How much company stock in your investment portfolio is too risky? Can series I savings bonds act as the cash in your portfolio? In the sequence of retirement savings, would contributing to a brokerage account instead of maxing out your 401(k) or 403(b) ever make sense? How should a 20-something self-employed couple, investing monthly in Vanguard’s Total Stock Market Index Fund (VTSAX), get retirement-ready? Is it possible to pay for the construction of a new home and keep the earned income tax credit and child tax credits? Should Roth conversion funds come from an inherited IRA, 401(k), brokerage account, or Social Security?
- (00:59) How Much Company Stock is Too Risky? (podcast survey)
- (03:54) I-Bonds in an Investment Portfolio? (Kevin, Denver)
- (06:54) Sequence of Retirement Savings: Save to Brokerage Instead of Retirement Accounts? (Kevin, Denver)
- (12:37) Self Employed Retirement Planning in Your 20’s: VTSAX and What Else? (Preston, AL)
- (16:26) How to Pay for New Home Construction and Retain Tax Credits? (Nick, Omaha, NE)
- (24:07) Roth Conversion from Inherited IRA, Brokerage, 401(k), or Social Security? (Rose, Southeast WI)
Free financial resources:
Today on Your Money, Your Wealth® podcast 355, YMYW listeners are dialing in their retirement saving and investing strategies: is it too risky to have 7 or 8% of your portfolio in your employer’s stock? Are series I bonds a good investment for the cash portion of a portfolio? Would it ever make sense to save to a brokerage instead of maxing out a retirement account? Besides investing each month in VTSAX, Vanguard’s Total Stock Market Index Fund, how else should a self-employed 20-something couple begin setting themselves up for retirement? What’s a good strategy to pay for construction of a new home and retaining the earned income tax credit and child tax credits? And finally, does it make sense to convert to Roth from an inherited IRA, brokerage, 401(k), or Social Security funds? Visit YourMoneyYourWealth.com and click Ask Joe and Al On Air to send in your money questions. I’m producer Andi Last, and here are the hosts of Your Money, Your Wealth®, Joe Anderson, CFP® and Big Al Clopine, C PA.
How Much Company Stock is Too Risky? (podcast survey)
Joe: All right, “I started participating in my ESPP plan earlier this year. The company gives me a 15% discount on stock price. I deferred the maximum allowed 15% of my pay. The first accumulation period just ended and the stock purchase has taken place. These shares represent about 2% of my total portfolio. To avoid paying ordinary income tax on the gain, I’m considering holding stock for 18 months after the purchase period. But since a new purchase period happens every six months, I will go through three more accumulation purchase cycles before I sell any shares. So it’s possible that the stock could grow as much as 7-8% of my portfolio. Is it too risky to have this much invested in my employer stock? Would it be wiser to sell shares immediately after the purchase, even though it would mean paying ordinary income tax on the gain?” Gives us the ticker, but I think it doesn’t necessarily matter. So ESPP plans, a really good plan for individuals that they can buy their company stock at a discount.
Al: Employee Stock Purchase Plan. Only a few companies offer it. It’s not common, but when your company does, it’s a great plan because you can buy stock at 15% discount. And so the rule is that once you buy the stock, you’ve got to wait a year to sell it. And you still pay ordinary income tax on the discount portion. That goes on your W-2. But the other part, the gain on sale of the stock, is capital gain. And there’s a couple more rules, but that’s the basic rule.
Joe: So if the stock does not change, you automatically gain 15%. If the stock goes up 15%, you just made 30%. If the stock goes down 50%, you didn’t lose anything besides the taxes that you paid. So, 7-8% of your total portfolio? No, I don’t think that’s too risky.
Al: I’m fine with that, too. I would go up 10% or 15% even.
Joe: Yeah, without question. At that big of a discount, you got wiggle room to see if the stock is super volatile.
Al: Yeah. And given 7% or 8%, the only reason you would sell before the one year period is if you felt the stock was overpriced and was going to go down. Then, forget the taxes, cash out and get what you can.
Joe: Yeah, exactly. But from a diversification standpoint, I like the ESPP plan. I would follow the rules on that. I would hold the stock. And then if you do want to diversify, pay the capital gains on any of the gains.
Al: Yeah, it’s a great plan. As you said, right from day one you get a discount of 15%, so you’ve got a gain immediately. So why not?
