Financial Confessions: The Money Mistakes You’ll Never Forget

You (the financial mutants) submitted your most jaw-dropping, hilarious, and painful financial confessions - and we’re unpacking them all. From underwear that depreciated too much to haunting Bitcoin regrets, these stories will make you laugh, wince, and maybe rethink your own money habits. ⁠⁠⁠Jump start your journey with our FREE financial resources⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Reach your goals faster with our products⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Take the relationship to the next level: become a client⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Subscribe on YouTube for early access and go beyond the podcast⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Connect with us on social media for more content⁠⁠⁠⁠⁠⁠ Bring confidence to your wealth building with simplified strategies from The Money Guy. Learn how to apply financial tactics that go beyond common sense and help you reach your money goals faster. Make your assets do the heavy lifting so you can quit worrying and start living a more fulfilled life. Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Your sausage McMuffin with egg didn't change, your receipt did. The sausage McMuffin with egg extra value meal includes a hash brown and a small coffee for just $5. Only at McDonald's for a limited time.

• 0:12Speaker 01

  Pricing participation may vary. Promotion pricing may be lower than meal pricing.

• 0:16Speaker 02

  This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18 plus.

• 0:41Speaker 03

  This is a big L. It's not a money win. I'm so nervous. Here's what I'm nervous about.

• 0:45Brian Preston?

  If there's a part three.

• 0:46Speaker 05

  That account now has $255,000 in it.

• 0:49Brian Preston?

  Man, Bitcoin just is chasing this guy around.

• 0:54Brian Preston?

  What a special day. The content team has asked you guys to give us your financial confessions. Can't wait to see how this goes, Bo.

• 1:03Speaker 03

  Brent, I am so excited because this is, these are our people. These are our financial mutants explaining some of their money decisions. I'm curious to see how this goes. Let's dive right in.

• 1:14Speaker 05

  So I hate buying clothes. I don't place any value on clothing other than just a utility. And so I wear them beyond what maybe a reasonable person would do. So I had a pair of underwear that had fully started coming apart at the seams, but I kept wearing them because why replace them if they're still functional, right?

• 1:35Speaker 03

  They're not functional. They're coming apart at the seams.

• 1:37Speaker 05

  Well, it got to the point, and not too distant past, actually, 2025 this year, that the entire supportive nature of these underwear, the briefs, was non-existent. So one day I happened to be in the kitchen in said underwear, checking under the dishwasher because I thought I saw maybe a leak or something. So I was on my hands and knees. Without getting into the explicit details, let's just say that I was hanging out, doing some home maintenance that day. And my wife walked in and was not too impressed at the sight that she saw. Told me that I had to throw them away immediately. So I gave in and. Threw him away. Needless to say, those underwear had been fully depreciated and had served in my army of dollars to the full. And I'm still trying to figure out if this is

• 2:21Speaker 05

  a money win, or maybe frugal to a fault.

• 2:25Speaker 03

  This is a big L. It's not a money win. This is a big L.

• 2:28Brian Preston?

  I was gonna pick at the end and be like, obviously he's single. Because nobody, I mean, because I look, I'm Mr. Thrifty Underpants. I am exactly like you, is I see no functionality in the clothes, except for one key difference, one key thing. My wife. I like to look, anything I can do, so that my wife finds me more attractive, I do it.

• 2:50Speaker 03

  You do it, yeah.

• 2:51Brian Preston?

  I've got some shirts and pants that are either too tight, or I think are too scratchy, but you know what? If she gives me a compliment, I'll wear it more often. So it, so to hear you say, first of all, I see no function in my clothing, I'd love to know what your spouse says about that. Because I mean, I think we all want to kind of present ourselves to our spouses in our best foot forward way. The other thing is, underwear is starting to fall apart. What are we doing? I mean, I mean, if you look at total cost for return, I mean, this is, even divide it by how many years? I mean, obviously, you got probably at least 10 years out of this underwear?

