No Retirement Savings at 40? Here's Exactly What to Do First (SB1827)

Summary

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Podcast Summary: The Stacking Benjamins Show

Episode: No Retirement Savings at 40? Here's Exactly What to Do First (SB1827)

Date: April 10, 2026
Host: Joe Saul-Sehy
Contributors: OG, Jackie Cummings Koski (Catching up to Fi; author of Fire for Dummies), Roger Whitney (Retirement Answer Man)

Overview

This episode tackles one of the most anxiety-inducing personal finance questions: What should you do if you hit age 40 with no retirement savings? Through a blend of practical advice, personal stories, and the show’s trademark humor, Joe Saul-Sehy, OG, Jackie Cummings Koski, and Roger Whitney explore the realities and solutions for so-called "late starters" to investing, why it's not too late, and how action, habits, and simplicity can lead you to financial independence.

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Key Discussion Points & Insights

1. Psychological & Emotional Realities of Starting Late

• Waking Up Late to Retirement: Many discover in their late 30s or 40s that they haven’t started saving for retirement, likened to the panic of a forgotten school science project deadline.

  “I’m 40 years old. I’ve done nothing.” – Joe Saul-Sehy (02:40) “I talk about it all the time. Because ... I was 38 when I woke up and got started.” – Jackie Cummings Koski (04:35)

• Grace & Self-Forgiveness: Recognize this is common—most people weren’t taught these skills, so don’t be too hard on yourself.

  “Give yourself a little grace. This stuff is not taught in schools.” – Jackie (12:08)

• The Power of Realization: Starting late is not a crisis; it’s a wake-up call that can fuel major changes.

  “It’s absolutely fixable, but it can feel like it’s not...” – Jackie (11:30) “You have to see a better future for yourself. You have to be able to identify agency ... and you have to find different pathways.” – Roger (13:37)

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2. Know Your Numbers & Pause Before Acting

• Step One: Know Where You Stand: Assess all your numbers—savings, debts, income, and expenses.
• Debt Matters: Many late starters also have debt. Addressing high-interest debt is crucial.

  “That’s why I say, you kind of need to pause and look at where you're at. If you've got a lot of debt…” – Jackie (15:32)

• Avoid Quick-Fix Panic Moves: Don’t chase flashy investments to “catch up”; focus on consistent, proven approaches.

  “The wrong way to catch up is to jump on Reddit and go like, what is the hottest stock right now?” – OG (16:26)

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3. The Magic of Compounding & Time

• It’s Not Too Late: Even at 40, time is still on your side for compounding to work its magic.

  “There is so much time. We do not, as humans, understand the power of compounding.” – OG (17:41)

• Trajectories Change: A small change now can make a huge difference over the next 20-25 years.

  “The key is how do I change the trajectory of that compounding...” – Roger (18:25)

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4. Taking Action: First Steps

• Start with Employer Retirement Plans: If available, maximize contributions to your 401(k) or similar plans, aiming above just the match if possible.

  “Most people start investing through their employer sponsored plan. So if you have that, take advantage of it.” – Jackie (19:45)

• Micro Adjustments Over Drastic Overhauls: Sustainability is key.

  “There’s a risk with getting shot out of a cannon... it’s not sustainable. What I think is probably an approach that we should consider... is actually to go micro and start to connect dots and pay attention to every dollar...” – Roger Whitney (26:04)

• Automate and Increment: Automate contributions and slowly increase savings rates.

  “If you can say, well, every six months I’m going to add 1% to my savings rate ... in five years you go from 3% to 13%.” – OG (24:00)

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5. Building the Investment Portfolio

a. Dividends and Stocks

• Dividend Investing: Pros and Cons
  • Not “free money”—just a distribution of profits; real focus should remain on total return.

  “Sometimes people do want the blue chip stocks because of their great dividends... but you really should be focusing on the overall return.” – Jackie (41:16)

  • It’s not inherently superior; dividends or capital gains both work toward portfolio growth.

  “A return's a return, isn’t it?” – Joe (44:16) “Dividends are neither good nor bad.” – OG (45:24)

b. Real Estate

• Not a Silver Bullet for Late Starters
  • Your home can be an asset, but real estate investing (rentals, Airbnb, flipping) is a business with risk.

  “It’s probably not the time to really start something new. But if you do it, make sure it’s something that lights you up...” – Jackie (46:01) “The real returns in real estate typically are with leverage. And leverage introduces a lot of risk.” – Roger (47:27)

  • Publicly traded REITs (Real Estate Investment Trusts) can offer diversification and liquidity without the management headaches.

  “If I'm going to have real estate, I want it to be as diversified and as liquid as possible...” – OG (48:37)

c. Simplicity Beats Complexity

• Default to Index Funds via Employer Plan or IRA

  “Stock index funds are very common now. They’re very easy, they’re very low cost. So that’s probably the low hanging fruit for most people.” – Jackie (51:29) “Just own one of everything. It takes all the guesswork out of this.” – OG (56:56)

• Boring > Exciting: Resist getting lured into complex or high-maintenance strategies; simplicity is more reliable.

  “Because it’s boring stuff that is the right stuff to do.” – Roger (54:05)

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6. The Power of Savings Rate

• Your Savings Rate Drives the Timeline: The more you save, the fewer years to independence.

  “If you only want to save 10%, then that's probably going to take you about 40 years. If you want to save 30%, then that might shave it down to 20 years.” – Jackie (57:56)

• Grow Your Income and Control Lifestyle: Income isn’t always the issue—sometimes, it’s lifestyle creep.

  “Life today in the way.” – Joe (58:39) “Even for high income earners, unfortunately, this can be a problem as well.” – Jackie (58:40)

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7. Key Mindsets

• Action Beats Perfection: Don’t get paralyzed seeking the perfect plan; small steps compound.

  “Just get started and it's going to make it better than it was yesterday... it'll be better than it was yesterday.” – OG (59:40)

• Multiple Valid Paths, but Simplicity Wins: There’s no one “best” investment, but keep it diversified and simple.

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Notable Quotes & Memorable Moments

• On Self-Compassion:

  “Give yourself a little grace. This stuff is not taught in schools.” – Jackie Cummings Koski (12:08)

• On the Commonality of Starting Late:

  “Oh, it’s crazy. It's totally common... they're so far behind. Even the way we frame the problem can really influence how someone might address it.” – Roger Whitney (13:37)

• On Market Behavior:

  “On average the stock market is up about 80% of the time. That will help keep you from selling when we have ... a down market.” – Jackie (51:29)

• On Real Estate Risks:

  “The return only works when you use leverage... nobody does [margin investing] with stocks because 'it's risky,' but we do it with property all day long.” – OG (48:37)

• On Savings Rate:

  “Your savings rate and a decent sale beats some complex investment strategy.” – Joe (57:40)

• On Simplicity:

  “Just own one of everything, it takes all the guesswork out of this.” – OG (56:56)

• On Micro-Adjustments:

  “You don’t diet, you get healthier; you don’t become a crazy saver, you become a better spender and saver of money. And those happen in the micro moments.” – Roger Whitney (27:16)

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Important Timestamps

• Introduction & Setting the Stage: 00:00–05:44
• Panelists Discuss the Panic of Starting Late: 11:30–19:10
• First Steps upon Realization (Assess, Numbers, Debt): 19:45–26:04
• Automating & Incrementing Savings: 23:16–25:32
• The Myth of Catching Up with High-Risk Investing: 16:26–17:41
• Dividend Investing Discussion: 40:58–45:24
• Real Estate in the Portfolio: 46:01–50:56
• Building a Simple Investment Plan / Index Funds: 51:29–55:15
• Savings Rate as the Key Lever: 57:56–58:40
• Summary of Key Mindsets: 59:40

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Engaging Moments & Additional Resources

• Trivia Segment Banter and the “Banana Stand” Story (29:35–39:57): Lighthearted interlude with a running joke about "money in the banana stand," reminding listeners that easy (or hidden) wins rarely exist in finance.
• Jackie’s "Great 401(K) Cleanup" Resource: Catching Up To FI podcast hosts a step-by-step 401(k) cleanup guide for those overwhelmed by choices.
• Upcoming Content Plugs: Roger’s upcoming month on “Decluttering for Retirement” on The Retirement Answer Man; Jackie’s continued focus on late starters and 401(k) clarity.

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Final Takeaways

• You’re not alone if you’re starting late; it’s common and fixable.
• Start with self-forgiveness and a clear understanding of your numbers.
• Prioritize savings rate over hunting for complex investments or “home run” returns.
• Automate, increment, and keep your investments simple—index funds are usually best.
• Explore your superpowers—income growth counts as much as frugality.
• Don’t get distracted by investment fads; focus on the boring stuff that works.
• Action trumps perfection. Just start.

