April 8, 2025 • 25 mins
Episode 130 focuses on dismantling the myth that filing for a tax extension is negative or indicative of a financial faux pas. Instead, the hosts reveal how a tax extension can serve as a powerful tax planning tool, particularly useful for business owners and real estate investors.
Chris passionately explains why tax extensions should not be feared but embraced to ensure accurate and optimal tax filing. With an emphasis on complex tax returns, the episode highlights reasons to file an extension, ranging from waiting on key documents like K1s to managing major life events such as marriage or changes in employment.
The episode stresses the importance of utilizing the additional time a tax extension affords to make strategic financial decisions, thus ensuring a comprehensive, accurate, and beneficial tax return.
Key Takeaways:
- Filing Extensions is Strategic: Extensions allow for thorough preparation and ensure that key documents are in place, particularly important for business owners and real estate investors.
- Avoid Rushed Filings: Hasty tax filings can lead to an increased audit risk and inaccuracies. Extensions provide the time to prepare accurate and beneficial tax returns.
- Major Life Events: Situations such as marriage, divorce, or significant changes in employment are valid reasons to file an extension, allowing time to navigate complex tax implications.
- Extensions Provide Flexibility: Additional time enables strategic financial planning and consideration of deductions and credits that may reduce overall tax liability.
- Interest and Penalties: While extensions allow more time to file, they do not extend the payment deadline. Interest and penalties may apply if taxes owed are not paid by the original due date.
Notable Quotes:
- "A tax extension is not something negative... tax extensions could be an amazing tax planning tool." - Chris Picciurro
- "You don't throw a pizza in the oven... make sure you have all the ingredients before you put a pizza in the oven." - Chris Picciurro
- "How many times has someone been, think about this, everyone... guess what happens? Traffic hits." - Chris Picciurro,
- "If you're planning a major deduction or strategy, that's major, file the extension." - Chris Picciurro
- "The relief people get when you file the extension for them and they realize the world’s not ending." - Chris Picciurro
Listeners are encouraged to delve deeper into the nuances of tax extensions by tuning into the full episode. Stay tuned for more insights and actionable advice on the podcast, ensuring clarity and confidence.
Episode Sponsor:
Integrated Investment Group
- (00:00) - Who Should File a Tax Extension and Why
- (01:35) - The Benefits and Misconceptions of Filing Tax Extensions
- (07:25) - Reasons and Benefits of Filing a Tax Extension
- (13:18) - Real Estate Investors and the Importance of Tax Extensions
- (15:06) - Reasons to File a Tax Extension Amid Major Life Events
- (19:41) - The Stress of Being Late and Finding Solutions
- (20:21) - Filing Tax Extensions and Managing IRS Penalties
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
John Tripolsky (00:04):
Hey, everyone, and welcome back to the teaching
tax full podcast episode 130today. We are gonna dive into
who should file a tax extension.So before we do that, as always,
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John Tripolsky (01:07):
Alright, everybody. Clearly, you know why
you're here. We're talking abouttax extensions. It's that time
of year where either you feelextremely prepared and ready to
file your returns or havealready, or you are in the
frantic actually, I should saythere's three things, or you're
in the frantic mode of, oh, boy.I only have a very, very, very
limited time to get this done,or you've actually filed an
(01:28):
extension already, and you're ingood shape here for a couple
months.
So let's talk about it. ChrisBacchero, welcome back to your
own show, sir. How are doing?
Chris Picciurro (01:35):
I'm doing fabulously. Fabulously. And, how
are you today?
John Tripolsky (01:39):
I'm doing good, man. Doing good. I know we we're
coming off of a little, we'llcall it an Eastern Seaboard
there with a conference downthere and some other things over
the past few weeks and andmonths, but, it is. It's it's
that time of year. Right?
So this is this is something Iknow a lot of people are afraid
of. I know we were down inRichmond, Virginia, not long
(02:00):
ago, and it seemed like thatgroup was pretty aware of the
power of a tax extension, butnot everybody is. Right?
Chris Picciurro (02:08):
Absolutely. A tax extension is not something
negative. I'm very passionateabout spreading the word that
tax extensions could be anamazing tax planning tool, and,
we use it quite often. I couldtell you in our private CPA
practice, we're probably about a75% tax extension rate. Even
(02:29):
though we're working very hardduring the peak compliance time
of year, which is February,March.
Tax extensions are not a badthing. And what we wanted to
talk through on this topic orthis episode is who should file
a tax extension. You are right.When you start working with
experienced business owners andreal estate investors, the vast
(02:49):
majority of those people will beextenders, and there's a very,
very good reasons why you wouldwant to be. Ultimately,
remember, the goal is to legallyand ethically reduce the tax you
pay in your lifetime and get youthe best result possible on your
tax return.
That doesn't mean the quickestresult, the fastest turnaround
(03:10):
result. It's the best resultpossible. That's a team sport.
The majority of people thatlisten to this podcast, I
imagine, work with a taxprofessional. But even if you
don't, it it could be a teamsport when it comes to
collecting information.
So let's jump into who shouldfile a tax extension. If you're
listening to this, you mightlike be like me. I filed a tax
(03:33):
extension. I have not a worry inthe world about it. I have
until, you know, on the personaltax return.
So let's talk about personalreturns real quick. On the
personal return, I have an extrasix months to file my tax
return. I have till OctoberOctober 2025 to file my 2024 tax
extension. And there's a lot ofthings that can happen during
2025, that could affect what Ido on my '24 return. To see what
(03:57):
happens.
So then come real estatetransactions and that sort of
thing. So if you might be inthat situation, I I you know, we
have some other content. If youhurried and hastily filed your
return and think that you didn'tget the best result possible,
the positive is is you can amendyour return for up to three
years. But right now, we'retalking about who should file
(04:18):
that extension.
John Tripolsky (04:19):
And kinda staying true to that question,
right, of who should. Right? Ithink it's I'd wager a bet that
a lot of people that couldbenefit the most from it
probably think it's like a it'sa death wish if you file that.
Right? And and I think one ofyou know, I know we talked about
this much earlier on.
I think it was in in the earlyepisode 20. So roughly about two
(04:42):
years ago, you know, we touchedon this topic specific, but it's
not and tell me if I'm wrong,but in no way, shape, or form is
filing an extension an automaticyear on the audit list per se
for the upcoming years. Right?
