BiggerPockets Money Podcast - The Middle Class Trap: Why $750,000 Doesn't Feel Like Enough (Financial Plan)

Episode Date: March 10, 2026

Are you a high earner in your 30s or 40s with a growing net worth — but somehow still feel financially stuck? You might be caught in the "boring middle" — a phase where your wealth is locked in ho...me equity and retirement accounts, leaving you cash-poor, inflexible, and far from the financial freedom you've been working toward. In this episode of the BiggerPockets Money podcast, Scott Trench and Mindy Jensen sit down with CFP David Jackson of  Domain Money to break down the middle-class trap and reveal why the conventional advice to max out your 401(k) may actually be slowing your path to financial independence. David shares three powerful strategic options for DEWK households (dual-income, employed, with kids) to build liquidity, optionality, and tax efficiency — without sacrificing long-term growth. You'll learn the Liquidity First Optionality Framework (LaFaF), how to think about diversifying across Roth, pre-tax, and brokerage accounts, and why psychological freedom matters just as much as portfolio size. Whether you're chasing FIRE, reassessing your retirement strategy, or simply tired of feeling trapped by your own financial success — this episode is your blueprint. To go beyond the podcast: Kick start your financial independence journey with our FREE financial resources - https://biggerpocketsmoney.com/ Subscribe on YouTube for even more content- www.youtube.com/biggerpocketsmoney  Connect with us on social media to join the other BiggerPockets Money listeners - https://www.facebook.com/groups/BPMoney Interested in learning more Domain Money and working with David Jackson? Visit: https://biggerpocketsmoney.com/cfp/ Early Retirement Group, LLC (“BiggerPockets Money”), is acting as a promoter for Domain Money Advisors, LLC (“Domain”) and receives a flat fee for each client who enrolls in or purchases the promoted services. In addition to the compensation provided to Bigger Pockets Money, Scott Trench is a current client of Domain and received non-cash compensation related to his promotional activity. This compensation creates a conflict of interest because the promoter has a financial incentive to recommend the service. Clients should independently evaluate whether the service is appropriate for their needs. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript
Discussion (0)
Starting point is 00:00:00 Mindy and I are so grateful for the following sponsors who make Bigger Pockets Money possible. Tax season is one of the only times all year when most people actually look at their full financial picture, including income, spending, savings, investments, the whole thing. And if you're like most folks, it can be a little eye-opening. That's why I like Monarch. It helps you see exactly where your money is going, and more importantly, where your taxed refund can make the biggest impact. Because the goal isn't just to look backward.
Starting point is 00:00:23 It's to actually make progress. Simplify your finances with Monarch. Monarch is the all-in-one personal finance tool designed to make your life easier. It brings your entire financial life, including budgeting, accounts and investments, net worth, and future planning together in one dashboard on your phone or your laptop. Feel aware and in control of your finances this tax season and get 50% off your Monarch subscription with the code pockets. What I personally like is that Monarch keeps you focused on achieving, not just tracking.
Starting point is 00:00:47 You can see your budgets, debt payoff, savings goals, and net worth all in one place. So every decision actually moves in Edle. Achieve your financial goals for good with Monarch, the all-in-one tool. that makes money management simple. Use the code Pockets at monarch.com for half off your first year. That's 50% off at monarch.com code pockets. When I evaluate debt funds, I look for things like first position loans, personal guarantees, deep experience by the fund operator, low fund leverage, fast liquidity, and consistent returns.
Starting point is 00:01:14 These are some of the reasons why I'm excited to partner with Pine Financial Group. Their fund six offers investors exposure to real estate credit, largely for construction and rehab, with loans originated by an experienced originator with over $1 billion in origination volume. They offer investors an 8% preferred return paid monthly and a 70-30 LP-GP split of everything over 10% paid annually. The lock-up period is nine months with liquidity available within 90 days after that nine-month commitment. The fund is open to accredited investors only. The fund's minimum investment is typically $100,000, but Pine Financial is able to reduce that minimum for bigger pockets money listeners to a minimum of $25,000. Full disclosure, I am personally invested
Starting point is 00:01:52 in this fund through my self-directed IRA. Pine Financial is sponsoring this message and our podcast. Go to biggerpocketsmoney.com slash pine, P-I-N-E. Please note that returns are not guaranteed and may vary based on fun performance. I love Matt, said no one ever. Nobody starts a business thinking, you know what would make this more fun? Calculating quarterly estimated taxes, but somehow every small business owner ends up doing it. Your dreams of creating, selling, and growing, get replaced by late nights chasing receipts, juggling invoices, and wondering if that bad sushi lunch with Scott counts as a write-off. Change all that with Found. Found is a business banking platform built to take the pain out of managing money. It automatically tracks expenses,
Starting point is 00:02:29 organizes invoices, and even preps you for tax season without you doing the heavy lifting. You can set aside money for business goals, control spending with virtual cards, and find tax write-offs you didn't even know existed. It saves time, money, and probably a few years of life expectancy. Found has over 30,000 five-star reviews from owners who say, found makes everything easier, expenses, income, profits, taxes, invoices even. So reclaim your time and your sanity. Open a found account for free at found.com. That's fowundd.com. Found is a financial technology company, not a bank.
Starting point is 00:02:59 Banking services are provided by lead bank, member FDIC. Don't put this one off. Join thousands of small business owners who have streamlined their finances with found. You're in your mid-30s. You're married with kids earning $175,000 a year with $750,000 in net worth. On paper, you're winning. But you've got home equity, retirement accounts, a rental property. you're approaching millionaire status. So why do you feel stuck in the boring middle?
Starting point is 00:03:32 Hello, hello, hello, and welcome to the Bigger Pockets Money podcast. My name is Mindy Jensen, and with me as always is my loves a good financial plan co-host, Scott Trench. Thanks, Mindy. Even more than a good financial plan is my love for duking it out, D-E-W-K, fully employed with kids duking it out about the best approaches for the middle-class trap. We are super excited to be joined today by David Jackson from Domain Money. David is a CFP with Domain Money, and BiggerP's Money is lucky enough to be partnering with Domain Money and David. David is also my CFP and is working on the financial plan for me and Virginia.
Starting point is 00:04:10 It's the first time I have worked with a CFP. We are promoting domain money here at Bigger Pockets Money on a go-forward basis. We have an affiliate relationship with them. and if you work with domain money, bigger pockets money will get paid. We hope that you are impressed with David and that you choose to interview domain money as at least one of the financial planners that you consider. We believe that he's very aligned with fire, real estate investing, and all the things that we talk about here on bigger pockets money. We're going to talk about today the middle class trap, this concept that Mindy and I have talked about several times here on bigger pockets
Starting point is 00:04:42 money and we've invented a average of the middle class trap as it relates to the bigger pockets money audience. We know that a lot of you are duly employed with kids in your 30s and you have built up a substantial net worth. You have a good income, but it doesn't feel flexible. It feels like it's all trapped in your home equity and your retirement accounts. We're going to attempt to articulate that problem and then the consequences of a strategic choice to stop maxing out the 401k and instead pay taxes and do something else to that. We're going to block that plan by David Jackson here for his professional input. So looking forward to that. Without further ado, actually with one more further ado, big shout out to David here as well. David is getting married today, March 10th,
Starting point is 00:05:27 when this episode releases Tuesday, March 10th, 2026. Yes, on a Tuesday. This is his wedding day. Congratulations, David. He will be responding to any comments or follow-ups following that, you know, Wednesday or the next week or whatever in here if you drop a comment in the YouTube channel. But please give him a big shout out. Congratulations. David, to you and your wonderful bride here. So thank you so much for joining us. And without further ado, let's get into it. Scott, we have one more disclaimer. This is a promotion for domain money, a registered investment advisor with the SEC. Bigger Pockets money may receive compensation if you choose to work with domain money as a client. Scott trenches a current client of domain
Starting point is 00:06:06 money and received non-cash compensation related to his promotional activity. This is not personalized investment advice. For the full disclosures, please visit biggerpocketsmoney.com slash CFP. With that lengthy disclaimer, David, thank you so much for joining us. Thanks, Scott. Thanks, Mindy. I'm excited to be here. I am excited to introduce you to our fake couple.
