Financial Advisors React to Massive Money Mistakes

Summary

Money Guy Show — "Financial Advisors React to Massive Money Mistakes"

Hosts: Brian Preston & Bo Hanson
Date: May 18, 2026

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Episode Overview

In this episode, Brian and Bo dive into real-world examples of major financial blunders, reacting to stories from listeners and interviewees who’ve made costly money mistakes—from ill-advised car loans to risky entrepreneurship, student loans, botched real estate decisions, and beyond. The hosts don’t just critique; they break down where things went wrong, offer actionable advice, and remind listeners that while mistakes come with a cost, they’re also powerful teachers. The tone is approachable, candid, and laced with their trademark humor and skepticism for “too good to be true” financial strategies.

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Key Discussion Points & Insights

1. Massive Money Mistakes: Kicking Things Off

• Costly Car Loans
  • [01:16] TK, a guest, describes financing a Dodge Charger: “300 monthly payments for only 10 years.”
  • Brian quips: “He's going to pay it off and then be able to put an antique tag on.”
  • Bo clarifies the Money Guy car buying guidelines ([01:36]):
    • Put 20% down
    • Finance for no more than 3 years (36 months)
    • Payments should not exceed 8% of gross income
  • Bo warns: “If you [break these rules], you can prevent your car from becoming financial napalm.”

2. Entrepreneurship & Home Equity Risk

• Using Home Equity to Fund a Business
  • [02:12] Robert shares: He borrowed against his property to fund his business, leading to foreclosure on his childhood home.
  • Bo explains: Replacing unsecured debt (like credit cards) with secured debt (like a mortgage) puts your house at risk ([02:46]):
    • “It is not a sound strategy, and it adds a lot more risk to your financial life.”
  • Brian’s “3D Glasses” Planning ([03:35]):
    • Dream: Ideal scenario
    • Down-to-earth: Realistic scenario
    • “Doo doo”: Worst-case scenario
    • “If he had done that, you'd have still had grandma's house.”

3. Student Loans & Life Decisions

• Regret Over Degree Costs
  • [04:28] Interviewee reveals: “Paying $100,000 for my bachelor's degree.”
  • Still owes $40,000; uses the degree but questions the cost.
  • Bo points out:
    • Many take on huge student loans without understanding the magnitude (“you can end up taking that student loan well into ... your working career” [04:44]).
    • “You want to make sure you do that well.”
  • Brian adds on relationships:
    • “Don’t let it just be how much somebody gets you excited because you think they're pretty or attractive … If you're not talking about religion, kids and how you do money, you're probably skipping a lot of the steps.” ([05:05])

4. Investment Fails & the Importance of Due Diligence

• Taking Bad Stock Advice
  • [05:21] Interviewee recounts losing money following a family member’s stock tip.
  • Shares: “Only person responsible for your money is you.” Mentions Oprah signs every company check over $10k.
  • Bo underscores:
    • “Not all financial advice is created equal.” ([05:57])
  • Brian advises:
    • For beginners, seek structured mentorship and follow proven steps like the Money Guy “financial order of operations.” ([06:08])

5. Costly Home Improvements & Poor Loan Choices

• Solar Panel Loan Mistake

  • [06:46] Caleb owes over $30,000 on a solar panel loan, unsure of interest rate or payment term.
  • “There is a small window … where solar panel loans work. That's when they're like 2 to 3, maybe 4% ... This is not returning the value.” ([06:58])
  • Bo notes:
    • Many end up financing upgrades for longer than they’ll use them.
  • Brian emphasizes:
    • “Don’t assume the person that's selling you the product is going to do math for you … their incentives are not aligned with your incentives.” ([08:10])

• Red Flag: Not Knowing the Details

  • Bo: “A big red flag … they always know their payment, but not the term or interest rate. … If you're borrowing money, you can’t tell me for how long, what the interest rate is … you don’t know enough about the money.” ([08:45])