• 3:28Speaker 03

  What it sounds like.

• 3:29Brian Preston?

  I mean, so that's not where you're going to fund your Roth IRA. Go buy some new drawers.

• 3:33Speaker 03

  You know the moral that I heard of this story? Who, who does their like, home improvements in their underwears? Right? Like that, like, like that, for step number one?

• 3:42Brian Preston?

  I've seen enough of you on social media, you, Bo, once you leave the house, I mean, leave the office here, you're Matthew McConaughey. You walk around shirtless everywhere on social media. I'm like, Bo Hanson doesn't know what a shirt looks like. So, so you are halfway to where this guy is.

• 3:59Speaker 03

  Pop on the top makes all the sense in the world when you're doing home repairs. But not having on pants, that's just a bridge too far. I say, do, do your chores with pants on.

• 4:09Speaker 05

  So, back in 2016, I contributed $2,400 to my Roth IRA for the year. And the very next month, beginning of 2017, the head gaskets went in my hoop-dee car that I was was driving at the time and wouldn't you know the repair bill was exactly $2,400. I didn't feel confident taking the money from my maintenance sinking fund or my emergency fund because I didn't think I had enough in there and yeah, I withdrew my, my contribution for the year.

• 4:39Speaker 03

  That's what the maintenance fund is there for. The reason why you keep a maintenance fund is when you have maintenance issues come up, you go and draw from it. So I'd be curious like why he made the decision instead of using the fund for the very thing that it's there for, he decided to go into the Roth and pull off those contributions.

• 4:55Brian Preston?

  The, the challenge I'd have for Hank now is because like a $2,400 mistake you can recover from and you had an immediate emergency there. So I'm going to give a lot of grace, but I think if you went and actually put that $2,400 from late 2016 into an S and P 500 fund and go calculate what it's worth now. You'll realize that from an opportunity cost or incremental decision standpoint, I wouldn't do pull that lever again.

• 5:20Speaker 03

  But it is one of the reasons why we love Roth IRAs, that, that lever does exist, even though we never ever want you to pull on it. It is an option. You can get to your basis, penalty free, tax free before age 59 and a half, if you have to. But our hope is that you never actually have to do that.

• 5:34Brian Preston?

  Especially if you have an emergency fund.

• 5:35Speaker 03

  That's right.

• 5:36Speaker 05

  I'm 43 years old. I've been working for about 23 years now. I've been really only saving to my 401k. That's been my only investment that I've been contributing to for the last 23 years. I've also been contributing 5% of my paycheck to a regular savings account. Not a high yield, a regular savings account, earning just point zero, 1% interest. It was just a set it and forget it. I didn't think about what's the best place for my money. So that account now has $255,000 in it and it's killing me knowing what that could have been had I actually invested it in say a Roth IRA or something like that back when I was in my twenties.

• 6:15Brian Preston?

  This is the story of my childhood.

• 6:17Speaker 03

  This, that, that's painful.

• 6:18Brian Preston?

  It wasn't $250,000, but my parents were great at saving money, meaning being disciplined, living on less than they made, but never put their army of dollar bills to work and that, that, that stuff breaks my heart.

• 6:29Speaker 03

  Even worse than that, it wasn't even a high yield account. I mean, even if you're going to build up cash, at least if you're making, you know, Recently, four or as high as 5% on that. That's something, but this is hundreds of thousands of dollars that sat there earning less than 1%. That's Rick, that's devastating. But as you sit here today, what I want you to recognize is that you still have an opportunity move moving forward. You can't go back and make up for lost time, but what you can do is you can adjust your behavior and your strategy today. So that your future looks brighter, but oof, that's a tough one.

• 6:58Brian Preston?

  And you're a vehicle for change, Rick, because you shared this experience. Other people go see this, they go resemble it and they're not going to make the same mistake.

• 7:06Speaker 05

  So my financial confession revolves around Bitcoin. I will never forget in 2008, 2009, my dad telling me in the kitchen table about Bitcoin.