I-Bonds in an Investment Portfolio? (Kevin, Denver)
Joe: Kevin writes in From Denver. “Hey Andi, Joe, and Big Al. After the beating I took from Joe on my last question in podcast 290, it’s taken me a year of therapy and a lot of barrel aged stouts to seek your insights on another topic.”
Al: You must have been pretty tough on Kevin.
Joe: Come on, Kev, we’re boys.
Al: It’s all in good fun.
Joe: I don’t remember beating up on Kevin. He probably gave us one piece of information and asked for answers on five. Barrel aged stouts.
Al: You like stouts?
Joe: Not really.
Al: I didn’t think so. I do like Guinness.
Joe: OK, let’s see what Kevin’s got here. “What is your take on I bonds in the cash portion of a portfolio? What is the downside beyond the purchase limits and penalties for early withdrawal? With the recent rate increase, it seems like a better alternative than what can be earned in a high interest savings CD account. Historically, I’ve had $100,000 in the CD ladder, but with my higher rate CDs, all my training over the past year, I’m trying to find a low risk alternative that can earn at least a little bit more interest.” Big Al, what’s your take on I bonds?
Al: I knew you’d ask me that. That’s for you. That’s an investment question.
Joe: I bonds. It’s a Treasury bond. Go for it. If you’re going to get a little bit better rate. There’s some liquidity issues there, but it sounds like it’s a cash reserve and emergency fund. If you really need to get out the money, I would imagine you would cash out your CDs early and pay the penalty there. Or not necessarily a penalty, or discount your interest. I bonds are somewhat similar.
Al: Well, that’s a good point about CDs because people are so nervous about the prepayment penalty and all that is, is receiving less interest. That’s how it’s calculated.
Joe: So, I like I bonds. It’s not like I would recommend them. But if that’s something that you want to do. Kevin, I think that’s…
Al: The thing about any bonds, you have a chance for a higher rate of return than a CD, there is a little bit of potential for volatility because the bonds can go up and down in value if you don’t hold them to maturity. So, just be aware of that.
Sequence of Retirement Savings: Save to Brokerage Instead of Retirement Accounts? (Kevin, Denver)
Joe: OK, “second question, if you’re willing, as a follow up to episode 350…” What? How many questions has Kevin asked? He’s got 290, 350, what episode are…
Al: Well, 350 wasn’t his question because he’s finally got the courage to ask it now.
Joe: All right. Sorry, Kevin. My sincere apologies. I’ll have a stout with you. We’ll hang out and have a couple of cold ones. So he’s got “a second question, if you’re willing, as a follow up to episode 350 in the sequence of retirement savings.” So 401(k) to the match, then you go to the max out Roth IRA, go back to the 401(k) and then money into a brokerage. “My wife and I plan to retire in 5-8 years, respectively. We max out our contributions to an HSA, my Roth 401(k), her 403(b) account, along with her annual $7,000 backdoor Roth. But there just isn’t enough extra income to also establish a brokerage account. We currently have 80% in pre-tax and 20% in Roth, with a conversion strategy of eventually reaching a more even mix by utilizing farm rental income for paying the taxes on the conversion. My question: would it ever be feasible to put money into a brokerage account in lieu of maxing out a 403(b)? It seems counterintuitive to continue to put money into the pre-tax savings, only to convert it to a Roth after my wife retires. We’re in the 24% tax bracket and our projected retirement spending will probably keep us within that tax bracket range or even higher. FYI – I am neither an engineer nor a professor as Joe has surmised in the past. I’m a nurse who has become a transition project manager helping hospitals move in open new hospitals, and thus a walking spreadsheet who needs to plan for everything. Thanks again for taking my question, Kevin in Denver.”
Al: So Kevin, you used your excel skills to churn out all these scenarios. What do you think?
Joe: Let’s say you get a tax deduction, 24%. And then you’re going to pay 28% later. So the whole purpose of a retirement account is to get a tax deduction today, have the money grow tax deferred, and then when you pull the money out, you’ll be in a lower tax bracket. That was the whole concept of the 401(k) and IRA plan. Back when they were established in 1974, the highest tax rate was a lot higher than it is today. 50%, 75% or something like that.
