March 25, 2025 • 24 mins
In Episode 128 of the Teaching Tax Flow podcast, hosts Chris Picciurro and John Tripolsky about the top five tax hacks for real estate investors. Known for his dynamic approach to tax strategies, Chris elaborately discusses the importance of proactive tax planning. He emphasizes that, whether you're a seasoned investor or just starting out, these strategies not only serve investors with direct benefits but can also be adapted by those not yet fully immersed in real estate investments. John, with his characteristic enthusiasm, highlights the non-conventional methods and the sophisticated planning that can transform an amateur investor into a financially savvy entrepreneur.
The thorough discussion includes insights into popular strategies such as the 1031 exchange, cost segregation studies, and Roth conversions — concepts that maximize tax efficiency and financial gains. The episode navigates through the intricacies of income shifting and S-corporation election, bringing to light lesser-known tactics that can generate significant savings. As the conversation unfolds, the synergy between smart tax planning and profitable real estate investment becomes evident, triggering a call to action for the audience to dive deeper into these methods.
Key Takeaways:
- The 1031 Exchange allows real estate investors to defer capital gains taxes by reinvesting proceeds into a similar property, enhancing cash flow potential.
- S Corporation Election can be a powerful tool for real estate business owners looking to reduce payroll taxes, though it’s important to apply it in the right circumstances.
- A Cost Segregation Study can accelerate depreciation deductions for real estate investors, providing immediate tax benefits and improving cash flow.
- Income Shifting to family members or related entities can offer tax relief and benefit from lower tax brackets or create additional opportunities for tax-efficient savings.
- Roth Conversions paired with real estate strategies can turn potential tax liabilities into tax-free growth opportunities for retirement savings.
Notable Quotes:
- "Either you pick your tax, or the IRS picks your tax. It's up to you." — Chris Picciurro
- "Tax strategies should be blended or stacked together. They don't live on an island." — Chris Picciurro
- "Ideas are cheap. Implementation is valuable. That's where the Teaching Tax Flow community comes in." — Chris Picciurro
- "Cost segregation study is pretty much the best bang for your dollar when it comes to tax strategies in real estate." — Chris Picciurro
- "If you're going to eat a lot, it's worth it. If you don't have a lot of profit, it's not worth it." — Chris Picciurro
Resources:
- Teaching Tax Flow - Official website for more tax strategy resources.
- Previous podcast episodes on related topics such as S-Corporation elections, Cost Segregation, and the short-term rental loophole are available on the podcast's YouTube channel.
Listen to this enlightening episode of the Teaching Tax Flow podcast to explore the dynamic connection between effective tax strategies and successful real estate investment. Stay tuned for more
Episode Sponsor:
Sunsets & Dinks
www.teachingtaxflow.com/pickleball
CODE: TTF15
- (00:00) - Top Five Tax Hacks for Real Estate Investors
- (06:07) - Maximize Real Estate Investment Returns with 1031 Exchange Strategies
- (08:58) - Planning and Humor in Podcasting Strategies
- (11:05) - Maximizing Tax Savings with S Corp Election in Real Estate <
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
John Tripolsky (00:04):
Welcome back to the Teaching Tax Flow podcast
today, episode 128. We arelooking at those top five tax
hacks for real estate investors.Before we get into this one, of
course, let's take a briefmoment and thank our episode
sponsor.
Ad Read (00:23):
Hi. Chris Pacquero here, founder of Teaching Tax
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John Tripolsky (01:23):
Hey, everybody. Welcome back to the podcast. If
you read the title here, we'regonna talk about some tax hacks
for real estate investors. Sowhy bring that up and why make a
point of that? Even if you'renot a real estate investor yet
or even if you have no intentionof ever doing it, I promise you
by the end of this, you're gonnalearn something.
Because even though the contentin this is really geared around
(01:44):
REIs, that real estate investor,a lot of it is actually gonna be
somewhat applicable to you atsome point your life. And heck,
even if it's not, you can atleast bring up some, knowledge
bombs, drop them at theThanksgiving table, and sound
like a genius. So let's stop BSing around it. Let's jump into
it. Chris Pacquero, welcomeback, sir.
Are you ready for this one?