Chris Picciurro (04:58):
Exactly. If someone has some information
that ties filing extension to ahigher auto rate, I'd love to
see it because I've been doingthis for almost twenty five
years, and I've yet to see anyinformation. Now inherently,
okay, returns that are extendedare typically more complicated.
So maybe there might be a higheraudit risk on returns that are
(05:19):
extended. However, I have yetnever seen anything that says
filing extension causes theaudit risk to go higher.
In fact, I would think theopposite. Because if you're
scuffling and and hurrying andscurrying to file a return by
April 15, that's not accurate.Your audit risk is going to
(05:40):
skyrocket.
John Tripolsky (05:41):
That's a great point because, yeah, if people
are in a rush to do it rightthere, you know, say it's a two
weeks or or a week or haven'tforbid a couple days before
before a deadline, your chancesof missing something I mean,
small as it is is, know, addingan extra zero to something, you
know, when you go to file couldthrow you throw you right off a
cliff. Right?
Chris Picciurro (06:02):
Right. I mean, how many times has someone been
think about this, everyone, andthen we're gonna jump into this.
How many times have you beendriving to the airport and
you're kind of in a hurrydriving to a meeting, and guess
what happens? It's that timewhere one, traffic hits. Two,
you need gas.
Right? Because, oh gosh, Ishould've got gas yesterday when
I wasn't in a hurry. Or three,just something stops you because
(06:27):
your margin for error is verylittle due to time constraints.
So don't put that pressure onyourself. File the extension and
and move on.
Now remember, a tax extensiongives you an extended time to
file but not pay. So if youthink you're going to owe, I
highly advise you make anextension payment. And one of
(06:49):
the cool things is this. Let'ssay you're not sure if you owe
on your let's let's say it's04/10/2025. You're not sure if
you're gonna owe on 2024, butyou know you're gonna have a
first quarter estimate that'sgonna be due for 2025.
One of the hacks out there isthis. Instead of making your
first quarter twenty twenty fiveestimate, make it as 2024 tax
(07:10):
extension payment. Guess what?If you're overpaid, big whippety
do. All you do is carry thatforward to your 2025 estimated
tax payment, or you get yourdarn money back.
John, you could see I get alittle fired up about these
things.
John Tripolsky (07:26):
Yeah. Yeah. The we're, you know, we're we're
gonna have to add this one tothe the list of, you know, poke
the bear topics. Kind of likesaying somebody is a ten ninety
nine employee. I know you lovethat one.
Chris Picciurro (07:37):
Oh, yeah. That's another that's another
good one. But Oh, good. Great.
John Tripolsky (07:41):
So Anyways, let's lower your blood pressure.
Chris Picciurro (07:43):
Yes. Let's get you back down. So when should
you file an extension? Okay. Thenumber one reason we're gonna go
through five reasons.
The number one reason is quitefrankly, you can't file a dang
return because you're waiting onkey documents. You know, you
might be waiting for even thoughw twos are due by, let's say,
the January, that doesn'tnecessarily mean you're going
(08:04):
receive it. What if you workedfor an employer that went belly
up, that has no accounting, nobookkeeping? This happens quite
often. Now there are ways youcould do what's called a
substitute w two by taking yourlast pay stub, but and and
trying to do trying to do areturn, but you might be waiting
most likely for k ones.
So if you are waiting forinformation and key documents,
(08:26):
bookkeeping, anything, wait.File an extension because you
have incomplete information. Youdon't you you don't throw a
pizza in the oven. And then whenit comes out, John, if you did
this, I'd be mad. Right?
Don't put a pizza in the oven.Break take it out, and then you
(08:47):
say, oh, jeez. We forgot to putsauce on it. You can put that
cold sauce on some burnt cheese.So get all your darn ingredients
together before you put thepizza not to say we're baking
your tax return or cooking yourbooks.
We're just saying make sure youhave all the ingredients before
you put a pizza in the oven.That's a great disclaimer.
Keeping tax law, you're gonnarealize we're starting to use
(09:07):
more pizza examples.
John Tripolsky (09:08):
We are. We you know, it's funny that when I
think the hamburger came up insomething. The pizza came up.
Yeah. We're just here to makepeople hungry.
Hungry for tax strategies.
Chris Picciurro (09:19):
Exactly.
John Tripolsky (09:20):
I like it.
Chris Picciurro (09:22):
Second reason, if you're a business owner or
real estate investor, which isthe vast, vast majority of our
private CPA firm client base,your returns are gonna be
complex. Remember, I think Iknow we have some content out
there in teaching tax law. Bythe way, if you're listening to
this, thank you. Number one.Number two, we're doing this for
(09:43):
free.
And number three, go subscribeto the YouTube channel. We're
just at this conference. Peepand I'm not trying to brag,
John, on on your editing, butpeople loved our content. And
they're like, wow. We love thevideos.
We love the podcast. Yeah.That's just a tip of the
iceberg. Go check out theteaching tax slow YouTube
channel because we've gothundreds of longer form videos,
(10:04):
not to five, ten minute videosthat dive into all these all of
these topics. Okay.
So we'll move off of our off ofmy my ban myself proclamation of
the YouTube channel. But ifyou're a business owner or real
estate investor and you have acomplex return, definitely file
an extension, and that goes forbusiness returns now. If you're
(10:26):
a s corp or partnership or a ccorp, you might be figuring out
your depreciation schedules. Youmight be waiting on a cost
segregation study. You mighthave bookkeeping cleanup.
There's a lot of things that goin to preparing those type of
tax returns that it's extremelycommon to file an extension.
John Tripolsky (10:44):
And it makes sense, and it's it's easy to do.
Right? Especially if you'reworking with a tax professional.
You could say, hey. You knowwhat?
I mean, maybe this is badadvice. You know? This is coming
from the marketing guy. I Iknow, Chris, you guys in in your
private practice, right, is Iwouldn't say that you assume an
extension, but I think it's justkind of built into y'all's
workflow. Right?
Like, you you have thatunderstanding. The client has
(11:06):
that understanding where it'snot you know, where's your
stuff? Where's your stuff?Where's stuff? Okay.