Starting point is 00:06:25 This is a couple that Scott and I made up based on some ideas from the people that listen to our show and have reached out to us. So Scott, do you want to give our overview of who we're talking about? about? Yes. Are we going to go through your LaFaf? We're going to just make up acronyms. Here we go. Liquity first optionality framework LaFoff. Okay. The liquidity first optionality framework LaFoff as Mindy has called it, otherwise known as the middle class trap, right? So this is, what do I do if all of my net worth is stuck in my 401k and my home equity? And I'm approaching millionaire status, but I don't feel free, right? This is a very common problem for the bigger pockets money
Starting point is 00:07:04 listener. We have chosen this persona. This is a Duke duly employed with kids, D-E-W-K, biggerpockesmoney.com slash D-E-W-K if you want to check out this plan. They're high income, $175,000 in household net income. They're strong at savings. They invest in index funds. They've done a lot of things right. But the problem is that their $750,000 net worth is almost entirely in their home equity and their retirement accounts. So they have a choice to make. over the next couple of years. Are they going to continue doing that and continue to stash away almost all of their wealth in their 401k or their home equity? Or are they going to make a pivot? Are they're going to make a tradeoff, a conscious tradeoff that is going to come with real costs
Starting point is 00:07:47 that could enable some optionality earlier in life? So you're with us so far, David? Is this something that you commonly come across? Oh, 100%. Yeah. I mean, I primarily work with folks who are high earners have kids, but there's a liquidity problem, right? So this is right in my willhouse. So let's talk about the balance sheet for this couple. They've got a primary residence with $300,000 in equity. They've got $350,000 in their retirement accounts. They have their three to six month of cash and emergency reserve of $35,000. And they've got a little bit in their taxable brokerage, about $65,000, giving them a total net worth of $750,000, right there in their mid-30s with two young kits. So this is a good result, right? This is a strong financial position,
Starting point is 00:08:33 but again, it comes down to this liquidity crunch. So the cash flow situation is we have $175,000 in gross income. Both spouses are maxing out their 401K contributions. That's why they've been massed so much in their 401K. They're taking home about 97,600 after those 401K matches and their taxes. And essentially all of that is then being spent on lifestyle. Maybe say, a few thousand bucks every year and that's how they've amassed the after tax brokerage account. So their spending pattern is not very unusual, about 34,000 on housing, 21,000 on child care and kids, 15,000 on food and household, 10,000 on transportation, 7,200 on health care and insurance, 3,000 on phones, internet, and subscriptions, 4,800 on clothing, giving, and other miscellaneous categories,
Starting point is 00:09:22 and 2800 on travel and family fund. This is very consistent for a household of four in a medium-cost-to-living area per BLS data. So again, the result here is we've got a very limited surplus in our lives with these numbers. So the problem that we've diagnosed here at Bigger Pockets Money is that this person is basically committing all of their wealth to their 401k and their home equity. And the result is that they just don't feel free. And what this does is this is a very efficient way to build for maximum retirement level net worth. But most of the people on listening to Bigger Pockets Money want something more than that. They want liquidity earlier in life. They want optionality earlier in life. And they don't want to feel stuck with the entirety of the time that their kids, for example, might be growing up.
Starting point is 00:10:03 So, David, so far, are we reasonably accurate with this persona in your experience with, you know, a mid-30s couple that's reasonably good with finance and, you know, starting a young family? 100%. Yeah, I see these types of clients all the time. So, Scott, with the problem that we have is that our fictitious customer, the Dukes, are actually wanting to retire early. They want some relief from the stress of constantly putting money away. And they don't have a lot of money to play with. Their income is about $97,000 after all of their contributions. And they're spending $95,000. There's not a lot of room in their budget. If they did have a big emergency, of course, they could pause their 401k contributions so that they would have the money to do it. But they don't have
Starting point is 00:10:55 a huge emergency fund just a couple of months. They don't have a lot of flexibility in their reality. The goal here, they want to save up $2.5 million for their retirement. But they're in the, what do we call this, the boring middle, the slog, the part of the financial independence journey where you have discovered financial independence, you're doing the right moves, and you're not there yet. And that time period can be 10 or 15 years. And they're finding themselves without a lot of fun in their lives, for lack of a better term. And they're kind of stuck in their jobs. If one of them leaves their job, then all of this plan kind of goes away. This plan is all or nothing. It's get to the end number or it doesn't work at the end of the day. Because if one spouse,
Starting point is 00:11:47 stops earning, you can't really withdraw from the 401k at that point because that puts you in a high income tax bracket and is terribly inefficient or crazy almost to set up a 72T at that point. You can't really begin doing rough conversions if one spouse is still working and take advantage at these tax optimized brackets. So it's really finished the play to $2.5 million in five. And in the meantime, it's going to feel really tight the entire way through. And that is what we call the middle class trap because this couple is on the very upper end of the middle class for sure and they're approaching millionaire status.
