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Jill Schlesinger
advice Are you the kind of person
Podcast Host/Announcer
friends turn to when they need help planning a trip?
Jill Schlesinger
I know I am. That means you gotta dig into the
Podcast Host/Announcer
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Jill Schlesinger
welcome to the Jill on Money Show. It's Wednesday, May 27th. Ah do I love a holiday shortened week?
Podcast Host/Announcer
Just four days and then you're on your way, gang.
Jill Schlesinger
So essentially this is like even better than hump day. Cause he didn't work on Monday. Most of you at least. And if he did work, sorry about that. I take every possible day that I can. So any day the stock market is closed, that's a day I don't work. Thank you. Thank you. It's one of the tricks of the trade. Hey gang, are you thinking about something going on in your financial life? Is there an issue that has cropped up that you need maybe another set of ears and eyes on the situation? Why not get in touch with us? Just go to jillonmoney.com and in the upper right hand corner there is a contact us button. When you click that button, a form will pop up. If you're going to write us an email, don't forget to give us a lot of information. Most importantly, don't forget to tell us how much money you spend. That's usually the one piece that we're missing. But that's the cornerstone of reaching any financial goal. Knowing what you spend every month, really important number here. If you are going to join us on the program, you don't have to be quite as detailed. Just check the box. Mark will follow up and do everything else while you're on the website. Don't forget to subscribe to the free weekly newsletter. Comes out on Fridays and we love that newsletter. That is a great way to keep in touch with us and track what's going on. As I've been talking about, gang, our Money Watch show is going to be morphing into a new show. It's called Money Moves and there's going to be. Yes, wait for it video. So it's going to be a lot of fun. Make sure you subscribe to Money Watch right now so you don't miss the beginning of this program. We'll tell you when it is live on YouTube and it'll be so much fun. Check that out. Okay. Today we are joined by Mary from the Bay Area. Hello Mary, how are you? It's early for you. We're talking to you. It's 8 o' clock in the morning for you. 11 o' clock here on the East Coast. So thanks for joining us.
Mary (Caller/Guest)
Thanks for having me.
Jill Schlesinger
What's going on? How can we help you out?
Mary (Caller/Guest)
Yeah, I just have some questions about mega backdoor, Roth versus investing in brokerage. I also have a lot of RSUs vesting this year so I'd like to dig into that.
Jill Schlesinger
All right, I love. This is a Mark, this is what we like to call just. These are like the code words for Mary's got Money. How about that? Maybe you should call that episode Mary's got Money. What should she do? First and foremost, Mark, get ready. I'm ready for you. Are you ready to explain the mega backdoor Roth to the folks listening there? Before we get into Mary's whole story, are you ready to do that for me?
Mark (Financial Expert)
Talking to me?
Jill Schlesinger
Yeah, you.
Mark (Financial Expert)
It's nice that her company offers it because not all companies do.
Mary (Caller/Guest)
Yeah.
Jill Schlesinger
So explain what it is.
Mark (Financial Expert)
It's basically just a mechanism that some companies will allow employees to contribute additional post tax dollars to their retirement plans at work. So you can go way above and beyond the usual. I think it's 24,500 this year.
Jill Schlesinger
And so what's cool about it is that if you can afford it, it's a way to shovel in even more money into the Roth environment. So we're going to get to Mary, to your situation. First of all, how old are you?
Mary (Caller/Guest)
I'm 39.
Jill Schlesinger
Young and bright eyed and bushy tailed. Fantastic. What is your status? Partner, Married, single, What?
Mary (Caller/Guest)
You got partnered, but everything is completely separate.
Jill Schlesinger
Kids or no kids?
Mary (Caller/Guest)
No kids.
Jill Schlesinger
Okay, plan for kids or no kids? What do you think?
Mary (Caller/Guest)
Yeah, no kids.
Jill Schlesinger
Animals or not?
Mary (Caller/Guest)
Nope.
Jill Schlesinger
What?
Mary (Caller/Guest)
I got nothing.
Jill Schlesinger
All right, you got a partner, that's fine, don't worry. Okay. So Mary, how much do you earn right now?
Mary (Caller/Guest)
So my base is 235 and then the RSUs that I have vesting this year by end of year will be 175.