Joe: 70%. So if I’m In the top marginal rate of 70% of getting the tax deduction- and the tax deduction there was a lot larger because the tax rates were so much higher. But over time, tax rates have gone down. and now they’re scooting back up, potentially. They’re slated to go up in 2026. So I know for a fact Kevin from Denver has done the planning, he’s done the spreadsheets and he’s taken a look at, with the conservative growth rate, conservative inflation, what tax bracket potentially do I think I’m going to be in? And I think he’s right on. If you’re going to pay 24% tax, do you put that in a retirement account? Have it grow tax deferred, and then when you have to pull the money out, you pay 28% in tax? That doesn’t make a lot of sense to me. Do I want to just pay the 24% in tax, and then put that into a brokerage account?
Al: So you got more tax diversification and you stay out of the higher bracket.
Joe: Yeah, because you’re just loading up. 80% of your money is in a pre-tax account. Another thing I would look at, depending on where his money’s held, if I’m in that 24% tax bracket, you might want to do a conversion at the 24% tax bracket. So convert today versus waiting for your wife to retire if you have money that can convert. If all of your money’s in an employer plan that doesn’t view in-plan conversions, then you don’t do that. But I would do an in-plan conversion or do a conversion to the top of the 24% tax bracket before not saving. Because as I’m saving into the retirement account, that’s lowering my tax bracket and I’m just converting now because you’re already maxing out all your Roth plans, given your income.
Al: Excellent point. It also depends upon what bracket you’re going to be in when your wife retires and how much you should convert, and that would help you figure out what to do today. But I think you’re right on.
Joe: All right, Kev. Again, please accept my apologies. I’m a new man. I was going through a little crabby spurt.
Al: Back in episode 290?
Joe: Yes, it was a totally different man. I’m back. Thank you for all your support.
Kevin asked about investing in I-Bonds – with so many sexier investments out there, why would you want to own bonds? We’ve got a new guide on that very topic and you can download it for free from the podcast show notes at YourMoneyYourwealth.com. Learn about the different types of bonds, the pros and cons of owning them, and the role bonds play in a diversified investment portfolio. If reading financial literature or asking questions on a podcast with a financial advisor going through a crabby spurt aren’t providing the in-depth answers you need for your retirement plans, why not click the Get an Assessment button also there in the podcast show notes? Schedule a financial assessment with one of the experienced professionals on Joe and Big Al’s team at Pure Financial Advisors. It’s free, like the guides and the podcast, but unlike them, this comprehensive financial assessment is expressly tailored for you – your tax situation, your ability to tolerate risk, your retirement needs and goals. Click the link in the description of today’s episode in your podcast app to download the guide to bonds, and to schedule your free financial assessment.
Self Employed Retirement Planning in Your 20’s: VTSAX and What Else? (Preston, AL)
Joe: We got Preston from Alabama. He writes in, “I’m currently 24 years old, I’m getting married in June and my fiancee is 22. We’re in the process of setting up retirement accounts. We are self-employed, so we’re setting up our own accounts. My plan as of now, is to open up two separate Roth IRAs with plans to max them out every single year. Along with that, I want to have one or two accounts that offer a tax benefit. I just finished reading A Simple Path to Wealth. I’ve done my research in considering opening up a Vanguard account and contributing to the VTSAX with a percentage of my salary each month. I was curious to know what else I should be doing and how to set up for the most successful moving forward? I appreciate the advice you can offer.” How to set up for the most successful…
Al: For the most successful retirement savings plan?
Joe: Most successful life? Most successful marriage moving forward?
Al: Well, first of all, VTSAX is the Vanguard Total Stock Market Fund.
Joe: We did a show on that one.
Al: In fact, I recommended that fund to both of my kids.
Joe: Really? I own that fund. OK, Preston, 22 years old here. You’re self-employed. So it’s kind of funny, “well, I’m self-employed, so I’m setting up my own account. I’m going to set up a Roth IRA.” Well, if you’re self-employed, you can do something a little bit different.
Al: You can. You might want to set up a self-employed Solo 401(k), then you can put more in if you have years where there’s more profit than just the $6,000 for the Roth.
Joe: So you and your wife are both self-employed, so I would set up a Solo 401(k) for you and your wife. I would make sure that the Solo 401(k) has a Roth provision in it, so you could put up to $19,500 for both of you because you’re under 50, you’re 22 and 24, and you can put those in your own qualified plan. Unless you have multiple employees. But I’m guessing you don’t because you said you work on your own, you’re going to do this on your own.
