
Loading summary
A
The following is a paid sponsorship, not an endorsement by NerdWallet's editorial team. Today's episode is sponsored by Bilt.
B
You guys have heard me talk about BILT as the loyalty program that lets you earn points on rent wherever you live. And guess what? They just leveled up even more. As of 2026, renters and homeowners can also earn up to 1.25x points on their housing payments.
A
This is thanks to Bilt's three new credit cards, the Palladium Card, Obsidian Card and Blue Card. All three can turn your housing payments, rent or mortgage into flexible rewards so you can choose the card that fits your lifestyle without missing out on points and exclusive benefits.
B
Built Points can be redeemed at top airlines and hotels, Amazon.com purchases, future rent payments and more. Built Points have also been ranked by top publications as the industry's most valuable point currency.
A
Your housing payment is most likely your biggest expense. Make it your most rewarding. Find the card that fits your lifestyle and Apply today at joinbuilt.com smartmoney that's J-O-I N B I L-T.com smartmoney make sure to use our URL so they know we sent you. Terms and limitations apply subject to approval and eligibility.
B
BILT cards are issued by column NA member FDIC pursuant to license for MasterCard.
A
International, Inc. Today's episode is sponsored by.
B
Quint's Quince is all about elevated essentials that feel effortless. They're designed for layering and mixing and every piece helps build a timeless wardrobe made to last with versatile silhouettes and thoughtful details. They're the kind of styles that you wear again and again.
A
They've got wardrobe staples with quality that's made to last 100%. Organic cotton sweaters, premium denim made with stretch for all day comfort luxe cotton cashmere blends perfect for the changing seasons.
B
And Quint's works directly with safe ethical factories and cuts out the middle so you're not paying for brand markup.
A
Quint uses the highest quality materials like 100% European linen and organic cotton. Everything is built to hold up season after season.
B
One of the pieces that I recently got from Quint was Carry On Luggage so I needed to upgrade mine because it broke and I got this beautiful neutral cream colored Carry on suitcase. It is perfect for international travel, very durable and I look stylish when I go to the airport.
A
Quint came in so handy over the holidays for me. I did not know what to get my mother in law but I found the perfect cashmere zip up hoodie and she loves it. So I'm glad I could use Quince to get me through the holiday season.
B
Refresh your wardrobe with quince. Go to quince.com smartmoney for free shipping on your order and 365 day returns.
A
Now available in Canada too. That's Q-U I N C E.com smartmoney to get free shipping and 365 day returns. Quints.com smart money self employment can be lucrative. It can also be expensive if you don't plan for taxes. This episode learn about how to navigate self employment taxes. Welcome to NerdWallet's Smart Money podcast where you send us your money questions and we answer them with the help of our genius nerds. I'm Sean Pyles.
B
And I'm Elizabeth Ayola. Later this episode we'll be talking about navigating self employment taxes is but first of all, we have our weekly Money News roundup where we break down the latest in the world of finance to help you be smarter with your money. Now, there are some huge athletic events coming up. All gather here if you're a sports fan. The Winter Olympics in Milan officially begins on Friday. Woohoo. The New England Patriots and the Seattle Seahawks are facing off at Super Bowl 60 on Sunday. And NCAA March Madness is just on the horizon.
A
So today we're talking about the rise of sports betting and what happens when betting apps stop feeling like a game. Our news colleague Ana Hilhosky is here to dig into it with us. Hey, Ana.
C
Hey, Elizabeth and Sean. Yeah, the Super Bowl, Olympics, March Madness, we've all seen that before. Betting on sports also isn't particularly new, but what's changed is how easy it is to bet instantly on your phone in real time while the game is happening. So a January 26 report from Ipsos found that the share of Americans who have placed a bet on a live sporting event has has doubled since 2022. It found that 17% of Americans surveyed had placed a legal sports bet, up from 13% in 2024 and 8% in both 2022 and 2023.
A
So, Ana, can you give us some background on this? Because it's all pretty new, this huge rise in sports betting, right?
C
Yeah.
A
Or at least legal sports betting, I should say.