6. The Condo Money Pit

• Confusing Ownership with Investing
  • [09:25] Condo Owner: “Buying a condo … is actually just a money pit. Every year I have a tenant paying $2400 a month … not covering my overhead cost … I’m out $6,000 a year.”
  • Bought due to comparison with others—felt left behind, assumed property is always an investment.
  • Bo:
    • “Personal finance is personal. … If the reason [for buying] is to check a box … you're not doing it for the right reason.” ([10:39])
    • “Renting is giving yourself future flexibility and options, and sometimes that is more valuable than trying to build equity.”
  • Brian:
    • Warns about condo association fees: “[They] are getting to be as large as the mortgage ... imagine how hard it is to sell that property with that large condo association fee, too.” ([11:21])

7. Rapid-Fire Money Regrets

• Assorted Mistakes Shared ([11:57]-[12:34]):

  • Using home equity for car purchase
  • Investing too quickly without knowledge
  • Traveling on maxed credit cards (“That stays with you. It takes a long time and it multiplies.”)
  • Cashing out a 401k (with penalties) to buy a boat

• Brian’s tongue-in-cheek take:

  • “Did he say that's how he met her? ... He got a dividend from his horrible financial decision.” ([12:37])

• Bo sums up:

  • “A lot of these were impulsive financial decisions ... but when you're doing them impulsively and you're making poor financial decisions to allow those things to happen, you are getting your financial life out of order.” ([12:46])

8. The Job-Hopping Debate

• Staying Too Long at Your First Job
  • [13:39] Career expert: “There is a study that shows people who stay in the same company for more than two years on average make 50% less over their lifetime.”
  • Brian challenges the advice:
    • “Not all jobs are created equal ... Sometimes the grass is greener where you water it.” ([14:21])
  • Bo:
    • “If you look like you're bouncing around, [as an employer] we’re like, why would we invest in this person that's not going to actually set roots ... Self-evaluate and really look at the scenario … don't just assume because you watch some content ... that your career opportunity might not be just incredible.”
  • Brian: “Context matters … advocate for yourself if you are getting, you know, if things aren't going well. But don’t just assume … you need to go change jobs because not all jobs are created equally.” ([15:24])

9. Core Theme: Personal Finance is Personal

• Bo wraps up:
  • “Personal finance is incredibly personal. So be careful listening to a 30 second clip or a minute clip of somebody telling you something you must do … it may or may not make sense in your situation for your unique variables.” ([16:30])
• Brian closes:
  • “A side effect of making mistakes is that you get wisdom, guys.” ([17:02])

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Notable Quotes & Memorable Moments

• Bo ([01:36]): “We want you to do 20, 3, 8. We want you to put 20% down. We don't want you to finance for any more than three years. … We do not want your total monthly payment to exceed 8% of your gross income.”
• Brian ([03:35]): “Make sure you put on your 3D glasses ... dream, down to earth, and doo doo plan. … If he had done that, you'd have still had grandma’s house.”
• Interviewee ([05:21]): “Only person responsible for your money is you. … Oprah told me that she signs every check in her company above $10,000.”
• Bo ([08:45]): “If you're borrowing money, you can’t tell me for how long, what the interest rate is … you don’t know enough about the money.”
• Condo Owner ([09:25]): “Buying a condo … is actually just a money pit. … I felt like a failure because I did not own property.”
• Bo ([10:39]): “Renting is giving yourself future flexibility and options, and sometimes that is more valuable than trying to build equity.”
• Career Expert ([13:39]): “People who stay in the same company for more than two years on average make 50% less over their lifetime.”
• Bo ([16:30]): “Personal finance is incredibly personal. So be careful listening to a 30 second clip ... it may or may not make sense in your situation for your unique variables.”

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Important Timestamps

• 01:16: Outrageous car loan example
• 02:12: Using home equity to fund a business—losing the family home
• 04:28–04:44: Regretting $100,000 student loan
• 05:21: Losing money on bad investment advice
• 06:46–07:42: Solar loan confusion & the problem with only knowing your payment
• 09:25–10:39: Condo as a money pit; peer pressure and homeownership myths
• 11:57–12:34: Rapid-fire money regrets (home equity for a car, credit card travel, cashing out 401k for a boat)
• 13:39–15:24: Staying at a job too long; challenging “job-hopping” conventional wisdom
• 16:30: The episode's core lesson: “personal finance is personal”

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Summary Takeaway

Financial mistakes come in all forms—from buying cars on terrible terms and leveraging home equity for risky ventures, to misunderstanding homeownership, taking bad investment advice, overspending on advanced degrees, and more. The Money Guy approach stresses due diligence, understanding the numbers, and making personal, context-driven decisions—not just following what “everyone” says or does. Mistakes are inevitable, but they’re incredible teachers if you pay attention.