Al: Yeah, that’s what I’m assuming, too. And if $6,000 is your number, then that’s what you can put into the Solo 401(k), but it just gives you the flexibility to put a lot more, and we completely agree it should be a Roth IRA. The principal reasons for that is you think about decades and decades of tax free growth, what that’s going to be worth later on. And secondly, thinking about if you’re 24 and 22 years of age, likely your income will go up, so you’re in a low bracket right now, which is the best time, absolutely, to take advantage of the Roth.
Joe: Yeah, without question. And then you can set up a brokerage account. What we like to look at is tax diversification. As your self-employment income increases, then you might go with the pre-tax component of your 401(k) plan. Or you might just stick with a Roth. You could do a Roth 401(k), and then you can also do a Roth IRA. So you can double dip here a little bit. You can really maximize the amount of money that you’re putting in tax free. If you want to save more than that, then we would recommend going into a brokerage account because there you’re going to be taxed at capital gains rates. So I think you’re doing a good job. You’re doing your research, you’re reading books, calling this stupid show. Yeah, I like it. Thanks, Preston. Good luck.
How to Pay for New Home Construction and Retain Tax Credits? (Nick, Omaha, NE)
Got Nick from Omaha, Nebraska, writes, “Hey, Joe, Al, and Andi. Love your show and I appreciate you answering my last question regarding the earned income tax credit. By the way, my four kids do have clothes and eat plenty.” This is the guy that lives off of like, $7 a year.
Al: Yeah, and is getting the earned income credit.
Joe: Crazy. Good for you, Nick. “I have another question regarding the earned income tax credit in paying for a new construction home with cash versus a 30 year loan. Is it best to take the loan for around $300,000 at 3 or 3.5% interest for 30 years or just pay cash? Normally, I would not be on the fence about the decision with interest rates where they are, and I would just take the loan and invest the difference in the market. However, with a paid off house, I can continue to max out on my retirement accounts, 401(k), 457, HSA, around $46,000 annually or close to that. Then I can reduce my AGI from the $26,000 to $30,000 range to get the max earned income tax credit and child tax credit. For 2021, these credits come out to about $6,728 and $1,380 for child tax credits, fully refundable. If the tax credit is not extended into 2022, it would still be over $14,000 per year going forward in return or refund. To sum it all up, is it better to take a 30 year loan at $300,000 at about 3, 3.5% and invest the difference, or get a guaranteed rate of return from Uncle Sam with the tax credit?” This is a very good question. I like it. So the child tax credits ranging from $14,000 to $20,000, that’s 46 to 67 rate of return on the $26,000/$30,000 AGI would need at least 5% to 7% return on the $300,000 annually to keep up with Uncle Sam’s generosity. So here’s the gist: he gets a child tax credit anywhere from $14,000 to $20,000 a year. Because he saved so much money that it reduces his income to pennies.
Al: So he gets the earned income credit and the child tax credit, and it comes out to 20 grand.
Joe: So if he gets a mortgage, now he cannot save as much into those plans because he’s got this mortgage. So it’s like, do I pay off the mortgage and pay cash? So that $300,000 is not earning me any money, but then I also get a $20,000 additional income. So what do you think?
Al: Here’s what I think. First of all, there’s actually another option that you might be missing, Nick. If you get the mortgage, you’ll have $300,000 in your account. You can have less of a salary. You still can have your full withholding. You still can end up with that AGI, just more slowly over time and you’re not paying that interest. That isn’t an option. I think when we look at something like this, the classic statement is if the loan is 3, 3.5% and you can earn 6, 7, 8%, why wouldn’t you do that? Of course, then it’s not guaranteed. There’s more risk. And I don’t know whether you’re good with that or not, with risk. But anyway, what would I do? I mean, it’s kind of a toss up, really.
Joe: I love where your head’s at here. Your mortgage is going to cost you about $16,000. You’re going to receive a $20,000 tax credit. So if you take a mortgage and it’s going to cost you $15,000, you still save. What Al was saying is like, fully fund your 401(k), 457, HSA plans, your AGI is still going to be that low because you’re maxing out all these plans. And you’re thinking, “Well, what are you guys talking about? I still owe the $16,000. I know I can live off of $7 a year, but come on, let’s be realistic, I got a mortgage now.” But you still have $300,000.