Starting point is 00:12:17 This is what the logical end result of following a order of operations, for example, like the Foo order of operations, financial order of operations from the Money Guy Show, or the ones that we've talked about here at Bigger Puckets Money, this is the obvious end result for an excellent adherence to a structure like that. And it's a problem. And I think that's the question is, how do we create a new path that gives us some psychological relief, some ability to feel like, hey, I'm almost a millionaire. Why are things so tight in my household right now? That's the challenge. And at bigger pockets money, we have kind of like three options that we've come up with. And this is what we're going to debate with David, a real CFP here today, right? Or debate or we're going to get feedback from David on. We said, okay, the three options that you have are first, just keep doing what you're doing and feel good about it, right? You're doing great. You're approaching
Starting point is 00:13:07 millionaire status. You're doing the optimal approach from a tax planning perspective, arguably, over a very long period of time, if you just keep maxing at your retirement, except your thin liquidity, your stress is going to slowly age off on this approach over the next 10 to 15 years. And the reason that's going to happen is because your housing costs, your mortgage are going to stay flat relative to inflation, and eventually that will roll off and get paid off. You're probably going to get some kind of raise or some kind of promotion or some kind of advancement at work. And if you keep your, again, housing costs and other fixed costs flat, that's going to create the option for more liquidity to come into your life and increase your savings
Starting point is 00:13:44 rate in a natural sense over those 10 to 15 years. That's option one. That's what a lot of people take, not really a very complex or difficult diagnosis or something that's difficult to understand, but something that's very reasonable. The second step is one, you know, and this goes back to things that I talked about in set for life. People think I'm anti-retirement accounts. I'm not anti-retirement accounts. I just think that for one to three years, if you don't max out the retirement account and instead apply those funds elsewhere. You're going to at some opportunity costs, some theory we'll try to quantify this in a little bit, but at a small opportunity cost, you're actually going to bring in a lot of liquidity into your life. You're going to build a major buffer,
Starting point is 00:14:21 and you're going to feel much better about your option set, whether that's taking a riskier job, taking a lower paying job, like a riskier, like a job at a startup, for example, on that has upside, but has lower base pay, entrepreneurship, all those kinds of things. So this is my, my bias here is that, hey, just declare coastfire. to some degree and stop maxing out the 401k. Either don't contribute at all for one to three years or contribute at a much lower capacity. Of course, I'll take the match during this period. We're going to take free money. But just deprioritize that and pay your taxes and rack up some after-tax liquidity. I believe that that is the fundamental solution to the middle class trap, as hard as it is to give up
Starting point is 00:15:02 that tax optimization for that period of time. And I believe that that will translate to really powerful optionality for this person, a very simple and powerful diagnosis. And the number one thing I want to beat up here with David. And then the third option is to just go whole hog. At this level of income, if you could house hack or sell your cars and, you know, downgrade to economy vehicles or relocate to a very low cost of living area or go into some kind of high risk business venture or sales job that produces enough income or cuts expenses enough to obviate the problem entirely, you can kind of have your cake and eat it too, right? You can max out the entire retirement and accumulate a tremendous amount of liquidity, bringing that freedom into your life or that
Starting point is 00:15:41 optionality into your life sooner. Very few people are willing to do this, but we should acknowledge it as a possibility. So I'll stop here for a second and say, David, how do you feel about this diagnosis of the option set for the middle class trap? No, Scott, I think it's a spot on. You know, I would say in the decade plus that I've been working in financial planning, the typical model is fork one, right? Hey, continue to max out 401. case where you can. Let's get all that pre-tax deduction on your current taxes. And then once you retire, then we can talk about Roth conversions between retirement and requirement distribution age, RMDA, currently at age 75. But again, as we're going to talk, the more we go into this,
Starting point is 00:16:24 fork two is typically my recommended strategy, especially for folks that are bigger pockets money listeners who are more self-directed and driven to say, hey, I want to be a good saver, but I also want to enjoy life with my kids. And you can do both. I think a lot of people say you've got to grind it out. And there's still some grind there, of course. But it's not to the point of where fork three might be. And again, kudos to those people who can do fork three.
Starting point is 00:16:50 But it's not so disruptive to your life that it's causing extra stressors and enforcing a major decision or defining moment in your life. So again, I think, yeah, really focusing on how, do we start to make that turn and discuss how we can diversify, not just our investments, but our income strategies in early retirement too. Awesome. And so the core strategic insight for Fork2 is you have this liquidity in your life. It's just all going to your 401k.
Starting point is 00:17:19 So what we're going to do is we're going to switch for a period of time, one to three years, perhaps, stopping all excess contributions to the 401k in this particular example. This captures the employer match. You're going to take your employer match, but it's not blindly matched. maxing out the 401k to its limit every year, literally the amount of discretionary spending that you can put in there. Everything else, because you're not maxing out the 401k, is going to go to your taxable brokerage account. We're specifically not prioritizing the Roth here either because this is a liquidity challenge. The diagnosis is you're going to get rich either way.
Starting point is 00:17:52 Stop blindly adhering to the most tax-efficient strategy and take some suboptimal approach for a couple of years to bring optionality into your life during the prime of your life while your kids are still, young, while your family is still young, while you can still enjoy some of that liquidity. So you're not going to end up with a huge pile of money you can never spend at retirement. And again, this diagnosis is only for the pretty strongly positioned student of personal finance who is in this problem, who is already coast-fi, who is already likely to build a huge retirement account balance at traditional retirement age and can afford to take some sub-optimization to get that balance of trade-off here. This amount that we're going to max into our taxable brokerage,
Starting point is 00:18:31 we're going to call this the optionality fund, which is going to give us, again, that optionality, that feeling of peace or freedom or flexibility in our life that we're lacking with the current approach. The cost of this transition is real. There is a real tax drag that we're going to assume at retirement. And David, I think this is actually where you, analyzing the situation, might push back a little bit. But I calculated this as you're going to pay taxes now instead of investing in your 401k. and at the end of your journey, that's going to result in a lower terminal net worth if you just take those funds and invest them in your brokerage account, for example, in the same types of low fee index funds at the end of that journey.
Starting point is 00:19:10 But David, I think you have a different opinion on this. You think that the opportunity cost is not the $50,000 to $90,000 that I'm estimating this to be for each year that you deprioritize the 401k and instead invest in your after-tax brokerage account. I can appreciate the model and the thought behind it. I think where the opportunity lies is for most people, it may not be as tax efficient now, but in working with a financial planner, yes, we do care about your tax efficiency today, but we also care about your tax efficiency tomorrow. And so what is the best way to give you the highest level of tax optimization over your entire livelihood is more so what we're talking about
Starting point is 00:19:52 here. So yeah, Scott, just as you pointed out, you're going to give up a little bit on the tax efficiency in the current year. But as we're going to discuss and what I discuss a lot of my clients is, hey, would you be willing to give up a certain level of tax efficiency while still taking your current marginal income tax bracket into effect? That's important. But are you willing to do that now so that when you get to retirement, you are not in the same position as unfortunately a lot of retirees who all they've been told is just save, save, put it away and it's in pre-tax money. and now they're paying way more in taxes than they ever thought they should be in retirement when if we would have just had a more diverse approach like we're talking about here, we could spread out
Starting point is 00:20:38 that tax liability over time instead of taking it all at the end. So I think in a way, is it less tax optimal in the current moment? Yes. But it could create a more tax optimal position over the course of your entire life. Tax season is one of the only times all year when most people actually look at their full financial picture, including income, spending, savings, investments, the whole thing. And if you're like most folks, it can be a little eye-opening. That's why I like Monarch. It helps you see exactly where your money is going, and more importantly, where your taxed refund can make the biggest impact. Because the goal isn't just to look backward, it's to actually make progress. Simplify your finances with Monarch. Monarch is the all-in-one personal finance
Starting point is 00:21:16 tool designed to make your life easier. It brings your entire financial life, including budgeting, accounts and investments, net worth, and future planning together in one dashboard on your phone or your laptop. Feel aware and in control of your finances this tax season and get 50% off your Monarch subscription with the code Pockets. What I personally like is that Monarch keeps you focused on achieving, not just tracking.
Starting point is 00:21:35 You can see your budgets, debt payoff, savings goals, and net worth all in one place. So every decision actually moves the needle. Achieve your financial goals for good with Monarch, the all-in-one tool that makes money management simple. Use the code Pockets at Monarch.com for half off your first year. That's 50% off at Monarch.com code pockets. When I evaluate debt funds, I look for things like first position loans, personal guarantees, deep experience by the fund operator, low fund leverage, fast liquidity, and consistent returns.
