In short
Tax season anxiety; why audits/penalties are unlikely; how filing works (mostly reconciliation of info already reported by employers/banks/brokers); three tax credits; and a “playbook” to make taxes manageable (organization, choosing how to file, using extensions/payment plans).
Guests
No episode guests; hosts are Austin Hankwitz and Robert Croak.
Key claims
IRS audits less than 0.5% of individual returns; W-2/standard returns are usually not complex; refunds aren’t “bonuses”; filing is reporting/crediting/deducting and reconciling amounts already sent to the IRS.
Notable examples
Three key documents—W-2, most recent pay stub, last year’s tax return; extension vs procrastination (failure-to-file penalties 5%/month up to 25%); credits with thresholds—Earned Income Tax Credit (e.g., MFJ AGI ≤ $68,675 with 3 children up to $8,046), Child Tax Credit (up to $2,200/child under 17 if MFJ income < $400k), Saver’s Credit (MFJ income < $79k up to $2,000). Playbook examples: start a folder Jan 1; use IRS Free File if under $79k; file even if you can’t pay; consider AI suggestions but verify with a CPA.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VODemystifying Tax Season Anxiety
4:09 to 11:04
Understanding the causes of tax season anxiety and how to tackle it effectively.
“My name is Austin Hankwitz, and I'm joined by my co-host, Robert Croak.”
Essential Tax Documents and Extensions
11:04 to 13:52
Learn about essential tax documents and the importance of filing an extension.
“And the third document, which is more of like a pile of documents, but it is last year's tax return because that old tax return, right?”
Episode Discussion
14:00 to 28:00
“So yeah, I'm itemizing every single year.”
Listener Question: Rental Property Mortgage Decision
28:26 to 30:10
Rich seeks advice on whether to pay off a rental property mortgage or invest.
“And as a reminder, if you have a question for the podcast, follow us on Instagram at rich habits podcast and DM us.”
Advice on Real Estate and Passive Income
30:10 to 33:39
Robert provides insights on real estate management and investment strategies.
“And then maybe look at it down the road after you've made more money and built more of this base we talk about, and then maybe go back and look at paying off that mortgage.”
Listener Question: 401k and Property Purchase Strategy
33:39 to 35:43
EB seeks guidance on using a 401k for buying a new property.
“Congrats on all you've built and definitely check out some of these tax optimizations, credits, and strategies that we've alluded to in this episode.”
Navigating Mortgage Options for Self-Employed
35:43 to 38:22
Discussing mortgage options and strategies for self-employed individuals.
“Yeah, I think from a landmines to look out for perspective, there's a couple things that jump out.”
Listener Question: Retirement Concerns in Uncertain Times
39:14 to 42:11
Anna questions the viability of saving for retirement amidst societal changes.
“To obtain a prospectus containing this and other important information, please visit neosfunds.com.”
Navigating Financial Futures
42:11 to 44:16
Learn about the importance of financial preparedness and asset ownership.
“Robert, I don't think I have an answer for Anna here.”
The Balance of Investing and Living Goals
44:16 to 46:34
Discover how to balance retirement savings with personal life goals.
“And we might be in this dystopian future where it is all tokens and through the government and who knows how on the blockchain.”
Transcript
Automatic transcript. May contain errors.0:00Austin Hankwitz:Get in the game with the college-branded Venmo debit card. Wreck your team with every tap and earn up to 5 % cash back with Venmo Stash, a new rewards program from Venmo. No monthly fee, no minimum balance. Just school pride and spending power. Get in the game and sign up for the Venmo debit card at Venmo.com slash college card. The Venmo MasterCard is issued by the Bancorp Bank N.A. Select schools available. Venmo Stash terms and exclusions apply at Venmo.me slash Stash terms. Max$100 cash back per month. Every soda's got something to say. Colas brag. Probiotics give TED Talks. Then there's Mr.
0:37Austin Hankwitz:Pibb. No pitch, no promises, just bold cherry bringing the flavor. Bold kick of cherry. Hey, yo, Mr. Pibb. Hey, everyone. Robert here. Before we get into this episode, I'm super excited, and I wanted to announce our first ever Rich Habits event, the Rich Habits Retreat. It's coming up on May 1st and 2nd, the weekend in Austin, Texas. I couldn't be more excited about this event. You guys have been talking to us for two years now, telling us to get out there on the road, and we're finally doing it. And this event is going to be special because it's going to be all about venture capital, how to invest, how to build a portfolio, and all of the things that we do to build these portfolios.
1:20Austin Hankwitz:And we're going to have a ton of special guests. Chris Camillo, our friend, is going to be there. Zayde Admani is going to be there from public. So it's going to be a blast. You're going to get some FaceTime with Austin and myself. And just so much is happening. But here's the kicker. There's only about a dozen tickets left. So if you're interested, make sure you look in the show notes below. There is a link and it'll tell you all the good stuff about the weekend and the Rich Habits retreat May 1st and 2nd in Austin, Texas. And I'd love to see you there.
1:49Robert Croak:This is going to be an intimate event with Robert and myself. You all wanted intimacy. You wanted those one-on-one conversations. Like you have the opportunity to look us in the eyes and ask us a question, talk about your business, whatever you want to do. It's an intimate event with about 30 to 40 of you showing up with us in Austin, Texas from May 1st and 2nd. Like Robert said, Chris Camillo from Dumb Money, he's going to be there. Zaded Mani from The Rundown with Publix Podcast, he's going to be there. Brian Chambers, the co-founder of Capital Factory, the largest seed fund in Texas. He'll be there.
2:24Robert Croak:Colin West from Ensemble is going to be there. Christine Healy from Pre-IPO Investing. She's going to be there. Like so many incredible speakers. We're going to be talking all things venture. And with the craziness we've seen with VCX lately after Fundrise listed it a week ago, like venture is pretty important. And it's pretty obvious that people should have some sort of exposure to it in their portfolios. So if you wanted to get into venture, you want to learn about venture, anything about venture capital is interesting to you and you want some face time with Robert and I, this event is for you.