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For more resources and detailed guides, visit Catching up to Fi and The Retirement Answer Man. Full show notes and links at stackingbenjamins.com.

Transcript

[OG]

I sold my car in Carvana last night.

[Jackie Cummings Koski]

Well, that's cool.

[Roger Whitney]

No, you don't understand.

[OG]

It went perfectly.

[Joe Saul-Sehy]

Real offer down to the penny.

[OG]

They're picking it up tomorrow.

[Joe Saul-Sehy]

Nothing went wrong. So what's the problem? That is the problem.

[OG]

Nothing in my life goes to smoothly. I'm waiting for the catch.

[Joe Saul-Sehy]

Maybe there's no catch.

[OG]

That's exactly what a catch would want me to think. Wow.

[Joe Saul-Sehy]

You need to relax. I need a knock on wood.

[OG]

Do we have wood? Is this table wood?

[Joe Saul-Sehy]

I think it's laminate. Okay, yeah, that's good. That's close enough. Car selling without a catch. Sell your car today on Carvana. Pick up fees may apply.

[OG]

Is this your place?

[Doug]

No, no, no, no, no, no, no.

[OG]

I live with my ma. Oh yeah. You hungry? Hey ma, can we get some meatloaf?

[Doug]

Live from the basement of the YouTube headquarters, it's the stacking Ben. I'm Joe's mom's neighbor Doug. And let's set the stage. It's your 40th birthday party. No retirement savings, no plan. Just a vague memory of buying dogecoin once. And maybe a strong desire not to eat cat food. At 75 years old, how would you begin to invest for retirement? We'll tackle the good, bad and ugly on today's show. But that's not all. Halfway through this shindig will roll out to our contributors another episode in our year long trivia competition. And now a guy who's going to help you compete when it comes to setting up a great retirement portfolio, it's Joe. Saul Sehi.

[Joe Saul-Sehy]

Hey, thanks Doug. We're super happy that you're here with the Stackers. Welcome to Friday and man, we do have a great show today, Doug. So many times people wake up and go, oh wait, I'm supposed to do what?

[Doug]

There's this thing that's been like nagging at me. I can't remember what it is like.

[Joe Saul-Sehy]

In fact, it's funny when we talk about, we talk about and a lot of people start at 40. In fact, one of our guests was a late starter and has done incredibly well. You've heard her on the show before. We're going to get to her in a second. But let me show you the person who thought that he was about to have a bad day. And you and I know, Doug, it can get worse than what this person said. This is comedian Brian Regan.

[Roger Whitney]

I think the worst day that was

[Joe Saul-Sehy]

the day the science project was due. Waking up that morning, that was fun, huh? Your headed pop off your pillow. Oh no. Oh no. That's due today. This is like the adult equivalent, I think, Doug, of that. Oh, no.

[Doug]

Oh, no.

[Joe Saul-Sehy]

I'm 40 years old. I've done nothing.

[Doug]

It's the worst feeling in the world.

[Joe Saul-Sehy]

Too many people have had that. A guy who helps people make sure they don't end up on the right foot. Everybody, I think, starts on a different foot, but Mr. OG is here across card table from me. How are you, man?

[OG]

We make sure people don't end up on the right foot.

[Joe Saul-Sehy]

We want them don't end up on the wrong foot. Didn't I say wrong foot?

[OG]

Yeah, you said right foot.

[Joe Saul-Sehy]

I hope I said.

[OG]

I was like. I mean, I guess left foot's okay, too. If you want to end up on

[Joe Saul-Sehy]

that, you end up on the left foot. The left foot's very comfortable in the

[OG]

right shape for everybody.

[Joe Saul-Sehy]

Were you the kid with the science project going, oh, no, it's due today?

[OG]

No, no, I was. I'm a firstborn man. I'm a rule follower. I'm a people pleaser. I'm all those things wrapped up.

[Doug]

Yeah, you are a people pleaser. We all almost pulled that off. Almost. I was the youngest, so I would wake up that day, have that feeling and say, well, guess I'm sick today. And then I would start heating up the forehead, you know, getting my nose all stuffed up to talk to mom.

[Joe Saul-Sehy]

And a woman who. Actually, the woman who I referenced earlier who started late is here. She is the co host of the Catching up to Five podcast. She's the woman behind a great book about the fire movement. Fire for Dummies. Jackie, Koski Cummings is here. How are you, Jackie? Hello.

[Jackie Cummings Koski]

I am doing great. How are you guys?

[Joe Saul-Sehy]

Were you the person with the science project and said, oh, God, it's today.

[Jackie Cummings Koski]

You know what? I was it. But I'm finding myself as an adult. It's almost tax time. I haven't even started. So that person today.

[Joe Saul-Sehy]

I like how Fire for Dummies is just kind of casually there behind you.

[Jackie Cummings Koski]

Yeah, I need to move that. It's over a year old now, so is it time to, like, scoot that to the side?

[Joe Saul-Sehy]

I don't think so at all. Because those lessons are timeless, and we're going to talk about some of them today. You are, by the way, not just somebody who really appreciates the fire movement and talk about it with your co host, Bill. You're somebody who actually talks a lot about how you started late. You talked about it on this show.

[Jackie Cummings Koski]

I do. I talk about it all the time. Because a lot of the fire movement, the way that it started, had a bunch of 30 year olds and I was 38 when I woke up and got started. So just under 40. And I wanted. And as well as my co, I want to represent that piece of it because to the general public, anything before 65 is considered early.

[Joe Saul-Sehy]

Yeah, it is wild that inside the movement they're like, what, you're 40? But to the average person, I bet there's a lot of people that saw this title of this episode and they're like, oh, good, perfect. I'm getting started right now.

[Jackie Cummings Koski]

That's right, that's right. Most people have almost nothing for retirement. You know, you see all the statistics out there and all the research and things like that. So 40, you know, some people will consider that late. I was a little bit younger than 40, but, you know, most people, that's when they're starting to think about retirement. Maybe they have a little something, maybe not.

[Joe Saul-Sehy]

Jackie, 40 is the new 30 now, right?

[Jackie Cummings Koski]

That's right, baby.

[Joe Saul-Sehy]

40, 30, the new 30. And a guy who is hoping that very soon he has his 40th birthday. He is the guy behind the retirement Answer man podcast. Our good friend Roger Whitney is back. Roger, you turned 40, what, in a year or two?

[Roger Whitney]

Oh, exactly. I'm 59. I had a month and a half period when my wife just turned 60. I'll just say that on air. And she was two years ahead of me for about a month and a half. It was awesome.

[Joe Saul-Sehy]

Because you had an older woman you were married to.

[Roger Whitney]

Yes, by a month and a half. And I was totally like Doug, except I didn't even go try to explain it to my mom. I didn't care that much.

[Joe Saul-Sehy]

Roger, I don't. Roger, I don't know that we've ever talked about this. Were you an early starter, a late starter? How did you start your retirement journey?

[Roger Whitney]

Oh, I was a late starter. I was a late starter in. In my 20s. I made way too much money and was way too cocky about my trajectory and spent future earnings. And I took all of my 30s cleaning up my 20s. So I started relatively late from a traditional retirement savings. The difference is I was investing in a business that could really compound my income quickly, and that was what ultimately saved me. And maybe we'll talk about building a shovel a little bit in this conversation.