Oh, crap. What can I do now? Oh,let's file an extension. Like,
everybody knows it's kindacoming. And like you mentioned
too, it's it gives you theopportunity to take care or, I
should say, take advantage of alot of opportunities that would
have been missed.
So I think, you know, somebodythat's working with a tax bar
already, if you haven't filed anextension in the past, maybe
(11:30):
talk to them about it. Probablynot on April 14, but at some
point, you know, leading up tothat date.
Chris Picciurro (11:37):
Okay. Yeah. How many times you've been to a
restaurant and the restaurantgets behind? You complain to the
waiter or waitress. They hurryup and get your food out, and
it's wrong.
Right? You don't want thatsituation. Do you want your tax
professional half awake on April11 pounding down coffee at, you
know, 09:30 at night working onyour return, your biggest bill
(12:01):
of the year. You have someoneworking on that's half awake
that's super competent, and ifyou just waited two weeks,
you're gonna get their best. Notsmart.
John Tripolsky (12:10):
Another another food and restaurant reference,
by the way.
Chris Picciurro (12:13):
Hey. It's easy. It's easy to make. Alright. The
third thing.
It kinda ties in with the secondthing and the first thing, but
let's say you're planning amajor deduction or strategy. We
talked about cost segregationstudies. You might have a cost
segregation study that you'reusing for the previous year that
you're still waiting on thereport to come in. That's no
(12:34):
normal when you own a businessor have real estate. You might
be funding a retirement account.
Guess what? For many selfemployed people, if you file a
tax extension, that gives youextra time to contribute to your
retirement account from the yearbefore. So the fact of the
matter is give yourself moretime by filing the extension if
you're looking at implementing atax strategy that you can
(12:57):
implement post year end. And,actually, John, you referenced a
wonderful trip to our friends inRichmond, Virginia in a real
estate we'll just call it say itout, deal makers, real estate
group, that many of those peoplehave extensions, and many of
those people wanted extra timeto implement the strategy. So if
(13:18):
you're planning a deduction orstrategy that's major, file the
extension.
John Tripolsky (13:23):
Hey, Chris. If I could play off that here for a
quick minute to, again, kind ofyou know, we we had a table
there. You were you werespeaking at some of them, and a
lot of the times, you know, Ifound myself kinda kinda hover
around our table a little bitand then obviously, ease
dropping some conversations thatyou were having with some
attendees there. And, again,back to, you know, that
audience, very well versed inwhat they do. You know, they are
(13:45):
and I wouldn't even say a lot ofthem are just real estate
investors.
A lot of them are, like, mastersof real estate investing, we
should say. And it was veryinteresting to me to listen. You
know? I can't remember exactlywhat conversation it was
specifically. I know there weremultiple, but where, you know,
you guys kinda discussed alittle bit on, you know, where
they're at, what their goalsare, just very briefly.
(14:07):
It wasn't like a, you know, adiscovery meeting or session at
all. Right. But then I feel likea lot of those conversations
right around the mid you know,midway point a little bit more
towards the end, I feel like taxextensions came up on every
single one of them. I mean,given the time of year it was,
but I feel like you asked themif they had filed an extension.
And then if the answer was yes,I'm again not referencing a
specific one that I I can'trecall, but immediately, it went
(14:30):
into a very deeper conversationon just how you have a lot of
opportunity from the previousyear to take advantage of stuff,
but it's not something that youcan do, you know, with, the
click of a button and thenstacking, you know, stacking and
blending all these opportunitiesand strategies.
It's incredible. And even thesepeople that were incredibly,
like I said, well versed in whatthey do, their eyes kinda light,
(14:53):
you know, light up a little bit.Like, oh, man. Like, I didn't
think of that. Or, wow, thiscould be a a bigger play, or it
just it was very interesting tosee how that works, and that's
not something they could havedone, obviously, if if an
extension wasn't in play.
Right?
Chris Picciurro (15:06):
Yeah. The thing is April 15 is the due date for
any tax that you owe for theprevious year. That's what it
is. If you if you pay that on atax return, then you filed. If
you wanna pay that, you know, ifyou wanna pay that on a tax
extension, great.
But it's not necessarily the endall be all due date of filing a
(15:29):
tax return. So number four,reason you should file a tax
extension. We have no drumrolls, but we should have one.
We'll talk to the editingcompany on that one. Major life
event.
(15:50):
Typically, it's going to be achange in marital status, you
know, especially if there's aseparation or divorce. Many,
many times, there'll be a youknow, that's something that gets
negotiated if they're if they'refine. First of all, can they do
they have to file together? Werethey was there a legal
separation? Who's claiming thecertain deductions?
(16:10):
Who's claiming certaindependents? So if you have a
major life event, many, manytimes, you should file the tax
extension. Now it could be thatyou got married, and you're
trying to figure out the lastthing on your mind was taxes.
You're a newlyweds. You've gotto, let's say, rent a new
apartment or you buy a new homeor there's just a lot going on.
(16:32):
You're trying to figure out yourfinances, and it's this sneaks
up on you pretty, prettyquickly. It could be you had a
child or you could you know, itcould be something. And, again,
a life event. You could haveinherited a home from a
relative. There's a lot ofthings.
Life happens. Life happens allthe time. So you've got to
(16:53):
realize that, hey. A life eventoccurred. It might make sense
for me to file an extension.
And then the the relief peopleget when you file the extension
for them and they realize theworld's not, you know, it's
like, John, remember 1999? Gosh,everyone thought like the world
was gonna end and all this allthese guys were thinking their
(17:16):
computer's gonna crash and allthat stuff.
John Tripolsky (17:18):
Why two k? I never
Chris Picciurro (17:19):
Yeah. I never fig I never thought anything
would happen. And if it did,okay, so it did, but nothing
happened, really.
John Tripolsky (17:25):
Right. It's like somebody saying, okay. Well,
here's the date. It could happenby that, but I will give you
twelve more months to go out orsix more months to go on. Get a
new computer if you're reallythat worried about it.
That's a y two k referencethere.
Chris Picciurro (17:40):
Look at the look at the life of that moving.
John, look at your situation,not to get too personal. When
you, you know, when you have achange in life, you you've moved
from different states. You'veowned businesses. You've gotten
married.
You've had a child. You've,again, moved back to another
state. So you've you've owned ashort term rental property.