C
Correct. So before 2018, legal sports betting was pretty much limited to Nevada. So you're in Reno, you're in Vegas. That's where you can bet. And it meant that the illegal sports betting market was thriving. Then in 2018, the Supreme Court ruled in Murphy vs. NCAA that the states have the authority to decide what laws remain in force in their own states, which meant they could legalize, regulate and tax sports betting. And that last one is really key. States saw legal betting as an opportunity to earn revenue. And today sports betting is mainstream. And more than 30 states and D.C. will allow some form of legal sports betting and that include mobile apps and online wagering.
B
Wow, that's over half of the states that allow legal sports betting now.
C
Yeah, it's everywhere.
B
Anna, talk us through app based betting. Because betting is becoming so accessible, people can literally do it on their phones now using an app.
C
App based sports betting is dominated by companies like DraftKings, FanDuel, BetMGM, and Caesar Sportsbook. And these apps work by letting users place wagers before and during events. Now, the sportsbooks set odds that reflect probabilities and public betting as and then an algorithm adjusts those figures. But they become so popular that at any point these apps are handling millions of transactions at once.
A
Wow, this is a world I am so not a part of. And that's fascinating to me. What I also find really intriguing is just the variety of bets that you can make. It's not just simply which team is going to win. Right. So, Ana, talk us through the different types of bets that people might be able to make.
C
So there are a lot of different types of betting you can make at legal sportsbooks. And I do want to say a couple caveats so I don't have to repeat it every single time. If you win in any of these cases, you're going to get the amount that you bet in return along with your winnings and then another one. Betting lines and odds are always changing. Remember those algorithms and sportsbooks will adjust them in real time. So by the time that you're listening to this, the numbers that I'm quoting might be slightly different. So if you go and check and they're not the same, don't get mad at me. All right, so starting off, money lines are the simplest. You're just going to pick who wins the game. Now DraftKings shows that for the super bowl, the Seahawks are the heavy favorite at minus 2 40. And that means that you'd have to bet $240 to win $100. Once again, you'd get your $240 back. Now the Patriots are the underdog at plus 1. 95. And that means if you made a hundred dollar bet and the Pat's upset, you'd win $195 and get your $100 back.
B
I have never done sports betting myself, but this sounds like the most straightforward kind of betting. And if I were to do it, it'd probably be this again.
C
It's the easiest, it's the simplest, and you're just saying who wins.
A
Okay, so what's maybe a step more complex than this one?
C
So the point spread. The favorite has to win by a certain number of points or the underdog loses by less than that. In order for you to win, there's also an over under, and that's known as totals. This is how it works. Instead of picking a winner, you're going to be betting on the combined total score of both teams. Now, the sportsbooks set a number and you wager if the actual total will be higher or lower, hence over under. So For Super Bowl 60, DraftKings puts the over under set line at 45.5. If you want the over, you're going to be betting that the two teams together will score 46 points or more. If you want the under, you're betting the total will be 45 points or less.
A
So you're kind of losing me here, but this is why I don't follow sports. But we'll just roll with it. I want to talk now about props because this is a form of betting that I find really fascinating just by the sheer number of options, which seems to be infinite.
C
Yeah, this is definitely like the weirdest world in sports betting. So props focus on really specific things happening in a game. There are novelty bets along with this. Who's going to win the coin toss, who's scoring a touchdown, what color is the Gatorade that the players pour on their coach's head when they win, et cetera. Here's one of the real wagers that DraftKings is showing right now. The bet is on whether the jersey number of the first player to score a touchdown is higher or lower than 10.5 over. 10.5 means that you think the players numbers will be 11 or higher. That's the favorite outcome. So you'd have to bet $160 to win $100. Now, under 10.5 means the player's jersey number is 10 or lower, which is less likely. But if you bet $100, then you're going to win $120 if it hits. And finally, one you may have heard of are parlays. And those bundle multiple specific bets together in order to get a bigger payout. But every single one of your picks has to win. So if you bet on three things happening, but only two hit you lose.
A
I think a lot of people listening might be focused on how much money they could make or lose doing this. Me, I'm thinking about taxes here and the fact that people are probably going to have to pay taxes on their earnings. So what's going on with that?