Philopsophy this episode:
Before you make a big money move, slow down, do the math, understand your personal context, and don’t let comparison, emotion, or impulse drive your decision. At the end of the day, your choices are personal—and so is your path to wealth.

Transcript

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[Brian]

Why go small when you can go massive? That's what we're covering today. Massive money mistakes.

[Bob]

I am so excited to see what the content team has in store for us today.

[TK]

Going on, folks, it's your boy.

[Ashley]

Score got me rolling and Ashley got me rolling.

[TK]

And today we got my dog TK. We got him approved on this Dodge

[Brian]

Charger, 120 bucks, 10 years.

[TK]

Great experience. I highly recommend it. They got me on 300 monthly payments for only 10 years.

[Brian]

He's going to pay it off and then be able to put an antique tag on.

[Bob]

That's yeah buddy, that's oh I if it's still rolling.

[Brian]

Like unlike Steve O, we believe that

[Bob]

there's a better way to buy cars. We want you to do 23, 8. We want you to put 20% down. We don't want you to finance for any more than three years or 36 months. By the way, 120 months is more than 36 months and we do not want your total monthly payment to exceed 8% of your gross income. If you can do that, you can prevent your car from becoming financial napalm

[Brian]

in your financial I'm surprised Steve O hasn't figured out how he can slap a tent in the trunk and then give him the mortgage interest deduction for how long he's financing these cars.

[Bob]

I don't know that I want Steve O to get me rolling.

[Brian]

People willingly go in to get slaughtered financially.

[Robert]

Holding company is very successful. Made it to seven figures. They have no coaches, no mentor, none of that. What I did was I was borrowing from my property to invest into my clothing company. I didn't know about credit, didn't know about funding. I didn't even know that I could borrow from my own property to invest, so I was using my own cash. So when we started to have issues where with cash flow, I wasn't paying my mortgage.

[Bob]

That's correct.

[Robert]

So then my house got foreclosed on. And it was a house that I grew up in. It was a house that my grandmother fought for to purchase when she moved from, you know, a different state. She was living in New Jersey. So when I lost that house, bro, I was super embarrassed.

[Bob]

You know, this is a great example. Obviously, his was an entrepreneurship thing. He took equity out of his home to invest in a business. But we see this all the time. Someone might have credit card debt or auto debt or student loan debt, and they come up with this great idea, hey, you know what? My mortgage or mortgage rates are lower than the rates that I have on my credit card and lower than the rates I have on my car, lower than the rates I have my student loans. So what I'm going to do is I'm going to go take a home equity line, I'm going to refinance my mortgage, take that cash out, and I'm going to consolidate that debt into the mortgage. And one of the problems is if you replace unsecured debt like credit cards, like student loans, those sorts of things, with secured debt, like a mortgage which is backed by your house, you have now taken that hole that you've dug and you've put your house at risk to try to satisfy that debt. It is not a sound strategy, and it adds a lot more risk to your financial life.

[Brian]

I always share with people. If you're thinking about doing anything with an entrepreneur, been to it, or you're thinking about even changing jobs, anything is going to just radically change your life. Make sure you put on your 3D glasses. What I mean by that is I want you to run it three different ways. I actually want you to create a plan for the next five to seven years where you say, hey, here's the dream. Everybody's good at doing the dream plan. But then no. And then take it from there. Go the down to earth. And then don't forget the most important step, the doo doo plan. Go ahead and say, if this doesn't work, how am I going to come out on the other side? I think if he had done that, you'd have still had grandma's house.

[Bob]

Before you start investing in unique things or executing complicated investment strategies, make sure you understand the ins and outs. So you know that what the negative consequences of that Decision could be if it happens to go the doo doo

[Interviewer 1]

route, what is your all time biggest mistake?