2:57Robert Croak:There's going to be a link in the show notes below to purchase tickets to attend the Rich Habits Retreat in Austin, Texas, May 1st and 2nd. And the best part, 10 people who are purchasing tickets to the event will randomly be selected to join us the following Monday at the New York Stock Exchange for an event from 1 to 5 p.m. with all of the biggest ETF issuers to learn about their global strategies, their market outlook for the rest of the year, everything with the macro and things like that. It's going to be an incredible event. These are the events that Robert and I get invited to, to attend to learn from.
3:36Robert Croak:And so what we've done is we figured out a way to have 10 people from the retreat meet us at the New York Stock Exchange on May 4th, the following Monday for an awesome event on the floor of the New York Stock Exchange. Get to watch a bell ringing. It's going to be incredible. So go check out the Rich Habits Retreat, link in the show notes below. And maybe you're one of those 10 lucky ticket holders that will join us at the New York Stock Exchange the following Monday.
4:01Austin Hankwitz:All right, Austin, great breakdown. So excited that we have some tickets left for all of you out there, and I'm ready to jump into the episode.
4:08Robert Croak:Hey, everyone, and welcome back to the Rich Habits Podcast, a top 10 business podcast on Spotify brought to you by public.com. By the end of today's episode, you will learn Robert and I's three favorite tax credits, as well as have the entire playbook that you need to feel more prepared when it comes to filing your taxes in a very stress-free manner. My name is Austin Hankwitz, and I'm joined by my co-host, Robert Croak. Robert is a seasoned entrepreneur with lifetime revenues of over$300 million, and I'm a multimillionaire in my late 20s with a background in finance and economics. As the show name might suggest every episode, we talk about rich habits as they relate to business, finance, and mindset.
4:52Robert Croak:With that being said, Robert, what are we specifically talking about in today's episode?
4:57Austin Hankwitz:In today's episode of the Rich Habits Podcast, we're going to explain the cause of immense anxiety tied to filing your taxes, demystify what's actually happening when you do file your taxes, and number three, share your favorite tax credits you all should be taking advantage of right now, and number four, give you the knowledge to stop fearing a process that is a lot more manageable than it looks.
5:20Robert Croak:And y 'all got to stick around for that fourth one, the playbook, the knowledge, everything you need to stop fearing the tax filing process. Robert and I think we do a pretty good job here near the end of this episode, really walking you all through how to think about taxes, not just here in 2026, but every year going forward. I think a term that kind of goes synonymous with taxes is the word anxiety. So let's talk a little bit about what causes that anxiety for people during tax season.
5:49Austin Hankwitz:Yeah, Austin, the number one source of tax season anxiety is fear of making a mistake and triggering an audit or incurring penalties. But here's the stat that should immediately take the edge off for everyone. The IRS audited less than a half percent of individual returns in recent years, which means your actual audit risk is extremely low, especially if you're a W-2 employee and you have straightforward income. So I don't think everyone needs to be worrying about that. They hear it all the time, but rarely, rarely do people get audited as by the numbers I just shared.
6:24Robert Croak:Yeah, another big stressor that causes a lot of anxiety, Robert, during tax season is the complexity of it all. About half of Americans report that they have little to no understanding on how to actually file their taxes and what the forms mean and things like that, which makes sense because the U.S. tax code is enormous. It's full of acronyms and jargon and numbers that might not be completely transparent on the surface. But the thing is, the average person filing a standard tax return is not dealing with most of that complexity. If you have a normal W-2 job, maybe you make some investment income, and you take the standard deduction, which again, 90 % of Americans fall into that bucket, your return should not be that complicated.
7:11Austin Hankwitz:And let's not forget all of the uncertainty tied to taxes. People genuinely don't know whether they're getting a refund or writing a check, and I think that unknown creates anxiety that festers for months. And here's the truth about refunds that I wish everyone understood. A refund is not a bonus. It means the government held your money interest-free all year and is finally giving it back your money, giving it back to you. A tax bill doesn't mean you did something wrong. It means you got to use that money throughout the year. So understanding that distinction alone should take a lot of the emotional charge out of the outcome.
7:50Robert Croak:So, Robert, we've talked about what really causes this anxiety, right? You mentioned fear of making a mistake, the audit, a penalty, things like that. I talked about the complexity of it all, and you kind of rounded off here with the uncertainty of, am I going to owe? Am I going to get a refund? I don't really know what's going on. So that's like what causes a lot of the anxiety for people. But let's now peel the curtain back on that anxiety and begin to demystify what actually is going on when you file your taxes and explain why you should not be scared. You should not be intimidated by tax season.
8:20Robert Croak:So here's the process. When you file a tax return, all you're doing is reporting to the IRS what you earned, accounting for any deductions or credits that you're eligible for, and calculating what you've already paid throughout the year to say, do I owe more money or am I owed a refund? That's it. That's all you're doing, right? So you file your return. You're saying, here's the money I earned. Let's now figure out those deductions and credits I might qualify for. Let's calculate what that comes out to. And if I owe money, I got to pay that. If I'm owed a refund, I got to receive that. What people forget about is their employers have already sent that W-2 income to the IRS.
9:04Robert Croak:Your bank has already reported the interest you've earned in your high yield savings account to the IRS. Your broker, public.com, right? They've already reported what your gains and losses might be like. So in many cases, the IRS already has a rough picture of what your financial year is going to shape up as before you even file anything. So what you're doing is you're just largely confirming information that already exists. The filing process is more of a reconciliation, not really a build from scratch. Let me tell this story. It's like the story already exists. You have all the information. Let me just confirm it for you.