C
Taxes on sports betting can be really tricky and we could probably fill a whole other episode on this, so I'm not going to dwell too much. But sportsbooks will show the total that you get back and that's your original bet plus your winnings. But for taxes you're only going to be paying on the winnings. You can also deduct losses, but only up to the amount that you won.
B
Anna I've been hearing a lot about prediction markets and what I've been hearing is pretty wild because you can bet on almost anything under the sun. Talk us through prediction markets Prediction markets.
C
Are fascinating to me and I kind of won't shut up about them, so I'll try and keep it brief. App based gambling has been around for a while, but in the last year or so there's really been a pivot to prediction markets and that's like Polymarket and Kalshi and those turn your beliefs into tradable assets. So prediction markets let people make money by betting on real world outcomes. You see it with things like elections, economic data, awards, weather, pop culture. But obviously sports are huge on these platforms. Now here's how they work. They use tradable contracts that are priced to reflect the crowd's belief about the likelihood of something happening. So if you're right, you get a payout and if you're wrong, it's going to be pretty much worthless. So let's look at something a little bit more specific in this case. So as of this recording, The Seahawks are at 68 cents, which means that the market thinks Seahawks have a 68% chance of winning. If you buy a yes contract at 68 cents and the Seahawks win, you get a dollar which would be a 32 cent profit. Meanwhile, the Patriots are at 33 cents and that means that the market thinks they have a 33% chance of winning. If you buy a yes contract at 33 cents and they win, you pocket 67 cents. It's fun, it's potentially profitable. But as with all betting, the losses are still very real.
A
And something we've seen with platforms like Kalshi is that it's not just about what you believe might happen sometimes it's what you are rigging to happen. There have been Some controversies in sports betting about this recently, right?
C
Yeah, there has.
A
So all of this is leading to a really new world for sports betting. Can you talk us through how it's changing?
C
You're seeing these commercials for things like DraftKings everywhere. It's become ubiquitous. None of this existed at scale five years ago. And I think it's sometimes difficult when we just see things all the time that you forget how quickly they change. App betting has just become normalized. And prediction markets have also exploded in both volume and visibility. So last year, following the Super Bowl, DraftKings reported that it set a new record for the amount that customers spent betting with them at $436 million.
A
Wow.
C
Yeah.
A
On a single game.
C
On a single game, on a single day. Now, the American Gaming association expects that roughly $1.76 billion will be legally bet on the Super Bowl 60 in the U.S. that's a 27% year over year increase and a record number. This year is also going to be the second super bowl for Cali and the first for polymarket.
B
Are any of you guys betting in the Super Bowl?
A
No, no. You mean are any of you betting on the Bad Bunny concert? Yeah, here. There's some game going on around it.
C
But now there's something else obviously happening, and we mentioned it up at the top. The Winter Olympics, they're starting and there are 116 events. That creates a lot of opportunity for wagers. During the Summer Olympics in Paris a couple years ago, betting really spiked and people were making wagers on all kinds of things, like medal counts by country to specific athletes. Now here's a weird one. The proverbial super bowl of sports betting is actually March Madness. And last year, the American Gaming association estimated that Americans legal wagers would hit $3.1 billion on men's and women's college basketball tournaments during March Madness. We're still waiting to see what the AGA predicts for this year's tournaments, but it's likely to be pretty high.
B
Ana, as you're talking, all I can think about is risk, risk, risk, risk, risk. And also how addictive gambling can be. Talk to us about the risks involved with all of this betting.
C
Right. So, I mean, that's what we're paid to do, right? We're paid to think about how this actually can affect people and their finances. The concerning thing about these apps is how frictionless they are. It's legal, it's on your phone. It's easy for the casual better to get drawn in. But apps are addicting. We know that they are gambling can be too. So then combine the two with some highly energetic sports fans and it can become a problem. There are also regulatory concerns, concerns about gambling addictions, debates about tax rates, and a lot of public frustration with the ubiquity of ads. Now, a Pew Research survey published in October found that while half of Americans didn't see legal sports betting as good or bad for society, an increasing number of Americans do view it as harmful. And that's 43% in 2025, up from 34% in 2022. There's also concern about sports betting impacting the integrity of the game. A Pew Research survey published in October found that 40% of Americans think sports betting is bad for sports, up from 33% in 2022.