Al: Yeah, that probably makes the most sense because it’s cheap money.
Joe: It’s cheap money and the credit is paying his mortgage. Because he wouldn’t receive the $20,000 if he didn’t have the AGI as low as he has it. So he takes the mortgage. He takes $15,000 from the $300,000 each year to pay the mortgage, but he’s also getting an additional $20,000 of tax, so he gets it right back.
Al: And the way that you do that is you fully fund your retirement plans, but now you just have a lower net pay and you supplement that lower pay with the $15,000 you’ll take out of your account, or whatever the number is.
Joe: So here’s the planning or spitballing for everyone else, is people are like, “Oh, I can’t really afford to max out my 401(k) plan”, but they have $200,000 sitting in a brokerage account, or maybe $100,000 sitting in cash. It’s like, no, fully fund your 401(k) plan. Yeah, your paycheck is going to be lower, I get it. But you have other capital to supplement. The only way to get money into the 401(k) is from your paycheck. So you just kind of play with the money a little bit.
Al: Yeah. And we hear this from different people when we tell them to max fund their 401(k) so that they can create a deduction so they can do a Roth conversion, they’ll say, “Well, I can’t live on that net pay.” It’s like, well, you got $500,000, why not just supplement your savings? And you end up with the same money, it’s just more is in a Roth IRA.
Joe: Your net worth isn’t changing, but how your net worth is going to be taxed in the future changes. So it’s making sure that you’re utilizing all the plans and maneuvering the money in such a way that you’re taking advantage of the tax code. Like Nick here, he’s like “here I want to buy this house. Should I just pay cash? So I get the $20,000?” Wait a minute. You can still get the earned income tax credit because you can still save that much, but you’re just paying your mortgage from another account and then the credit comes back to you and you just plop that right back in. So good luck, Nick. Thanks for the question. Hopefully, that helps.
We’ve got two new free guides ready for you to download from the podcast show notes at YourMoneyYourWealth.com: First, find out how to maximize the tax deduction you receive from your donations to charity in our Charitable Giving guide with Steps on Informed Donating. Next, learn how to fast track your retirement savings, regardless of your current account balance with our Tips to Fast Track Your Retirement. Download both of these new guides, and revisit that episode that touches on the Vanguard Total Market Stock Index Fund, where the fellas answered the question, why not just go “all in” on VTSAX? Access all three by clicking the link in the description of today’s episode in your podcast app to go to the show notes and look for Free Resources.
Roth Conversion from Inherited IRA, Brokerage, 401(k), or Social Security? (Rose, Southeast WI)
Joe: Rose writes in From Southeast Wisconsin. “Hi Andi, Big Al, and yo, Joe.” Yo, what’s up, Rose? Here’s for the important stuff, “Call me Rose. I drive a 2006 Toyota Prius. Got to love the 57 MPG”. Have you ever driven a Prius, Big Al?
Al: I test drove one once.
Joe: I knew you did, you green vegan.
Al: I’m for saving the Earth and making us healthier. Have you driven a Prius?
Joe: I’ve never been in one.
Al: Annie was getting a new car and she wanted a small car, so she drove the Prius C that had just come out. That’s a little one. Tiny. And to try to get on the onramp of a freeway, that was an adventure. So I said, I don’t think this is the one.
Joe: Rose has no pets anymore. “I’m 57 and retired, retired at age 55. I own my home with no mortgage. I have no earned income.” So everything’s coming from her investments.
Al: Investments or pensions or both.
Joe: “This is about Roth conversions. Sorry, no back door. I don’t want to deal with the pro-rata nonsense.”
Al: You can’t do a back door with no earned income anyways, so that works.
Joe: I think you’re fine. Rose. Yeah, no worries. “I can take money from one or more of four sources to do Roth conversions from traditional IRA 401(k) accounts.”
Al: So she’s probably talking about paying the tax, I’m guessing.