9:41Austin Hankwitz:I love this episode already because I want everyone to take a deep breath and just really listen and take notes in this episode because I do feel like this is one of the biggest stressors of the year for most people, and it doesn't have to be. I know the forum looks intimidating, but most of them follow the same basic logic. The W-2 tells you what your employer paid you and what was already withheld. The 1099 family of forums covers everything else. freelance income, investment dividends, interest, and so on and so on. And your job is to gather those documents, plug the numbers in whatever software preparer you use, and let the math happen.
10:19Austin Hankwitz:Most people find that once they actually start and sit down, it takes far less time than they feared. And if you remain organized throughout the year tracking your income, investment dividends, interest earned, and other qualifying transactions, you will find the tax season is a lot less stressful because you're not doing it all at once in a couple weeks because you were prepared along the way.
10:41Robert Croak:So if you're taking notes and taking action right now, write this down on your notepad. There are three documents that are going to answer 90 % of your questions before you even start your whole tax filing process. The first document is your W-2. You have that. Your employer gave it to you. It's got all the details in it. The second document is your most recent pay stub. that's got a ton of information as it relates to retirement contributions, healthcare, all that fun stuff, right? It's all on there. And the third document, which is more of like a pile of documents, but it is last year's tax return because that old tax return, right?
11:18Robert Croak:2025 tax return in this situation is going to tell you all the different accounts and forms that, oh, I had mortgage interest. I reported, I reported a 1099 for interest I earned on a high yield savings account. I reported a 1099 for this brokerage account because I made some trades, right? Last year's tax return is going to have all that information. So it's your job to look at that tax return and say, okay, I now need to essentially go find all of the updated forms as it relates to these specific transactions that took place last year and likely took place again this year.
11:53Austin Hankwitz:And if you're like us and you own multiple businesses, you own real estate, reach out to your CPA and file an extension. It's not illegal, it's not frowned upon, and it's actually encouraged so you're giving yourself more time to comb through everything that you might have missed and ensure you file properly. So stop being afraid of filing an extension. I do it every year. I'm sure Austin does it most of the time, if not every year, because we need more time as your tax returns get more complex. Yeah.
12:23Robert Croak:And let's be clear, right? An extension is different from procrastination.
12:28Austin Hankwitz:That's right.
12:28Robert Croak:An extension does not mean failure to file. It just means I'm going to file a couple of months after April. Failure to file means, oh, I just, I didn't even file my taxes for the last year, right? That comes with a penalty. That's 5 % of your unpaid taxes per month up to a 25 % penalty. Failure to pay is another 0.5 % penalty per month. If you can't pay your full taxes by the deadline, that's fine. Just file them anyway, because filing without paying is dramatically less expensive than just like not filing at all. Now, Robert, we alluded to it earlier in this episode. We're talking about our favorite tax credits that we think everyone should be taking advantage of.
13:11Robert Croak:So here are some of those, because this is the biggest way a lot of people leave money on the table, the tax credits and the deductions. Remember, the standard deduction for 2025 is$15 ,750 for single filers and$31 ,500 for married filing jointly. If you itemize your deductions and they do not exceed those numbers, you should take the standard deduction and move on. But if you are itemizing your deductions, think mortgage interest, state and local taxes, health care expenses, charitable contributions, things of that nature, and you itemize those deductions and it's above that$15 ,750 or the $31 ,500, then that's how you should proceed when it comes to filing your taxes.
13:58Robert Croak:I itemize. Unfortunately, my mortgage interest is every year beyond just the$15 ,750. That's out the window, Robert. So yeah, I'm itemizing every single year. But y 'all should consider doing the same if it's a larger deduction than just that$15 ,750 or$31 ,500, depending on single married filing jointly.
14:18Austin Hankwitz:And these credits are even more impactful than deductions because they reduce your tax bill dollar for dollar. So, for instance, the earned income tax credit is a good example. If you're married filing jointly and your adjusted gross income is$68 ,675 or below and you have three children, you're likely eligible for an$8 ,046 credit. And this could even be straight up in your refund if you don't already owe taxes for some reason. Number two for me, I really like this one as well. Super simple. The child tax credit, very popular. So if you're married filing jointly and make under 400K a year, you can get up to$2 ,200 per qualifying child under 17.
15:03Austin Hankwitz:This is major, this is easy money. You just have to know what you're looking for. And number three for us is the saver's credit for retirement contributions. I know that's a mouthful, but let me explain. If you're married filing jointly and make less than$79 ,000 a year and contribute to your retirement accounts, you can qualify for up to$2 ,000 in tax credits. This is so important to go out and find if you qualify for these credits and actually take advantage of them. You know, we're always trying to find you guys the free money, the tax credits, and all the hacks to help you keep more money in your pockets.
15:39Austin Hankwitz:And this episode is a great example of that.
15:42Robert Croak:Yeah, I'm going to call it that earned income tax credit. If your AGI is below that$68 ,675 and you have three children, that's a no-brainer$8 ,000 tax credit. And again, like Robert said, there's a difference because it's like, oh, you owe taxes and we're going to give you a credit down to zero. But no, this is like zero and then also a refund. So this will count toward a refund, not just like lowering your tax bill. And again, go look up all this stuff. Go do your own research. Talk to a CPA. I'm not a CPA. Robert's not a CPA. We're just here trying to find the gems, share them with you all so you're not as intimidated about taxes on an annualized basis.
16:22Austin Hankwitz:Yeah. And I want to get into our next call out and that is the knowledge to make tax season work for you. That's what this entire episode is about. So let's round off this episode talking about how to make tax season manageable. The single most important thing you can do is start a folder. I don't care if it's a manila folder or a digital folder, do that on January 1st of every year and label it for that tax year. Because every time a tax document arrives that could be tax related, it goes into the folder. I have one of these. So does Austin. You're going to put the W-2s, the 1099s, the receipts for charitable donations, mortgage interest statements, anything that is relatable to your taxes goes into this folder.