Jill Schlesinger
Okay, so those are the RSUs that are vesting and the taxation of those restricted stock units. If you were to sell them, let's say they all vested tomorrow and you sold everything available, what is the tax liability?
Mary (Caller/Guest)
I guess this is a question for you because historically I have held onto them for a year and then sold them and then put them in like a Vanguard index fund.
Jill Schlesinger
Yep.
Mary (Caller/Guest)
But another option is to just sell them day of or whatever and then put them in the index fund. Just different taxation. So.
Jill Schlesinger
Right. You would be so in your way. It's like they become available, you wait a year because the day they become available, that's your cost basis. But if you wait a year you would be subject to capital gains, long term capital gains rate. But if you needed the money and you or you were like a little freaked out, like oh I don't want to wait or something's going on with the company or you just, maybe you just needed the money because you were, say, buying a house. If you then sold it immediately, you would be subject to short term capital gains. Yeah. Which would be a higher rate for you. Okay. So that's really the difference. So I understand the waiting and it's worked out well for you, theoretically. I'm just wondering like, how that has. It sounds like it probably has. Yes.
Mary (Caller/Guest)
Yeah. I've never needed the money. And so typically I just let it sit there for the year and then once the year hits, I sell it and then put it into a Vanguard fund.
Jill Schlesinger
Okay, great. All right, so let's talk about. Maybe you can do that again. I mean, obviously there's some risk, Right. Like the stock goes down and you're like, oh, God damn it, why didn't I sell that? Right. You look back, oh, I should have sold it. But you know, whatever. With the benefit of hindsight. So right now let's talk about how much is in that brokerage account.
Mary (Caller/Guest)
875.
Jill Schlesinger
Wow. You're so young. You got a ton of money. It's amazing. And what about retirement savings?
Mary (Caller/Guest)
I have 560 in my 401k.
Jill Schlesinger
And that's traditional or Roth?
Mary (Caller/Guest)
Traditional.
Jill Schlesinger
Okay. And any Roth money?
Mary (Caller/Guest)
I have 145 in my Roth IRA. No, traditional Roth.
Jill Schlesinger
When you came on and you said about the mega backdoor Roth, do you have the cash flow to be able to absorb doing a mega backdoor Roth?
Mary (Caller/Guest)
I can. So historically, whenever I've had a couple thousand extra dollars, I'll just dump it into my brokerage. But instead I could stop doing that and then just calculate whatever percentage I, I want to.
Jill Schlesinger
Right.
Mary (Caller/Guest)
And then funnel it in that way. I just, I've never done it for no particular reason.
Jill Schlesinger
Right. It's because it's like a tiny bit complicated. Like the brokerage account is pretty easy.
Mary (Caller/Guest)
Yeah.
Jill Schlesinger
Is there any reason you need money from that brokerage account? Do you own a home or do you and your partner own a home? Or do one of you own a home? Or do you want to own a home?
Mary (Caller/Guest)
I don't own a home and I don't want to own a home.
Jill Schlesinger
Wow. Tell me why. It's like the opposite of what everybody says. What? How do you know so much about yourself? Tell me why.
Mary (Caller/Guest)
I love having one payment that I know of every month and I pay it. Nothing more, nothing less. I hate maintenance. I don't want to deal with anything. And I watched my parents deal with just all sorts of homeownership and property management stuff. And I just want nothing to do with it.
Jill Schlesinger
I think that is hysterical. It's like I want you to be the poster child for why renting makes sense.
Mary (Caller/Guest)
Running the numbers, it actually makes more sense for me to rent than to buy, especially where I live.
Jill Schlesinger
Yeah. I mean, even though you live in a high cost of living area where not just housing costs a lot, but rent is expensive, right?
Mary (Caller/Guest)
It is. I'm afraid to tell you what I pay. Tell me it's okay for a one bedroom. It's about 4,000.
Jill Schlesinger
That doesn't.
Mark (Financial Expert)
We're from New York, you're from New York. That's why it doesn't.
Jill Schlesinger
Yeah, I mean, don't worry. We're very much, you know, adaptive I think. Mark, I don't know if you saw this, but I think that the like the median rent in Manhattan is 4 or 5,000 now. So that's incredible. Especially in a place like New York where we have a lot of housing stock that's cheap. We have a lot of assistance by the city and the government. So we actually have some low cost options. I mean it's not as much as everybody wants, but we have rent stabilized buildings, we have rent control buildings. So that just means that like everyone else is paying a lot more. So. Okay, so we're thinking like maybe a couple thousand bucks a month that is available for the mega backdoor. But I'm not going to say you have to. I'm just saying that would be the availability. And right now are you maxing out your retirement account?