Starting point is 00:22:02 These are some of the reasons why I'm excited to partner with Pine Financial Group. Their fund six offers investors exposure to real estate credit, largely for construction and rehab, with loans originated by an experienced originator with over $1 billion in origination volume. They offer investors an 8% preferred return paid monthly and a 7030 LP split of everything over 10% paid annually. lockup period is nine months with liquidity available within 90 days after that nine-month commitment. The fund is open to accredited investors only. The fund's minimum investment is typically $100,000, but Pine Financial is able to reduce that minimum for Bigger Pockets Money listeners to a minimum of $25,000. Full disclosure, I am personally invested in this fund through my self-directed IRA. Pine Financial is sponsoring this message and our podcast. Go to biggerpocketsmoney.com
Starting point is 00:22:46 pine p i and e please note that returns are not guaranteed and may vary based on fun performance audible has been a core part of my routine for more than a decade i started listening years ago to make better use of drive time and workouts and it stuck at this point i've logged over two hundred and twenty nine audiobook completions on audible alone and i still regularly re-listen to the highest impact titles lately i've been listening to bigger leaner stronger for fitness the anxious generation for parenting perspective and several Arthur Brooks' audiobooks that have been excellent for mental well-being. What makes Audible so powerful is its breadth. Beyond audiobooks, you also get Audible Originals, podcasts, and a massive back catalog
Starting point is 00:23:27 across business, health, parenting, and more, all accessible in one app. If you're looking to turn everyday moments into real progress, Audible has been indispensable for me over over 10 years. Kickstart your well-being journey with your first audiobook free when you sign up for a free 30-day trial at audible.com slash BPMoney. I think this is an important point that I didn't actually model through correctly when I did this the first time until I submitted to you for feedback. But I basically said, hey, you're going to go in at a pretty high marginal tax bracket today. And you're going to come out at a lower tax bracket at traditional retirement under this approach.
Starting point is 00:24:02 And you're saying that that may not be true, that your marginal income tax bracket may be much higher in this situation than what I originally called for. Can you explain that dynamic one more time without, you know, getting so far in the weeds? that it's hard to follow for a listener? I certainly can. So, you know, in our example, we have a household making about 175,000. And taking out, going away with all the extra math of standard deductions and things, that puts them right in the middle of the 22% tax bracket.
Starting point is 00:24:31 So it doesn't really matter if they're putting into their 401ks or not. They're going to be in the 22% marginal bracket. Of course, their effective rate would drop or be raised if they did or didn't contribute to their pre-tax 401Ks. But the whole point is if we say, okay, Let's back off on 401Ks a little bit for now. Let's instead put that into your taxable brokerage accounts. Well, when you get into early retirement and you are pre-age 55, pre-age 50 even, and you're retiring,
Starting point is 00:25:00 well, yes, we can do 72T. We can do substantially equal periodic payments or SEPP. We can do that with our retirement assets. And we probably will to a point. But our goal is during that time, a lot of our cash flow should come. from these taxable brokerage accounts, because the IRS does not see those taxable brokerage accounts, those long-term capital gains,
Starting point is 00:25:23 they don't see that as ordinary income. So when you're looking at tax brackets, it's very likely that if you do this the right way, you could be in the 12% marginal income tax bracket, which means any long-term capital gains taxes are 0%. And that's a massive after-tax win based on current tax law. that's a huge part of this strategy. Yeah, I think what a lot of people forget is that when you sell that $100 stock,
Starting point is 00:25:52 $100 isn't your capital gain. It's the difference between what you paid for the stock and what you're selling in it now. Even if you paid a dollar for it and it grew $99, you're still not paying taxes on that $100. Although most people aren't having such luck, they're buying it at $75 and selling it $100. So you're paying taxes on $25, but you're getting all. $100. So when you're thinking about selling stocks to pay for your lifestyle, your after-tax brokerage, you're looking at a tax bill that's far less than you might be thinking about. 100%. So, David, this actually changes some things in the head because, you know, I like being
Starting point is 00:26:31 intentionally right, not accidentally right on the middle class trap there. It's good to be right. What I'm hearing is, what I'm hearing is I took it for granted when I've been articulating this mechanism that by foregoing the 401k or the pre-tax deferral, I'm going to be sacrificing some tax efficiency. But again, you're saying that in this situation, again, a person who is very heavily concentrated in the pre-tax 401k already, that in their early retirement or certainly traditional retirement, they may actually be better off, or the opportunity costs may be very small or negligible for going into it a taxable brokerage account, because of the different tax treatment of capital gains and qualified dividends versus ordinary income that will come out eventually of the pre-tax accounts. Is that the right way to kind of put a pin in it
Starting point is 00:27:23 for why the opportunity cost is not nearly as much as it might be at first glance in modeling it out? It is. Yeah. And Scott, to that point, I think the biggest thing that some people miss is, well, I'm going to have to pay taxes anyway. And honestly, that's just really not true necessarily. It really depends on your tax situation, both now, but also in early retirement. The next question I have is for the Roth piece. I'm certainly because I'm intentionally not giving up the current tax break in the 401k, the current tax deferral in the 401k, I am also in this situation not getting the Roth benefit. That is a real opportunity cost, right, that we should acknowledge as part of this plan
Starting point is 00:28:06 if I choose to put it in the after-tax account instead of the Roth. Is that right? That's right. Yeah. And I think that there is an opportunity if you're working one-on-one, you know, with clients who I work one-on-one with, that's something I can certainly model out for them, right? I mean, from a general standpoint, it's hard to say because obviously the tax-free growth against potential tax-efficient growth in a brokerage account, whether it's 0% cap gains or 15%. That is something that you really need to get into the weeds to model out for sure. I really think this is a breakthrough. It's very technical, and I'm probably, probably losing some folks. I've got to state it one last time before I move on here, is if you follow the financial order of operations logic too far and too blindly and too well across a personal finance journey, you may actually be under-optimizing relative to for some years, a small percentage of those years, contributing to an after-tracked brokerage account instead. Is that actually a true statement for a good portion of the personal finance community here, including those pursuing financial independence retire early, David? I would, yeah, especially in your client base and those bigger pockets money listeners
Starting point is 00:29:16 that are in that allocation. I would say to kind of close the loop on it, in my experience over the past decade, roughly half of retirees that I helped coach and helped provide plans for were paying requirement distributions in excess of what they actually needed. And so it actually can be less beneficial to do it the traditional way. So I'm excited to talk about a more modern structured approach. Awesome. And by the way, a bunch of the stuff we talked about is even prior to factoring in RMDs,
Starting point is 00:29:44 which are often discussed as, hey, that's an overblown risk or whatever. I think they're pretty real for someone who's optimized on the pre-tax side for a lifetime and shouldn't be dismissed. But even discounting those, your logic holds for a portion of the fire community who wants to heavily rely on the pre-tax accounts. early retirement. Yeah, those pre-tax accounts are key to the bridge years, right? Bridging the gap between the rule of 55, if you're going to retire at 55, or just 59 and a half without taking into account 72T and SEPP distributions for sure. Great. And then one last qualification here I'd like to make because
Starting point is 00:30:18 I think we're going to get some really good feedback on this, or I hope we get some really good feedback on this, is the logic that we're talking about here applies to somebody more in the two and a half million and perhaps more fire target number. For a lean fire portfolio, someone who is looking to spend less than $40,000 a year and build a million dollar portfolio, I don't think our argument holds. And I think that you should contribute the max to the pre-tax retirement accounts in your high-income earning years because your plan implicitly assumes a super low spending target and therefore super low withdrawals from these accounts. Would you agree with that? I would actually disagree, Scott, respectfully, I would say that I would argue that it can be still beneficial for someone
Starting point is 00:31:02 who is only in that lien million dollar portfolio. It can be beneficial to not contribute to the 401k, not max out the 401k for a small number of years. Is that what you're saying? Yes, I'm sorry. Yes, that's correct. Yeah. So if you don't max out, it really depends on the age at which you're retiring. And, of course, when those retirement assets can be in full force. Got it. Okay. And again, I want to keep hammering this thing here. We're not saying that it's bad to max out the 401K much or even most of the time, right? We're saying that if you have only done that across your entire career and you're blind to these other dynamics, you may or you have a very good chance of being under optimized despite thinking that you're pursuing an optimal approach. That's what we're saying here, right, David?