17:05Austin Hankwitz:It might seem old school. I have my folder sitting right here. Austin's got his big red folder there, but it is so important because everything that is related to these transactions needs to be there. So when April rolls around, you're not scrambling, you're just opening a folder, organizing it and getting it sent off. Or if you're doing your own taxes, it's all right in front of you. So there's no stress.
17:28Robert Croak:Yeah. Like welcome to adulthood, right? I mean, like seriously, congrats. You have to file taxes, go get yourself a folder from office max or staples. Like that's what I did. I got this red folder. I showed Robert when we were making notes on this episode. In my red folder, it's just that year and it's got all the stuff. It's got the mortgage interest, the high yield savings account, 1099, my broker stuff, like all of the things. It's all right there in the folder. So when I'm ready to say, hey, Mr. CPA that I work with, here's all the stuff. Robert's doing the same thing. He's got his folder right now on screen.
18:01Robert Croak:You need to get a folder. And what you need to also do, because I know a lot of y 'all are receiving these 1099 broker statements in email and digital, go make a Google Drive, go make a Dropbox folder, go do something digitally as well. So you have everything. What I've done is I scanned using the Notes app on my iPhone, every single physical piece of paper that I get in the mail that has to do with these tax transactions, email it to myself, and then I upload it into that Google Drive folder that I use. and I have it for every single tax year. And that's how I organize everything. So seriously, y 'all got to be doing this.
18:37Robert Croak:It's so simple. It takes no time at all. Love this call out. The second thing y 'all need to consider when it comes to having a manageable approach to filing taxes every single year is to understand how you want to file those taxes, right? And figuring that out before you actually have to file. So here's an example. You can file yourself with software, TurboTax, H &R Block, stuff like that. It's going to cost maybe$100 or so. You can use a CPA or some sort of tax professional, several hundred dollars, but really comb through all your stuff. Or you can take advantage of the IRS free file program, assuming your income's under$79 ,000 a year.
19:18Robert Croak:You can do this on Cash App and it's just no brainer, super simple. It literally is free. It's really cool. So go do that if you want. We're also going to have a link in the show notes below for that IRS free file program. But understanding what you want to do before you even get started is going to help you a lot because if you're doing the CPA thing, Robert, your CPA is going to want to have all this stuff physical, maybe print it out. Maybe it's going to want to, you know, oh, upload it to our specific software or share it with us digitally or whatever compared to maybe you want to use a TurboTax.
19:49Robert Croak:You got to make an account. You got to make sure you've got the stuff figured out there. There's a little, you know, nuances here and there, but having them figured out ahead of time is how you're going to get in the game and stay in the game and not fall victim to anxiety along the way.
20:02Austin Hankwitz:Yeah, I love that because each of these have their trade-offs, but the more organized you are ahead of time, the less stress you're going to be having. And that is what this entire episode is about, is giving you the playbook so you don't have stress around taxes and you don't leave money on the table because you weren't prepared. And software is inexpensive and works well for most returns, for those of you that are W-2 employees. But a CPA costs a little bit more in itself. But if you have more complexities, say you have freelance income, you have rental properties, significant investments, it's always good to get a CPA's eyes on that to make sure you're filing correctly.
Read the full transcript
20:41Austin Hankwitz:And free file is genuinely underused, and it is genuinely free. So the worst approach here is making the decision under deadline pressure in April. That's why we want to stress to you guys to get ahead of it, get that folder started and get everything organized. And the next way to help your filing become more manageable is if your situation changed significantly in the past year. Maybe you got married, you had a child, started freelancing, bought a home. Maybe you inherited some money. That's the year to spend at least an hour or two with a tax professional. Life changes are where people miss the most money.
21:14Austin Hankwitz:And a one-time consultation oftentimes more than pays for itself five times over.
21:20Robert Croak:And finally, Robert, this just goes without saying, right? But if you owe money to the IRS and you can't pay it all at once, the IRS has a payment plan option, an installment agreement that lets you pay it over time. It is far better, Robert, to owe the IRS money and be on this payment plan than not filing your taxes at all because you don't have the money, right? Do not ignore the problem and watch those penalties compound on themselves. The IRS would much rather work with you and your situation than chase you down. Most people who engage with the process directly find it far more workable than they originally feared.
22:02Robert Croak:Remember, Robert, it is illegal to not file your taxes. It's perfectly fine to file them and not have the money to pay the IRS. There's a big difference between the two. One is a payment plan. The other is jail time. It's okay to be on a payment plan. It's not okay to go to jail.
22:21Austin Hankwitz:Yeah, I just talked about this the other day with a friend, a dear friend, actually. And he owns multiple businesses. He has two or three real estate properties. and he was telling me how he hasn't filed the last two years because he was behind. He didn't know what to do. He didn't have all the information. And I said this exact thing to him, what you just spelled out. Get it filed. Doesn't matter if you don't have the money because you want to get it filed and then work out the payment plan. It's better than trying to dodge it because guess what? It's never going to go away. And then one day they're going to show up at your business or your home.
22:53Austin Hankwitz:They're going to start knocking and you're going to go to jail. That's why we want to make sure everyone gets ahead of this and stays organized as best as they can.
23:02Robert Croak:Yeah, maybe we should talk about this for a second. So personally, I've never been behind on my taxes, but I know a handful of entrepreneurs that I respect. I really respect that they simply didn't have the right tax guidance in the beginning to help them navigate how much money to set aside. If it's sales tax or if it's, you know, federal income tax. And they had to go on a payment plan with the IRS. Like it's okay. That's totally normal. It's, I would much rather have a payment plan. Oh, a little bit of interest and have like this sort of loan with the IRS to get them their money paid than just, uh, figure it out, figure it out.