[Bob]

Oh, God, there's been a few.

[Interviewee 1]

Paying $100,000 for my bachelor's degree.

[Interviewer 1]

Are you currently using the degree?

[Interviewee 1]

Yes.

[Interviewer 1]

Are the loans paid off?

[Interviewee 1]

I got 40k left.

[Interviewer 1]

All right, okay, that's progress. My ex wife, when that cost you

[Bob]

couple million, we make one of the biggest financial decisions we'll ever make in terms of how much student loan we take on not recognizing the gravity of that decision that we can end up taking that student loan well into the rest of our life, well into our working career. So you want to make sure you do that well. And then when it comes to getting married, you probably want to make sure you do that one well.

[Brian]

Also, don't let it just be how much somebody gets you excited because you think they're pretty or attractive. Make sure there's a lot more substance. It's going to carry you through the future. And then talk about the heavy stuff. You know, you're not talking about religion, kids and how you do money. You're probably skipping a lot of the steps.

[Interviewee 1]

Biggest investment mistake ever made was listening to other people and not my gut feel. Long time ago, one of my family members who I thought was really smart told me to buy this stock. I bought it, the company went under, I lost all my money. I mean, it wasn't that much money back then, but at the time it was a lot of money. So do your own research. Only person responsible for your money is you. You know, I met Oprah one time and unbelievably, she told me that she signs every check in her company above $10,000. So it's your money, it's your responsibility.

[Bob]

You have to be so careful of what advice you let into your head and whose advice you take when it comes to making financial decisions. Because not all financial advice is created equal.

[Brian]

Well, I think Robert needs to differentiate entrepreneurship wise. I completely agree with him. One of the biggest things, when I was in accounting and working with small business owners, I was like, nobody's going to know your business like you. So you can't just skip over understanding how the bookkeeping everything is. But I will say for, for if you're just starting out on the financial journey and you're just trying to figure out how do I fund my Roth ira, how do I get into the basics, Find somebody who's done it, go. Let that be your mentorship or step. And that's what I like to do with the financial order of operations that Way you can get your life for you and you cannot waste a dollar because the experience is baked into the system.

[Financial Advisor]

How much you owe?

[Brian]

Here's Caleb.

[Caleb]

Over 30,000.

[Financial Advisor]

Okay, what's the interest rate on them? If you're gonna say eight or nine, it's 12.

[Caleb]

Oh, I sent all the paperwork for him.

[Financial Advisor]

There is a small window. Small window. And I'm going to be very clear that it is a small window where sold panel loans work. And that's when they're like 2 to 3, maybe 4%. This is not returning the value. It can't be the break even point with the interest rate and how long you're going to be paying them. Has to be a ridiculous amount of time. Has to be.

[Caleb]

We're paying $120 a month.

[Financial Advisor]

Yeah, but for how many months?

[Caleb]

32, 36.

[Financial Advisor]

What's your monthly payment?

[Interviewer 1]

Are you sure?

[Caleb]

I don't.

[Financial Advisor]

Oh. What's your monthly payment?

[Caleb]

120.

[Financial Advisor]

That's more like a 250month thing. So I don't know what you're talking about. You said 30 months.

[Condo Owner]

Well, I didn't know.

[Financial Advisor]

You have no idea what you're talking about and you think these are. How many years is that? Dude, this is like a 20 year thing. You have this debt for 21 years, you're not going to live in the house of 21 years.

[Bob]

Statistically we see this all the time. People want to do upgrades to their home, add it, do solar, whatever the thing is, and they end up financing it. This like improvement or this thing they want to do for longer than they're even going to be able to utilize this thing. Solar panels are a great example of people that we've seen in the past where you can do it and you look at the economics and it might make sense, but in a lot of cases it is not economically viable to try to do it. And yet a lot of people still fall into that trap.

