Financial Advisors React to the BEST and WORST Tax Advice

Summary

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Money Guy Show: Financial Advisors React to the BEST and WORST Tax Advice

Hosts: Brian Preston & Bo Hanson
Date: April 6, 2026

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Episode Overview

This episode of the Money Guy Show takes listeners on a spirited tour of popular (and polarizing) tax advice found around the internet. Brian and Bo, both seasoned financial advisors, react in real time to TikTok clips, “expert” hot takes, and client stories, breaking down the strategies, half-truths, and outright myths behind each claim. Throughout, they blend laughs, personal anecdotes, and practical pointers to help listeners demystify tax planning, avoid costly mistakes, and ultimately build wealth with more confidence.

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Key Discussion Points and Insights

1. Understanding W-4s and Tax Withholding (01:17–03:43)

• Internet advice dissected: Chef Mei Lin and 'Dave' discuss manipulating W-4 dependents to minimize tax over/underpayment.
• Brian’s reaction:
  “The more dependents you claim, the less taxes they withhold. She should have claimed zero dependents…if she didn’t want to get a refund…” (02:17, Brian)
• Main takeaway:
  Do a tax projection if you want accuracy, but for most, simply monitor your refund each year and adjust withholding as needed.
• Bo’s ‘hassle factor’ tip:
  “First year, you get a job… fill out the form the way it is… then when you do your taxes, pay attention. If there’s a huge refund, you immediately know you need to do a new W-4…” (03:07-03:30, Co-host)

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2. The Real Estate “Never Pay Tax Again” Strategy (04:37–05:51)

• Strategy explained by a Real Estate Tax Expert:
  • Become a real estate professional (IRS definition).
  • Acquire property; use 1031 exchanges to defer capital gains.
  • Borrow against real estate equity for living expenses.
  • Transfer property via estate for a basis step-up.
• Brian’s reaction:
  “You have to be comfortable always being in debt…you’re never actually going to have a really impressive-looking net worth statement because your liability column is always going to be substantial.” (05:21, Brian)
• Legislative insight:
  “The lobbying arm of the real estate professionals is pretty spectacular…they got carved out of the QBI exclusion. It’s almost like they helped write the legislation.” (05:51, Co-host)

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3. Cost Segregation and Passive Losses “Paper Law” (06:41–08:23)

• TikTok “Paper Law strategy” summarized:
  Buy property, do a cost segregation study, write off assets, use passive loss to offset other income.

• Brian and Bo’s reality check:

  • Only real estate professionals truly benefit at the W-2 offset level.
  • Most people will only offset passive income, not W-2 or investment income.
  • Those earning over $150,000 usually carry losses forward until the sale.

• Quotes:
  “You have to be a real estate professional…You can’t just on your tax return say, ‘hey, I’m a real estate professional, give me all these benefits.’ The IRS is going to call you on that.” (07:29, Co-host)

  “Most people…will have losses against the passive income on that property for a few years, which is great. But it likely is not going to offset the other income sources.” (07:56, Brian)

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4. Mythbusting Big Tax Refunds as “Free Money” (11:21–12:00)

• Brian clarifies:
  “The government didn’t give you money…All they did was give you back money that was already supposed to be yours.” (11:21, Brian)
• Bo’s old-man moment:
  “All that video did was make me feel old…I guess it’s a generational video meme. Maybe we should just…” (11:54, Co-host)

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5. Employee vs. Business Owner Tax Realities (12:55–13:52)

• Viral claim:
  “Owning a business beats earning six figures any day” because of deductions.
• Brian’s real world perspective:
  “Depending on the business, that W2 salary might actually have more money than that business owner.” (13:02, Brian)
• Bo’s caution:
  “Entrepreneurship is somewhat of a calling. If you’re doing it because of tax savings, you’re probably not starting a business for the right reason.” (13:33, Co-host)

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6. Maximizing Deductions: The “Shelter 66% of Your Income” Approach (13:52–15:27)