You've sold that rentalproperty. You owned a primary
(18:00):
residence.
You sold that. You built a newpro you have a new primary
residence. You've had a lot oflife events that have made made
it make sense to fileextensions.
John Tripolsky (18:09):
Right? Yeah. Without it, it's like, oh, man.
I mean, hey. Like you mentioned,I think, you know, one of the
ones that I feel like comes up alot, right, is the k ones.
I feel like a lot of people,they stress because they haven't
received those. Right? Andthey're sitting there like,
where they at? Where they at?Where they at?
Where they at? But Mhmm. Youknow, who knows what's happening
with those? Right? And then,like you said, that extension
(18:30):
buys you the time to to gohunting and then find where
those are floating around at.
Chris Picciurro (18:37):
And you go and and the thing is is k ones are
and we have a a a episode k onefor dummies. They are very
complicated forms. You know, ifyou so there's the the the tax
professionals that preparethose. You know, some of the
ones in our private practice,we've got 200, two hundred 50 k
ones that go out on one entity.It could be a real estate
(18:57):
syndication.
Syndication. That's a lot of ofreconciling. And a lot of times,
it comes down to the operator'sbooks and records, so it could
have nothing to do with your taxpreparer. Right? So it's natural
for those to come out a littlelater.
And, you know, that's justthat's just the way it is. So
(19:18):
major life event is number four,and then you kinda ran into
number five. And I've mentionedit a little bit. Some of these
blend together. When you'redriving, when you don't leave
enough self enough time, let'ssay you're rushing your child to
a practice, you're going to ameeting, you're meeting your
friend for a coffee.
It always happens. There'salways, oh, I got there, but I
can't find parking. Oh, I've Ineed gas. Oh, there's traffic.
(19:41):
You're rushing or stressed.
Wouldn't it be nice that onetime, John? I'm sure everyone's
been in this situation. You'regoing to meet somebody. You're,
like, looking at your GPS.You're gonna be about two
minutes early because you'realready knuckleheaded around,
and you're you're gonna almostgonna be late.
Traffic hits. Now you're gonnabe two two minutes late. Now you
start feeling terrible andyou're like, oh, should I tell
(20:03):
the person I'm gonna be twominutes late? Once it gets to,
like, three or four minutes, Ialways tell people. Then you get
there and you can't findparking.
What if you could just push abutton and say, hey, friend.
I'll be give me fifteen extraminutes. I and then I'll come
in. And now you're not runningin flustered and stressed.
You're coming in early.
John Tripolsky (20:21):
Right.
Chris Picciurro (20:21):
So if you're rushing or stressed, just file
the extension. And, honestly,most of the extensions, if you
talk to tax professionals, ifthey had some truth syrup,
they're gonna say, yeah. I couldprobably get that done within
the next thirty days betweenApril 15 and May 15 really well
while I'm still fresh. So it'snot like just because you file
(20:43):
an extension, you have to waitsix more months. But extended
tax returns get done in thethirty days after they April 15.
That's very normal.
John Tripolsky (20:51):
Right. Right. And you and you bring up a great
point too that I wanna circleback around too if we can maybe
just touch on is, you know,that's the date that things are
due. So so what happens? Say youowe just we'll just use an even
number.
Say you owe a thousand dollarsthis year. You file an
extension. Don't make thatpayment to the IRS by April 15.
(21:15):
What happens there? What whathappens between that and, you
know, the time they file, say,in May, October, whenever it is.
Chris Picciurro (21:23):
Alright. So you're you're saying you
John Tripolsky (21:25):
So they owe.
Chris Picciurro (21:26):
Didn't make the payment, and you filed a month
later. Oh gosh. You'll probablyget penalized, like it depends
on how much you owe, but let'ssay a couple percent. You know?
John Tripolsky (21:34):
Let's say
Chris Picciurro (21:35):
if you owed the thousand bucks, you'd probably
pay in $30 a penalty in
John Tripolsky (21:38):
all reality. So there is the penalties, and
that's what I was getting at isthe penalties that are being
added on top of it. It's notit's not a get out of paying
jail free card. It's a get outof filing jail free card. The
payment You start to
Chris Picciurro (21:52):
pay by by April 15, but you can file an
extension.
John Tripolsky (21:55):
Perfect. Perfect. Just for those that got
too maybe they got too excitedabout the filing the extension.
I know we touched on a littlebit earlier, but I wanted to
circle back around on that justthat there there will be
interest penalties.
Chris Picciurro (22:06):
You will always but but and we're not advocating
this, but let's be real here. Ifyou owe the thousand dollars,
the IRS doesn't know you owe thethousand dollars until you file
the return. So you would justhave to pay that penalty once
you file.
John Tripolsky (22:22):
Right. Right. Exactly.
Chris Picciurro (22:24):
You're gonna get a bill on April 16 for the
thousand bucks.
John Tripolsky (22:28):
Right. Perfect. Perfect. And that's like you
said too, it's, you know, again,not to advocate for not making
that payment. Right?
But say you owe say you owe ahundred thousand. Right? You
file an extension. Not only areyou getting more time to file,
getting your ducks in a row, thelikelihood of you saving more
(22:50):
than what the penalty may be.Well, maybe not a hundred
thousand.
That might be a stretch. But itjust all in all puts you in a
much, much better spot. It's notlike you're getting hit with a
25% penalty and a, you know,$3,000 late fee or something
like
Chris Picciurro (23:04):
that. Correct. Awesome. I mean, it could be so,
yeah, definitely talk to someoneabout and and, again, like I
said, if you're if you'reconcerned about owing, just
Mhmm. Overpay.
I mean, you can get the moneyback. Right. Awesome. It's not
gone forever.
John Tripolsky (23:18):
And it's good advice. It's good advice. And
this one I like. I mean, it'sagain, I think now that you know
that this exists, for those thatwere listening, I mean, I'm sure
you've heard this come upsomewhere, but it's definitely
like we mentioned early on. It'snot a it's not a death wish.
It's not this big 30 page formyou need to fill out to make
this happen. You're just betterto do it. Just do it in in most
(23:42):
situations. Right?
Chris Picciurro (23:43):
Right.
John Tripolsky (23:44):
Awesome. Awesome. Well, I know we got
some great topics coming up asalways here on the podcast.