Starting point is 00:31:52 That's correct. I'm feeling real theme here, Scott. I feel seen as well here. And again, I feel like this is something that I could intuit, you know, in a lot of situations. I don't think I could have modeled out, hey, that there's optimal. I think until today, I've been approaching this as, yeah, you know, sometimes being suboptimal on the terminal net worth number is actually a boost to your freedom, life optionality, all the things that we want here in the fire community. to learn that it actually may be a boost to your terminal net worth or fire number or help you accelerate financial independence is actually pretty awesome here and pretty validating. Again, it depends on circumstances here.
Starting point is 00:32:34 But I think that makes sense in the way that David's explained here that there just needs to be other sources of wealth that can't all be in one place or we're going to be suboptimal. And I also think that depending on what you believe about future tax regimes and benefits like ACA subsidy evolutions and those types of things, the flexibility. word is going to be absolutely critical to a financial independence journey and having money in various buckets, including the Roth, the pre-tax, and the post-tax account is going to be the name of the game in that, which no one can model out or assign probabilistically at this point in time. Okay, so let's talk about what enough means in terms of feeling a lived experience in someone's behavioral change. So, David, you work with clients all the time. I've hypothesized that this couple would feel better with $100,000 in aftertax assets that are reasonably liquid.
Starting point is 00:33:25 They'd begin to not fear a job loss at $250,000. And if they got to the $400,000 mark, then the entrepreneurial half of the couple is going to have a very credible and serious case to the non-entrepreneurial spouse, hey, I should probably go out and start this business. I could lose, but I could also win. And it's not going to disrupt their lifestyle if we treat this as, a fallback fund for us. Is that the right way to think about it? How would you benchmark these
Starting point is 00:33:52 stepping stones in terms of the amount of liquidity needed to feel or see a lived change in your client's experiences? Yeah, Scott, I see this all the time where folks, even in our example plan here, clients a lot of times are grinding it out. They're doing what they feel like they should be doing, building up this net worth. Liquidity is key. Liquidity is key, and I can't say that enough because I have clients right now who have great real estate portfolios, and they should. There's nothing wrong with real estate. But at the same time, they have a liquidity crisis. And I'll say, well, you can't really take a brick out of your home and go sell it to pay a medical payment.
Starting point is 00:34:29 Right. So having that diversification across liquid assets and non-liquid assets, those non-liquid assets are good. But more liquidity definitely speaks for sure. What would you kind of advise someone in terms of how? How much is enough? This couple has been very clear for us, this fictional couple. They said, we want to feel like we have options in our life. And we don't right now, even though we have a $750,000 net worth and a pretty good household income here.
Starting point is 00:35:02 How would you quantify that feeling for them to some degree? The quantifying piece is really unique to the individual and the advisor relationship. You've probably heard the difference between risk. tolerance and risk capacity when it comes to investments, but it's the same thing here with liquidity risk, right? I could throw out a number and one couple will say that feels comfortable to me. Another couple says that doesn't. So I think listening to, you know, what are your priorities? Is it just an emergency fund? And you just want to make sure that you don't go into debt again? Okay, well, that number is probably going to be lower versus someone who is more entrepreneurial,
Starting point is 00:35:39 right? Or maybe wants to expand their real estate portfolio or other goals, non-retirement goals. That number is going to be higher based on that because, again, the liquidity risk is greater, depending on that situation, but also how they feel about the flexibility and the diversification across those accounts to make it liquid. It is also going to be important there. So to quantify it is to also speak to the qualitative aspects of that plan. We have a different range in terms of lived experiences here. I've tried to quantify it as if I were this couple, I would feel pretty good about that entrepreneurial bet if I had 400K, in after-tax liquidity, I'd feel okay about a job loss. I wouldn't fear that to the same extent at $250K. And I would still feel personally fairly anxious at $100,000 if one spouse lost a job,
Starting point is 00:36:27 but I wouldn't feel like that was quite enough. And so to me, this implies a two to five-year intentional flow of liquidity to building after-tax liquidity at the opportunity cost of maxing out the 401k. And they're at an annual opportunity cost that I had calculated at 50 to 90, thousand dollars. You say it might be much lower. That may change depending on the timeline and how long they decide to deprioritize the 401k, but the model actually will be closer in many cases than what I, what I estimated here over their retirement. Let's kind of zoom out here for a second and say, what are the aspects of a good financial plan here? And how do you describe, what are the ingredients to a good plan? I really appreciate the question because it's so core to my values and a lot
Starting point is 00:37:12 of advisors values that are trying to help people. So I think honestly, the core values of a good financial plan is truly the plan being holistic and not just focus on investments. Investments are important, but they are a piece of the puzzle, right? What we're talking about here is how these clients are feeling about their freedom, their liquidity, how the money is actually going to be impactful to still do things with their family, still make experiences for their kids and with their kids, but still be able to retire at the age in which they want to, right? That is a much more impactful plan and a sustainable plan than simply talking about, well, here's the numbers around investments. And again, I don't want to diminish that. It's important, but it's not
Starting point is 00:37:55 holistic. So really coming at it from all angles and saying, how is this part of the plan impacting another and what are your priorities? Getting that and laying that out in a holistic plan is of the highest importance. And I think about strategy at bigger pockets, right? As a C, A good strategy, it basically contains kind of three ingredients plus a bonus one, right, which is a clear diagnosis of the problem, right? We understand the factual current situation in crystal clear detail, including strikes, weaknesses, opportunities, threats, and income, in this case, balance sheet. The second is a set of guiding principles, right?
Starting point is 00:38:31 Implicit in that diagnosis is, where do we want to get to? So we know where we're at and we know exactly where we want to get to, right? A clear set of goals is imperative, otherwise if you don't know where you want to get to, There's a million paths you can take. And from there, there's a set of guiding principles, right? Is my plan going to be maximizing my retirement account assets at age 65? Is it going to be flexibility in my 30s, 40s, and 50s? Is it going to be, I'm going to make dang sure I have enough at 65?
Starting point is 00:38:58 And once I'm dang sure, then I'm going to maximize freedom in my 30s, 40s and 50s. Those have to be clearly outlined. And once those guiding principles are set, now we can move into specific action, which diagnoses exactly how, and models out, what these decisions are going to look like in terms of taxes paid today, taxes paid tomorrow, investment return assumptions under these guidelines. The last component of a strategy in this context, a financial plan in this context, is a checklist. Right. There's a bunch of things that are common to every financial plan, like insurance, like estate planning, those types of things that we put in there.