[Joe Saul-Sehy]

That is interesting. Yeah. Talking about income streams and how those work together. Well, you can see we've set the stage. Everybody, I'm going to give the three of you Jackie, OG and Roger, I'm going to give you like a fictitious person here in just a moment, we're going to help that person get retired. Maybe you see yourself in that person if you're hanging out with us, maybe there's little pieces of it. So grab wherever you take notes, whatever you take notes with. And we're going to dive in in just a moment to this topic. But first we got a couple sponsors who make sure that we can do all this live on YouTube and then on the podcast for absolutely nothing. We're going to hear from them. As our friend Paula Pant always says, it's absolutely free and worth every penny. We're gonna, we're gonna hear from them and then Roger, Jackie and OG are gonna help you. Even if you started late, even if it's way past 40. Get moving. In business, there is no room for guesswork. Every shipment matters, every deadline counts. And when you're trying to keep operations running smoothly, the last thing you need is uncertainty. That's why reliability is at the core of USPS Ground Advantage. From the moment your package is first scanned in, it moved through a secure nationwide network, aiding in a timely and accurate delivery. You get near real time tracking so you can keep up with your shipments. And with affordable upfront pricing, there are no hidden fees or surprise surcharges to throw off your cost sheets. It all adds up to predictable deliveries you can depend on because knowing your logistics are handled lets you focus on everything else. Your customers, your team, and the future you're building. Visit USPS.com ground advantage to start shipping with confidence. USPS ground advantage. We mean business. I remember when I got my first life insurance policy. Man, was it such a pain. First of all, I knew I needed to do it for a long time, but because I was in the business, which by the way, is another reason why why you should know how hard it was. Because I knew better and I delayed. But you know why? There was so much that had to be done. And yet when I got it done, it felt so good. It was just a relief that Cheryl and my twins were taken care of if something happened to me. And also then when we got life insurance on her, it was exactly the same. She said she felt exactly the same. Well, the cool thing is it doesn't have to be like it was back forever ago when I did this. And although life insurance isn't a fun topic, it is one you need to think about. So I'm glad that we found out about Ethos. Ethos makes getting life insurance fast and easy. It's 100% online, you can get a quote in seconds, apply in minutes, and get same day coverage. There's no medical exam. You just answer a few simple health questions. You can get up to $3 million in coverage. Some policies are as low as $30 a month. As of March 2025, Business Insider named Ethos the number one no medical exam instant life insurance provider. And Ethos has 4.8 out of 5 stars on Trustpilot with over 3, 000 reviews. Protect your family with life insurance from Ethos. Now by going to ethos.comsb in as little as 10 minutes, you can get your free quote and up to $3 million in [e-mail] SB that's spelled ethos.com SB ethos.com SB application times and rates may vary. I often write. Here is where I say today's discussion is based on this thing that I read. It was actually just a need that we get questions all the time. Jackie, on your show you get questions all the time. Roger on you sure, you get questions all the time. Hey, I'm starting late. What do I do? And I'm like, what a perfect panel of people to dive into this topic. So let me give you just this person that I made up. This person, 40 years old, as I mentioned, wants to retire at age 65. Their income, let's say they're middle class, maybe they make 75, $100,000, no savings. And let's do this too, guys. We're just going to take the pension today out of the game. They have absolutely no pension. All right, Jackie, how does this relate to where you are? Is this a crisis or is this totally fixable?

[Jackie Cummings Koski]

It's absolutely fixable, but it can feel like it's not. I think when people finally wake up, let's say in their 40s, and they're like, I have not saved near enough or I saved nothing. It feels like it is the end. But if you realize that you need to do something different, that could change the whole game. So it definitely fixable. I was close to my 40s when I woke up. I had a little something, but felt like I didn't have much of anything. And it's usually because people don't know their numbers. And that's usually a great starting place.

[Joe Saul-Sehy]

Just know how far behind you might be.

[Jackie Cummings Koski]

Well, I don't put it like, I don't put it like that, but I guess even before then, it's a psychological part. You know, give yourself a little grace. This stuff is not taught in schools. And if you didn't grow up around good role models where you were exposed to financial education. Why would you know?

[Joe Saul-Sehy]

Yeah.

[Jackie Cummings Koski]

So when you do wake up and your co workers all starting to talk about it, hey, I'm five years from retirement, 10 years away from retirement, you're thinking, oh my gosh. When you just pause for a moment, you start to realize, I know I haven't been doing everything right. You let that sink in, you give yourself a little grace, and then you start to say, okay. And it could be a while, it could be months. For me, it was almost two years before I realized that and I actually started doing something. And you kind of need that time to figure out, okay, what have I been doing wrong? What have I been doing right? And how can I start to fix it? Sometimes I think people kind of rush immediately to give me the best portfolio, give me the thing that I can get the biggest return, you know, so that's the natural response. But if you take a moment and kind of digest it all, see where you're at, that makes all the difference, and then you can start heading in the right direction.

[Joe Saul-Sehy]

I want to chat in a second about this sense of panic that people have, but Roger, Roger, you're already chatting it up with all our stackers hanging out on YouTube. Our friend B. Wayne says after I described the scenario, said totally brutal scenario, you said, not necessarily. This is very common. You see this all the time as well.

[Roger Whitney]

Oh, it's crazy. It's totally common. You look at the statistics of 60 year olds and how much they have for retirement. I don't have the number off the top of my head, but it's not much and it's normal. Some of the areas of the scenarios, we don't know how much debt they have. They likely a normal person would probably have debt as well as what you just described. But you have to start where you start. And I can hear it already in how we're talking about it, Joe, of how we frame it. Like B. Wayne, totally brutal scenario. They're so far behind. These framing, even the way we frame the problem can really influence how someone might address it. Just throw your hands up. Well, dang it, then I guess I don't have to worry about it. If you think of the. The science of hope, the science of hope has three pieces to it. You have to see a better future for yourself. You have to be able to identify agency where you can do something to get to that better self. And you have to find different pathways. And I think that's where someone needs to live when they have this aha moment. Otherwise you're just going to put your head in the sand.

[Joe Saul-Sehy]

Yeah. Oh, a hundred percent. Well, I might as well do nothing. I'm screwed either way.

[Doug]

I think that's really common, actually. I have a relative who did exactly that. They probably got to late 40s, early 50s in this same scenario and thought, you know what, I might as well have fun because I'm going to work till the day I die. And never made an attempt to get any roots or anything growing in there in a portfolio. So, yeah, I think that's probably pretty common.

[Joe Saul-Sehy]

How many times have those early retirees around us told us the tale of. They tell people that they've retired at X age and. And they hear. Must be nice, right? Must be nice. Jackie. Roger talked about debt. I think I remember when you and I chatted more deeply and I'll link to it in our show [e-mail], our longer conversation about your. Your whole journey. I think I remember. You had debt, didn't you, at first when you were starting out?

[Jackie Cummings Koski]

I did. I had just a little bit, but it was manageable. Even though I grew up poor, raised by a single dad with six kids, the one good lesson he did teach us or that I took away was was that debt was bad. So I didn't have a lot of debt, but I did have student loans and I did have some credit card debt. Luckily they were manageable. They didn't hold me behind. But the typical person probably does have a lot of debt, and that's a piece of the puzzle as well. That's why I say, you know, you kind of need to pause and kind of look at where you're at if

[Joe Saul-Sehy]

you got a lot of debt. That's the numbers you're talking about.

[Jackie Cummings Koski]

Yeah, that's the numbers. Yeah. All of those numbers.

[Joe Saul-Sehy]

Oh, gee. You know, Roger brought this up earlier. You hear this kind of sense of panic people have. Even the way I presented it, I might have done that a little on purpose. But I think this also clouds the way people invest. If they feel like at 40, I'm behind, they may get into some investments that might not be the right thing.

[OG]

I think that there's two, two great crimes in financial planning. And most people focus on the first one, which is what we're talking about today, which is under saving, and it causes a whole series of dominoes to fall. And. And one of those is that sensation of being behind and then that the next thing of like, I need to do something to catch up. That's the next phrase that happens. And the right way to catch up is by saving money and investing it appropriately and living within your means and, and stop digging a hole, you know, in credit card debt. Like, those are the right ways to catch up. The wrong way to catch up is to jump on Reddit and go like, what is the hottest stock right now? Or, you know, you see something on YouTube or something crazy about cryptocurrency and how come your crypto didn't go up 7,000%? And you know, you take these wild swings of bets when you have to remember the people who are having the success with that are the people that are largely the people that are investing that way have their security all taken care of. They're playing with their 5% money. Like this is the sandbox money. Not largely anyway, not the corpus of the portfolio, so to speak. I think the biggest message that I have for people, you know, people say, oh, it's a brutal scenario to wake up and be 40 and not have any saved, is it's fine. There is so much time. Like, we do not, as humans understand the power of compounding. It is impossible for our brains to do. If you think for a second that you're screwed because you're 40 and you haven't saved anything, I think you've got a great opportunity. Look, you're not going to retire probably at 51. Maybe that's not going to be the case, but you can have a great retirement at 60 or 65 or 70. You just probably have to do things a little different.

[Joe Saul-Sehy]

Roger, you just showed a graphic, which is great for the people that are live with us on YouTube, but for the audio listeners, they're not going to be able to get that. What's the graphic all about?

[Roger Whitney]

Well, he mentioned compounding, and that's what we're talking about. If you think of someone that's age 40, they compounded certain types of behaviors to get to where they are now. And obviously life throws you curveballs in every which way, but that's always going to happen. The issue that a 40 year old or any of us have to deal with is what do I, how can I influence the scope of that compounding, either positively or negatively and a little bit of change now, you know, if you keep doing what you've always done, you're probably going to be in the same place. But the key is how do I change the trajectory of that compounding when it comes to money? And yeah, drastic is nice, but any improvement is, you know, Better than nothing.