Mary (Caller/Guest)
Yeah, so I max out the 401k, I do the backdoor Roth and then I max out the HSA as well.
Jill Schlesinger
How much is in the HSA?
Mary (Caller/Guest)
85.
Jill Schlesinger
Great.
Mark (Financial Expert)
Your 400. 401K is pre tax or Roth.
Jill Schlesinger
Yeah, the, the traditional 401K is, is 560. And then she's got the her Roth, which is through the back door is 145. And then the question is whether, you know, she's got 875 in brokerage, which is incredible. You first of all, like maybe let me take a breath. You're doing an incredible job, Mary. Absolutely incredible. Amazing. Amazing. Okay. And I think because you have so much money in brokerage, I am inclined for you to do the mega backdoor. I really am. Could you shift to in terms of your just plain old 401k, is there any reason not to use the, the 401k Roth option?
Mary (Caller/Guest)
Not necessarily.
Jill Schlesinger
I mean, I guess in order. It's funny because you have the mega back door. I Guess Mark, there is a case to be made that Mary is in a high tax bracket because she's got, you know, that 235 grand of base, plus she gets these RSUs. So there's some tax. There's tax on top of that. She lives in California high tax state.
Podcast Host/Announcer
So there is a possibility that she
Jill Schlesinger
like finds herself in the, you know, maybe. I'm not saying always, but Maybe in the 35% bracket probably sometimes. Could she use the pre tax for traditional, then put in a bunch of extra money into the mega back door? Would you be game down for that or do you want her to use the Roth no matter what?
Mark (Financial Expert)
Oh, yeah, no, she should be using Roth in my opinion for sure. She's so young, she already has a nice chunk saved pre tax. She should be all in on the Roth. I would make that switch first. I would make all of your regular 401k contributions Roth. See how it impacts the paycheck, See what you're left with on a monthly basis after the fact. And then if you still are left with, you know, a couple grand each month, then that's when you would make the move into doing the backdoor Roth.
Jill Schlesinger
Can you split it between traditional and Roth for your contributions?
Mark (Financial Expert)
I'm sure she can.
Mary (Caller/Guest)
Oh, is that a question?
Jill Schlesinger
Yeah, that's for you. Yeah, for you. In other words, if you didn't want to go. So like it's almost like going cold turkey. Instead of doing that, you're maxing out your traditional right now. So let's just say that you said all right. Right now I'm putting, I'm going to make up the percentage. 15, 18 is going into traditional. Maybe you would do it just to get used to the cash flow implication. Maybe what you would do is you'd say, all right, I'm going to go 10 and 10 and 8. And then slowly but surely get yourself to all Roth. See how it feels. And then the, the mega backdoor would be interesting only if your cash flow feels comfortable enough to absorb it.
Mary (Caller/Guest)
Okay. Yeah, Right.
Jill Schlesinger
And you have a ton of money in brokerage anyway, so. Especially if those RSUs are coming, you know, fast and furiously. Do you get nervous about waiting the year or not?
Mary (Caller/Guest)
No.
Jill Schlesinger
Okay. If you're not nervous, I'm not nervous. You work for a company. It sounds like you had a good experience, gang. A lot of people who are in that situation, they don't want to chance it. So when you have those restricted stock units that become available, the reason to sell it immediately is that you're Kind of either you need the money, so that's number one. But because Mary has all this money in brokerage, it's really not like you need the money. The risk is the stock goes down in that year, you missed your opportunity. And maybe you either hang on or maybe you say, all right, well you know, I'll wait even longer. But that's the risk. The risk is the actual. The company's value drops and you've missed an opportunity. But the upside is you pay at a long term capital gain rate. And you know, again, we're talking about for you in the 30 something tax rate bracket for your money or maybe 35. And you know, as you make more and more money versus the top bracket that you could potentially be paying as a single is probably, you're probably at 18.8 is probably where you are for the long term capital gains. You're not. I mean if you make, if you're making a million dollars a year, it'll be more. But like for now, 18.8, it's like half of what you would pay for your short term. So it makes sense to me to take on that risk. Especially because you don't need the money if you knew you needed the money. I'm buying a house, I'm doing this, I'm going to grad school, whatever it is, then you're just gonna pay it. So Mary's got money. And Mary, you're doing a great job. You're awesome. And are you managing everything yourself?