Starting point is 00:39:33 And you and I and Mindy have worked on a very detailed checklist for this persona of, things here that, you know, walk us through what you think are those checklist items now that we've kind of articulated the starting point, the goal, and the core diagnosis here, which is, stop putting all your money in the 401K for some time and you'll have more freedom in your life here. Very simple. That is good strategy at the end of the day, right? It's a clear diagnosis and a very simple or almost obvious output from that strategy. But driving from that now are a number of decisions we need to make in a checklist form to really complete our financial plan. So can you walk us through what you think are the most important checklist items that this, this, this couple
Starting point is 00:40:12 should now put in place to implement this plan. Yeah, Scott, so for this client in particular, and, of course, a lot of our clients fall into this category, number one is insurance. I'm looking at their life insurance, right? Are their kids protected if heaven forbid something should happen to them? So I'm going to recommend like a term ladder, a 10-year term and 20-year term policies that reduce over time. For health insurance, if they're healthy, we're going to go with a high deductible plan with an HSA, right? We're going to max that out because, again, you can use that even in early retirement years for qualified medical expenses and get the triple tax break there.
Starting point is 00:40:49 We've already talked about retirement assets, but I'm going to double down and say, hey, let's get the match. Let's get that free money. But then let's also put in any excess cash flow into these tax efficient direct indexing types of accounts or even if you don't like the direct indexing approach, something that has tax loss harvesting available to maximize after tax returns. That's where I'm starting with these. clients. What about estate planning? What are some things that you're looking for at a very
Starting point is 00:41:12 baseline level for this type of person? I think for estate planning, I honestly, personally, really dig into estate planning. I think it's hyper important, especially if you're a homeowner, have kids. It's something that you're going to want to put together. Definitely at least a will, advanced directives. I know advanced directives are not something or a living will. Some people call it are not attractive, but your loved ones are going to want a piece of paper in their hand. They do not want to guess when they're going through situations in which you can't tell them what your wishes are. Powers of attorney, things like that are very important. And of course, if you have assets like a home and your net worth is in this case, you're approaching a million, you may want to discuss with an estate
Starting point is 00:41:52 attorney a trust or, of course, with your financial planner, a trust to discuss those non-retirement, those non-investment assets and how to accurately leave them according to your wishes to your heirs. What do you recommend in terms of the cadence for this couple in terms of approaching their finances? Yeah, Scott, so it really depends on are they doing it themselves or do they have somebody doing it for them? And of course, I think we're in the same boat. We like the do it yourselfers. I know I give specific guidance. Let's do low-cost index funds. Let's make sure we're rebalancing as appropriate to keep the portfolio the way it should be. Even if you're a do-it-yourselfer, I would say at a minimum, you're probably going to want to meet with your financial planner and rebalance, at least four times a year is key. If you can't do four times a year,
Starting point is 00:42:41 at least two times a year. But I think every quarter is important just to make sure that the portfolio is set up the way it needs to go. What are the other categories of kind of this checklist? What are some other things you're looking for or how do I know that I'm unset if I'm a DIY personal finance student that's applying a plan along these lines? The biggest things, again, are if you have kids, what does that look like for you, right? So I would challenge you. And if you have anybody else in your life, a partner or spouse who's helping with the kids, I would say talk, have a discussion about how you want that experience to be for your kids. Do you want to fund fully public or private? Do you want them to take on some of that? So that's part of that
Starting point is 00:43:18 checklist. And then, of course, meeting with the financial planner to determine the best vehicles, like 529s versus ESAs versus taxable accounts. Typically, I'm recommended 529s. There's also the tax picture, right? Taxes change all the time. We've seen that even though this year. We've already talked about a few things that have changed with ACA credits and things in the cliff there. So it's really important to stay up to date with somebody who's in this all the time. And I'm talking with clients all the time about those tax implications, both now and in the future. We're playing chess, not checkers, right? So how can we be tax optimal across their entire life versus just in the current year.
Starting point is 00:43:59 Awesome. I want to talk about education planning because this is something where I fell very short because of a misunderstanding about how the 529 plan worked. And I don't know if it just was different 20 years ago and has changed. I mean, I'm sure that's that case.
Starting point is 00:44:16 But I was under the impression that if you put money into a 529 plan, let's say I put a total of 10,000 in and it grew to 100,000 and then my kids didn't go to college or I didn't have kids or whatever, I was under the assumption that I lost that $90,000 and all I could get was that $10,000 back. So my thought was, why would I chance that? I'll just continue to invest in after-tax brokerage and then I'll deal with it when I get there. And now I've got a kid in
Starting point is 00:44:44 college. She's in her freshman year of college, and I've saved $0 for her college fund. And I feel like this is something that maybe everybody else understands it and I just made the mistake reading it. But I feel like people aren't contributing enough or they're over contributing to the 529 plan in a way that is detrimental to their retirement and their liquidity plans. I'll actually try being here and I'll say Virginia and I had this discussion with David last Friday, right? Like four or five days ago from when we recorded this. Our decision is to max out those contributions, like an absurd five times the annual contribution limit that you can put in, which we're not going to do. But we're going to take the maximum contribution, which is somewhere in the ballpark of $38,000 and put that in
Starting point is 00:45:29 for both girls this year into our 529 and then call it a day because with that contribution, plus the ones we made in previous years, by the time our three-year-old and infant, you know, turning one this year, go to college, that should be more than enough to cover many of the base expenses there. And I can call it a day. And that does two things for me. One, it gives me the Colorado tax break. and two, it allows that growth to grow and if used for college be used tax-free on that. But we just had that debate yesterday.
Starting point is 00:46:00 Give me your assessment of where we ended up. Did I articulate it reasonably well? Why we like that approach? Yeah, I've impressed, Scott. You know, you remember it a lot, which is good. I'm glad that something stuck with you. No, it was good. I could literally talk for an entire podcast episode about 529 plans and education savings.
Starting point is 00:46:18 So to really slim it down, right? I think especially in today, there are a lot more exit strategies, if you will, for 529 plans that, or excuse me, 529 funds that don't get used than there have been in the past. And so, number one, it's important to have that conversation, just like Scott and Virginia did with me. It's really important to have that conversation with your financial planner to determine really what's the goal, right? You know, are we talking public or private and full or partial funding? But to your point, Mindy, it's really, okay, let's say we get into a situation. The 529s are funded and we're funding them. And, oh, shoot, well, my daughter, my son just got a scholarship, which is great. But now I have all of this excess in my 529 plan. What do I do? Number one, the 529 plan under current tax law, you can roll $35,000 of unused 529 funds into a Roth IRA for that beneficiary. So if your daughter, your son is out of college and they got 35,000 left in their 529, that's just a jumpstart on their retirement, right? So that's an excellent way to use that. The other thing to keep in mind
Starting point is 00:47:28 is there's something called intra-family portability. And there are IRS guidelines around this, but essentially what it means is that any immediate family member, including any future descendants that that beneficiary may have. So if they have kids, you can actually save those 529 funds in that 529 plan and give them to a sibling back to a parent if the parents are going to grad school late in life and they're switching careers or even to their children one day if and when they should have children. So there is some flexibility versus taking it out and incurring the tax and penalty there to you. Is it a taxable event to roll it from the 529 to the Roth IRA? It's not. No. It's not a taxable event up to that $35,000 threshold. And that's once in a lifetime. So just to be clear, it's not
Starting point is 00:48:15 it's not an annual limit. It is a lifetime limit, but it's still a pretty significant event. David, at the, at the strategy level, though, comes back to, these funds are no longer yours, right? They're not part of your fire portfolio once you have used them. Once you have contributed to your kids' 529 plan, they're now your beneficiaries funds, right? I include them in a tracking of my net worth. That's one of the reasons why I created the personal financial statement at Bickerpocketsmoney.com slash resources. How about that plug? That's free, by the way, no email required. That separates out those kinds of things, right? Your 529 plan. are not part of your fire portfolio.