[Joe Saul-Sehy]

Jackie, I like your very thoughtful beginning. Think of where you're at. How did you get to this point? Where are you at? What's going on, you know, with you mentally? And then I also like then run the numbers and really it's almost like you're wearing a master shirt today. It's masters weekend. So it's almost like a golfer setting up their shot. I don't golf myself but you know, the golfer just rolls up and whacks it. It's probably not. I don't ever see pros do that. Let's though begin to get an action. Let's say it's time to take action. What is the first move? Not perfect plan, but I'm sure we're all going to have some candidates for what maybe the first move would be. What would yours be?

[Jackie Cummings Koski]

I think my first move would be of course, you know, like look at some important numbers. Okay. Investing certainly is a part of it, but also if you work for a company, how much are you contributing? Some people may have stuck with the company match all of that time or might not have it at all. So can you start there? Most people start investing through their employer sponsored plan. So if you have that, take advantage of that.

[Joe Saul-Sehy]

So that's a fine place to start is through your employer putting money in for 1k.

[Jackie Cummings Koski]

Yeah. Or whatever your company sponsored retirement plan is. If you don't have that, you know, make sure you're looking at the debt. We talked about the debt. A little bit high interest debt. So I'm not necessarily talking about your mortgage. But if you've got, let's start with the worst of the worst payday loan. Okay. Those need to be knocked out like as soon as possible. They deserve focus. Maybe you're living above your means and you've got a 28% credit card interest rate where you've got thousands of dollars that you're trying to pay off that should be lined up. You should have a plan for that. Now I'm a believer in the fact that we are all masters at multitasking. So you can invest and pay off your debt at the same time. It's just a matter of how much you go towards each. So as you pay the debt off, then maybe more should go towards the investing. The other thing, I really like people to tap into their superpowers. I mean we have a tendency to focus on the negative things and the fact that we don't have compound growth and things like that. Well, I guess another thing I like to mention is that we've been led to believe and convince that the trajectory to retirement is about a 40 year time horizon. And why that's because of pensions, right? Well, really, when we dove into it with some late starters and track them, and including myself, it's more like a 10 to 15 year journey. So you could have some compounding. So I started 38, woke up and by the time I was like 49, I was to the place where I'm like, wow, this is crazy. But waking up and realizing that you're far behind, that's a hell of a motivator. So you get motivated and you are going to surprise yourself with how fast you move. So looking at a 10 to 15 year trajectory, that changes your mindset right away. So that can help but find your superpower when you get a little bit older. Let's say you're in your 50s now. You are kind of through that bottleneck. And when I say bottleneck, little kids and expensive daycare, okay, you just got the big house, you just graduated, you got student loans, you got a bunch of debt. All those things are squeezing at you at one time. Well, by the time you're 50, maybe the kids are growing out of the house, maybe you don't need the big house anymore, you don't have the expensive daycare. There's just so many things that open up in your 40s and your 50. Typically you're at your. A lot of people are at their peak earning years. So there's a lot of things working for you that, that I think, you know, sometimes we're too hard on ourselves and we don't think about those things. So can any of those pieces help you move a little faster?

[Joe Saul-Sehy]

We talked about this on Monday. Show OG about ways to cut your spending. And Jackie's kind of talking about, do I value this stuff anymore? Right? But she also said that putting money into this retirement plan just the match. Didn't say this Jackie, but insinuated. I would believe that that's a mistake. What's the number we should shoot for? I mean, it might be individual, person to person, but is there, is there a number that I should say, hey, let's see if I can do this percentage and if I can, I'll back it down.

[Jackie Cummings Koski]

Well.

[Joe Saul-Sehy]

Oh, wait a minute. That was for O.G.

[Jackie Cummings Koski]

okay, that's for. Okay.

[OG]

He's on a roll, man. I'm just a willing participant.

[Jackie Cummings Koski]

I'm throwing it to you.

[OG]

Stay out of the way. She got it all handled. I was thinking about the scene from Austin Powers where he goes, $1 billion. Like I was trying to, I was trying to think about that.

[Joe Saul-Sehy]

Yeah, yeah, yeah.

[OG]

I don't know that there's a correct number, you know, like a percentage to have or.

[Joe Saul-Sehy]

Yeah, like 20. And if you can't do it, go 15 or.

[OG]

I guess the way that I would think about it is a little bit more about progress and not like this ideal number. And what I was kind of encouraged people to look at is can we figure out a way to increase our savings in such a way that it doesn't hurt? And there's two different ways to do that. There's the tear the band aid way off and you go, okay, this is just gonna suck. And I need to go from nothing to I need to be saving 20% and that's gonna cause a lot of upheaval, you know, and maybe you're the person that has been doing the 401k to the match and you're getting your 3% and 3% match and so on so forth. Can you set it up so that in June you increase it to 4%? I mean, if you're making $100,000 and you increase your savings by 1%, that's a thousand bucks, right? Divided by a month, it's $83 a month. If you can pay twice a month, it's like 40 some odd dollars a paycheck. I'm guessing that we probably don't miss the 40 bucks. You know, like for some people and I get for other people, they would. So a lot of this is trial and error and you know. Yeah. I would also say for some people the right answer is put it at 20, find out where the pain is and then back it down to 15. You know, like put the heavy weight on the bar and see if you can lift it and see what happens. Right. I mean, as long a spotter, you're good, right? You kind of know thyself there a little bit. But if I was setting this up, if I was 40 and saying, okay, hey, I have been doing the match, I, I, I do recognize I'm a little behind air quotes and I need to do a little bit more. How can I automate this? If you can say, well, every six months I'm going to add a 1% to my savings rate. Yeah, it's going to take you five years, but in five years you go from 3% to 13%. Like that's a pretty profound change and it's going to feel like a non event the entire time. So see if you can automate the change to make it something a little bit more palatable on the lifestyle.

[Joe Saul-Sehy]

I love that idea of Jackie saving through work. Roger. And this will be our last question before we take our mid session break. What if you are working for a company that doesn't have that retirement plan? Is there a way to set up the thing that Jackie's talking about? Because essentially what I love about that, Roger, you hide money from yourself, right? I mean, it just, it's automatically gone. Can you set that up on your own?

[Roger Whitney]

Yeah, well, you can set up an individual retirement account and contribute. You're not going to get a company match. But can I go back to another point that I think is really important in terms of where to start?

[Joe Saul-Sehy]

Of course you can.

[Roger Whitney]

When you realize you have this moment, I'm 40, I have no money and I got to deal with retirement. Our tendency is to want to take drastic action and there's a risk with getting shot out of a cannon, with motivation to totally change your life and then you slowly come back down to earth because it's not sustainable. What I think is probably an approach that we should consider, and I'll use a health approach as an example because I've been doing this for 15 plus weeks, is actually to go micro and start to connect dots and pay attention to every dollar you spend and every dollar you save and make micro adjustments. So as an example, let's use food as an example. If I have a target of a certain amount of calories for the and I'm tracking every single calorie that I eat, my choices change. I'm not going to eat mixed nuts because they're calorie dense and low protein. When I'm at the store, I'm going to say, oh wait, do I want to spend that much calories on, you know, ravioli? When it's not going to give me what we want? It helps to change the individual habits.

[Joe Saul-Sehy]

I thought the answer, and that's what real change.

[OG]

But anyway, I know I was like, ravioli is so yummy, Roger.

[Jackie Cummings Koski]

I know it is.

[Roger Whitney]

But until we start connecting those dots, then because you don't diet, you get, you get healthier, you don't become a crazy saver, you become a better spender and saver of money. And those happens in the micro moments. And I think if you don't connect those dots, there's a risk of going out, out of the canon and then slowly coming back down to what normal is.

[Joe Saul-Sehy]

I love that looking at every line, I'd have been going, how much do I actually enjoy this? It's almost like Roger, you're putting, who was that Marie Kondo on this. Every single thing go through your, your banking app and go does this spark joy? If it doesn't spark joy, then they get rid of it and add it to that IRA or that 401k.

[Roger Whitney]

And because that sustainability of whatever changes you're going to make is the most important thing because otherwise, oh, it doesn't work. I give up and I'm going back to what was.

[Joe Saul-Sehy]

Well and I think that's also a key is, is you're going to fall off the horse, get back on. I mean, you're going to fall off. It's just going to happen. At the halfway point of our Friday shows. If you're brand new to stacking Benjamin's, we have this year long, completely professional very high stakes tournament going on all year long between our three frequent contributors, og, Paula Pant from Afford Anything and Jesse Kramer. And so just to make it easy for me as the host, we'll have Jackie, you're going to be team Paula today. And then Roger, you'll be team Jesse. We're. Which means, guys, there's some good news and bad news for both of you. I think. Doug, well, jacket, let's ask you, do you want the good news or the bad news first?