• Viral tip from Tyler:
  • Max out HSA, IRA, 401k, and use the standard deduction to lower taxable income dramatically.
• Brian and Bo’s holistic advice:
  • Prefer Roth IRAs/401ks for younger/lower-income individuals, aiming for future tax-free growth.
  • Focus on lifetime tax minimization, not just this year’s refund.
• Quotes:
  “If you have a really good financial plan, you’re not thinking about how can I save the most amount of taxes today. You’re thinking about how can I save the most…over my entire lifetime.” (15:27, Brian)

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7. Tax Filing Negligence: The Consequences of Not Filing (16:05–18:05)

• Case Study: Caller confesses to not filing taxes for eight years.
• Tax professional’s response:
  • Not filing is riskier than not paying; eventually, the IRS will act.
  • File as soon as possible; sometimes, only the last six years are required.
  • Installment/payment plans are available but can place you on the IRS’s “naughty list.”
• Brian’s warning:
  “You do not want to be on that side of the federal government.” (17:27, Brian)
• Final advice:
  “Pay your taxes. If you get nothing else out of this video, pay your taxes.” (18:05, Co-host)

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Memorable Quotes & Moments

• On withholding confusion:
  "The more dependents you claim, the less taxes they withhold." (02:17, Brian)
• On real estate loopholes:
  “You’re never actually going to have like a really impressive-looking net worth statement because your liability column is always going to be substantial.” (05:21, Brian)
• On business deductions:
  “Just because you’re a W-2…doesn’t mean that’s necessarily a bad thing. You should try to figure out how you could go…out on your own.” (13:02, Brian)
• On the importance of tax filing:
  “They literally have the authority to come take your stuff…You do not want to be on that side of the federal government.” (17:27, Brian)

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Important Segment Timestamps

| Timestamp | Segment | Key Topics | |------------------|---------------------------------------------------|---------------------------------------------------------------------| | 01:17–03:43 | W-4 Withholding | Dependents, refunds, tax projection vs. simple adjustments | | 04:37–05:51 | Real Estate “Never Pay Tax” Strategy | Real estate professional status, debt, 1031 exchanges | | 06:41–08:23 | Paper Law Cost Segregation Strategy | Passive vs. active losses, IRS rules, high income limitations | | 11:21–12:00 | “Big Refunds” Myths | Why refunds are not a windfall | | 12:55–13:52 | Employee vs. Entrepreneur Tax Debate | Deductions vs. business risks | | 13:52–15:27 | Sheltering 66% of Income | HSA, IRA, 401k, Standard Deduction, Roth vs. Traditional | | 16:05–18:05 | Ignoring Taxes: Not Filing for Years | IRS enforcement, options for late filers, consequences | | 18:05–18:56 | Final Advice | Pay taxes, distinction between legal avoidance and illegal evasion |

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Tone and Style

Brian and Bo keep the tone energetic, accessible, and playful, even as they tackle complex, often intimidating tax topics. They consistently pump the brakes on viral “hacks” and internet bravado, emphasizing responsible, legal strategies over shortcuts or risky moves.

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Bottom Line/Takeaways

• Adjust your W-4 thoughtfully by monitoring your annual refund or tax owed, not by gaming “dependents.”
• Real estate tax deferral schemes can work but usually entail high debt and complex requirements.
• Cost segregation largely benefits professional real estate investors—not most wage earners.
• Massive tax refunds are not “free money”—they’re interest-free loans to the IRS.
• Entrepreneurship isn’t a magic tax solution; passion and business basics matter far more than potential deductions.
• Focus your retirement contributions on lifetime tax minimization, leveraging Roth accounts where appropriate.
• Not filing taxes puts your finances and assets at very real risk; always file, seek help if needed, and avoid IRS enforcement actions.
• Legal tax “avoidance” is smart; illegal evasion can ruin lives.

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Final Thought:
“Who would have thought coming in here talking about death and taxes could have been this much fun?” (18:56, Co-host)

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Transcript

[Real Estate Tax Expert]

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[Brian (Money Guy)]

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[Co-host / Commentator]

Death and Taxes. Everybody's favorite subject, so why not make it as fun as possible?

[Brian (Money Guy)]

I am so excited about this. Is death really people's favorite? Okay, whatever. I'm so excited about this because right now, the Internet is gonna tell us what we need to know about our tax system. Let's dive right in.