A
Yeah, I'm among that 40% of people and I don't even care about sports besides the Olympics. Okay, so Ana, how can people protect themselves? Because we know that people love sports betting. It can be a recreational activity if you budget for it. It might not be a bad thing. But there are still a lot of risks as we were just talking about, right?
C
There's a slippery slope and I'm not gonna sit here and judge people. I'm not gonna say don't gamble. If you wanna gamble, you're gonna do it. But there are very real concerns to consider. So as you said, treat it like entertainment, not income. Decide what your limits actually are before you go into it. If you're not having fun, stop doing it and go do something else that is fun. And most of all, if it's not feeling within your control anymore, you might need to seek help.
A
And what's a good place for people to get that help?
C
Yeah, a good place to start is probably the National Council on Problem gambling. And at 1, 800, my R E S E T that's 1, 800, my reset. There are also typically area specific support options that'll be likely listed on your state's website.
B
Well, thank you so much, Anna. I will not be betting on the color of Gatorade and I will instead be using my money to buy tacos and margaritas.
A
There you go.
C
Far more practical.
B
All right, up next we answer listeners question about navigating self employment taxes and I will be sharing my tax blunders as a self employed person. But before we get into to that, a reminder to send us your money. Questions. Do you want to know how to budget for your leisure activities? Maybe you want to know how to save for a summer vacation or you're in the market for a new credit card. Whatever your money question, we want you to send it to us. And you can do that by calling us and leaving us a voicemail or texting us on the Nerd Hotline at 901-730-6373. In case you missed it, it's 901-730-Nerd. We love emails, but please send them to us@podcasterdwallet.com youm can also leave us.
A
A comment on Spotify or YouTube. And speaking of taxes, we're doing a whole episode about tax season 2026. So if you have any questions about taxes this year, I'm sure you have a pile of documents just staring at you on your desk. I know I do. Let us know. So send us your question any way you want to and we'll answer it in a few weeks. Okay, in a moment. This episode's money question Stay with us. The following is a paid sponsorship, not an endorsement by NerdWallet's editorial team. Today's episode is sponsored by Bilt.
B
You guys have heard me talk about Bilt as the loyalty program that lets you earn points on rent wherever you live. And guess what? They just leveled up even more. As of 2026, renters and homeowners can also earn up to 1.25x points on their housing payments.
A
This is thanks to Bilt's three new credit cards, the Palladium Card, Obsidian Card, and Blue Card. All three can turn your housing payments, rent or mortgage into flexible rewards, so you can choose the card that fits your lifestyle without missing out on points and exclusive benefits.
B
Built points can be redeemed at top airlines and hotels, Amazon.com purchases, future rent payments, and more. Built points have also been ranked by top publications as the industry's most valuable point currency.
A
Your housing payment is most likely your biggest expense. Make it your most rewarding. Find the card that fits your lifestyle and Apply today at joinbuilt.com smartmoney that's J-O-I N B I L T.com smartmoney make sure to use our URL so they know we sent you. Terms and limitations apply subject to approval and eligibility.
B
BILT cards are issued by column NA member FDIC pursuant to license for MasterCard International, Inc.
A
We're back and answering your money questions to help you make smarter financial decisions. Here's this episode's listener question. Hi Elizabeth and Sean. I would like to know if you have any advice on how to navigate tax status for contract work. Previously, when I did contract work, I received Form 1099 NEC. If I'm remembering correctly, during that time I paid estimated taxes during the year and noticed additional tax for self employment, but I only filed as single and personal taxes. I'm looking back into doing contract work again and curious if there is any guidance you can offer on tax setup. Also, in the past year I've invested in a Roth IRA and Hyatt savings account. Is there any guidance on how to anticipate and prepare for taxes with these accounts? Thank you for your nerdy advice. Double exclamation point.
B
Thanks for the detail Sean. Yes, this is a loaded question. Like a loaded sandwich. I'm hungry. All right, so Sean and I are tackling this solo today and that's because the tax team is busy getting us prepped for our favorite season Tax season. This is your chance to say Yay Sean.