Starting point is 00:48:47 They're going to go to your beneficiary at some point in life. And there's a strategic tradeoff there about your fire destination and your children's education fund, which I think today the question is like what Mindy asked, right, around is there going to be a scholarship or something that offsets those funds? And do you see some people that take this, you know, too far way over funding those those accounts at a significant opportunity cost. Is that fairly common in your experience? I would say it can be common. A lot of the folks that I work with right now at least are, again, in their 30s and 40s, they still have kids that are in elementary high school. But in the instances where I've worked
Starting point is 00:49:30 with retirees who are in retirement, yes, I mean, their kids still would have these 529 funds. And they're typically now using that for their children. So it works out. I think the biggest thing, Scott, that we need to talk about. And it's something that I do a lot with clients. I actually just had a client who had 529 accounts for their kids upwards of a million dollars. And they said, yeah, we could pay for 10 years of private school. And we kind of laughed about it. Right.
Starting point is 00:49:57 So yes, it does happen. But I think that's then generational wealth that right, that you can pass down to to your kids if and when you get there. Do we want to avoid that? Absolutely. For sure. Right. But that really comes down to what is more important to you. as a client, right? Is it, I really want to make sure that college is funded and I would rather
Starting point is 00:50:17 overfund a little bit than underfund? Or is it, no, I want to really focus on my retirement. I'm going to do the best I can for my kids, but if they've got to take on a little bit of this, hopefully I can help them with cash flow during college. But if not, we can help them in different ways pay that off over the years afterwards. So it's really a matter of perspective at that point. That's kind of my plan here is what you just stated, right? Which is I'm going to, I'm a, yeah, I think I funded it. based on reasonable assumption returns. And hopefully it's just a hair short. That means I've nailed it.
Starting point is 00:50:49 And I pay just a little bit with non-529 plans for college in there. Hopefully, hopefully it's short enough where I can transfer that 35,000 rollover to their rods or something like that. Well, let's go back to this couple, right? So because this is a real kind of additional fork here is do I max out my 401K? Do I amass after tax liquidity or do I begin funding kids, education. I can't do all of them, right? I can't, I do not have the liquidity to max out the 401k, max out the Roth, max out the HSA, max out the 529 plans. I have to choose here in my early 30s. What is kind of the bias you would bring to the situation, given what we know about our, our fake
Starting point is 00:51:29 couple in this situation? And knowing the, the cost that Mindy is now paying because she's paid tax, this is all after tax dollars that are going to, to her children's education costs here. I think fork two still fits really well for a multitude of reasons, right? Number one, if we go fork one, maxing out 401Ks, yes, there's a tax optimization for current year. But then we have to get into 72T distributions, SEPP, all that stuff. And what a lot of people don't realize is you don't get to determine the amount of your 72T distributions. There are tests that the IRS allows you to do. And you can only do, there are three different ways you can take them. And so there are limits. So to say that you could fully pay for, your early retirement using those is a lot of times inaccurate. So it gives you a lot more space. It gives you a lot more freedom. Again, diversifications, a hot word, right? Not just investments, but in income. But also to your point, Scott, let's say we get to the point where Mindy is, right? 10 years down the road, this couple that we're talking about, they may have had better jobs or in a much better cash flow position. And all of a sudden they say, oh, well, shoot, we forgot about
Starting point is 00:52:36 the kids or we didn't know about this for our kids. Well, they have built up. a massive liquid account to where now they can front load five years if they want to, right? So priorities change, things change, tax law changes. The importance of fork two is that it gives you the diversification and the ability to mitigate risks when it comes to the future because you have different buckets you can take from. So I guess I'll end it by saying this. My worst cliche or best cliche, depending on if you like cliches, is clients will say, well, what's tax law going to be like in five years?
Starting point is 00:53:09 I say, oh, shoot, I forgot my crystal ball in the trunk, you know, my fault. We don't know, but at least this empowers us and gives us the flexibility we need for the future going down that forked two path. I think that that's an interesting take. And I want to address the seriousness of that decision because I think this is a hard choice for this person. And this is a lived experience for many people who listen to personal financial podcasts on their way to work or at the gym instead of the chain smoker. here is you are reasonably optimized. And there's a decision, right? It's the 401k. It's the after-tax brokerage account. It's the Roth or it's the 529. And I think that the recommendation that we're coming with for this particular financial plan for the reason to be stated is after-taxed brokerage,
Starting point is 00:53:54 build the flexibility and come back to the maxing out of the 529 or the 401k at a future point after we've amassed some liquidity to give ourselves a really nice buffer against the world over the next five to 10 years. That's the hard tradeoff of strategy that is the result of good strategy. Bad strategy is doing a balance across all of those things every year. Good strategy is the decision based on your goals and the objectives and the forced rank ordering of that. And I think that's where we should leave it here, right? That's where it comes down to. And there's many right answers to the question here. But that is the strategy that we've put together in this document. Again, this will be available at bigger pockets money.com slash duke d ewk duly employed with kids d ewk um you can also find
Starting point is 00:54:40 all this at the broader resource library at bigger pocketsmoney dot com slash resources and if you'd like to chat with david who works not just with dukes of course but with a variety of situations including very complex real estate positions and those types of things you can go to bigger pockets money money.com slash CFP. And yes, we are partnered with domain money and yes, bigger pockets money will profit financially, including me and Mindy, if you do choose to work with David. But we really appreciate the partnership, endorse David, and look forward to continuing to work with him. Yeah, thanks, Scott, Mindy. This was fun. Thank you, David. This was a lot of fun. I learned a lot. And I really love learning more about finances. And I have already shot off a email to my
Starting point is 00:55:20 husband saying, we need to talk about 529 plans for both girls. So thank you. you. That's great. Yeah. All right, Scott, that was a fantastic episode with David Jackson. I learned a lot. I'm sure you learned something, too. What did you think of his advice? I love being accidentally right, Mindy. I like being it right on purpose more than more than being right by accident. But I have not thought through the entire implications of what is likely to be, again, likely to be true for somebody who has amassed essentially all of their wealth, all of their financial portfolio, at least, inside of a retirement account and how having a balance can actually dramatically change the tax profile that you can experience in a lived fire or traditional retirement. So I think that was a really
Starting point is 00:56:04 interesting piece there. And I think that the modeling there is going to be very complex. That's going to be something I need to add to my vibe coding toolkit and modeling approach here. But I think that's a really interesting point. And I had not considered that. Our approach does come with a clear opportunity cost in terms of the tax advantages of the Roth IRA, however. I had also not considered the tax implications at the end where I'm starting to withdraw from my 401 accounts and I will be facing RMDs. And I know boo-hoo, what a horrible problem to have. But I didn't optimize for my entire life's tax burden. I optimized in the beginning of our savings and investing for reducing my taxable income now versus reducing my taxable income later. I think I'm going to
Starting point is 00:56:50 ultimately be paying a lot more taxes over my lifetime because I optimized incorrectly. Thanks a lot, David. Wish I wanted to talk to you 20 years ago. I want to call out where and why you are in this position and why it applies. Because your strategy never fully really actually considered the fact that you did and were going to win. And I think this is a huge problem in the fire community. People start out, they're making 50 grand a year.