[Brian]

You have to be careful when things feel like you're doing the right thing. And then you get these government subsidies that are also put on top. It feels like, well, heck, two of the three boxes are checked for why I should go ahead and do this. This has to be a great idea. Otherwise there wouldn't be all these companies doing it. The government wouldn't be incentivizing it. And then I feel good because I'm now going to be self sufficient and you know, and I'm solar powered. But if the math doesn't work. But don't just skip that step and don't Assume the person that's selling you the product is going to do math for you too. Their incentives are not aligned with your incentives.

[Bob]

A big red flag. I always see around when I'm talking to someone and I ask them some questions. They always know their payment. And in this case, she's, oh, 120. For how long? Oh, I don't know. What's the interest rate? Oh, I'm not sure. You need to understand the specifics of your financial situation. So you know, if you're actually making a nightmare of a decision, if you're borrowing money, you can't tell me for how long, what the interest rate is and what the payment is. You don't know enough about the money.

[Brian]

You know who else does that? Steve. Oh, Steve. O got you rolling into solar. You know, we could, we could help because that's exactly right. If you don't know, if you're only paying, focusing on the payment, you don't really know what you're paying for the entire product.

[Bob]

Stevo got me solar.

[Condo Owner]

I'm going to tell you guys the number one financial mistake I made in my entire life. That cost me almost $100,000, and that was buying a condo. I credit this decision to two main factors. Number one, I compared myself to every single person around me. My coworkers felt like majority of them own property, family members, majority of them were homeowners. People that I knew from back in the day, Homeowners. Why does that matter to my life? I don't know. At the time, it mattered. I felt like a failure because I did not own property. Number two, I was under the misconception that owning property, more specifically a condo, was an investment. And let me tell you, it's not an investment. I did not know that growing up. Just everyone around me was always like, if you own property, that's an investment. An investment is something that generates you income. Buying a condo in 2021, 2022, when I purchased that, is actually just a money pitch. And every single year I have a tenant in my condo right now paying $2400 a month. That is not covering my overhead cost, like property taxes, mortgage and condo fees doesn't even come close. So every single year I'm out like $6,000.

[Bob]

Personal finance is personal. Sometimes home ownership does make sense. Sometimes it does make sense to even perhaps buy the condo or whatever that is. But the reason that she bought it was not the reason why you want to buy real estate just because other people did it or you think it's the next box to check in your financial life. If that's the reason you're doing it, you're not doing it for the right reason. You need to make sure that I want to be on the home ownership side. It makes sense for my current life situation, life stage. And if it doesn't, it's totally okay. Renting. A lot of people say that renting is just throwing money away. Throwing money away. I would disagree. I think renting is giving yourself future flexibility and options, and sometimes that is more valuable than trying to build equity.

[Brian]

Condos are unique upon themselves because they have these association fees and because, you know, we've seen, especially if you're looking in places like Florida, where they're now having to do, do some rehabbing to make sure these things are structurally sound in the state of Florida. So you're seeing condo association fees go in crazy directions up, and you have zero control over that. And that's a lot different than just a normal HOA fee. So just pay attention to those condo association fees. In a lot of cases, they're getting to be as large as the mortgage is. If you're having trouble just making the cash flow, imagine how hard it is to sell that property with that large condo association fee, too.

[Interviewer 2]

What's been your worst money mistake?

[Bob]

We took a home equity line out and we bought a car.

[Interviewer 2]

What was your worst money mistake?

[Ashley]

Buying that stand. And then the estate went bankrupt.

[Financial Advisor]

Maybe trying to invest too quickly.

[Interviewer 2]

Don't get into it too quick when you don't know what you're investing into.

[TK]

Exactly.

[Interviewer 2]

What has been your worst money mistake?

[Ashley]

When I was traveling by myself, I used every limit of credit card I had to do it. That stays with you. It takes a long time and it multiplies.

[Boat Buyer]

I pulled a bunch of my 401k money, paid the penalty to buy my boat. It's very expensive to buy a boat in the Virgin Islands. And that was awesome.

[TK]

And I met her.

[Boat Buyer]

And now looking back, like, you know, being older with a mortgage, better do that stuff when you're younger, probably, or,

[Bob]

or, or hear me out. Don't do that stuff maybe.

[Brian]

Did he say that's how he met her?

[Bob]

He did say that's how he met her. He did say that.