A
Yay. I'm more into the tax refund side of things, but you know, it's an important time of year whether we like it or not.
B
Now back to the question for today. I nerded out when I read this question because I have so many related lived experiences which I'm going to share later in the episode. Now Sean, you are officially a business owner now yourself, so you might have some related experiences too.
A
I think I'm about to have some horror stories of my own potentially. This is my first time filing taxes as a business owner and I got married last year, so I'm going to be in a whole different world of filing my taxes. I'm excited about it. I'm a little bit nervous. I wouldn't be surprised if I have an unexpected bill, but we'll talk about that when the time comes.
B
Finally, something that we can share.
A
Yes. Well, the listener seems to have three primary questions. One how to navigate their tax status, two how to set up their taxes, and three how savings and investment accounts might impact their tax bill. So let's start by talking about tax status, which defines your household situation for the irs. Our listener wants to know how to navigate their tax status for contract work, and mentioned in their message that previously they filed as single and filed their contract work on their personal taxes, which isn't uncommon.
B
No, it's not. I personally think that determining your tax status is pretty straightforward, but actually I did read on the IRS website that incorrect filing status is one of the most common mistakes that people make. So maybe I am mistaken.
A
Well, it can get confusing because there are five different filing statuses. People may not be aware of that, so let me just tick through them super quickly. They're single, there's married filing jointly, there's married filing separately, there's head of household, there's also qualifying surviving spouse. So some of these are pretty specific niche circumstances, but knowing which one might be best for you isn't always super clear cut. Now, being self employed, whether part time or full time, shouldn't impact your tax filing status all too much. But the filing status you choose can affect things like your tax rate, your standard deduction, tax credits, other deductions. And you really do want to get this right. And most self employed people report business income on their personal tax return, as the listener did previously.
B
Status aside, another important thing that you should be aware of of when you're filing your taxes as a contractor is your self employment category. Elizabeth girl, what are you talking about? I'm going to explain soon. So you need to know which category that you fall into so your income is properly reported to the IRS. Now, the IRS recognizes five primary business categories. All right, Sean, pop quiz. Mr. CFP. What are they?
A
Okay, I'm going back into my CFP knowledge because I haven't touched this stuff in a little bit, but here they are. Sole Proprietor Partnership llc. C Corp and S Corp. Ding, ding, ding. We need some like confetti, some like a kazoo or something. Yeah, throw in all the sound effects here, please.
B
All right, so Sean, you did get all those right, but you do not win anything but bragging rights. I'm sorry.
A
Okay. And sound effects important.
B
I do want to add that the business categories also tell you what forms you need to file with your personal income tax return, which is also important. The listener sounds like a sole proprietor, which is a business that hasn't been registered as a legal entity and that's separate from the person who owns it. And you might also hear that being called an incorporated business, sole proprietors likely need to file using Form 1040 and then they report their business income and calculate self employment taxes using schedule C and se. I know, very boring. But all has its purpose. Many people fall into the sole proprietor category, such as independent contractors and gig workers. All of this can get really confusing real fast. So it may be best to consult a tax professional before filing like I do every year. On that note, let's answer the listener's question on tax setup as a self employed person. This is so important. I can't emphasize how important this is because you do not want to end up in the IRS's black book.
A
And we have a few tips that can help people figure this out. So first one is choose A business structure where you need to, you know, not everyone needs to register a business, but doing so could actually help you save on taxes. And Elizabeth, I know that you actually changed your tax status from an LLC to an S corp to reduce your tax bill. Can you talk about how that worked?
B
I sure did. And again, I am not a tax professional. So please don't run if you have an LLC and you're trying to reduce your tax bill and copy me. But I will say that it did cut my tax bill in half. Self employment taxes are high. You're paying your part and what an employer would pay. And currently that's 15.3% on net earnings of $400 or more. So that can get pretty pricey. And that's basically Social Security and Medicare payments that again an employer would usually handle for you, but you're doing yourself.
A
So why did you make this change then?
B
Well the long and short is my tax person told me to do it to save money.
A
But following your advice of listening to a tax professional here.