[Jackie Cummings Koski]

Always bad news first.

[Joe Saul-Sehy]

Doug, what's the bad news?

[Doug]

The bad news is you are sitting squarely, firmly, uncontestedly in last place.

[Joe Saul-Sehy]

And the score overall is bad news for Roger.

[Doug]

Yeah. Because he is also sitting in a very comfortable second place.

[Joe Saul-Sehy]

Yeah.

[Doug]

No one's really challenging you for second. So our overall score is the Prince of Darkness. OG he has seven points. Jesse, slash. Roger has two points. And Paula, Jackie clinging to life with just one point.

[Joe Saul-Sehy]

But they're on the board. Finally. It took a couple of weeks ago to actually get on the board, which is super exciting. So now, now the stage is set for Q2. And that means we need a trivia question. Doug, you've got it, man. What are we talking about today?

[Doug]

Did we explain that that means that because Jackie's in last place that she gets to go last and get the benefit of hearing everybody else's guesses ahead of us.

[Joe Saul-Sehy]

That does mean, Jackie, thank you. That you're going last. Roger, you'll go in the middle and oh gee, because he's in the lead is going to have to guess first. So here we go. Doug, I won't explain margin calls to everyone. If you're new to this show, we have a thing called margin calls. There will Be none today, because we have two guests on the show, so no need for that. There will be none. So let's do some trivia.

[Doug]

Here we go. Hey there, Stackers. I'm Joe's mom's neighbor, Doug, and holy cow, I'm going bananas over here. Remember how on that one show there was always money in the banana stand? Heck, yeah. While that might have been fiction, turns out it really occurred back in London one day. Londonians, London heirs, Londonites, London drapers. Anyway, people who live there, they woke up and found a banana stand smack dab in the middle of town. Here's your big question for today. What year did London first go bananas for bananas? I'll be back right after I find out if maybe I can smuggle a smuckle. I'm not gonna smuggle anything, but I'm gonna figure out if I can smuggle a couple of bananas down to the basement. Come on over if you want to try one. They're delicious.

[Joe Saul-Sehy]

Bananas are delicious. And Roger, to your point, they're healthy, right? Got all that Potassium.

[Roger Whitney]

Potassium, yes.

[Joe Saul-Sehy]

All right. OG Bananas first appeared in London for sale in what year?

[OG]

Okay, I was going to ask a little bit of a clarifying question in a banana stand being like, a gimmick thing or like, literally the first time somebody saw a banana in London, it

[Joe Saul-Sehy]

literally was the first time a banana was for sale.

[OG]

So this is. This is more like the 1970s, not the 1990s.

[Roger Whitney]

Okay.

[Joe Saul-Sehy]

It might have been 83.

[OG]

Oh, 83. I hadn't thought about the 80s. All right, so I am going to say that a banana first appeared. Interestingly enough, I actually know this because it was a monkey who brought it. So they brought the monkey. Monkey carried a banana. They beat up the monkey and took the banana. It's a weird story, but it's a part where Doug didn't want to do that part of the story, but it had to do with smuggling monkeys from the rainforest. And the first person to do that was Ponce de Leon. Old Ponce did that in the year

[Doug]

of our famous Londoner.

[OG]

Yeah. Yeah. Well, he made a pit stop on his way back to Spain.

[Doug]

Stelion. He was from the south side of London.

[OG]

No, he was from Spain.

[Jackie Cummings Koski]

But he.

[OG]

He played both sides of the alley.

[Joe Saul-Sehy]

Jackie, backstage, I told you, we pontificate about the answers.

[OG]

No, this isn't pontificating. This is. This is how it went down. But anyway, old Ponce, that's what we call him, he captured that Peruvian monkey and all the bananas in sometime around the same time that Columbus sailed the Ocean Blue. So 1505, 1505.

[Joe Saul-Sehy]

What do you think about that answer, Roger?

[Roger Whitney]

I don't know what he was talking about, but I love that he talks with confidence. Yes, I love that he talks with confidence. I'm not going to pontificate as OG did, but I was spending the whole time. Did bananas come from South America? Africa? Both places I was still working on where the hell a banana comes from.

[Joe Saul-Sehy]

I actually don't know where the bananas originally came from in London. I, I didn't look up that part of the trivia. That is interesting.

[Doug]

Walmart.

[OG]

I know.

[Roger Whitney]

I'm going to say that it was from Africa, not South America. And obviously it had to do with colonialism and all of that, but I'm going to go earlier. When did they have the first sail ships? I need to figure this out.

[OG]

Magna Carta.

[Roger Whitney]

I'm going to go 1476.

[Joe Saul-Sehy]

1476. So, Jackie, we've got 1505 and 1476. We're several hundred years ago and there's only a 31 year delta between their answers.

[Jackie Cummings Koski]

Look, I, I was never the best in history, but I feel like I need to phone a friend, but I'm thinking logically. So we're saying in the, in the uk, right? Did you say the uk?

[Joe Saul-Sehy]

Yep, yep. In London.

[Jackie Cummings Koski]

Okay.

[Joe Saul-Sehy]

In London, not London. Ontari scenario. To be.

[Jackie Cummings Koski]

To be correct. Okay. So when I don't know the answer to something, I just try to apply the logic of what I do know, just like I did on the CFP exam. Okay. So I think. So I'm thinking about transportation things because if they couldn't grow it in the uk, they had to bring it over here. So I'm thinking more recent. So I'm going to go with, for my gaming strategy, I'll say 1550.

[Joe Saul-Sehy]

1550.

[Jackie Cummings Koski]

Because it's closer to what OG said, but I feel like it was more recent than that. So I'll go up just a little bit.

[Roger Whitney]

Box you in, OG. We boxed you in, buddy.

[Joe Saul-Sehy]

We've got Roger at 1476, OG at 1505, Jackie at 1550. We'll see who's right. We'll be back. Did you know Fast Growing Trees is America's largest and most trusted online nursery with thousands of trees and plants and over 2 million million happy customers. Whether you're planting fruit trees, adding privacy, brightening things up with flowers, or bringing in houseplants, Fast Growing Trees has it all. Even better, they can help you find options that are right for your climate, your space and lifestyle. Click order, grow Every plant arrives healthy with the alive and thrive guarantee straight to your door. So if you're ready to get planting, this is the moment. Right now. They have great deals on spring planting essentials, up to half off on select plants. And listeners to our show get 20% off their first purchase when using the code WWO at checkout. That's an additional 20% off. Better plants and better growing at fastgrowingtrees.com using the code WWO at checkout fastgrowingtrees.com code WWO now is the perfect time to plant. Let's grow together. Use WWO to save today. Offer is valid for a limited time. Terms and conditions go to growingfasttrees.com for details.

[Jackie Cummings Koski]

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[Joe Saul-Sehy]

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[Jackie Cummings Koski]

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[OG]

Hey there.

[Joe Saul-Sehy]

I'm Paula Pan. I help people make the smartest money decisions possible. Do not ever worry about your salary. You need enough to make sure that you aren't in a bad financial position. Once you have that, your salary becomes moot. What matters from that point forward?

[OG]

Upside, gains, any type of ownership stake or ownership potential.

[Jackie Cummings Koski]

That's the money.

[Joe Saul-Sehy]

Remember, you can afford anything. Just not everything afford anything.

[OG]

Follow and listen on your favorite platform.

[Joe Saul-Sehy]

OG began at 1505. Feel pretty confident about that number. No, Roger, 1476. You've got if it is 1200. You got it?

[Roger Whitney]

I got it.

[Jackie Cummings Koski]

What on earth?

[Roger Whitney]

We got the Romans that came over to London. You know, they had monkeys. They probably went to Africa or wherever beforehand.

[Doug]

I think I'm good.

[Jackie Cummings Koski]

Oh, well, that one completely threw me off.

[OG]

No, he was saying, if it is, it's not.

[Joe Saul-Sehy]

And then. And then. Jackie, you got 1550. Feeling good?

[OG]

No.

[Jackie Cummings Koski]

Oh, I thought you said Roger's answer was right.

[OG]

No.

[Jackie Cummings Koski]

Or the closest. Oh, it was.

[Roger Whitney]

Well, he will say that, Jackie, in a moment. Okay.

[OG]

Okay.

[Jackie Cummings Koski]

Got you. Gotcha.

[Joe Saul-Sehy]

We're about to find out. Andrea hanging out with us says OG it's called a handicap. You ever play golf? It's a handicap.

[Jackie Cummings Koski]

That's right. We talked about golf today.

[Joe Saul-Sehy]

Yep. All right, Doug, you got the answer. Who's bringing this one home?