[Chef Mei Lin]

Is there a magic formula or some way to figure out how many you can claim on your W4 so you

[Brian (Money Guy)]

get the smallest tax return back?

[Dave (Taxpayer Example)]

There's a formula, but it's not based on the number of dependents. The IRS tables are wrong, of course. Okay, so thus you. You know, you can claim. Like for instance, my daughter, when she first got out of college, claimed six dependents. She didn't even have one, and it still got her a refund. Okay, so she still didn't have enough coming out. So that's how bad the tables. They're not minorly off. They suck. The way you would do it is one of two ways. The. The most accurate way is to actually do a fake tax return for the year. Actually prepare your tax return and let it tell you exactly what you would owe in taxes, your total tax bill, and then divide that by the number of months, and that's what needs to come out of your check per month. And so if your actual tax bill is $4,800, then $400 a month needs to come out. Right.

[Brian (Money Guy)]

Dave said that when his daughter graduated,

[Dave (Taxpayer Example)]

she had like, six dependents and it still got her a refund.

[Brian (Money Guy)]

Well, yeah. The more dependents you claim, the less taxes they withhold. She should have claimed zero dependents if she didn't want to get a refund so it makes sense that she still got a refund because I think she likely did it wrong. Now, no W4 forms, they'll. They'll kind of walk you through. Okay, answer this question, Answer this question, Answer this question. And I do think that Dave is right. You can do a tax projection. You can arrive at what you think your tax bill is going to be, and you can reverse engineer your withholding. But a lot of people don't have to do that. So what I would say is, this year, when you do your taxes, pay close attention. Do I owe a big amount? If that's the case, I probably need to increase my withholding. Or if I get a big refund, maybe I need to decrease my withholding. And I would do it that way rather than trying to go out and figure out, okay, well, how do I do a tax rejection? How do I do if that's not something that's sort of in your wheelhouse?

[Co-host / Commentator]

The hassle factor is high for the way Dave laid this out. I think it's the right way, but I wouldn't do it this way. Here's what I would do. First year, you get a job, actually fill out the form the way it is. If you're married, put married, and you can still check a box that says, hey, but I want to be treated as single because I want to have the maximum amount withheld. If you think you're going to get a refund, you don't have to check that box.

[Brian (Money Guy)]

Right.

[Co-host / Commentator]

And claim both. And then when you do your taxes in that first year, pay attention. If there's a huge refund, you immediately know you need to go do a new W4, change the numbers, and then grip and rip and let it go until the next tax season.

[Brian (Money Guy)]

Where's all your money gone, Daddy?

[Shopify Representative]

Taxes.

[Co-host / Commentator]

Uh oh, he's crying.

[Brian (Money Guy)]

Let me fix my houses.

[Co-host / Commentator]

But it's okay. It's part of the community.

[Brian (Money Guy)]

Is it Monopoly?

[Co-host / Commentator]

It's not fun to what? It's the worst part of the case. It's what? Taxes.

[Tax Professional / Advisor]

Amen, brother.

[Brian (Money Guy)]

He got it. How many times, Brian, have you sat down with a small business owner? They launched their first business, they start their first side gig, Go ahead. And maybe they're not laying in front of the couch crying, but that same realization, holy cow, why on earth do I owe so much taxes? I finally just made my business profitable. It is something that if you do not plan for it and don't know that it's coming, you may also find yourself in tears.

[Co-host / Commentator]

Probably a proud parent moment, though. Like okay, he's going to be a hard worker and not want to pay taxes. He's an American.

[Real Estate Tax Expert]

Here's how to never pay tax again. So this is what I would do if I was solely basing my decisions off of tax and nothing else. First, I'd become a real estate professional under IRS definitions because they receive by far the best tax advantage is I would purchase real estate. And third is whenever I sell the real estate, I would only do 1031 exchanges so that the capital gains is deferred. And finally what I would do is you could borrow against that property to use that cash to live off of. And then I would only transfer the real estate by leaving it in my will or in my estate, not by gifting it while I'm alive, but so that the people that receive it get a step up in basis. And as long as you're under that estate tax threshold of 11 million per person, that's your tax free formula.