Mary (Caller/Guest)
Yeah, I feel comfortable managing everything myself. Maybe once a recovery, couple years, I'll meet with a fee based financial advisor and just run things by them.
Jill Schlesinger
But otherwise, who's going to inherit all of your money?
Mary (Caller/Guest)
Part family and part charities. Which is actually another question I had.
Jill Schlesinger
Tell me more.
Mary (Caller/Guest)
Yeah, so in my living will, I have a portion allocated, a large portion actually allocated to charities. And right now what I do is I, I just, I don't know, I kind of spend some money, you know, buying food, buying clothes, whatever, and donate it. But I'm wondering if I should be looking into like a donor advised fund and.
Jill Schlesinger
Okay, I, I have the best idea. I'm so excited right now. Okay, so you know that 175 that you have in your RSU?
Mary (Caller/Guest)
Yeah.
Jill Schlesinger
Okay, so let's say I'm talking to you where it's the end of May. Let's say you're, this money is live, available for you, invested on June 1st. Okay. Just pretend. And let's say that you determine that, at least for now, while you're making a chunk of money. You would really like to get your charitable giving pre funded. Meaning you want to put money into an account that doesn't have to be given away all at once, but that you want it while you have these RSUs, while you have this income, you want to build yourself a little like it's, it's like the mini Mary Foundation. Okay, here's how it would work. So again, let's pretend you're 175 of RSUs. It's now your money. It's the stock, it's the company. It's publicly traded, right? Okay. Now on June 1st, it's in your power to sell it. But if you sold it, what would happen? You'd get whacked with taxes. We've already talked about that. Let's say you were set. You said, hey, I'm going to take. Instead of, let's just, for argument's sake, pretend that you just want to put it all away at once. You could take that 175 of stock, it can be moved into a donor advised fund in one fell swoop. For this tax year, you would be getting a deduction for the whole $175,000 that went into the donor advised fund. So it is a massive tax write off for you. Okay. The second order effect is when you gift it into a donor advised fund, you don't have to pay capital gains on it. It goes in as a charitable contribution. The money that goes into the donor advised fund doesn't go in as stock. Actually, it's sort of like a two step mechanism where it kind of, you say, I'm giving the stock of my company, I'm gifting it into my own donor advised fund. It comes in as cash. You can take the 175 that comes in cash. You can keep some portion of it in cash to give away and you can invest the rest. So you could literally create your own little mini fund to give away to charity. Now it is not the same thing as buying food or clothes. It doesn't have that grassroots effect. But what you could do, Mary, is you could say every year you could say, I'm going to give 10 or 20 thousand dollars away to organizations I care about. You do it directly from the donor advised fund. You don't get the tax deduction when you give the money from your donor advised fund. You've gotten it on the way in. Okay, you could do this. You could do this every year. Again, you don't have to do the whole 175. You could take 50 a year and do that so that by the time you're 45 years old, you've got hundreds of thousands of dollars that you can use to give away if something were to happen to you. And instead of having like the charities listed in the living will, all you would have in the living will is so and so who is, you know, the executor is the person who will make a decision about my donor advised fund, whatever cash is left in that account. This could be an incredibly powerful tool for you while you're making a lot of money. And it does so many things at once. It's sort of like the, the most efficient way to have a slug of money. And this way when you know your annoying friend Jill is saying I'm doing a bike ride for charity, you can just use your donor advice fund to give money to that. If you are invited to do something. If you're in an. If you're like just really into an organization and you say I want to give a significant amount of money away over the course of time, you can make that happen. It's amazing. So the fact that you are charitably inclined. I usually don't have the donor advised fund conversation with people who are 39, but since you said you're charitable, it's a no brainer. Where are you managing your money? Where's the brokerage account?
Mary (Caller/Guest)
Vanguard.
Jill Schlesinger
Vanguard has a donor advised fund. You can do it directly at Vanguard.