[Doug]

Hey there, stackers. I'm banana lover and guy who accidentally Made it awkward again. Joe's mom's neighbor, Doug. So I sneak upstairs to grab a banana and I heard Joe's mom's coming around the corner. So just as I reached for the fruit basket, well, I panicked. I just shoved it in my pants. She took one look at me and said, is that a banana in your pants? You know how you can never think of a clever thing to say, like right when you need to say it? All I could think of at that moment was thank you. So I went with that. Turns out that was not the best answer I could have said. So we're just gonna move on. What year did Londoners wake up to a banana stand that was making whatever they called their version of Benjamin's right downtown for the first time? Well, the answer is 157 years after Roger Guest, 128 years after OG Guest, and just 83 years after Jackie Guest. Because the correct answer is 1633, making Jackie slash Paula our winner.

[Joe Saul-Sehy]

It's amazing.

[Jackie Cummings Koski]

Hey, how about that, Paula? You owe me one. Yeah.

[Doug]

Yes, she does.

[Jackie Cummings Koski]

I just thought. I thought their days was just too far back. So I went with 18. I was gonna go with 1800. No matter what I would have won, Right?

[Joe Saul-Sehy]

No matter what, you would have won.

[Doug]

Yeah, yeah, yeah. But what's interesting here is that of how long it took a plantain to make it to London because they actually originated. Roger, you were pretty much half the globe away. They originated in Southeast Asia and were sort of domesticated as it were. Apparently they were wild and uncontrollable prior to this 5000 BC. So they looked pretty different than what the bananas look like today. But nonetheless, people were using them as a crop 5000 years BC and didn't make it to London until 1633.

[Roger Whitney]

How do you fact check that? Seriously.

[Doug]

I got a guy. I got a guy.

[Joe Saul-Sehy]

We're going to go bananas for the second half of our conversation about. You start at age 40, you think that you're late. What are you going to do? And I love the conversation so far. You're not late. And we've got this miracle of compounding. And we're not just compounding returns, we're also compounding behaviors. We're compounding the things that we do to make a difference when it comes to getting what we want for ourself, which is in this case, the goal is a great retirement. All right, you got money to invest, where does it go? I want to give you some types of investing. And I know, Jackie, in your book, you go over all these different strategies of investments. But there's a lot of talk from one corner of the universe about dividend investing. Right. And about, I want more dividends in my portfolio. For people that don't understand dividend investing, could do you mind just doing a very brief. Here's how that works, what that means. But then how do you like it? Let's, let's, let's put your, your take on dividend investing versus maybe other ways to invest.

[Jackie Cummings Koski]

Are you throwing that to me, Joe? No, I. So as far as dividend. So for me, I also have a single stock portfolio, so that's looked at a little bit differently. So sometimes people do want the blue chip stocks because of their great dividends. We know that dividends isn't really giving you more money overall. It's just giving you a portion of their, you know, profits of the company, and they pay it out to you by, you know, sending you a check every quarter. I look at dividends as a representation of other areas of strength of the company or not. So. So I keep that in mind. I think some people might be attracted to the whole idea of dividend because they don't have to sell shares to be able to get it. But you really should be focusing on the overall, you know, return, you know, the growth of the stock or the index fund versus well, and the dividends along with it. And because most people, like, don't really understand how dividends work, sometimes an explanation of that will start to make sense to them because some people just think that's just a free extra bonus that I get every quarter. So. So the education piece of any type of investing is probably one of the most important things. And I suppose if you are thinking about retirement, it's a nice way to get sort of some fixed income or cash. So that's okay. But I think there's some education around doing that because it could work for your strategy, whatever your strategy is. Dividends might have a place for that. I just don't immediately discount it. As in, oh, yeah, dividends create. No, you know, that's really nothing. You shouldn't be focused on that. I want to talk them through and walk them through. Here's, you know, some benefits, some ways you can use it, and things like that. But, you know, it's really not getting them much more of.

[Joe Saul-Sehy]

Yeah, it could be a piece of the puzzle.

[Jackie Cummings Koski]

Yeah, I think it could be a piece of the puzzle, but a lot of times people are confused about how that even works. It probably warrants a little something.

[Joe Saul-Sehy]

Well, and I Think my brain was ringing the bell on what Jackie was saying, Roger, because when I hear about dividend investing, the number one thing is you don't ever have to sell your stock. It's like you still got the mountain of stock and now I'm just taking the dividends. Right. Is there a flaw in that argument?

[Roger Whitney]

The mountain of stock never really grows as much because dividends are simply profits that are given back to the shareholders, meaning that they didn't have anything else better to do with the money in terms of reinvest, reinvesting it in the company separately. If you're taking the dividends, you're not reinvesting in the company or in a, say even a mutual fund. You can reinvest or take it out. I think for someone that's 40, the key issue is I have to build wealth. I need capital appreciation and I have a 15 year time frame in the fact set that you gave us. We hear all these things because we love to talk tactics, but tactics are after you have a bigger strategy and it's really capital appreciation, keep it as simple as possible because. And which is going to be not thinking about dividends or sectors or all of that. Buy a portfolio and focus on the things you have the most agency over. So I think it's premature for someone at 40 thinking about retiring at 65 to even being thinking about these tactics.

[Joe Saul-Sehy]

I really like OG the other thing that Jackie mentioned too, which is it's all kind of same, same like dividend capital gain. Your stock goes up. Yeah. It might send you to panic a little bit because you're selling some of your stocks. But a return's a return, isn't it?

[OG]

I mean it is. And the taxability of it is virtually the same too. So it's like, well, I didn't want to sell a stock and pay taxes. It's like, well, but you get dividends and you pay taxes. So tomato, tomato, it's all returned to shareholder like Roger was talking about. One way or the other. It's the company made money and now they have to decide how best to use the money. And sometimes they decide to use it to buy more stuff or build more product or invest in research or whatever. Sometimes they use it to reward existing shareholders, sometimes they use it to line their own pockets. There's all sorts of ways you can use profit as a company. And I think what's most important, especially like Roger was talking about here, dividends, capital appreciation, whatever, it's all return. And if you're taking some of that return off the table every year, you're going to have a slower growth of your overall net worth in the time where you are trying to compound it as fast as possible. So dividends are neither good nor bad. It's just if you're going to use it to supplement your lifestyle, especially when you're 40 or 50 or not retired yet, basically then you're taking a little bit off the table in terms of your compounding in the future.

[Jackie Cummings Koski]

Fun fact. Did you know that Nvidia pays a dividend? Oh, they do a tiny little one, but you know, hey, that right something I guess their leadership get the hot

[Joe Saul-Sehy]

company and the dividend.

[Jackie Cummings Koski]

Right. And, and that's what I love to have both. And it also depends on where you have the money. If you have it in your retirement account at work, then the dividends are going to get reinvested, so you don't have a choice. But if you have a brokerage account, you then you have all those things that Og was talking about.

[Joe Saul-Sehy]

We see lots of channels, Jackie, in the personal finance space that talk about real estate. The magic of real estate. This person, 40 years old, just starting out, doesn't have anything. Where does real estate fit in that portfolio?

[Jackie Cummings Koski]

Yeah, in my way, the first thing would be if you own your own home, you're. You're owning real estate. Arguable. You know, some people don't even call that an investing, but it can be beneficial to you. Like for instance, I've been in my house for a really long time and some people that are 40 or older, potentially they could have been in their house for a while, maybe they have a really low interest rate. So that may be something working to their benefit. But if you have not done real estate before as a wealth building tool, like you know, you are investing in rental properties or something like that, Airbnb, it's probably not the time to really start something new. But if you do it, make sure something that lights you up, like real estate may not be your thing thing. But there's a lot of buzz out there that says hey, real estate is a quick way to do it and that could help you catch up. Maybe if you're interested, but you're not going to stick with it if it's not something that really interests you. And if you've never done real estate before, I don't know if turning 40 and being behind is the right time to do it. If you already got experience with that,

[Joe Saul-Sehy]

then maybe might not be the right fit. It certainly didn't light me up, Roger. I Don't know if real estate lights you up, but when you see people

[Roger Whitney]

trying to figure that out. Joe,

[Jackie Cummings Koski]

I just.

[Joe Saul-Sehy]

The real estate thing is so, was so ugly. Where do you stand on real estate for this person?

[Roger Whitney]

I agree with Jackie. Real estate. And I'm assuming we're talking about single family properties or buying a commercial building, etc.

[Joe Saul-Sehy]

Yeah.