B
That's right. But I did do some research myself of course. Now how it saved me thousands of dollars. With an S corp you only pay self employment taxes on whatever in quotes is a reasonable salary according to the IRS that you pay yourself. But the rest of your profit is exempt from self employment taxes. But as an LL you have to pay self employment taxes on 92.35% of their net earnings.
A
Gotta love that hyper specific number. Yes, I know, right?
B
It's so specific.
A
And again this really underscores how important it is to just talk with a tax professional. Maybe just hire someone for a season or every year if you want to and just have someone do this heavy lifting for you because you don't want to get something wrong.
B
All right, so the next thing, I actually really like this one because again it was a real life learning. But decide on how you're going to pay taxes throughout the year. My first year as an llc I did not know anything about estimated taxes because I didn't check. So I wasn't paying them. But luckily I was withholding enough from my W4 so I didn't end up being fined by the IRS. But with that said, you are required to make quarterly estimated taxes by the IRS and you can make those payments using IRS form 1040es.
A
So note that estimated tax payments are what they say they're estimated. So you could end up paying a little bit more come tax time or possibly getting a refund depending on where you land at the end of tax season. The listener mentioned that they previously paid estimated taxes throughout the year and it's common to do it quarterly. But then they also had to pay additional self employment taxes when they filed. So they probably underpaid their taxes there. That's what that sounds like to me.
B
Sounds like that to me too. But I will say if you're going to diy, use a self employment tax calculator to make sure that you're withholding or rather paying enough estimated taxes taxes. Now, I say withholding because I'm excited to get to my next point because I save myself a lot of time by doing this. Now another option that you have if you happen to have a 9 to 5 like myself, is to withhold enough taxes from any W2 income that you might have. So I spoke with my tax professional and they actually helped me calculate how much I should withhold from my W2 and all I had to do was submit a new W4 with my new withholding and that was it. So I don't pay estimated taxes.
A
That also makes me think that it's really important to be on top of how you're tracking your income and your expenses for your business. That leads us to talking about having an accounting or bookkeeping system in place to follow all of this so you don't miss something. How do you track your expenses for your business?
B
Elizabeth I am pretty straightforward. I just use an Excel sheet because I generally do not have many expenses. I am a one man band and I just do some contract work so I just don't really have that much to keep track of.
A
Yeah, I'm in the same boat for my firm. I mean I just got my firm started midway through 2025 and then I had that whole like getting married and going on a three week honeymoon thing. So I didn't have a lot of income and expenses for my business maybe going into this year. Depending on how things go, I might, you know, adopt something like Quicken, which I know a lot of people love.
B
People do use Quicken. There are so many we actually have on the NerdWallet website a list of different kind of softwares that you can use to keep track of your expenses.
A
Love the plug.
B
Yes, we love a plug. All right. Speaking of which, you want to keep track of your deductible expenses when you're doing bookkeeping. You want to keep your receipts on whatever that you're spending. The IRS also does have a list of deductible expenses and categories such as your home, your vehicle, energy, travel, and more. One of the most surprising things that I saw that I could deduct was the actual space that I use. So my office space. And there's some calculation that's done and you know you can get some deductions for that. So you want to check that list and make sure you have receipts for.
A
Everything, but make sure you're doing it correctly because a lot of folks might think, oh, I can just deduct my entire apartment or my house because I work here. No, the IRS has some pretty specific definitions of how the space is used or not used, so do not run a bowel of that.
B
And my second to last tip is you want to keep track of all the tax forms that you need when it's time to file. At one point I think I had like four or five clients all at once and those were freelance writing clients and I was getting tons of 1099 Necs and I had to make sure I kept track of all of those and use them when I was filing my taxes. People who receive at least $600 in non employee compensation should receive a 1099 NEC from the person who is paying them. And I also want to point out that the one big beautiful bill has changed that threshold from $600 to $2,000 in 2026. So if the listener makes under that amount, they may not receive a form, but they still do need to report that income.
A
People should also consider contributing to a retirement savings account for self employed people. This could be a sep which is a simple employee pension or a simple ira. And this can help you save for retirement, but also do keep track of those contributions too. That can help you reduce your taxable income.
B
I use a SEP IRA and it does help reduce my taxable income every year.