• 7:19Brian Preston?

  He's probably billionaire now then.

• 7:21Speaker 05

  And I was still in high school. He was saying how he had some extra money around and he had around $10,000 to invest. And he was kind of just looking for something to diversify in. He heard about this newfound thing called Bitcoin. He got all excited and said, oh, they think it could go up to $500.

• 7:42Brian Preston?

  Back then.

• 7:43Speaker 05

  I convinced him that it was a scam and that he shouldn't do it.

• 7:49Speaker 05

  I think he would probably be in the tens of millions had he bought back then.

• 7:55Speaker 03

  Here's the problem, Bill. Hindsight is always 2020 because okay, yes, for Bitcoin, that's true. Had he done that back then. But we could name all the cryptos that have come along since then and all the meme coins and all the NFTs. And for every one Bitcoin story, there's probably a hundred other stories of the thing that did not turn into that. So I don't think that your guidance was off. I don't think your guidance was crazy because that was a very speculative investment in 2008. It just happens to be a speculative investment that turned out okay.

• 8:26Brian Preston?

  You could, you could swap out Bitcoin for Amazon, Apple, whatever stock or investment back. Cause I think he said 2008, everything was super cheap back then. But here's the reality, I'll go ahead and play this out so you can release yourself from this prison of mental traps you're putting yourself in. Even if your father would have bought. Ten thousand dollars worth when it was worth twenty thousand, more than likely he'd have sold it.

• 8:47Speaker 03

  He's probably gonna get out, right?

• 8:48Brian Preston?

  He was gonna get out and then go put his money somewhere else. So, I mean, this was not a ten thousand dollar mistake that could have become twenty million dollars, like you said. Yes, if you'd have left it, but there's also all kind of data out there that if you had put a thousand dollars into Amazon at the certain date, it'd be worth millions of dollars now. That opportunity cost thing is gonna be something you'll always deal with. And that's one more reason why I don't like buying specific individual holdings, is because now all of a sudden, your daily emotional happiness is driven by the volatility, the ups and downs of that. It's much better if you're just buying index funds and generalized things that lets you kind of just enjoy your money versus letting your money kind of be the dominion over your daily happiness.

• 9:32Speaker 05

  I worked for a company with branches all over the country, and I got transferred from one branch to the other. The branch they got transferred to was the DC branch, and when that happened, they also transferred my state income tax withholding. However, even though it was called the DC branch, the actual physical location of the office was in Virginia. And I lived in Virginia, so even though it said DC branch, I lived and worked in Virginia. But they switched my tax withholding to DC, and for whatever reason, I could not get them to change that tax withholding. And when it came time to actually file my taxes at the end of the year, my taxes had been taken out for DC the entire year,

• 10:14Speaker 05

  and then Virginia came and said, hey, you didn't pay us any taxes this entire year, so here's your tax bill, and also here's a penalty for not paying any of your taxes throughout this year. And I got so flustered that I just paid the Virginia taxes as well, while also having previously paid my

• 10:29Brian Preston?

  Did you file a mandate?

• 10:30Speaker 05

  DC state tax bill, which I couldn't figure out how to get refunded. I actually worked at that location for three years. The same thing happened for three years. And so, for a three-year period, I paid state taxes to two different states in their entirety, including for a state that I did not live or work in.

• 10:47Speaker 03

  I feel like this is a common theme that we see happen. We've seen this happen with clients before. They get a letter from the IRS, or something happens, it's scary, and the Immediate default response is I'm just gonna write a check to make it go away. I I I'm so nervous. I'm so I'm gonna make this go away. There's probably, if you add up those three years of taxes that she was paying to two separate municipalities, I bet it was substantial material and she was entitled to get that money back. She could have gotten that money back as she'd gone through the process.

• 11:12Brian Preston?