[Roger Whitney]

The beauty of real estate is leverage. That's where the magic happens. If you go into real estate, you're going into a business. So it's really, do you want to be in a business that happens to be real estate? And, and the way to get the real returns in real estate typically are with leverage. And leverage introduces a lot of risk. And I think it's do you want to go into business? Is that really where you want to spend your time? And are you willing to do it for a long period of time? And that's a really different kind of decision. I think it's better for, you know, the fact that you gave us somebody to walk and build the habits before you start thinking about going into a business such as real estate.

[Joe Saul-Sehy]

Yeah, I think, and it's funny, you see, we saw, we had a tick tock minute. OG if you remember this guy saying not only going to real estate, but flipping houses, Roger, of all the businesses out there, you know, real estate as a business, buy a house and long term hold it, maybe have a renter is maybe low impact business can flare up from time to time. But the flip, somebody was telling somebody to do a flip right out of the gate and I was like, what do you. You're telling them to do a flip. Full blown business. Where do you see OG Real estate in a portfolio?

[OG]

This person, from an investment standpoint, I have a hard time. Unless your expertise is in real estate using individual, individual property. I mean just, just conceptually from a diversification standpoint, what's going to be better? A real estate mutual funder ETF or one rental property in hometown usa? Like if I'm going to have real estate, I want it to be as diversified and as liquid as possible and not literally have one thing unless that's my expertise. If I'm a Realtor or, you know, I have some family connections or something like that. Your real estate story and mine are very similar. We both hated doing it. I think mine's a little different. And I got lucky on timing and so on paper it looks like I hit a home run, which I did, but it's because I like closed my eyes as I had the bat in my hand. And just swung and the bat hit the ball. You know, I didn't actually try to hit the ball, it just happened. And it looked like it was like this magical outcome. And I think it's true. You know what Roger said about leverage. And this is really the thing that to me puts the nail in the coffin about individual real estate investing. Because the return only works when you use leverage. Like you have to put $100,000 down to buy a $500,000 property. That's how that works. And when that $500,000 property goes up 10%, you made 50 grand on your 100. And that looks like you're a genius. I would submit to you, you can do the same thing with your stock account. You can call Schwab and say, hey, I've got $100,000. You guys let me buy 500,000 worth of stock. They'll go, yeah, absolutely, sure. And nobody does that because, oh, that's risky. Wait a second. What's riskier? The biggest, biggest, most well run, most well capitalized companies in the entire universe or property in hometown usa?

[Joe Saul-Sehy]

And to be clear, that's not an endorsement of taking out the margin.

[OG]

I'm not saying you should do that. I'm just saying, like to me, that's the trade. That's the. When you do the math on both of those, you go, well, I would never do that. I'll go, well, why would you do it this way then if you're going to do it that way?

[Roger Whitney]

And that's a great point, OG and you're adding a lot more execution, risk of vacancies and repairs and all the other stuff that comes with it.

[OG]

You would never do that with your stock account. Right. You'd never take a million dollar brokerage account and go buy 5 million of stock on margin at 7% and go, oh, it's just leverage, it's great. But we do it with commercial property all day long. I like real estate as an investment. Publicly held, very liquid, diversified as an ETF or mutual fund.

[Joe Saul-Sehy]

Well, and let's talk about that because Jackie, you're nodding your head like there's this wide world of investments. We said dividends only. Probably not. Even though you're going to read about that a lot, you're also going to read as a newbie, you're going to see people getting rich off real estate. We just said, yeah, it can be great, but probably not a place to start. If I'm this 40 year old person and I got this wide world of investments. What types of investments? Maybe Even what type of packaging am I looking at first to start to get comfortable with where I'm probably more likely to invest?

[Jackie Cummings Koski]

Yeah, I think for most people it's back to the employer sponsored retirement plan, just like an index fund. And I think just a little bit of education around how the stock market performs. I guess the bond market as well, but mostly the stock market. For instance, the stock market will have years where it goes down. No need to take all your money out, no need to panic, sell or anything like that. Look at market history. I've gone all the way back to 60 years, even, even further. But on average the stock market is up about 80% of the time. That will help keep you from selling. When we have two or three weeks or a couple of months or even a year of a down market, even if it's a sharp decline like it is right now, we're in, you know, near the first quarter of 2026. So I think that is something that happens more often than not. They want to go real aggressive. All stocks, you know, I want the thing that's going to grow the most. And then when we hit a downturn it's like oh my gosh, this is too crazy. And they start to understand their real risk tolerance. So that would be where I would look at it, know how stocks are behave. Stock index funds are very common now. They're very easy, they're very low cost. So that's probably the low hanging fruit for most people. But make sure you understand how that performs and that a market downturn is a normal part of the cycle.

[Joe Saul-Sehy]

Roger, all these places to look at. Jackie says this index fund is a great thing to look at first. Do you agree and if so, what's the attractiveness for you of, of starting to dig into index funds and begin your research there?

[Roger Whitney]

You want to do as little as possible because the more you make it something you have to think about like real estate, the more you have a chance of screwing it up, the more complicated the system is. One is, I want to go to your point a little bit earlier related to this Joe is you know, this 40 year old, oh my goodness, I have no savings. You're like a person that's dead in the water feeling like they're just trying to keep their head above and now they want to swim a direction. And it's easy when you're in that mental state to grab for the, the easy button. The risk is becoming more susceptible to man go on the Internet, you find it all over the place. Everybody has a strategy Real estate millionaires and people sitting outside in front of their Rolls Royces. You could potentially be a sucker for a lot of these things that are just really bad for you because it's boring stuff that is the right stuff to do.

[Joe Saul-Sehy]

That actually is funny, Roger, because as you're talking, I'm going back through the three things we talked about. If we go with the index fund guys, it's okay. Do you have dividends, Jackie, to your point earlier about Nvidia and some of these companies, Coca Cola, whatever, you're like, yeah, you got some of that. It's not all, but yeah, you got some. And then real estate. Yeah, all these companies own some real estate. Maybe not all of them, but a bunch of them. Yeah, you got a little bit of real estate. Yeah. So Roger, it's. You're saying it's not the winner to research first because you're going to win, it's because you're less likely to lose. Is that what you're saying?

[Roger Whitney]

I'm saying that you should keep it really simple. I do think just invest in the current of the economy. And that's essentially what, you know, the economy is this current, it has a current that is going to growth. And there are rapids periodically of bear markets and corrections. And that's the price for being on the river for this 40 year old build the habit of saving in the most efficient way and you want to be on Tom Sawyer's raft in the river, something that costs not much to build, you don't have to think about navigating it. You're just trusting that every now and then you're going to get wet when you hit the rapids. But because you have the proper time frame, you can grow with it. And I think the simpler you make it, the better at this stage.

[Joe Saul-Sehy]

But it's funny in the comments today, man dividend gypsy hanging out with us says, hey, but to play devil's advocate, historically, oh gee, don't companies that grow dividends annually have a greater total return than non dividend payers? You could not only get dividends but also be in the hottest stocks.

[OG]

Well, I think it's just cherry picking data. It depends on how you analyze it. I mean, is the dividend paying the reason for the high long term performance or is the fact that most dividend payers are companies that have been around 25 years? Those are backward looking statistics. I don't think you can look at a stock today and say, oh well, Nvidia is a bad example because it is kicking everyone's ass. But this company pays a dividend, therefore it's going to outperform. There might be a trend of over the last 30 years or 50 years, if a company historically raises its dividend, it also has outperformed. But why did it do that? It did that because it was a great business that created a lot of value for a lot of people. The problem is that you don't know what those great businesses are that are providing a lot of value for a lot of people in advance. And also I would say you don't know because they've been a great business that provided a lot of great value for a lot of people for the last 20 years that there's any indication that they're going to do that for the next 20 years. There's no statistical evidence of the persistence of performance. So I think that the best solution to that is, yeah, you probably will have some dividend payers in your portfolio, but you should also have some non dividend payers in your portfolio and big and small and international and you know, us based and like a wide variety of basically all the companies in existence. Because then you get everything all the time, like it's the easiest way to do it. Roger said something about being on a raft with Tom Sawyer. I don't, I didn't really follow that. But you know, at the end of the day it's like just own one of everything. It takes all the guesswork out of this.

[Roger Whitney]

Well, I think the key here, Joe, is, you know, we go back to agency. If you're 40 years old, do you want to spend your mental energy thinking about investment strategies or more important things that are like levers that can really impact your life? So a lot of this is just simply time management.

[Joe Saul-Sehy]

And that's important, Roger, because what do you need to really do? I mean, you need to grow your income. If you really feel like you're behind, the cool thing to do is to grow your income. If you can grow your income and save more of that income, then that's great. Because Jackie, as I thought through, you started this cavalcade of Roger and Og saying yes, I believe looking at the index fund, what you're really saying is that your savings rate and a decent sale beats some complex investment strategy.