23:39Robert Croak:And it never gets figured out. Fast forward two, three, four years, Robert. And then you got this big mess staring at you in the face.
23:46Austin Hankwitz:Yeah. A lot of people with successful businesses and careers end up in this boat because they feared what to do and they didn't have the right knowledge. Like you alluded to, so they do nothing. Don't run from this. Be organized. Get yourself a 50 cent folder. Get everything put together and give it to somebody. If you have to, go to a CPA and say, hey, I'm sorry. This is where I'm at. Help me fix this and spend the money because it's better now than being stuck with all the penalties like Austin's talking about.
24:14Robert Croak:So here's what you need to do. You need to understand that every dollar that you recover through those credits that we talked about, every penalty that you avoid by filing on time, And every specific deduction you make along the way that is actually, you know, real transaction, you can really, you know, claim this deduction. That's money that will be saved and put in your pocket and will compound for you in your favor over a decade. So take this tax stuff pretty seriously.
24:43Austin Hankwitz:Because building wealth isn't just about making more money. It's about keeping more of the money you already made. And understanding taxes is one of the most direct paths to doing that exactly. You guys hear us say that all the time on the Rich Habits podcast and in the Rich Habits Network. It's not what you make. It's what you keep. And that starts by filing your taxes and understanding how to get the most benefits from the tax code.
25:06Robert Croak:And I will say this too. I literally had a date with Claude on my computer a couple weekends ago. I shared with it all of my tax situation. you know here's my brokerage gains here's what i did in this here like i just i was way transparent with it and i told it my whole situation i said help me optimize how do i save what can i do what levers can i pull to optimize my taxes i used opus 4.6 by the way for those asking and it laid out a path for me to make seven changes in my specific business to net positive save or maybe add $220 ,000 to my net worth in 2026 that I was not planning on doing. This comes with solo 401k contributions, QBI deductions, putting Ireland on salary, we get married, like all this stuff, right?
26:00Robert Croak:Like it came up with a bunch of different ideas. So if you don't or can't afford a CPA or a tax professional or tax strategist, congratulations. Artificial intelligence is here. It's in your pocket. It's on your iPhone, your laptop. It's everywhere right now. Go to Claude, go to ChatGPT, go to Gemini, and just start talking with it and share your situation. And again, this is AI telling you stuff. So I took it, I screenshot it, and I sent it to my CPA and said, hey, is this legit? Right? So that's what you need to do with it. Don't just go do it without figuring out if it's legit or not. All of the resources are available to you right now.
26:35Robert Croak:It's never been easier to try and optimize and do everything you can to ensure that you are doing the tax stuff as effectively as possible.
26:44Austin Hankwitz:What an incredible episode. I feel like I could run through a wall right now because I just love putting together episodes like this where it can change the lives and the future finances of tens and tens of thousands of people that follow this podcast. So what an incredible episode, but let's get into the Q &A now.
27:02Robert Croak:Well, before we get into the Q &A, Robert, got to give a shout out to public.com, the investing platform for those who take it seriously, because on public, you can build a multi-asset portfolio of stocks, bonds, crypto options, and now generated assets, which allow you to turn any idea into an investable index using AI.
27:23Austin Hankwitz:And it all starts with your prompt from renewable energy companies with high free cash flow to semiconductor suppliers growing revenue over 20 % year over year, you can literally type any prompt and put the AI to work. It screens thousands of stocks, builds a one-of-a-kind index, and even lets you backtest against the S &P 500, all with just a few clicks.
27:44Robert Croak:Generated assets can be thought of as ETFs with infinite possibilities. They're completely customizable based on your thesis, not someone else's. So when you're ready to go try it, Go to public.com slash rich habits and earn an uncapped 1 % bonus when you transfer your existing portfolio through our affiliate link. 1 % bonus, right? You got$100 ,000, transfer it to public and get your free$1 ,000, right? 1 % match. Robert, imagine you have a million dollar portfolio sitting, you transfer it to public and you get$10 ,000 completely for free. How cool is that? public.com slash rich habits. Go check them out.
28:22Austin Hankwitz:Paid for by public investing and full disclosure in the podcast description.
28:26Robert Croak:And as a reminder, if you have a question for the podcast, follow us on Instagram at rich habits podcast and DM us. All the questions from today came from Instagram DMs over the last seven days, right? So like we're trying to get through them as often as we can. We also have questions asked to us via email that we answer all the time on the show, richhabitspodcast at gmail.com. Let's dig in. First question coming from Rich on Instagram. Rich says, I work a W-2 earning$107 ,000 a year while my wife earns$93 ,000 a year. We own two rental properties. One of them cash flows$1 ,600 a month at 2.75 % interest and the second one cash flows at$600 a month at a 4 % interest rate.
29:13Robert Croak:That one, we owe$103 ,000 still on the mortgage. Our primary residence is at 3 % with$500 ,000 left on the mortgage. We each have Roth IRAs worth about $80 ,000 combined and a traditional IRA worth about$115 ,000. We have a bridge account on public with $20 ,000 in it and a Schwab account with$40 ,000. Our 529s for our children each have$5 ,000 in it. My question is, do I pay off the mortgage on the 4 % interest rate rental property? It's a loan of $103 ,000, effectively raising our cash flow from$600 to$1 ,500 per month, or do I take the$103 ,000 that I would have paid off with the mortgage and instead invest it into the markets?
30:00Robert Croak:Our overall goal is a more passive income lifestyle, spending time with our children. Really love the show and would appreciate your feedback. Robert, what advice do you have for Rich?
30:11Austin Hankwitz:I love this situation, Rich. You guys are crushing it. You're making a lot of money. You've really done a lot of things well, but I would prefer to see you take that$103 ,000, get it working into the markets, into one of these taxable brokerage accounts that you have versus paying off one of these low interest mortgages, because even at 3.99%, I still think you're going to have the positive arbitrage of 2, 3, 4, 5 % if you had the money working for you in the markets versus paying off the mortgage. And then maybe look at it down the road after you've made more money and built more of this base we talk about, and then maybe go back and look at paying off that mortgage.