  Yeah, I mean, I I don't I don't know DC's tax rate off the top of my head, but it's probably at least six, seven percent. So you you take that and you did it by multiple years. And then you think about the penalties back in Virginia. This is something, guys, I look, I get it. A lot of do it yourselfers, you don't like to pay fees. You you you just think you go do it all yourself. But this is a perfect example that if you go see the right tax preparer CPA, they can help you unwind this situation because you realize you have three years to go back and perfect and correct the record where you can file amended returns. You can write letters of of of explanation of what actually happened here. And I'll tell you, just from my experience of writing hundreds of tax letters for for clients, is that I think a well-written letter with the right correspondence and attachments,

• 11:56Brian Preston?

  I could have gotten you out of the penalty for Virginia. And if you especially showing the withholding for DC and the and the mix up there from your employer. But then also, you probably could have gotten all of that DC and gotten your name taken off of the DC rosters so that they're not looking for you to be paying in future years. Because that's something that I always tell people with I've had states where they've come after individuals. When you're like, wait a minute, you gotta make sure they understand. Well, yeah, because you want to make sure they understand you're not really a taxpayer in that state. So they can not hold you accountable for for income that you're earning. It's just not going to be taxable in their jurisdiction.

• 12:30Speaker 03

  A lot of us want to be penny wise, but we end up being pound foolish. And this is a great example of that. You likely in this situation, you should have hired a tax preparer or hired an accountant and said, hey, I've got this problem. I don't know how to fix it. I'm going to pay you a fee to help me fix this. And there's a good chance that had you done that, you'd actually ended up in a better spot.

• 12:47Brian Preston?

  I know you said three years, so probably go lose at least one of them. But if any of those three years are still within the three-year window, go get this fixed. I mean, you can still go file an amended return within that three-year window. I'm money, guys. I pull.

• 12:59Speaker 05

  The bow and took $7,000 out of my emergency fund to fund my Roth from 2024.

• 13:06Speaker 03

  You know what?

• 13:07Brian Preston?

  That's not the craziest thing.

• 13:08Speaker 03

  Let's not say I pulled a bow there, but that is a great thing that you can do because one of the beautiful things, we said this earlier about a Roth IRA is that if you put the money in, you can actually access the basis penalty free and tax free if you absolutely have to. Now, don't mishear me. I'm not saying go take all of your emergency fund and dump it in the Roth IRA. But let's say that you have a few months, maybe you got five, six months in the emergency fund and you can pull that 7,000 and fund that Roth. And it brings you down just a touch and you have time to replenish that. I don't think that's the craziest thing in the world because you can't go back in time and fund that Roth. You can only fund this year's Roth, this year, or this year plus up until the tax filing deadline. I don't want you to miss out on that opportunity.

• 13:46Brian Preston?

  As much as I love the coin term, I pulled a bow. I think that, look, you have to ask yourself, is this decision a seasonal decision? Meaning that in this moment to maximize this unique opportunity, this is what I need to do. Or is this, are you now making a behavioral change that you're going to skimp on emergency reserves? Just so you can have this Roth IRA and you keep making that same mistake every year? Then that's a problem, but if this is a season and you're like, it's just, I'm just getting jammed up on the timing of this. I've got some future income coming in and I'm going to do this because it allows me to get the money in the Roth and I could quickly be able to replenish that emergency fund. I'm never going to punish you or, or, or, or give you trouble for a seasonal decision. I just want to caution you from turning this into a longstanding behavior.

• 14:31Brian Preston?

  That's what, that's the mistake I made when I fell into the access to cash trap is that instead of keeping emergency reserves, I was using my home equity line as the emergency reserves instead of just letting it be an additional tool in the safety belt of all the financial tools I had. So that's, that's the only thing I would say is just make sure that this was a seasonal decision, not some new behavior or habit that you're doing. That's going to keep you from having emergency reserves.

• 14:54Speaker 05

  And then fast forward about four more years, my roommate in the Navy told me that he was mining Bitcoin in our barracks room. And he had a couple hundred Bitcoin and I still thought it was a scam. And he tried to get me to start mining it with him with our computers and I I told him I didn't want to get into it because it could be illegal and jeopardize my Navy career. He is probably a multimillionaire right now, too.