[Jackie Cummings Koski]

Yeah, it's so true. I love to show that chart. One column, it'll show your savings rate and another column, how many years with that savings rate will it take you to get to financial independence? And that becomes very powerful. So if you only want to save 10%, then that's probably going to take you about 40 years. If you want to save 30%, then that might shave it down to 20 years. And some people that are 40, it doesn't mean that the income was their problem. It could be higher income earners. As you know, my co host, Bill Yount, he's a physician and his wife is a doctor as well. So their problem was not income, it was other things like spending every, you know, more, more money, more problems. So they just.

[Joe Saul-Sehy]

Life today in the way.

[Jackie Cummings Koski]

Yeah, exactly. So they still was living paycheck to paycheck, living a big life. And when they realized that they did have a big shovel because there were just a lot of crumbs falling out of the bottom. And once he identified that, he just became smarter with how he spent his money. Before he spent first, save last, he reversed that and said, now I'm going to save first and spend last. And in about 10 years he got to that place. So even for high income earners, unfortunately, this can be a problem as well. And that's why you kind of stop for a minute and say, wait a minute, let me see where things are at. Because the income might not be the problem, the debt might not be the problem. It could be a lot of different issues. The better you are at identifying the problem that caused you to be behind, the more likely you can start to close that gap and start your path in the right way. Because it's just not the same for everybody.

[Joe Saul-Sehy]

I love this, guys. If you're 40 years old and you're hanging out with us, listening, it's not too late. Savings rate matters more than be getting clever. Simple beats complex. There are multiple valid paths, but some are more valid than others. So do some, do some research. And I think action beats perfection. Like, don't try to, don't try to create the perfect thing. Just get moving, get moving. I like what you said earlier, OG that you know what, just get started and it's going to make it better than it was yesterday. Might not be perfect, but it'll be better than it was yesterday. I think that's a fantastic place to leave it. It is Masters weekend and Jackie, you've been to the Masters twice?

[Jackie Cummings Koski]

Yeah, three times actually. I went to the practice rounds. Yeah, the practice rounds twice. And the actual Sunday tournament once when I was in college.

[Joe Saul-Sehy]

Well, the cool thing is I'm gonna ask OG what he's doing on a bet is sitting on the sofa watching the Masters.

[OG]

You know, I've got a little after school activity this week, kind of middle of the spring for that. So I will try to watch as much golf as I possibly can. Between that and pedaling my rear end up and down.

[Joe Saul-Sehy]

I was going to ask you about that because a lot of stackers asking

[OG]

about how the bike is going so far, so terrible. It's.

[Joe Saul-Sehy]

But you're doing it.

[OG]

You're doing it. No, it's fine. I enjoy being outside. It's very structured, which is what I need every day. I don't. I don't make stuff up. I just, like, literally look at the calendar and see what the coach put in there. It's like, oh, four hours. Okay, here we go. I'll see you later. And I just get up, get my

[Jackie Cummings Koski]

ass on mic and go.

[Joe Saul-Sehy]

So you've seen every trail in the area?

[OG]

Yeah, yeah. Trail, road. I'm going to start going to Roger's house pretty soon. I was going to say, you need

[Roger Whitney]

to come up for some altitude training, buddy.

[OG]

He's in the mountains and I'm going to go. He doesn't. He didn't invite me and he doesn't know it's coming. But I'm going to show up one day with my, like, hat in hand and a bicycle and be like, roger, can you ride your bike with me, please?

[Joe Saul-Sehy]

From here to there. Might take longer than four hours, but

[Roger Whitney]

get some climbing in.

[Joe Saul-Sehy]

Spoiler. Jackie, thank you so much for hanging out with us again. We've got the beautiful book behind you. People can get that everywhere if they'd like. Fire for Dummies. Learn about the fire movement through the amazing. Jackie, I gotta ask you about two things. Number one, what's coming up with you and Bill on catching up to Phi?

[Jackie Cummings Koski]

Yeah. So catching up to five, we focus on late starters on the journey to financial independence. So this is squarely in our space. And the other thing is, I've been getting very frustrated about 401ks that are offered to employees. They're confusing the name of the funds are confusing. People don't know how to do them. And most people sit with the default for a very long time. And I hate that because that is a backbone of most people's retirement these days. So I created something called the Great 401K Cleanup, where I put a guide together on how to clean up your 401k in less than an hour.

[Joe Saul-Sehy]

Awesome. And you got to tell us where to get it.

[Jackie Cummings Koski]

Yeah, you can come on over to Catching up to five. We just did an episode that walked through the whole thing. And you can download the guide and just the one page checklist. Just from going to the podcast and it's in the show notes there. But that's where we've got it and I just am trying to share that with everyone. Listen to the podcast, download the guide and you'll be good to go share it with. You know, we got smart people on here, Joe, so they may not need it for themselves, but if you have younger friends, family, nieces, nephews, kids, they're going to be looking to you for help. And that guide kind of helps you do that.

[Joe Saul-Sehy]

87 choices and there are four good ones buried in there.

[Jackie Cummings Koski]

Exactly. I see that all the time. It's a shame.

[Joe Saul-Sehy]

It's great seeing you.

[OG]

Good.

[Joe Saul-Sehy]

And thanks so much for helping our stackers today.

[Jackie Cummings Koski]

Yep.

[Joe Saul-Sehy]

Mr. Whitney, what's coming up at the Retirement Answer Man? By the way, you are permanently now in Colorado.

[Roger Whitney]

No, I am officially a resident of Texas, but in Colorado, apparently.

[OG]

Yes, occasionally visit Colorado. Yeah, I'm with you, Roger.

[Joe Saul-Sehy]

But we got to talk about what's happening at the Retirement Answer man, the Rock Retirement Club.

[Roger Whitney]

Well, this month in April, we're answering listeners questions, but I'm excited about May because May we're going to have an associate of Marie Kondo come on and talk about decluttering for retirement.

[Joe Saul-Sehy]

Wow, I didn't even know that I brought up Marie Kondo earlier.

[Roger Whitney]

It's amazing. Not, you know, you can declutter obviously your home and everything else to re nest I call it, for your new phase of life. But also there's a lot of decluttering that has to happen financially because you sort of gather old 401ks and IRAs and these things that you thought you were going to do. So we're going to have a whole month long series on decluttering and that's

[Joe Saul-Sehy]

at the Retirement Interman podcast where finer podcasts like Catching up to Fi and Stacking Benjamins are found. We'll link to all these great shows in our show notes@stacking benjamin's.com we also have a friends page and you guys are both on our friends page on Stacking Benjamins as well. You can find the shows we think are pretty damn cool on that page as well. All right, that's going to do it for today. Thanks to everybody hanging out with us on YouTube. We're super happy that you're here. Speaking of if you got a friend, if you've got a friend who is this 40 year old who's just starting out, maybe send them to this episode because that you guys really nailed. I think a lot of the key issues to begin what's going to be a much, much longer journey than the one hour we took, but it's a wonderful place to start the trip. Doug, you got it from here, man. What should we have learned on today's show?

[Doug]

Well, Joe, first, take some advice from Jackie. No matter how late you are saving for retirement, you're never too late to start starts to slow start simple and before you know it, the power of compounding will make a bigger difference than you'd ever believe. Second, don't forget what Roger said. When you're trying to get up to speed, don't put all your eggs in one basket looking for the silver bullet that's going to hit a home run. You've got to diversify. But the big lesson, don't rely on some pile of hidden money suddenly showing up at the last minute. Turns out there isn't always money in the banana stand. Thanks to Roger Whitney for joining us today. Want to learn more about Roger? Just Google Retirement Answer man or head to rogerwhitney.com we'll also include links in our show [e-mail] thanks to Jackie Cummings Koski for hanging out with us today. Check out her book Fire for Dummies or her incredible podcast Catching up to Fi wherever you listen to the finest podcast. And finally, thanks also to OG for joining us. Looking for good financial planning help? Head to stackingbenjamins.comog for his calendar. This show is the property of SB Podcast, LLC, Copyright 2026 and is created by Josal Sehai. You'll find out about our awesome [e-mail] along with the show notes and how you can find us on YouTube and all the usual social media spots. Come say hello. And oh yeah, before I go, not only should you not take advice from these nerds, don't take advice from people you don't know. This show is for entertainment purposes only. Before making any financial decisions, speak with a real financial advisor. I'm Joe's mom's neighbor, Doug, and we'll see you next time back here at the Stacking Benjamin Show.

[Joe Saul-Sehy]

What's wrong with you? It's either this show or indigestion.

[Roger Whitney]

I hope it's indigestion.

[OG]

Why? It'll get better in a little while.