30:52Austin Hankwitz:But right now, I'd rather see that money going into the markets, dollar cost averaging over the next few months rather than taking out a loan to pay off what I consider is a low interest mortgage.
31:03Robert Croak:Yeah, I'm just kind of looking at it. And again, you guys have crushed it. You've got a cash flowing rental property at$1 ,600 a month. You've got another one at$600 a month. I'm sure you're doing all the normal things as it relates to setting money aside for vacancy and maintenance and repairs and things like that. So you're doing just fine here. But you've only got about$250 ,000 in the markets. And I don't say only as if that's not great. That's a lot of money for anybody. $250 ,000 here at about 40 years old is incredible. However, I would love to see that be$350 ,000. I really would. I personally wouldn't pay off a 4 % interest rate mortgage, especially if it's cash flowing$600 a month.
31:43Robert Croak:That just doesn't really make too much sense to me. And the thing is though, you mentioned, hey guys, I want passive income. That's my whole deal. Okay, cool. Take that $103 ,000, build a portfolio of NEOS funds with that money, SPYI, QQQI, maybe a little bit of BTCI or IAUI for Bitcoin and gold or IYRI, their real estate income index ETF there, and start earning passive income on that$103 ,000. You play your cards right, you'll start getting paid between maybe$1 ,000 and$1 ,200 per month from NEOS funds, all tax-efficient income deposited to your brokerage account. So if you're looking for that passive income tax efficiency, I think a NEOS funds portfolio, assuming again, you're optimizing for that passive income over growth, that NEOS funds portfolio could do wonders for your situation.
32:37Austin Hankwitz:I love that takeaway. I'm so glad you added the NEOS funds portfolio. So smart. And it's just safer to me because if you're so overly leveraged in real estate, especially you guys did a great job with the low interest mortgages, I still like to have you more base, like Austin alluded to, going into your 40s than that$200 ,000.
32:58Robert Croak:Well, I mean, it kind of reminds me too of like, you know, the pandemic. I don't know what state riches in, but you know, I think it was in California and New York and a couple other states out there. It was like tenants don't have to pay their landlords rent, right? for a little bit, right? And so like, as a landlord, what are you supposed to do? So Rich, I don't know your situation. But to Robert's point, it's like, there's a lot of uncertainty sometimes when it comes to building a real estate portfolio around vacancies or around different laws and different things of that nature, you know, maintenance repairs that normally pops out of nowhere.
33:28Robert Croak:But something I think much more durable and predictable from a monthly income perspective, because you're talking about this, this income that you want to have passive income, NEOS funds. So again, go check those out. Love the situation, Rich. Congrats on all you've built and definitely check out some of these tax optimizations, credits, and strategies that we've alluded to in this episode. Maybe you should go to Claude, talk about all the stuff you're doing with your rental stuff or chat GPT or Gemini or whatever and ask it, how do I optimize taxes in favor of my situation with these rental properties, right?
33:58Robert Croak:Maybe that's something to consider. So our next question on Instagram comes from EB. EB says, I'm 60 years old. I'm self-employed, and I have a 401k from a previous employer. I have an opportunity to purchase a property. I need to sell a property that I own, use some of my 401k and the gains from the property to qualify for a mortgage loan. Do you all know of any smart purchasing strategies or maybe even landmines I should be looking out for? I know you all own your own businesses, So how do you all go about qualifying for mortgages while being self-employed? Good question. Robert, you want to kick it off?
34:36Robert Croak:You've bought a lot of homes as a self-employed individual throughout your life.
34:39Austin Hankwitz:Yeah, this is a tough one because at 60 years old, I hate to see money come out of 401k and have to sell another property to be able to buy this property. But if I'm understanding the question right, he could sell the current property, do a 1031 exchange into the new property to get some benefits there. but I would just be careful because we don't have the totality of the numbers of how much you're taking out of a 401k, even though it's an older one and it's probably been sitting for a while, which helps, but I don't know the totality of the numbers, but I don't know of a smart purchasing strategy other than doing the 1031 exchange into the new property and using as little funds as possible.
35:19Austin Hankwitz:But I also don't know your situation. Could you qualify for an FHA loan? Could you qualify for some of these other rural loans like a USDA loan, but without knowing more about where EB lives and the other situation with the numbers, it's tough to give too much of a strategy. But I hope that helps some to help you understand that you do have options. I just don't know what all options you have.
35:44Robert Croak:Yeah, I think from a landmines to look out for perspective, there's a couple things that jump out. The first one's the tax impact, right? The 401k, the traditional 401k you're alluding to, all the money you take out of it is taxed at ordinary income. So if you're like, oh, I need to go take out a massive down payment for this house from my 401k and that down payment is$200 ,000 or$100 ,000, whatever it is, you owe ordinary income taxes on that money in that lump sum, right? So the more you take out, the higher your effective tax rate is going to be because of tax brackets. The other thing to look out for is that self-employed sort of mortgage qualification, right?
36:22Robert Croak:That one's pretty hard because normally when it comes to qualifying for a mortgage, you need a couple years of income and showing reputable, predictable income as a business owner before a bank's going to want to underwrite you. You might have to pay a higher interest rate on this mortgage than what you might see online. So if you're seeing online an interest rate at 6.5%, you might have to come around 7 % or 7.5%, depending on your situation, because you're self-employed and you don't have that normal W-2 income. So just keep those two things in mind as you kind of budget and think about, can you actually afford this home?