Anybody that's listening tothis, the day that it comes out,
you literally have one week tofile that extension. Actually,
little bit shorter.
Don't wanna do it on thefifteenth, but take advantage of
it. If you have any questions inthe meantime, reach out to us.
Get on defeatingtaxes.com.That's their private Facebook
(24:05):
group. Well over 2,000 peoplethat are in that now.
Post some questions. Post somequestions. Any questions you
have. Oh, maybe how do I file anextension? Or has anybody else
in this group filed anextension?
What did you do? Any of thosequestions, reach out to the
group. Reach out to us here atTeaching Tax Flow. Literally, we
are here to answer questions andmake your life easier. So until
(24:26):
next time, next week, differentday, completely different topic,
roughly the same time.
We'll see everybody back hereagain on the Teaching Tax Flow
podcast. Have a great week,everybody.
Disclaimer (24:41):
Purposes only. We encourage you to seek
personalized investment advicefrom your financial
professional. For all tax andlegal advice, please consult
your CPA or attorney. Investmentadvisory services are offered
through Cabin Advisors, aregistered investment advisor.
Securities are offered throughCabin Securities, a registered
broker dealer.
The content of this podcast doesnot constitute an offer of
securities. Offerings can onlybe made through an offering
(25:03):
memorandum, and you shouldcarefully examine the risk
factors and other informationcontained in the memorandum.
Hey, everyone, and welcome back to the teaching
tax full podcast episode 130today. We are gonna dive into
who should file a tax extension.So before we do that, as always,
let's take a brief moment andthank our episode sponsor.
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John Tripolsky (01:07):
Alright, everybody. Clearly, you know why
you're here. We're talking abouttax extensions. It's that time
of year where either you feelextremely prepared and ready to
file your returns or havealready, or you are in the
frantic actually, I should saythere's three things, or you're
in the frantic mode of, oh, boy.I only have a very, very, very
limited time to get this done,or you've actually filed an
(01:28):
extension already, and you're ingood shape here for a couple
months.
So let's talk about it. ChrisBacchero, welcome back to your
own show, sir. How are doing?
Chris Picciurro (01:35):
I'm doing fabulously. Fabulously. And, how
are you today?
John Tripolsky (01:39):
I'm doing good, man. Doing good. I know we we're
coming off of a little, we'llcall it an Eastern Seaboard
there with a conference downthere and some other things over
the past few weeks and andmonths, but, it is. It's it's
that time of year. Right?
So this is this is something Iknow a lot of people are afraid
of. I know we were down inRichmond, Virginia, not long
(02:00):
ago, and it seemed like thatgroup was pretty aware of the
power of a tax extension, butnot everybody is. Right?
Chris Picciurro (02:08):
Absolutely. A tax extension is not something
negative. I'm very passionateabout spreading the word that
tax extensions could be anamazing tax planning tool, and,
we use it quite often. I couldtell you in our private CPA
practice, we're probably about a75% tax extension rate. Even
(02:29):
though we're working very hardduring the peak compliance time
of year, which is February,March.
Tax extensions are not a badthing. And what we wanted to
talk through on this topic orthis episode is who should file
a tax extension. You are right.When you start working with
experienced business owners andreal estate investors, the vast
(02:49):
majority of those people will beextenders, and there's a very,
very good reasons why you wouldwant to be. Ultimately,
remember, the goal is to legallyand ethically reduce the tax you
pay in your lifetime and get youthe best result possible on your
tax return.
That doesn't mean the quickestresult, the fastest turnaround
(03:10):
result. It's the best resultpossible. That's a team sport.
The majority of people thatlisten to this podcast, I
imagine, work with a taxprofessional. But even if you
don't, it it could be a teamsport when it comes to
collecting information.
So let's jump into who shouldfile a tax extension. If you're
listening to this, you mightlike be like me. I filed a tax
(03:33):
extension. I have not a worry inthe world about it. I have
until, you know, on the personaltax return.
So let's talk about personalreturns real quick. On the
personal return, I have an extrasix months to file my tax
return. I have till OctoberOctober 2025 to file my 2024 tax
extension. And there's a lot ofthings that can happen during
2025, that could affect what Ido on my '24 return. To see what
(03:57):
happens.
So then come real estatetransactions and that sort of
thing. So if you might be inthat situation, I I you know, we
have some other content. If youhurried and hastily filed your
return and think that you didn'tget the best result possible,
the positive is is you can amendyour return for up to three
years. But right now, we'retalking about who should file
(04:18):
that extension.
John Tripolsky (04:19):
And kinda staying true to that question,
right, of who should. Right? Ithink it's I'd wager a bet that
a lot of people that couldbenefit the most from it
probably think it's like a it'sa death wish if you file that.
Right? And and I think one ofyou know, I know we talked about
this much earlier on.
I think it was in in the earlyepisode 20. So roughly about two
(04:42):
years ago, you know, we touchedon this topic specific, but it's
not and tell me if I'm wrong,but in no way, shape, or form is
filing an extension an automaticyear on the audit list per se
for the upcoming years. Right?
Chris Picciurro (04:58):
Exactly. If someone has some information
that ties filing extension to ahigher auto rate, I'd love to
see it because I've been doingthis for almost twenty five
years, and I've yet to see anyinformation. Now inherently,
okay, returns that are extendedare typically more complicated.
So maybe there might be a higheraudit risk on returns that are
(05:19):
extended. However, I have yetnever seen anything that says
filing extension causes theaudit risk to go higher.
In fact, I would think theopposite. Because if you're
scuffling and and hurrying andscurrying to file a return by
April 15, that's not accurate.Your audit risk is going to
(05:40):
skyrocket.
John Tripolsky (05:41):
That's a great point because, yeah, if people
are in a rush to do it rightthere, you know, say it's a two
weeks or or a week or haven'tforbid a couple days before
before a deadline, your chancesof missing something I mean,
small as it is is, know, addingan extra zero to something, you
know, when you go to file couldthrow you throw you right off a
cliff. Right?
Chris Picciurro (06:02):
Right. I mean, how many times has someone been
think about this, everyone, andthen we're gonna jump into this.
How many times have you beendriving to the airport and
you're kind of in a hurrydriving to a meeting, and guess
what happens? It's that timewhere one, traffic hits. Two,
you need gas.