[Brian (Money Guy)]

Look, it's true what she laid out is accurate. Now one of the things, if you're going to perpetrate the strategy, you have to be care, you have to be comfortable always being in debt because you heard where her cash flow comes from is borrowing the equity out of the properties that she has and then she does a 1031 and she exchange that, she borrows the equity out and borrows the equity out. So you're never actually going to have like a really impressive looking net worth statement because your liability column is always going to be substantial. But she is correct, that is a way to not pay tax.

[Co-host / Commentator]

Here, here's the thing, she did say something that that's very true. And I have often thought this is like the lobbying arm of the real estate professionals is pretty spectacular because a few years ago when they came out with the small business exclusion, was it the 120, the QB, the QBI business? QBI business exclusion, where essentially 20% of small businesses doesn't get taxed of the income they excluded. Most professionals, like if you go out there and look at your, you know, your CPAs, your attorneys, your financial advisors, your doctors, they don't get the small business exclusion on their stuff because they're considered professionals. But guess which professionals somehow got carved out of it. It was real estate professionals, it was architects. It's amazing. It's almost like they helped write the legislation.

[Real Estate Investor / Tax Strategist]

Here's how you can avoid 100% of your income taxes every single year. We call this strategy the paper law strategy. In order to use it every single year, you have to understand the rules. The very first thing that I'm going to need you to understand is you're going to need to buy an investment property. When you buy a rental property, it could be an Airbnb or a lot of long term rental, but as soon as you purchase the property, I want you to write off everything that's on the inside of the property. This could be applian, bathrooms, tubs, cabinets. And when you write off everything that's inside of the property, it creates a big expense. We call this the cost segregation study. Once you do the cost segregation study, it creates a big enough loss to offset your W2, your 1099, your stock and your crypto income, making you tax free.

[Brian (Money Guy)]

He left out a big thing.

[Co-host / Commentator]

I don't see a lot of people doing cost segregation on residential, but on commercial property for sure. We've even done cost segregation on real estate that we've bought. But the thing is, is you have to be a real estate professional to be able to take it against W2 and ordinary income. It's not the easiest test to pass. You can't just on your tax return say, hey, I'm a real estate professional, give me all these, these benefits. I think a lot of people are gonna be like, oh, because the IRS is gonna call you on that.

[Brian (Money Guy)]

Yeah. I think, Carlton, what happens for most folks is they buy the property, they do cost seg study, they get all those expenses front end loaded. And what you have is you have losses against the passive income on that property for a few years, which is great. But it likely is not going to offset the other income sources. If you do have W2 income or investment income, it's only going to serve to offset the income applicable to that type of property. That type of investment.

[Co-host / Commentator]

Yeah, I mean most people, it's just going to be a big carry for it. That's what especially, you know, a lot of people get into residential rental thinking they're going to be able to write off everything. And then you find out women I make more than like, was it $150,000? You're like, oh, I'm gonna have to carry this loss forward until I actually sell the property. Like, well, what the heck did we even do this for?

[Brian (Money Guy)]

Hello, Brian. I love being a business owner, but I think people underestimate how fast things move from I've got an idea to all right, now we actually have to build this thing.

[Shopify Representative]

That's right. The idea is the fun part. But then you've got logistics, operations, marketing, all the stuff that actually makes the business run and work.

[Brian (Money Guy)]

And that part can really slow you down. And it might even keep you from starting at all.

[Shopify Representative]

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[Brian (Money Guy)]

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[Shopify Representative]

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[Brian (Money Guy)]

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[Shopify Representative]

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[Brian (Money Guy)]

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[Shopify Representative]

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[Brian (Money Guy)]

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[Chef Mei Lin]

As a chef, I know flavor doesn't begin in the kitchen. It begins on the land. And West Home's nature led Australian Wagyu is a story written in the landscape of northern Australia. Cooking is storytelling. And West Home Wagyu carries a story of northern Australia itself. Raw, powerful and deeply authentic. It's a testament to the passion and care raised in the rhythm of northern Australia. I'm chef mei Lin from 88 Club in Los Angeles and I invite you to visit westhome.com meilin to learn more and taste a story only west home nature led Australian Wagyu can tell. That's W-E-S-T-H-O-L-M-E.com M E I L I N Hey, I can't come into work today. Is everything okay?