Mary (Caller/Guest)
Okay. Okay. Yeah, that makes sense. I just wanted to because I know I'm going to be giving a lot of money away and right now it's pretty much after I die. And so I.
Podcast Host/Announcer
So much more fun to do it while you're alive.
Mary (Caller/Guest)
That's true.
Jill Schlesinger
Yeah, right. You know, and it's like you can get involved in organizations, you can research the organizations. You can really have a hand in this I think is amazing. I'm excited for you, Mary. This is fun and you're real and it's a smart tax decision. By the way, all the money in the donor advised fund, even if it's invested and makes money, there's no tax implication.
Mary (Caller/Guest)
Okay.
Jill Schlesinger
So it's a great way to get that money that is now, you know, again, it was part of your compensation. Restricted stock units and options. And you know, these are the successor to options. This is all money that you would have had in, you know, in salary, but it's coming in stock. It's just that you are able to escape taxation because you are using a charitable organization to help you and it's so great. So if you run into any problems or any other questions, you know, let us know. But I'm excited for you. Congratulations. You've done an incredible, incredible job of amassing this. And I really may come back and talk to you about could you possibly come on our other show and talk about why renting makes sense? Yeah, I try to convince people all the time.
Podcast Host/Announcer
They don't believe me.
Mary (Caller/Guest)
No, I'm very passionate about renting something.
Jill Schlesinger
Oh, so you see, you might come on camera for that. Yeah, we'll blur you out or something. You're trying to figure it out right now. Thank you so much. Hey gang, if you receive compensation in the form of stock units or something that's a little bit different, this is the kind of conversation you can have. How can I best use this? How can I fund different opportunities? How can I be charitable? All these things, they are available to you. All you need to do is get in touch with us. Go to jillonmoney.com click the contact us button. Write us a note, let us know what's going on. If you want to come on the program live, check the box Mark. We'll do everything else you can subscribe to us on the Odyssey app or wherever you find your favorite podcast. Try to do do something nice for someone else today. Change your work, Change your wealth, change your life. Thank you for listening and we'll talk to you tomorrow.
Podcast Host/Announcer
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Jill on Money with Jill Schlesinger
Date: May 27, 2026
In this episode, Jill Schlesinger takes a detailed listener call from Mary, a financially savvy professional from the Bay Area. The core focus is on advanced retirement savings strategies—particularly the "mega backdoor Roth," the prioritization of different investment vehicles, and maximizing the benefits of equity compensation (specifically RSUs or Restricted Stock Units). The discussion expands to include cash flow management, the merits of renting versus homeownership, and proactive charitable giving via a donor-advised fund.
Jill and Mark’s Advice:
Tax Considerations:
On financial fortitude:
Jill: "You're doing an incredible job, Mary. Absolutely incredible. Amazing. Amazing." (11:54)
On renting:
Mary: “Running the numbers, it actually makes more sense for me to rent than to buy, especially where I live.” (10:28)
On charitable giving and DAFs:
Jill: “It’s like the mini Mary Foundation.” (17:25)
Jill: “So much more fun to do it while you’re alive.” (21:46)
On shifting retirement contributions:
Mark: "She should be all in on the Roth. I would make that switch first." (13:29)
On handling RSUs:
Jill to Mary: “The risk is the actual … The company's value drops and you've missed an opportunity. But the upside is you pay at a long-term capital gain rate.” (14:55)
| Timestamp | Segment | |-------------|------------------------------------------------------------------------------------------| | 05:36–06:15 | What is the Mega Backdoor Roth? | | 06:15–11:42 | Mary’s Financial Snapshot (income, investments, strategy, and cash flow) | | 07:15–10:04 | RSUs: Hold or Sell? Tax implications and behavior | | 09:54–10:48 | Why Mary Prefers Renting Over Owning | | 11:42–14:42 | Prioritizing the Mega Backdoor Roth, Retirement Contribution Strategy | | 16:38–17:17 | Self-Management, Considering Advisors, and Charitable Inclinations | | 17:17–21:48 | Donor-Advised Fund Explained and Why It’s a Smart Move for Mary |
For Listeners in Similar Situations:
For Mary:
Jill closes by encouraging listeners to seek customized advice on integrating compensation, investing, and giving (even if, like Mary, “you’ve got money!”), and teases future content on the new video show, Money Moves.
End of Summary