Right? Because, oh gosh, Ishould've got gas yesterday when
I wasn't in a hurry. Or three,just something stops you because
(06:27):
your margin for error is verylittle due to time constraints.
So don't put that pressure onyourself. File the extension and
and move on.
Now remember, a tax extensiongives you an extended time to
file but not pay. So if youthink you're going to owe, I
highly advise you make anextension payment. And one of
(06:49):
the cool things is this. Let'ssay you're not sure if you owe
on your let's let's say it's04/10/2025. You're not sure if
you're gonna owe on 2024, butyou know you're gonna have a
first quarter estimate that'sgonna be due for 2025.
One of the hacks out there isthis. Instead of making your
first quarter twenty twenty fiveestimate, make it as 2024 tax
(07:10):
extension payment. Guess what?If you're overpaid, big whippety
do. All you do is carry thatforward to your 2025 estimated
tax payment, or you get yourdarn money back.
John, you could see I get alittle fired up about these
things.
John Tripolsky (07:26):
Yeah. Yeah. The we're, you know, we're we're
gonna have to add this one tothe the list of, you know, poke
the bear topics. Kind of likesaying somebody is a ten ninety
nine employee. I know you lovethat one.
Chris Picciurro (07:37):
Oh, yeah. That's another that's another
good one. But Oh, good. Great.
John Tripolsky (07:41):
So Anyways, let's lower your blood pressure.
Chris Picciurro (07:43):
Yes. Let's get you back down. So when should
you file an extension? Okay. Thenumber one reason we're gonna go
through five reasons.
The number one reason is quitefrankly, you can't file a dang
return because you're waiting onkey documents. You know, you
might be waiting for even thoughw twos are due by, let's say,
the January, that doesn'tnecessarily mean you're going
(08:04):
receive it. What if you workedfor an employer that went belly
up, that has no accounting, nobookkeeping? This happens quite
often. Now there are ways youcould do what's called a
substitute w two by taking yourlast pay stub, but and and
trying to do trying to do areturn, but you might be waiting
most likely for k ones.
So if you are waiting forinformation and key documents,
(08:26):
bookkeeping, anything, wait.File an extension because you
have incomplete information. Youdon't you you don't throw a
pizza in the oven. And then whenit comes out, John, if you did
this, I'd be mad. Right?
Don't put a pizza in the oven.Break take it out, and then you
(08:47):
say, oh, jeez. We forgot to putsauce on it. You can put that
cold sauce on some burnt cheese.So get all your darn ingredients
together before you put thepizza not to say we're baking
your tax return or cooking yourbooks.
We're just saying make sure youhave all the ingredients before
you put a pizza in the oven.That's a great disclaimer.
Keeping tax law, you're gonnarealize we're starting to use
(09:07):
more pizza examples.
John Tripolsky (09:08):
We are. We you know, it's funny that when I
think the hamburger came up insomething. The pizza came up.
Yeah. We're just here to makepeople hungry.
Hungry for tax strategies.
Chris Picciurro (09:19):
Exactly.
John Tripolsky (09:20):
I like it.
Chris Picciurro (09:22):
Second reason, if you're a business owner or
real estate investor, which isthe vast, vast majority of our
private CPA firm client base,your returns are gonna be
complex. Remember, I think Iknow we have some content out
there in teaching tax law. Bythe way, if you're listening to
this, thank you. Number one.Number two, we're doing this for
(09:43):
free.
And number three, go subscribeto the YouTube channel. We're
just at this conference. Peepand I'm not trying to brag,
John, on on your editing, butpeople loved our content. And
they're like, wow. We love thevideos.
We love the podcast. Yeah.That's just a tip of the
iceberg. Go check out theteaching tax slow YouTube
channel because we've gothundreds of longer form videos,
(10:04):
not to five, ten minute videosthat dive into all these all of
these topics. Okay.
So we'll move off of our off ofmy my ban myself proclamation of
the YouTube channel. But ifyou're a business owner or real
estate investor and you have acomplex return, definitely file
an extension, and that goes forbusiness returns now. If you're
(10:26):
a s corp or partnership or a ccorp, you might be figuring out
your depreciation schedules. Youmight be waiting on a cost
segregation study. You mighthave bookkeeping cleanup.
There's a lot of things that goin to preparing those type of
tax returns that it's extremelycommon to file an extension.
John Tripolsky (10:44):
And it makes sense, and it's it's easy to do.
Right? Especially if you'reworking with a tax professional.
You could say, hey. You knowwhat?
I mean, maybe this is badadvice. You know? This is coming
from the marketing guy. I Iknow, Chris, you guys in in your
private practice, right, is Iwouldn't say that you assume an
extension, but I think it's justkind of built into y'all's
workflow. Right?
Like, you you have thatunderstanding. The client has
(11:06):
that understanding where it'snot you know, where's your
stuff? Where's your stuff?Where's stuff? Okay.
Oh, crap. What can I do now? Oh,let's file an extension. Like,
everybody knows it's kindacoming. And like you mentioned
too, it's it gives you theopportunity to take care or, I
should say, take advantage of alot of opportunities that would
have been missed.
So I think, you know, somebodythat's working with a tax bar
already, if you haven't filed anextension in the past, maybe
(11:30):
talk to them about it. Probablynot on April 14, but at some
point, you know, leading up tothat date.
Chris Picciurro (11:37):
Okay. Yeah. How many times you've been to a
restaurant and the restaurantgets behind? You complain to the
waiter or waitress. They hurryup and get your food out, and
it's wrong.
Right? You don't want thatsituation. Do you want your tax
professional half awake on April11 pounding down coffee at, you
know, 09:30 at night working onyour return, your biggest bill
(12:01):
of the year. You have someoneworking on that's half awake
that's super competent, and ifyou just waited two weeks,
you're gonna get their best. Notsmart.
John Tripolsky (12:10):
Another another food and restaurant reference,
by the way.
Chris Picciurro (12:13):
Hey. It's easy. It's easy to make. Alright. The
third thing.
It kinda ties in with the secondthing and the first thing, but
let's say you're planning amajor deduction or strategy. We
talked about cost segregationstudies. You might have a cost
segregation study that you'reusing for the previous year that
you're still waiting on thereport to come in. That's no
(12:34):
normal when you own a businessor have real estate. You might
be funding a retirement account.