37:00Robert Croak:Is it a good idea to tap in to the 401k? Things of that nature. And finally, I guess the good news is really depending on what type of property this could be, maybe you can qualify for a DSCR loan. So, Robert, maybe talk about what a DSCR loan is and how to qualify for one of those. I know you've done those before as well.
37:19Austin Hankwitz:Yeah, a DSCR loan, a debt service coverage ratio loan could be a good option here because they're not basing the loan on your qualifications. They're basing the loan on the comparables of the property itself. What does it rent for if it's multi-units? So if it works out that the numbers are in your favor based on the debt service, you could qualify for that. and I've used that many times. But one more that I want to mention before we move on is you could also look at a bank statement loan. Those have worked really well for me, but you will have to be prepared to pay around a half percent to one percent more than a traditional mortgage.
37:57Austin Hankwitz:But it helps you because they're not going directly off of your credit and your income. They're going off of the continuous deposits and what the average is over two years in your bank accounts. Those can work really well for people in your situation as well.
38:13Robert Croak:Yeah, that's actually how I paid for the house I'm sitting in right now is a bank saving loan. And unfortunately, it was 1 % higher than what the 30-year mortgage was. Before we jump into our final question, got to give a shout out to Neos Investments. Actually, we just talked about them, but they are a sponsor of this episode too, which I didn't even realize. Neos, they offer ETFs that seek high levels of monthly income with a keen focus on that tax efficiency that I was alluding to earlier in that answer. They also provide core portfolio exposure across equities, fixed income, real estate, cryptocurrency, and cash alternatives like T-bills.
38:48Robert Croak:Their ETFs may be especially interesting for investors looking to generate tax-efficient monthly income inside of their portfolios. Their funds may serve as a compelling income-focused alternative or complement to many of the investments already in portfolios.
39:03Austin Hankwitz:And if you're looking to add passive income-focused ETFs to your portfolio, consider learning more about NEOS ETFs at neosfunds.com. And as with all investments, investors should carefully consider their investment objectives, risks, charges, and expenses of NEOS exchange-traded funds before investing. To obtain a prospectus containing this and other important information, please visit neosfunds.com. Please read the prospectus carefully before you invest. An investment in NEOS ETFs involves risk and including possible loss of principal. There is no guarantee that NEOS ETFs will make monthly distributions and those amounts may fluctuate from month to month.
39:45Austin Hankwitz:Cryptocurrency is relatively new and the market has its own specific risks. NEOS ETFs are distributed by Foresight Fund Services, LLC.
39:53Robert Croak:So our final question here is coming from Anna on Instagram. Anna says, hi guys, I've been listening to your podcast for two years now and it is just awesome. Thank you, Anna. We appreciate that. Anna says, I'm 36 and I was trying to do some catch up on my retirement by maxing out my 401k for the last two years. But with all the uncertainty and fast AI developments I'm seeing in the world, I'm debating if I should even save for retirement. I'm concerned that in 30 years, we might not even exist as a society. The dollar might not even exist as currency and the banks, they just disappear. Should I save money, buy a farm in Italy that I've been dreaming about for years and go do that?
40:38Robert Croak:Or should I contribute to my 401k? Thank you. Wow, Robert, what a question from Anna. Anna's been looking at the headlines a lot. I think Elon Musk did an interview or something where he said that you don't need to save money for retirement because everything is going to be free in the future because the cost to make a widget is going to go down so much because humanoid robots and autonomous this and AI that, that widgets are going to be essentially free and we're going to run out of things to make and everyone's going to. Oh, Anna. So here's my perspective. I am just as scared as you are. I am.
41:16Robert Croak:I am just as scared as you are. I've got neighbors where they've got four little girls and they're between the ages of two and 12. And I don't know what their lives are going to look like when those kids are 30, 40, 50 years old. I can't even predict it. I don't know, to your point, if society will exist at all, if we're going to have a currency that's not the dollar, if it's going to be some AI agent thing or if humanoid wrote, or, you know, Sam Altman was saying we would get universal basic income, but it will be in the form of token compute, right? Like, I don't know. I have absolutely no idea.
41:54Robert Croak:And I'm just as scared as you are. It's very interesting to reflect upon, Anna, because I've seen, to your point, a lot of people talk about what you're talking about, where people that understand artificial intelligence, technology, they've been serial entrepreneurs, they're doing one of two things. they're either going all in on ai and using this technology to go make billions of dollars and build the next unicorn company startup or they're going to a farm in italy and they're living off the land because they know what the future is going to be and it scares the crap out of them and they want to be able to have some goats a couple cows and chickens and they're good to go right like there's no in between right now unfortunately the people that are stuck in between are just asleep at the wheel.
42:39Robert Croak:Robert, I don't think I have an answer for Anna here. Of course, Anna, max out your 401k, you know, do the things you're supposed to do, be responsible with your money, right? Assume, you know, whatever, but like, what's your take, Robert?
42:50Austin Hankwitz:I think this question hits home to me so much because I love that I get to wake up every single day and try to educate people on what to do with the mindset, with their money, with their 401ks, all of this stuff alongside you, Austin. But I love this question because I think it really opens the door for everyone watching this episode that's still here at the end of the episode to ask themselves this exact question. Where do I see my life in 10 or 20 years? And what do I care about the most? Because things are changing. If we end up in this abundance economy or we end up with no dollar and we're in this mess and who knows what's going to happen, owning a farm with goats and chickens and making your own cheeses and eggs and corn sounds pretty cool.
43:38Austin Hankwitz:But I think the number one takeaway for me is understanding what you need to do now until you buy the farm in Italy or you buy the farm in Nashville and have that land because it will certainly feel good for all of you that own an asset, that dirt, that home, that barn, those things that if everything goes south and we do end up in this controlled government environment when it comes to income, you know you're still safe. And that's going to be the key thing, I think, for most people thinking ahead for the next 10 or 20 years is how do I create safety? Because I do think the financial systems are going to change.