A
And one really big thing to emphasize too is to avoid commingling funds from the business side of your operation and your personal finances. So I would recommend opening a separate account for business expenses if possible. That can help you track them more easily and have a paper trail and just avoid having your own personal income potentially be in the hands of the IRS for your business activities.
B
When I first started I did not have separate accounts, so I was commingling all my monies. And when I tell you it was stressful and frustrating come tax going through all my statements and trying to figure out which was business and which was personal. So opening a business account was a lifesaver and also having a business credit card so that I can see where all my expenses are.
A
So now you've gotten organized and you keep it Totally separate. Right. Are you doing any commingling nowadays?
B
I'm not doing any co mingling, Sean. I'm learning from you. Be organized, Proud of you. I do want to put it out there that you guys should be aware of the tax deadline and give yourself enough time to prepare and file. I had a horror story last year. I was fined over $2,000 by the IRS because I converted my business, like I said earlier, from an llc, sole proprietorship to an S corp to save on taxes. And I didn't realize that the tax deadline was different just by a month. Yep, March versus April. And guess what? Apparently my accountant didn't know that either. Can you believe that?
A
Maybe you need to hire a new accountant, Elizabeth, because that's a pretty big oopsie.
B
Right? And he's like, don't worry, we're going to fix it next year. How are you going to give me $2,000 back?
A
Yeah. How are you going to make it right for this year?
B
Exactly.
A
The year where the issue happened.
B
Exactly.
A
Are you still working with them?
C
No.
B
No.
A
Okay.
B
No, absolutely not.
A
Yeah.
B
But luckily I was able to waive the fee thanks to the first time penalty abatement, AKA the fta.
A
So, Elizabeth, that's a really jargony term. What is first time penalty abatement?
B
Well, essentially it just lets qualifying taxpayers reverse the penalties for not filing a tax return or paying on time. So since I was basically a first time offender, the IRS said, okay, you've paid all your taxes on time. This is first time doing it. We'll let you slide. And I said a very hearty thank you.
A
Okay, well, now let's get to the second part of our listener's question about preparing for taxes with a Roth IRA and a High Yield Savings account. Elizabeth, kick us off with the IRA side of things.
B
Well, the IRA side of things, I am glad to tell the listener, won't be a big deal because with specifically a Roth IRA that's funded with after tax money. So guess what? You don't have to pay any taxes come tax tax time. Yay. But even if it was a traditional ira, you'd only be taxed if you made withdrawals from that account.
A
And since we're all about reducing your taxable income on this show, it's important to know that a traditional IRA can help you do just that, dollar for dollar, depending on your income and your filing status. So this in turn could reduce your tax bill for the year, which is great. So if you're a contractor and you want to save for retirement and potentially pay less in taxes. Consider funding an Iraq.
B
Since the listener is employed and doing contract work, I want them to keep an eye on the Roth phase out limits. Now for 2026, if you are single and your modified adjusted gross income is under $153,000, then you can contribute the full amount. But for the most part you don't need to worry about paying taxes on investments in the stock market come tax time unless you sell assets at some point during the year.
A
Now let's turn to that Hild Savings Account. Unfortunately, our listener will likely have to pay federal and maybe state income taxes on the interest accrued in these accounts. This is the downside of getting that nice yield on your savings.
B
That yield is considered ordinary income and it's taxed at your marginal tax rate. Sorry, it's not free money. Well, not exactly. You report it as regular income when you do your tax return, the High Yield Savings Account provider will usually send form 1099 int. I get that every year. If you've earned above $10, the form will let you know your interest income for the tax year. So you don't have to do any math around that.
A
Yeah, I was very lucky to put a lot into my Hylde Savings account last year and I was looking at the interest coming in each month thinking wow, I'm doing such a great job and I'm sure I will be kicking myself a little bit when I get my 1099 INT, which should be in the mail any day now. Boom. But hey, I'm not going to stop putting my money into one of these accounts because it's way better than having it sit in an account that's giving me no interest at all.
B
I agree, I agree. Something is better than nothing.
A
Absolutely listener.
B
We hope that we answered your question and we hope the rest of you listeners learned something about filing taxes as a self employed person and I'm sure.