[Co-host / Commentator]

I can't see.

[Dave (Taxpayer Example)]

You can't see something wrong with your vision?

[Chef Mei Lin]

No, I can't see myself working today. Bye.

[Co-host / Commentator]

Huh.

[Brian (Money Guy)]

So I think it's great. A lot of people, they get a big tax return, they get a big tax refund and they're like, boom, I'm rich. Look at all of this free money. The government just Gave me. I'm loaded now. And I think what they don't recognize is the government didn't give you money. They didn't say, hey, you know what? Congratulations on filing your taxes. All they did was give you back money that was already supposed to be yours. So if you're someone who's getting a big refund and that money comes back to you, I would not treat it as found money. I would treat it as money that you loan the government interest free.

[Co-host / Commentator]

For the last year, all that video did was make me feel old, elaborate. I was trying to pay attention, thinking I was actually going to hear something there, and I was like, oh, is this, what is this like a video meme? You know, because it had tax return, big refund and then, okay, enjoy it. Then you voice. Put the voice. So there was just a lot going on that I just, I didn't completely get. I guess it's like a joke came and I just. It wasn't funny to me. I'm sorry. I can tell you it was funny to you though. So it's all right. It's a generational video meme. Maybe we should just. Here's the problem with earning six figures as an employee at 100k, you're in the top 3%. Nice. After taxes, that hard earned salary could leave you with just 65k. Instead, imagine earning six figures as a business owner. You can write off expenses like the latest gadgets and business trips abroad, allowing you to keep more of what you earn. That's why owning a business beats earning six figures any day. Well, okay, look, I feel like I've got it on both sides is that we have lots of employees, but I've also been an employee and then I've been a business owner. It is true there's a few more things that are more deductible, but there's also a lot more things that cost.

[Brian (Money Guy)]

That's right. Entrepreneurship is wonderful and it's a great thing if that's something that makes sense for you. But it's not for everyone. And I would argue that there are a lot of people out there. If you compared someone who makes $100,000 of a W2 salary versus versus a business owner that has $100,000 in revenue, depending on the business, that W2 salary might actually have more money than that business owner. So just because you're a W2, just because you collect a paycheck doesn't mean that that's necessarily a bad thing. You should try to figure out how you could go how to Go out on your own.

[Co-host / Commentator]

I think entrepreneurship is somewhat of a calling. If you're doing it because of tax savings, you're probably not starting a business for the right reason. Believe me, it takes more than just tax savings. You need passion, you need cash reserves. You need to have talent that actually is so marketable that you get rewarded for bringing this out to the public.

[Tyler (Financial Advisor)]

Here's a quick way to shelter 66% of your income legally. I'm Tyler. I'm a former financial advisor and portfolio manager. Now I make financial content for free so that you don't have to pay for it. Make $75,000 a year pre tax. Number two. I would start by putting 4,150 bucks in a health savings account above the line deduction. Number three. Next, I'd put $7,000 into a traditional IRA above the line deduction. And we're rolling. Number four. Next, I'd put $23,000 into my traditional 401k pre tax contribution. Number five. Then I'd cap it off by taking the single filer deduction of 14,600 bucks. Number six. And I'd turn around and tell the government that I officially made 26,250 bucks of taxable income. Went from the 22% to the 12% tax bracket and at this rate and projected to be a millionaire in just under 14 years.

[Brian (Money Guy)]

There's one thing I would change and I have to think through this and I'd want to look at the taxes,

[Co-host / Commentator]

but I'd rather do a Roth.

[Brian (Money Guy)]

I'd rather do the Roth IRA than the traditional ira. That's exactly where I was going. I love maxing out the 401, but because, because imagine if he did Roth IRA contribution and imagine if he did a Roth Solo 401K or Roth 401K. Imagine those dollars growing tax free. I'd want to know more about what his income trajectory over the long term looks like.