• 15:16Brian Preston?

  Man, Bitcoin just is chasing this guy around. It's like he comes around the corner and Bitcoin's there like, you know, so it's just, so poor Bitcoin Bill here is just being haunted by this. I have to amend my previous answer because I was like, look, your dad would have sold it and doubled, but that still wouldn't have gotten you out of your Navy mate who all of a sudden is is mining it down in the corner, letting the US government pay the utility bills. By the way, you were correct. That probably was illegal.

• 15:39Speaker 03

  And I, I love that. Again, I don't even fault you on that advice. I think so often people get so excited about this opportunity, this thing that presents itself. If that thing or that opportunity that has come along might cause you to lose your J O B, the very thing that provides your livelihood, I would think two, three, four times about that before I jump headlong into it. Because if this is something that would have not been permissible in the position that you're in, by all means, it doesn't, it's not something that would likely make sense for you to do. I'm so nervous. Here's what I'm nervous about.

• 16:08Brian Preston?

  If there's a part three.

• 16:09Speaker 03

  I'm nervous that part three is he's gonna got, he would, he's gonna have gotten in at the very height. Like, ah, I finally pulled the trigger and ended up losing my underpants.

• 16:16Brian Preston?

  Okay.

• 16:17Speaker 00

  Your sausage McMuffin with egg didn't change. Your receipt did. The sausage McMuffin with egg extra value meal includes a hash brown and a small coffee for just $5. Only at McDonald's for a limited time.

• 16:29Speaker 01

  Price and participation may vary. Promotion pricing may be lower than meal pricing.

• 16:33Speaker 02

  This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses setup required. Compatibility and availability varies. 18 plus.

• 16:58Speaker 02

  Invested in worthy peer capital to about 25K currently being held for over two years now after a pause was put in place in July of.

• 17:11Speaker 03

  Twenty-three. I don't know if I'll ever get that money back, but we'll see. Right now, when I reach out to the company, they state that they're working on a resolution plan, but they're waiting on the S E C to approve it, which seems unlikely. Sounds like this guy got involved with an investment and that investment ended up going kind of belly up. Maybe it wasn't something on the up and up and so his money's trapped in there. Again, this is not something uncommon, not necessarily this investment, but we see all the time with clients who somebody comes along and they gotta get invested in a private equity deal or a private placement. They gotta do it and all they get excited and they're an accredited investor and they write the check for twenty-five thousand, write the check for fifty thousand and then they recognize, holy cow, I invested in something I didn't understand with some people that I did not know, uh, with a structure that

• 17:55Speaker 03

  I was not familiar with and all of a sudden now my money's trapped and I don't know if I'm gonna get any of it back. I don't know when I'm gonna get it back. If you do not understand something, if you don't know what you're putting your money into, you should immediately pause and think to yourself, man, should I really be putting my hard-earned dollars in this thing or might I be better served putting them somewhere else?

• 18:14Brian Preston?

  Yeah, I mean, that's, this is what, it's back to a point I made earlier. I like index funds. I like things that take the emotion out of investing because behaviorally, this is what us humans tears us up is, is the regrets and getting into investments, being sold something that was not exactly what we needed at that moment in time. I just would try to avoid those behaviors as much as possible.

• 18:34Speaker 05

  Fast forward a few more years later, twenty sixteen, twenty seventeen, I was stationed with the Marine Corps and I had Marines who were living in the barracks and they were mining Bitcoin and making thousands of dollars just by mining it. And I still thought, still thought it was a scam. So fast forward twenty sixteen, twenty seventeen, I finally decided to get into it and bought into Bitcoin right before it really took off and then it took off and it crashed and I sold and I had four or five Bitcoin. And had I just kept always be buying as as Brian says, I would have close to a million dollars.