[Brian]

But here's what I think is he got a dividend from his horrible financial decision.

[Bob]

Here was the common thread throughout.

[Financial Advisor]

A lot of these.

[Bob]

A lot of these were, like, impulsive financial decisions. Hey, I racked up all this credit card debt so that I could travel because I wanted the experience. I pulled money out of my 401k and I paid the interest and I paid or I paid the penalty, I paid taxes so that I could buy a boat. Traveling is not bad. Buying a boat is not bad. Those inherently are not bad things. But when you're doing them impulsively and you're making poor financial decisions to allow those things to happen, you are getting your financial life out of order.

[Brian]

Don't you wish that they could just put a sign on things, you know, like, like a contact sign everywhere you went. It's just like on his boat that he had down in the Virgin Islands, it had a sign that said finance. With my 401 previous 401k, she wouldn't have jumped on that. That boat train and dating train as life would be better if you saw like people with brand new cars and it said finance. With a home equity line, you'd be, you know, you just understand a lot better the situation people are in.

[Career Expert]

This mistake I made when it comes to money is staying at my first job for too long. There is a study that shows people who stay in the same company for more than two years on average make 50% less over their lifetime. And that stat was based on a 10 year horizon. Career is going to be longer than 10 years, but the longer you're working, the bigger that difference. If you're staying in the same company, you're getting on average a 3 to 5% pay rise. Whereas if you're moving and switching jobs, you can expect between 10 to 20% of a pay rise.

[Brian]

She just said if you stay at a job past two years, you're making a mistake. What job are you still on?

[TK]

Oof.

[Career Expert]

Ooh.

[Financial Advisor]

Ooh.

[Brian]

Should you have left? Oh, man.

[Bob]

Man, I bet life would be a lot better had I left inside the first two years. Here's what I think is interesting. Not all jobs are created equal. I will agree with one thing that she said. There's a difference in a job, a J, O, B and a career. Something that has a trajectory, a place where you can have an impact and create a future for yourself. Now you have to make sure the place that you are at allows for those things. But it's not a function of just hopping around. Oh, if I'm in a great job and I'm just going to leave and go somewhere else, then ipso fact, I'm going to be in a better situation a lot of times. The grass, grass is not greener. The grass is greener where you water it and if you're watering it in the job that you have in the company that you're with, with the firm that you're with. And there are opportunities there. You shouldn't have to constantly move in order to improve your financial stake. Now there are situations where it does make sense to move and look for something different. You lived that life, but there are others where you don't have to do that. And you have to define for yourself where are you and be realistic about what options are ahead of you.

[Brian]

Context matters. This is what sometimes look, we love career changers sometimes as employees because that way when they get here, they go,

[Financial Advisor]

oh, this is different.

[Brian]

I'm happy as pig and slop. I mean it is just you just so happy where you are and you realize this is what I've been looking for. It matters to have the context. And don't just watch somebody say, hey, you gotta jump jobs every two to three years so you can get the pay raises. Yes, that will work probably in the short term. But I will tell you as an employer, we look for that on the resume. If you look like you're bouncing around, we're like, why would we invest in this person that's not going to actually set roots and actually be a team, you know, building opportunity for the whole enterprise here. It's something to pay attention to. I would self evaluate and really look at the scenario and of course advocate for yourself if you are getting, you know, if things aren't going well. But don't just assume because you watch some content that your career of a lifetime opportunity might not be just incredible just because you know, you heard you need to go change jobs because not all jobs are created equally at the

[Bob]

end of the day. And I think we saw through all these videos, personal finance is incredibly personal. So be careful listening to a 30 second clip or a minute clip of somebody telling you something you must do in order for your life to get be different because it may or may not make sense in your situation for your unique variables. If you want to know more, if you want to go check out a better way to do money. We have tons of resources [e-mail] resources. You can check out all of our deliverables, all of our free calculators because we really do believe that there's a better way to do money.

[Brian]

A side effect of making mistakes is that you get wisdom guys. We load you up every week. So we love creating content. I'm your host Brian, joined by Mr. Bob Wisdom and Experience Out.

[TK]

They got me on 300 likely payments

[Brian]

for only two years.

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