Guess what? For many selfemployed people, if you file a
tax extension, that gives youextra time to contribute to your
retirement account from the yearbefore. So the fact of the
matter is give yourself moretime by filing the extension if
you're looking at implementing atax strategy that you can
(12:57):
implement post year end. And,actually, John, you referenced a
wonderful trip to our friends inRichmond, Virginia in a real
estate we'll just call it say itout, deal makers, real estate
group, that many of those peoplehave extensions, and many of
those people wanted extra timeto implement the strategy. So if
(13:18):
you're planning a deduction orstrategy that's major, file the
extension.
John Tripolsky (13:23):
Hey, Chris. If I could play off that here for a
quick minute to, again, kind ofyou know, we we had a table
there. You were you werespeaking at some of them, and a
lot of the times, you know, Ifound myself kinda kinda hover
around our table a little bitand then obviously, ease
dropping some conversations thatyou were having with some
attendees there. And, again,back to, you know, that
audience, very well versed inwhat they do. You know, they are
(13:45):
and I wouldn't even say a lot ofthem are just real estate
investors.
A lot of them are, like, mastersof real estate investing, we
should say. And it was veryinteresting to me to listen. You
know? I can't remember exactlywhat conversation it was
specifically. I know there weremultiple, but where, you know,
you guys kinda discussed alittle bit on, you know, where
they're at, what their goalsare, just very briefly.
(14:07):
It wasn't like a, you know, adiscovery meeting or session at
all. Right. But then I feel likea lot of those conversations
right around the mid you know,midway point a little bit more
towards the end, I feel like taxextensions came up on every
single one of them. I mean,given the time of year it was,
but I feel like you asked themif they had filed an extension.
And then if the answer was yes,I'm again not referencing a
specific one that I I can'trecall, but immediately, it went
(14:30):
into a very deeper conversationon just how you have a lot of
opportunity from the previousyear to take advantage of stuff,
but it's not something that youcan do, you know, with, the
click of a button and thenstacking, you know, stacking and
blending all these opportunitiesand strategies.
It's incredible. And even thesepeople that were incredibly,
like I said, well versed in whatthey do, their eyes kinda light,
(14:53):
you know, light up a little bit.Like, oh, man. Like, I didn't
think of that. Or, wow, thiscould be a a bigger play, or it
just it was very interesting tosee how that works, and that's
not something they could havedone, obviously, if if an
extension wasn't in play.
Right?
Chris Picciurro (15:06):
Yeah. The thing is April 15 is the due date for
any tax that you owe for theprevious year. That's what it
is. If you if you pay that on atax return, then you filed. If
you wanna pay that, you know, ifyou wanna pay that on a tax
extension, great.
But it's not necessarily the endall be all due date of filing a
(15:29):
tax return. So number four,reason you should file a tax
extension. We have no drumrolls, but we should have one.
We'll talk to the editingcompany on that one. Major life
event.
(15:50):
Typically, it's going to be achange in marital status, you
know, especially if there's aseparation or divorce. Many,
many times, there'll be a youknow, that's something that gets
negotiated if they're if they'refine. First of all, can they do
they have to file together? Werethey was there a legal
separation? Who's claiming thecertain deductions?
(16:10):
Who's claiming certaindependents? So if you have a
major life event, many, manytimes, you should file the tax
extension. Now it could be thatyou got married, and you're
trying to figure out the lastthing on your mind was taxes.
You're a newlyweds. You've gotto, let's say, rent a new
apartment or you buy a new homeor there's just a lot going on.
(16:32):
You're trying to figure out yourfinances, and it's this sneaks
up on you pretty, prettyquickly. It could be you had a
child or you could you know, itcould be something. And, again,
a life event. You could haveinherited a home from a
relative. There's a lot ofthings.
Life happens. Life happens allthe time. So you've got to
(16:53):
realize that, hey. A life eventoccurred. It might make sense
for me to file an extension.
And then the the relief peopleget when you file the extension
for them and they realize theworld's not, you know, it's
like, John, remember 1999? Gosh,everyone thought like the world
was gonna end and all this allthese guys were thinking their
(17:16):
computer's gonna crash and allthat stuff.
John Tripolsky (17:18):
Why two k? I never
Chris Picciurro (17:19):
Yeah. I never fig I never thought anything
would happen. And if it did,okay, so it did, but nothing
happened, really.
John Tripolsky (17:25):
Right. It's like somebody saying, okay. Well,
here's the date. It could happenby that, but I will give you
twelve more months to go out orsix more months to go on. Get a
new computer if you're reallythat worried about it.
That's a y two k referencethere.
Chris Picciurro (17:40):
Look at the look at the life of that moving.
John, look at your situation,not to get too personal. When
you, you know, when you have achange in life, you you've moved
from different states. You'veowned businesses. You've gotten
married.
You've had a child. You've,again, moved back to another
state. So you've you've owned ashort term rental property.
You've sold that rentalproperty. You owned a primary
(18:00):
residence.
You sold that. You built a newpro you have a new primary
residence. You've had a lot oflife events that have made made
it make sense to fileextensions.
John Tripolsky (18:09):
Right? Yeah. Without it, it's like, oh, man.
I mean, hey. Like you mentioned,I think, you know, one of the
ones that I feel like comes up alot, right, is the k ones.
I feel like a lot of people,they stress because they haven't
received those. Right? Andthey're sitting there like,
where they at? Where they at?Where they at?
Where they at? But Mhmm. Youknow, who knows what's happening
with those? Right? And then,like you said, that extension
(18:30):
buys you the time to to gohunting and then find where
those are floating around at.
Chris Picciurro (18:37):
And you go and and the thing is is k ones are
and we have a a a episode k onefor dummies. They are very
complicated forms. You know, ifyou so there's the the the tax
professionals that preparethose. You know, some of the
ones in our private practice,we've got 200, two hundred 50 k
ones that go out on one entity.It could be a real estate
(18:57):
syndication.
Syndication. That's a lot of ofreconciling. And a lot of times,
it comes down to the operator'sbooks and records, so it could
have nothing to do with your taxpreparer. Right? So it's natural
for those to come out a littlelater.