• 19:14Speaker 05

  I got in and out of Bitcoin a few times over the years and and sold when it would crash because I would get scared. And then foolishly buy in after it went back up. And and now I would, had I just always been buying small amounts, a couple hundred dollars here and there, I would probably have over a million dollars by now. So, yeah, that is my series of stories about Bitcoin and and how it could have been a great investment or and how I also kind of got burned by it.

• 19:42Speaker 03

  You know, when I hear Bill talk, I don't think your problem is that you weren't always be buying. Based on what I'm hearing, based on the emotions that you are suggesting you have when it comes to investing. I don't know that investing in something like Bitcoin matches your specific risk tolerance. Because you just said, when when it crashed, I got scared and I sold. And then when it came back and I felt like I was missing out, I bought back in. That's the exact opposite. You're not buying low and selling high. You're buying high and selling low. That suggests to me that you might not be the type of investor that makes sense to hold such a risky, such a volatile asset as a cryptocurrency. I don't think the issue was that you weren't dollar cost averaging, always buying. I think the issue is that you were investing in something that did not make sense for your unique investor profile.

• 20:27Brian Preston?

  Let it go. I mean, I just think that this is not healthy for you. Walk away from it. This is the spice of life. It could have been the same thing. You could have bought a piece of real estate in your hometown on this corner lot and it would be worth 10 times to 100 times what it was. You could have bought Apple or Amazon. You could, what if, everything in your life, the better decision is maybe go look at the financial order of operations. Start building your plan for success. So, yeah, you can look back and go, yeah, I could have, would have done this, but I'm still all right. That's the biggest thing. Are you all right in your own financial journey and in your own shoes and how you're making a decision? Because everything you've shared, your risk profile is never should have held Bitcoin in the first place. You're too risk adverse, which I would say is a healthy thing.

• 21:09Brian Preston?

  You just got to make sure that the rest of your actions match the journey and the walk. So you're building your own narrative that doesn't have this horror story of Bitcoin jumping out, doing jump scares every every few minutes or weeks of your life.

• 21:23Speaker 03

  Love it.

• 21:24Speaker 05

  Nice try, Feds.

• 21:25Brian Preston?

  Was that, is that it? That was it?

• 21:29Speaker 03

  Well, here's what I love about all of these, all these stories, all these things that we just said is that in our journeys, we might have financial missteps. We might have financial miscues, but that's okay. How your journey begins does not define how your journey has to end, even when it comes to financial mutants. For those of you who reached out, who shared this, thank you so much. We love, we get to share it with the world around us that we can all learn from your mistakes.

• 21:54Brian Preston?

  I still, sovereign citizen, pay your taxes. Thank you for sharing all the, the comments, the confessions, the haunts. We loved it. We love our audience and we love creating this type of content.

• 22:08Speaker 03

  Hey guys, we absolutely love this. If you'd like for us to hear your money miscue, you can go to moneyguy.com/confessions and share your story with us.

• 22:18Brian Preston?

  I'm your host, Brian Preston, Mr. Bo Hanson, Money Guy team, out.

• 22:23Speaker 03

  The Money Guy Show is hosted by Brian Preston and Bo Hanson. Brian and Bo are partners with Abound Wealth Management. Abound Wealth Management is a registered investment advisory firm regulated by the Securities and Exchange Commission in accordance and compliance with the securities laws and regulations. Abound Wealth Management does not render or offer to render personalized investment or tax advice through the Money Guy Show. The information provided is for informational purposes only, may not be suitable for all investors, and does not constitute financial, tax, investment, or legal advice. All investments involve a degree of risk, including the risk of loss.

• 22:56Speaker 00

  Your sausage McMuffin with egg didn't change, your receipt did. The sausage McMuffin with egg extra value meal includes a hash brown and a small coffee for just $5. Only at McDonald's for a limited time.

• 23:08Speaker 01

  Price and participation may vary. Promotion pricing may be lower than real pricing.

• 23:12Speaker 05

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