it at work.

41:47Evan Raidt:Oh, okay. All right. All right. Well, if you weren't at work, I think you'd be young enough to not have one. That's fair. That's fair. I'm going to just do it. Whether you guys like it or not, I'm going to drag you through this math problem. Through homework? All right. One of the sayings that Charlie Munger used to say, Charlie Munger, business partner Warren Buffett, billionaire himself as well. you always say the first hundred thousand is the hardest. Think about this for a second. Say you have 50 grand. What is 50 grand? What happens if you double 50 grand? How much do you have? 100 grand.

42:25Evan Raidt:100 grand. Good. Now, what if you earn 50 % on that 100 grand? How much do you have? 150 grand. 150 grand. That's a triple from what you had at 50 grand. Weird, right? The compounding of once you've doubled the money, you don't have to double it again to triple or quadruple. To triple it, you just have to earn 50 % on it. So that's the math behind compounding. Your snowball doesn't need much more once it's gotten bigger. And those numbers just start to get ridiculous. So if you can get to the 100 grand, the numbers really start to get magical.

43:08Andrew Sather:yeah going to 100 and that even though you know most of us aren't earning 50 in the stock market the numbers work out just the same even for lower returns you know something like 10 returns is going to behave behave exactly the same just to a to a less severe degree um yeah the longer you let that snowball ride and the bigger it gets it's going to get so much easier like you know if you started investing today you started dollar cost averaging today or lump sum what you had then started dollar-cruis-affering, whatever it is, 20 years from now, that snowball, even if you didn't change how much you're investing on a weekly, monthly basis, would be growing so much more quickly than it ever was before.

43:45Andrew Sather:And it's only going to grow more and more quickly. And then like you mentioned, you keep ratcheting that up of investing more as you earn more, or as your expenses decrease, whatever you can change in your life, it's just going to ratchet up faster and faster and freaking faster. And that's the kind of train you want to be on. So I hope that was helpful for some people out there. So to kind of summarize from the title of this episode, dollar cost averaging is absolutely not losing you money. It's absolutely not. However, there are definitely some situations out there where taking into account lump sum as an option could definitely be really good for you, really beneficial for your finances.

44:22Andrew Sather:And if you're somebody that can emotionally handle it, then it could be really, really good for your life and your financial future. So I really hope that helps some people. As always, if you have any questions or you want to email me at evan.einvestingforbeginners.com. I'd love to hear how you invest, whether you use dollar cost averaging and lump sum or just one or the other. You know, are you a massive risk taker or are you somebody that just wants this to be an easy, breezy, beautiful ride and that's all you want from it. As we mentioned before, also we have a free budgeting calculator available online at einvestingforbeginners.com slash budget.

44:54Andrew Sather:Really free, super easy tool to use to just to get started. And remember, financial freedom is built one smart move at a time. Keep it simple. Keep it steady. And at any rate, I'll see you next time. Peace. The information contained is for general information and educational purposes only. It is not intended for a substitute for legal, commercial, and or financial advice from a licensed professional. Review our full disclaimer at einvestingforbeginners.com.

45:29Evan Raidt:looking to upgrade your stock portfolio if you are a regular listener of investing for beginners then i have a great podcast to add to your rotation my name is brett schaefer co-host of chit chat stocks a podcast helping you find your next great investment on this show we study businesses interview best investing experts and riff on weekly market commentary whether looking for new stocks to buy or simply a fun weekly listen covering the stock market, we have episodes that you will enjoy. Discover new stocks and upgrade your investing game by following Chit Chat Stocks today on Spotify, Apple, or wherever you get your podcasts.

From the publisher

In today’s episode, Evan (aka Aaron) Raidt and Andrew Sather tackle one of the most debated questions in the investing world: Should you drip your money into the market slowly or dump it all in at once? We break down the psychological hurdles of "waiting for the dip," the math behind historical market performance, and why your emotional temperament might be the most important factor in your strategy.

Topics Covered:

The FOMO Factor: Why waiting for a market crash often leads to missed gains.

Math vs. Emotion: Breaking down why lump sum investing statistically wins, but feels terrifying.

The "Sleep Well at Night" Strategy: How to determine if dollar-cost averaging is the right move for your personality.

Costco & Cash Flow: Lessons from the titans of industry on managing capital.

Timestamps: 

00:00 – Intro: Two sick guys and two sets of background noise.

04:15 – Defining Dollar-Cost Averaging (DCA) and Lump Sum Investing.

12:30 – The "Cash Drag" Problem: Why sitting on the sidelines costs you.

22:45 – Case Study: Investing at the peak of 2021 vs. 2022.

31:10 – Andrew’s Take: When to ignore the math and protect your peace.

37:32 – Final Thoughts & Where to start.

Resources Mentioned

The Value Spotlight Newsletter: https://einvestingforbeginners.com/value-spotlight-newsletter/

Free monthly budgeting spreadsheet: https://einvestingforbeginners.com/budget/

Email Evan: evan@einvestingforbeginners.com

Have questions or want your story featured? Email the show at newsletter@einvestingforbeginners.com or comment below. Your feedback shapes the podcast!

Remember, financial freedom is built one smart move at a time. Keep it simple, keep it steady, and at any rate, we’ll see you next time.

Timestamps are generated by artificial intelligence, and are not 100% accurate depending on the platform used for listening.

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