And, you know, that's justthat's just the way it is. So
(19:18):
major life event is number four,and then you kinda ran into
number five. And I've mentionedit a little bit. Some of these
blend together. When you'redriving, when you don't leave
enough self enough time, let'ssay you're rushing your child to
a practice, you're going to ameeting, you're meeting your
friend for a coffee.
It always happens. There'salways, oh, I got there, but I
can't find parking. Oh, I've Ineed gas. Oh, there's traffic.
(19:41):
You're rushing or stressed.
Wouldn't it be nice that onetime, John? I'm sure everyone's
been in this situation. You'regoing to meet somebody. You're,
like, looking at your GPS.You're gonna be about two
minutes early because you'realready knuckleheaded around,
and you're you're gonna almostgonna be late.
Traffic hits. Now you're gonnabe two two minutes late. Now you
start feeling terrible andyou're like, oh, should I tell
(20:03):
the person I'm gonna be twominutes late? Once it gets to,
like, three or four minutes, Ialways tell people. Then you get
there and you can't findparking.
What if you could just push abutton and say, hey, friend.
I'll be give me fifteen extraminutes. I and then I'll come
in. And now you're not runningin flustered and stressed.
You're coming in early.
John Tripolsky (20:21):
Right.
Chris Picciurro (20:21):
So if you're rushing or stressed, just file
the extension. And, honestly,most of the extensions, if you
talk to tax professionals, ifthey had some truth syrup,
they're gonna say, yeah. I couldprobably get that done within
the next thirty days betweenApril 15 and May 15 really well
while I'm still fresh. So it'snot like just because you file
(20:43):
an extension, you have to waitsix more months. But extended
tax returns get done in thethirty days after they April 15.
That's very normal.
John Tripolsky (20:51):
Right. Right. And you and you bring up a great
point too that I wanna circleback around too if we can maybe
just touch on is, you know,that's the date that things are
due. So so what happens? Say youowe just we'll just use an even
number.
Say you owe a thousand dollarsthis year. You file an
extension. Don't make thatpayment to the IRS by April 15.
(21:15):
What happens there? What whathappens between that and, you
know, the time they file, say,in May, October, whenever it is.
Chris Picciurro (21:23):
Alright. So you're you're saying you
John Tripolsky (21:25):
So they owe.
Chris Picciurro (21:26):
Didn't make the payment, and you filed a month
later. Oh gosh. You'll probablyget penalized, like it depends
on how much you owe, but let'ssay a couple percent. You know?
John Tripolsky (21:34):
Let's say
Chris Picciurro (21:35):
if you owed the thousand bucks, you'd probably
pay in $30 a penalty in
John Tripolsky (21:38):
all reality. So there is the penalties, and
that's what I was getting at isthe penalties that are being
added on top of it. It's notit's not a get out of paying
jail free card. It's a get outof filing jail free card. The
payment You start to
Chris Picciurro (21:52):
pay by by April 15, but you can file an
extension.
John Tripolsky (21:55):
Perfect. Perfect. Just for those that got
too maybe they got too excitedabout the filing the extension.
I know we touched on a littlebit earlier, but I wanted to
circle back around on that justthat there there will be
interest penalties.
Chris Picciurro (22:06):
You will always but but and we're not advocating
this, but let's be real here. Ifyou owe the thousand dollars,
the IRS doesn't know you owe thethousand dollars until you file
the return. So you would justhave to pay that penalty once
you file.
John Tripolsky (22:22):
Right. Right. Exactly.
Chris Picciurro (22:24):
You're gonna get a bill on April 16 for the
thousand bucks.
John Tripolsky (22:28):
Right. Perfect. Perfect. And that's like you
said too, it's, you know, again,not to advocate for not making
that payment. Right?
But say you owe say you owe ahundred thousand. Right? You
file an extension. Not only areyou getting more time to file,
getting your ducks in a row, thelikelihood of you saving more
(22:50):
than what the penalty may be.Well, maybe not a hundred
thousand.
That might be a stretch. But itjust all in all puts you in a
much, much better spot. It's notlike you're getting hit with a
25% penalty and a, you know,$3,000 late fee or something
like
Chris Picciurro (23:04):
that. Correct. Awesome. I mean, it could be so,
yeah, definitely talk to someoneabout and and, again, like I
said, if you're if you'reconcerned about owing, just
Mhmm. Overpay.
I mean, you can get the moneyback. Right. Awesome. It's not
gone forever.
John Tripolsky (23:18):
And it's good advice. It's good advice. And
this one I like. I mean, it'sagain, I think now that you know
that this exists, for those thatwere listening, I mean, I'm sure
you've heard this come upsomewhere, but it's definitely
like we mentioned early on. It'snot a it's not a death wish.
It's not this big 30 page formyou need to fill out to make
this happen. You're just betterto do it. Just do it in in most
(23:42):
situations. Right?
Chris Picciurro (23:43):
Right.
John Tripolsky (23:44):
Awesome. Awesome. Well, I know we got
some great topics coming up asalways here on the podcast.
Anybody that's listening tothis, the day that it comes out,
you literally have one week tofile that extension. Actually,
little bit shorter.
Don't wanna do it on thefifteenth, but take advantage of
it. If you have any questions inthe meantime, reach out to us.
Get on defeatingtaxes.com.That's their private Facebook
(24:05):
group. Well over 2,000 peoplethat are in that now.
Post some questions. Post somequestions. Any questions you
have. Oh, maybe how do I file anextension? Or has anybody else
in this group filed anextension?
What did you do? Any of thosequestions, reach out to the
group. Reach out to us here atTeaching Tax Flow. Literally, we
are here to answer questions andmake your life easier. So until
(24:26):
next time, next week, differentday, completely different topic,
roughly the same time.
We'll see everybody back hereagain on the Teaching Tax Flow
podcast. Have a great week,everybody.
Disclaimer (24:41):
Purposes only. We encourage you to seek
personalized investment advicefrom your financial
professional. For all tax andlegal advice, please consult
your CPA or attorney. Investmentadvisory services are offered
through Cabin Advisors, aregistered investment advisor.
Securities are offered throughCabin Securities, a registered
broker dealer.
The content of this podcast doesnot constitute an offer of
securities. Offerings can onlybe made through an offering
(25:03):
memorandum, and you shouldcarefully examine the risk
factors and other informationcontained in the memorandum.
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