44:19Austin Hankwitz:And we might be in this dystopian future where it is all tokens and through the government and who knows how on the blockchain. And I love the idea of someone owning a farm. So I really enjoyed this question and it was a great way to finish this episode.
44:34Robert Croak:I completely agree, Robert. And the additional advice I'd give you, Anna, is not to think about it as a black and white. I can either contribute to my 401k or I can go to Italy and own a farm. Why not both, right? Why not contribute up to the match in your 401k and get that free money, max out your Roth IRA because you want to make sure that if society doesn't crumble, you're not a Walmart greeter at 80 years old. And anything above that, you are now setting money aside for that farm in Italy. Maybe you're working a side hustle right now for that farm in Italy. Maybe working a second job right now to save for that farm in Italy, right?
45:11Robert Croak:You have that goal. And that goes for anyone else, right? It's like until there truly is a collapse of society and the dollar is not the, you know, all the, we could talk about this stuff. We've been talking about this, you know, Y2K, the Cold War, you know, COVID, 2000, everything was crazy in the past. We've always had these big hoo-hum, rum-drum, get all scared and crazy stuff with headlines, but it's the wall of worry. It's the wall of worry. And the stock market continues to climb the wall of worry is what they say. And I know no technology like AI has ever existed. So it's a little bit different this time.
45:48Robert Croak:When you kind of get over that and you realize maybe it's not, I need to still look out for myself, my future, my retirement, things of that nature. And I love Robert's point, right? Owning assets. It'd be really cool to own a paid for plot of land with a nice home on it and some chickens and a garden. Like I love that. That's the end game for me, certainly. Right. I really think that's a great idea for you, Anna and anyone else listening, but I don't think it's black and white like you gave it to be. I think there's a lot of why not both in this question for you, Anna?
46:20Austin Hankwitz:Yeah, and I think to put a bow on it, it's not about stopping your investing. It's not about one or the other because everyone needs to prepare for the future, but it's really digging deep and asking yourself, what do I really need as a person? What do I wanna do for retirement? Do I need three cars in the driveway in my neighborhood with my high HOA? or would a cool small farm be better for my kids to grow up on, maybe on some water or whatever? Everyone's different. Personal finance is different. So everyone listening, figure out what works for you. We can't predict the future. We can only try to help you prepare for it.
47:01Robert Croak:Everybody, thanks so much for tuning into this week's episode of the Rich Habits Podcast, helping you demystify and approach your taxes in a very stress-free, manageable way. Hope that you guys learned a ton. We are super grateful that so many of you come back every single week to listen to the show. If you've not yet signed up for the Rich Habits newsletter, go check that out. Every Thursday morning, we publish a nice market update as to what happened, what Robert and I are thinking about the headlines or portfolios or ideas, things like that. Just Google Rich Habits newsletter. It'll pop right up or use the link in the show notes below.
47:37Robert Croak:If you've not yet checked out the Rich Habits Network, that is our community for our biggest fans. Those are people that want more FaceTime with Robert and I because every Tuesday evening, Robert and I host a live stream on Zoom where we talk with everyone about their questions, our ideas, our portfolios. We open up the playbook and make sure everyone understands what we have our eyes on, what we're doing with our money. And we're also talking about investment opportunities. We just invested into So Aptronic, a humanoid robotics company, secondary shares, which was really exciting. So we're doing stuff like that all the time in the Rich Habits Network.
48:13Robert Croak:Seven-day free trial to join that. You can join completely for free. Join a live stream. Figure out if it's right for you. If it's not, no hard feelings. Thanks for listening to the show and supporting us. And, of course, got to give a shout out to WallStreetFavorites.com, the best way to understand what Wall Street thinks about your own portfolio. It will rank your portfolio by highest upside, according to Wall Street. You can then go in and see what the institutions are buying and selling of the stocks in your own portfolio. It's got sector breakdowns. It's got technical analysis. WallStreetFavorites.com.
48:50Robert Croak:We built it for you all. A lot of it's free, a little bit of it's pay. Go check it out. It's awesome. We're so proud of it. Again, all the links to the Rich Habits newsletter, Rich Habits Network, and Wall Street Favorites will be in the show notes below.
49:03Austin Hankwitz:And to be clear about the Rich Habits Network, if you've been on the fence with joining and you've heard about it over and over watching the podcast, there is a seven-day free trial, but I want to make something very clear. When we do these Tuesday live streams, it is Austin and myself. I had a meeting last week with a company and they have all these communities that they help run. And I was surprised at how many of these communities, the actual founders, the people that brought the people into the community don't actually do their live streams. They pass them off to coaches and underlings and they pop in for five minutes here and there.
49:38Austin Hankwitz:No, Austin and I do two hours usually every single Tuesday with all of our best stuff. So if you've been on the fence, make sure you understand that we are there every single week sharing our best ideas, our best investment opportunities with each and every one of you in the Rich Habits Network.
49:55Robert Croak:Absolutely. People suck. How could they? Come on now. It's terrible.
49:59Austin Hankwitz:I couldn't believe when I heard it. I'm like, what do you mean? You have this community and you don't do them. Oh, no, I have my coaches do them. I have my underlings do it. I'm like, why would anyone want to pay for that? We're paying and people want to be involved in communities where it's really a community and it's not about a paywall. So I just wanted to clear that up for people that might think we're these two big brains that aren't in the call ourselves. No, we run the call. We do every single call. So I wanted to clear that up because some people might not know.
50:30Robert Croak:Well, we are in there every Tuesday night from, what is it, 8.30 to 10.30 Eastern time. We have a Zoom call, ask your questions, pop up on screen. It's a good vibe. It's awesome. Join us over there, Rich Habits Newsletter, Rich Habits Network, WallStreetFavorites.com. Everybody, thanks so much, and we'll see you on Thursday.
51:11We'll see you next time.
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