A
You probably have a lot more questions about filing your taxes this year. So as always, send your money questions, text or otherwise our way. You can hit us up on the Nerd hotline at 901-730-6373. That's 901-730-Nerd. You can text us or leave us a voicemail there. You can also email us@podcasterdwallet.com we want.
B
You to join us next time to hear about paying for senior care. Follow Smart Money on your favorite podcast app that's Spotify, Apple Podcasts and iHeartRadio to automatically download brand new episodes.
A
Here's our brief, we are not your financial or investment advisors. This nerdy info is provided for general educational and entertainment purposes and may not apply to your specific circumstances.
B
This episode was produced by Tess Viglin and Ana Helhoski. Hilary Georgie helps with editing. Nick Karismi mixed our audio and a big thank you to NerdWallet's editors for their help.
A
And with that said, until next time, turn to the nerds.
B
Want to see your brand on tv? Roku Ads Manager makes it easy to launch targeted ad campaigns in minutes, track results in real time, and drive on.
A
Screen purchases with just a click of the Roku remote.
B
Get a $500 match on your first $500 spent with code ROKU500@ads.roku.com that's code R O-U500. Terms apply.
Episode: Prediction Market Betting Hype and Self-Employment Taxes You Don’t Want to Miss
Date: February 5, 2026
Hosts: Sean Pyles, CFP® and Elizabeth Ayoola, with guest Ana Helhoski
This episode dives into two timely themes:
Throughout, Sean, Elizabeth, and Ana offer actionable tips, underscore common pitfalls, and share personal anecdotes, all in the podcast’s fast-paced, supportive style.
(03:10–15:33)
Background:
User Growth:
How Apps Work:
Variety of Bets:
“It’s the simplest kind of betting… just saying who wins.” —Ana (07:11)
“Props focus on really specific things happening in a game… like the color of the Gatorade the players pour on their coach’s head.” —Ana (08:09)
Tax Implications:
“Prediction markets let people make money by betting on real-world outcomes.” —Ana (09:52)
“DraftKings reported ... a new record... $436 million [bet] on a single game, on a single day.” —Ana (11:59)
“Apps are addicting. Gambling can be too. So combine the two with some highly energetic sports fans and it can become a problem.” —Ana (13:21)
“If you’re not having fun, stop doing it… If it’s not feeling within your control anymore, you might need to seek help.” —Ana (14:39, 15:04)
(18:00–33:45)
(18:00)
Filing Status:
Business Categories:
Tip: Consult a tax professional to ensure correct filings and optimize structure.
“It may be best to consult a tax professional before filing like I do every year.” —Elizabeth (22:05)
Business Structure for Tax Savings:
“With an S corp you only pay self employment taxes on whatever... is a reasonable salary… the rest of your profit is exempt.” —Elizabeth (23:59)
Estimated Tax Payments:
“Estimated tax payments are... estimated. You could end up paying a little more come tax time or possibly getting a refund.” —Sean (25:11)
DIY vs. Withholding Strategy:
“I save myself a lot of time by... withholding enough taxes from any W2 income...” —Elizabeth (25:35)
“When I first started I did not have separate accounts, so I was commingling all my monies. And when I tell you it was stressful… opening a business account was a lifesaver.” —Elizabeth (29:14)
“That yield is considered ordinary income and it’s taxed at your marginal tax rate. Sorry, it’s not free money.” —Elizabeth (32:25)
“Since I was basically a first time offender, the IRS said, okay, you’ve paid all your taxes on time. This is first time doing it. We’ll let you slide.” —Elizabeth (30:40)
Sports Betting:
Self-Employed Tax Tips:
Memorable Anecdote:
Elizabeth’s $2,000 IRS fine due to a missed deadline for S Corp filing underscores the importance of knowing your deadlines and holding your accountant accountable.
If you need help:
For gambling addiction: National Council on Problem Gambling, 1-800-MY-RESET.
Contact:
Listeners can submit questions by voicemail/text at 901-730-6373 or email podcasterdwallet.com.
Next Episode Teaser:
How to pay for senior care.
This summary covers all vital discussions and insights from the episode, captures the NerdWallet team’s approachable style, and provides clear takeaways for listeners new and experienced alike.