Starting point is 00:57:17 And they can't see. they don't understand that if they apply themselves, if they listen to financial podcasts instead of the chain smokers for a thousand or five thousand hours over the course of the next 20 years, and that's what they like doing, and they apply themselves at work, and they take advantage of the tax-efficient ways to invest, and they invest in low-cost mutual funds that reasonably reflect long-term average returns, that they're going to do much better than the baseline plan suggests, because they're going to get a raise at some point. They're going to be, you're going to find some opportunity that comes their way.
Starting point is 00:57:49 overtime. And that is not modeled into most people's plans. And because of that, many people are going to end up with way more wealth than they initially bargained for. The 4% rule is already implicitly extremely conservative. This is why I can be so optimistic on average across many conversations. Not everyone will win, but the more likely situation is that people will win far greater and far, far faster than their baseline conservative assumptions put in there. And for this reason, this is why I never prioritized the 401k until I was in a very high income tax bracket, a very high income tax bracket. It's because I'm arrogant enough and also, you know, I think reasonably educated enough as a personal finance to say, I probably am going to win. I'm probably
Starting point is 00:58:27 going to win in the sense that my long-term wealth is going to be very high. And that's going to produce a very high tax burden, especially if it's all inside of a pre-tax retirement account. And further, on top of that comes my bias towards David doesn't have his crystal ball, but I'm going to pull up my crystal ball here and say that you got to be really bold to think that this is going to be the highest tax bracket environment of your lifetime. Donald Trump's administration right here in 2026, I believe is going to be one of the more favorable tax environments, someone like me in the fire community or building a substantial net worth and earning a good income is going to experience. I think that that is a very reasonable bet to make, and I am willing
Starting point is 00:59:09 to play that out from a logic perspective, and I would rather pay taxes now on average than in whatever the future tax brackets come my way. So that's a very important. That is a controversial stance. People can disagree. I would love to discuss that with you, but that is certainly informing parts of my strategy here. So those are the reasons why you're now in this situation, Mindy. And I think a lot of people who are listening to this could find themselves at risk
Starting point is 00:59:33 of that as well, as they're over optimized for that. And they don't, they're not really understanding or internalizing the fact that they could win in a really real way. That will be suboptimal from a tax perspective. Sorry for my rant. No, I always thought that RMDs were just something you pay. But if you set up your accounts correctly, you don't have to pay any RMDs and still win. RMDs are the end result of a lifetime of enormous winning of money not spent, right?
Starting point is 00:59:59 So that's the other one there. So maybe you should start spending now. Yeah, money not spent. I'll say this, actually, let's put this one out there for feedback. Mindy, your net worth, you're not shy about this, is going to approach the eight figure mark within the next few years. Within the next year. And the bulk of that's in your pre-tax retirement. accounts, right? I would have to look up exactly where it all is, but yeah, I've got a lot in pre-tax
Starting point is 01:00:22 retirement accounts. I think that if you pay taxes now, you're going to really thank yourself later, even if you're paying them at the top possible marginal tax bracket for federal and state right now, because I do not believe that whoever the pendulum swings in politics and one day somebody's going to get in power who's going to change those rules at some point. I'll put that out that's a serious assertion. And I would love feedback on that from the comments here. But I would, I would be really interested to see how you and Carl, if you sit down and say, that is the bet you are making right now. You're saying, if I believe a stroke or returns are going to take place in 20 years, I'm going to this number is going to double three times. And then I'm going to be, you know,
Starting point is 01:01:02 or maybe two or two and a half times in real terms, inflation adjusted terms. And I'm going to be withdrawing those when RMD perspective. That's your bet you're making by keeping that in there. Is that the right way to frame it? Yeah, we're looking into 72 T's. But I'm also having like record income years. I know, poor Mindy, boo-hoo, but it's like which one of these levers do I pull? Oh my goodness, Scott, it's almost like I need somebody with professional experience to help me out. Mindy, by the way, you've won. So this is, this is like, but it's perfect to talk to you here about this because if you were in this situation,
Starting point is 01:01:35 the answer would have been, don't max out the 401k 20 years ago, right? It would have been to put them in the after tax bucket here. And we wouldn't have this item here. So you won and I think that's a good illustration of this. And I don't think this is widely understood by the personal finance community. You know, Scott, I think you are correct. I didn't have a 401k match at any company except one that I worked at like 30 years ago. And the match, well, this was back when I think the contribution limits were super low.
Starting point is 01:02:04 But like the match was like $6,000. And I think I was the only person in my department that was getting the match. I mean, I don't think anybody was even contributing to their 401k at the time. But even if I just did that, that would have been great. But then we went above. I mean, we max out Carls. We maxed out mine for years because that's what you do. But if we had not, if we had paid the taxes on it back then, and who knows what the tax
Starting point is 01:02:32 bracket was 20 years ago. I mean, the internet does, but I'm not going to look it up. Our RMD situation would be much different because we still would have invested. We just would have invested in the things that we were all. already investing in an after-tax accounts. So, yeah, it's interesting. All right. Well, if you listen to all of this, we really appreciate you.
Starting point is 01:02:49 You're our favorite. Thank you so much for listening to us. He is Scott Trench. I am Indy Jensen saying, bye-bye, Apple Pie. When I evaluate debt funds, I look for things like first-position loans, personal guarantees, deep experience by the fund operator,
Starting point is 01:03:03 low-fund leverage, fast liquidity, and consistent returns. These are some of the reasons why I'm excited to partner with Pine Financial Group. Their fund six offers investors exposure to real estate credit, largely for construction and rehab, with loans originated by an experienced originator with over $1 billion in origination volume. They offer investors an 8% preferred return paid monthly and a 70-30 LP split of everything over 10% paid annually. The lockup period is nine months with liquidity available within 90 days after that nine-month commitment. The fund is open to accredited investors only. The fund's minimum investment is typically $100,000. The
Starting point is 01:03:37 Pine Financial is able to reduce that minimum for bigger pockets money listeners to a minimum of $25,000. Full disclosure, I am personally invested in this fund through my self-directed IRA. Pine Financial is sponsoring this message and our podcast. Go to biggerpocketsmoney.com slash pine, P-I-N-E. Please note that returns are not guaranteed and may vary based on fun performance. I love Matt, said no one ever. Nobody starts a business thinking, you know what would make this more fun, calculating quarterly estimated taxes? But somehow every small business owner ends up doing it. Your dreams of creating, selling, and growing get replaced by late nights chasing receipts, juggling invoices, and wondering if that bad sushi lunch with Scott counts as a
Starting point is 01:04:14 write-off. Change all that with Found. Found is a business banking platform built to take the pain out of managing money. It automatically tracks expenses, organizes invoices, and even preps you for tax season without you doing the heavy lifting. You can set aside money for business goals, control spending with virtual cards, and find tax write-offs you didn't even know existed. It saves time, money, and probably a few years of life expectancy. Sound has over 30,000 five-star reviews from owners who say, found makes everything easier expenses income profits taxes invoices even so reclaim your time and your sanity open a found account for free at found dot com that's f o undd com found is a financial technology company not a bank banking services are provided by lead bank member fdic don't put this one off join thousands of small business owners who have streamlined their finances with found

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.