Joe: OK, we’ll see. “I could take about the same amount of money from each source. The four sources I could take the cash out of are…” So she’s getting an RMD through age 87 on inherited IRA, just for edification, everyone out there, you cannot convert an inherited IRA, but if you’re taking cash from the inherited IRA and you’re reinvesting it or spending it or potentially using it, to pay the tax on conversion, you can. Brokerage account. That’s just a non-qualified capital account. 401(k), the rule of 55 applies. So what she’s stating there is that if you have a 401(k) account, you can pull money from a 401(k) as long as you separate from service from that employer at age 55. Rose is 57. So she does not have a 10% penalty when she pulls money from the 401(k). And she could take Social Security starting at age 62. So she’s 57, Social Security is a couple of years down. So here’s just a few things, this is a pretty long question, but here’s what I’m trying to figure out now. She has no earned income, and so she doesn’t want to do the back door because she doesn’t want to do the pro rata stuff. “No backdoor, I don’t want to deal with the pro rata nonsense.”
Al: Unless you’re married and your husband has earned income.
Joe: But if you have a 401(k) account versus an IRA, there is no pro rata rule with the 401(K)s, it’s just the IRAs. So you could put everything into your 401(k). So there’s ways around the pro-rata rule. Maybe she’s got a big retirement account that she’s trying to convert, and she’s got these different areas of access money outside of the big 401(k) that she can use the money to pay the tax. OK, “I understand the tax implications of the RMD 401(k), that’s ordinary income tax.” So, brokerage account is going to be 15%. If she takes Social Security, 15% of that is going to be tax free. “As a note, the funds are being converted to get them into a tax free account and to reduce my future tax bracket,” which she believes is going to be in the 28% or 33% if she does nothing.
Al: Wow. OK, so she’s got a lot of income, other income.
Joe: “The longer it takes to move the funds, the more years I’ll be in a higher tax bracket. The plan below includes my personal spending budget and the rest is for conversions in taxes.” So she’s going to convert up to the 24% tax bracket and then she’s going to convert to the 28% tax bracket when the tax brackets change and then hopefully in 2030 and thereafter, she’s going to convert at the 25%.
Al: And by the way, the tax brackets change in 2026, at least they’re scheduled to right now.
Joe: “So ideally, I’d like to have most or all conversions done before the age 70 when RMDs kick in. This is my plan, unless certain presidential administrations mess up my plans again. I live in a state that collects tax.” She wants to move to a tax free state. We’re currently in low tax time. She’s in the 22% tax bracket versus the 25% when rates increase. “I know at the end of 2025 the brackets are planned to increase. If I use ordinary tax funds, the remainder of the tax bracket for conversion shrinks due to the higher ordinary income tax.” So she’s going to do a conversion, but she has to pay more tax on the conversion so the amount she can convert is lower. “However, the federal tax bracket percentages are lowered, so maybe it makes sense because I’m in a low tax environment. Maybe I use these lower ordinary income rates to get the money out versus using ordinary income rates in the future to get the money out.” I think that’s the gist of the question. What do you think? Because she’s going to be in the 28% or 33% tax bracket if she does nothing? Here’s the biggest rule of thumb: if you stay in the 28% or lower, that’s what your math should look like.
Al: And so it depends how much funds you have in your brokerage account or how much your required minimum distribution from your inherited IRA, which of course, is taxable. So let’s start with inherited IRA. With that, you’ve already got that income. It’s already factored in so you can convert up to the top of that bracket. Your brokerage account will be capital gains. You can then pay a 15% tax likely on that. 401(k), you’re going to have more ordinary income.
Joe: So I guess the question is should she use ordinary income tax or capital gains tax now in a low tax environment?
Al: Well, we don’t know enough about what these numbers are, so it’s impossible to say.
Joe: No, it’s not. If you’re going to take money from a retirement account and pay the tax, include the amount of money that you’re paying in tax and make sure that your effective rate is going to be the same or lower when you do a tax projection in the future. I think Al is still super confused on the question.
Al: I thought, that’s what I said. I think you’re confused about my answer.
Joe: No, because you just repeated, “the capital gains tax is 15% and ordinary income taxes are going up.” I mean, I just read the question. Maybe you weren’t listening.
Al: All right. Whatever.
They’re like squabbling brothers sometimes, aren’t they? They’re way behind on answering your voice messages and emails since Big Al has been vacationing in Tahiti, but we’ll start catching up next week. Make sure you’re subscribed to the YMYW podcast so you don’t miss a thing.
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