[Co-host / Commentator]

If you were just doing this as a thought exercise on how you minimize income as much as possible for taxes, then boom. Yeah, it's kind of cool that you made 60 of the money disappear from a taxability. What I like is because he just like right here on the screen is that you'd be a millionaire in under 14 years. Imagine if you're a tax free millionaire. And the other thing is, is because you did it with, you funded it with after tax money, you're actually getting more of the money into that, that account that's growing and compounding that won't have the headwind of taxes in the future.

[Brian (Money Guy)]

One of the beautiful things about financial planning is a lot of people focus on how can I save the most amount of taxes today? But if you have a really good financial plan, you're not thinking about how can I save the most amount of taxes today. You're thinking about how can I save the most amount of taxes over my ent lifetime? And that's why these lower income thresholds in the 12% bracket or even 22% bracket, we love building Roth assets.

[Tax Professional / Advisor]

Now we're going to take a call from a client who hasn't filed tax returns for many years. Most people, once they don't file for a lot of years, usually they're too scared to file. Also, they get in the process of if I didn't file for that many years, where should I file now? And I have to pay somebody to do it. So let's talk to him and see if he's different than everybody else.

[Brian (Money Guy)]

Eight years ago I switched jobs and

[Co-host / Commentator]

one thing led to another.

[Brian (Money Guy)]

So I have not filed taxes in

[Co-host / Commentator]

the last eight years, which is not good.

[Tax Professional / Advisor]

Why haven't you filed?

[Brian (Money Guy)]

I couldn't afford to file.

[Tax Professional / Advisor]

When you don't file, the IRS can charge you criminally. But if you don't pay, then there's so much you can do. But it's usually worse if you don't file than if you file and not pay. And how old are you?

[Brian (Money Guy)]

32.

[Tax Professional / Advisor]

Okay. Married?

[Brian (Money Guy)]

Yes.

[Tax Professional / Advisor]

And children? Who files with the children?

[Brian (Money Guy)]

My wife.

[Tax Professional / Advisor]

I think it was a good idea for a wife to file separately. This way she's not responsible for your tag there. Do you own any real estate?

[Brian (Money Guy)]

I have a mortgage on my main residence. The mortgage is for 150 right now.

[Tax Professional / Advisor]

How much would you say the house is worth?

[Brian (Money Guy)]

230,000.

[Tax Professional / Advisor]

It's easier to deal with it now because the more equity you have, the more the IRS will expect you to pay. I'll send you some documents. We'll contact the IRS and see what we need to file. And we'll just file the bare minimum. Sometimes they only require us to file a few years, usually the last six years. And if we owe money, then we'll figure out how we're going to pay for it. We set up a payment plan, see if you qualify for any of the tax relief programs.

[Co-host / Commentator]

There are programs where the government will let you get on an installment plan with them. Now, I will tell you that that kind of puts you on the naughty list with the irs. So you kind of really need to be careful. When you went before you go that route, it's better to do it now than to let this just continue to build up in the background and create a huge tax bomb for the future.

[Brian (Money Guy)]

Yeah, I always wonder where the mindset is. Someone you know, I don't follow this year and I go, I didn't follow last year and I kind of got away with it. So then I don't file the next year and the next year and the next year. If you are someone with income and assets and you have things that the government could come take away, like your assets, like your income, I don't think operating under the assumption, oh, they're just not going to catch this, I'll just fly under the radar. I don't think that that's what likely happens. And when you do get that letter, whether it be a year, three years, five years, eight years from now, they literally have the authority to come take your stuff, to come garnish your wages, to come repossess your assets. You do not want to be on that side of the federal government.

[Co-host / Commentator]

Pay your taxes. If you get nothing else out of this video, pay your taxes. We've, we've covered it earlier in the show is that tax evasion is illegal and that's when you don't file your taxes, when you, you purposely exclude stuff that's tax evasion, that's going to get you put in the clink. But if you are smart and you actually keep up with what's going on with the financial world, the tax policies, you can actually use tax avoidance, completely legal and maximizing your wealth journey. And that's why we love covering this type of content. Who would have thought coming in here talking about death in taxes could have been this much fun? I'm your host, Brian, joined by Mr. Bo Money Guy. Team out.

[Brian (Money Guy)]

To realize the future America needs. We understand what's needed from us to face each threat head on. We've earned our place in the fight for our nation's future. We are Marines. We were made for this.