Chris Picciurro (02:02):
Oh, I'm ready. You know that we, spend a lot of
time with real estate investorsand truly enjoy doing it, on our
in our personal lives. And andyou're you're right, John. I
mean, even if you're not a realestate investor, being aware of
this is is very important. Wehave a lot of content on the tax
advantages of primary homestead,ownership, but this is we're
(02:24):
talking about people that gobeyond investing in their
primary homestead as as realestate.
And and the other thing toconsider is you might not be in
a position or that you want tomaybe buy a single family home
or short term rental property,but some of these ideas might
spur some thoughts about maybepartnering with other people or
going into a syndication whereyou own like, I could say
(02:46):
personally, you know, I'veinvested in syndications where
we own mobile home parks, andwe've owned, multifamily and
apartment buildings. Like, Idon't personally wanna buy an 80
unit apartment building and andbe worried about the management
of it, but it's nice tounderstand those tax benefits
that come along with it. So,yeah, let's jump in on REIs, as
you said. You know, we like ouracronyms here at Teaching Tax
(03:07):
Flow.
John Tripolsky (03:07):
Oh, yeah. Oh, yeah. It's you know, I mean,
heck, you're basing off of, youknow, CPA, ARA, all I mean, you
got you have half the alphabetat the end of your name on your
LinkedIn page. But this one, Iremember specifically that we've
done a few no. We you've done acouple presentations on this
specifically.
So, again, if anybody'slistening or watching this and
you were at one of thosepresentations, I know one of
(03:27):
them, I think, was down inFlorida not too too long ago. It
might sound a little familiar toyou, obviously, but I can
definitely say this, that Iremember very vividly doing this
presentation or, again, being inthe audience for it, and there
were so many questions around itbecause people may have heard of
these concepts or these hacks,but they really didn't know kind
(03:47):
of the the full breadths of itall. Right? Like, they they
might know this much, and,again, those are watching. I'm
kinda holding my finger up justa little bit, but then how they
kinda play into each other aswell too.
So and which is really taxplanning. Right? If you don't
plan, then, you know, a lot ofthis, you can't take advantage
of, or you might miss the boat.
Chris Picciurro (04:05):
Absolutely. It's proactive planning. Either
you pick your tax or the IRSpicks your tax. It's up to you.
So these are our top five taxhacks.
There are I mean, there are tonsof hacks, and a lot of these
things, these strategies, can beblended or stacked together.
Well, I'm gonna just talk aboutour top five, Paint a picture.
Remember, in teaching tax law,we have a proprietary process
(04:28):
for tax planning and strategy,which means diagnose your
situation, prescribe differentstrategies, run through the IQ
test. Does it make sense for youfinancially and nonfinancially?
And then implement.
TikTok, Instagram, they arereally great resources for
ideas, but ideas are cheap.Implementation is valuable.
(04:51):
That's where the teaching taxtool community comes in, helping
you with these implementations.But let's just talk about our
top five tax hacks. I'll giveyou a 30,000 foot view on each
one, and we're gonna jump inwith with both feet.
John Tripolsky (05:04):
Sounds good. Let's do it, man. I got my
swimsuit on.
Chris Picciurro (05:07):
Oh, good. Well, John, I appreciate that you wore
your your normal shorts and notyour banana hammock this time,
as a swimsuit. You know, I knowyou've you've donned that many
times when we're on the road andwe go to the pool, you know, you
like to strut your stuff around.So
John Tripolsky (05:23):
Oh, well, how do you know that? You know, these
these webcams, they're they'revery good at, you know, cutting
off half of the body. I couldhave one that says TTF on it in
places that we do not mention.So
Chris Picciurro (05:35):
Well
John Tripolsky (05:36):
Talk about hacks. So
Chris Picciurro (05:38):
We'll we'll take that branding. And, anyway
There you go. So, like, numberand, again, these are in no
particular order. These are justthe ones we're seeing most
popular. First one's gonna bethe 10:31 exchange.
So remember, one of the threelaws of teaching tax flow. Tax
agencies are your involuntarybusiness partner. Tax laws are
in to encourage and discouragecertain behavior. So if you're
(05:58):
in a situation where you wannasell a piece of real estate,
maybe you're repositioning, andyou don't need the cash in your
pocket, you want to have anotherpiece of productive asset. A lot
of times, we find people thatare landlords, or rental
property owners, and they wantto be more passive, they wanna
shift their portfolio somewhereelse, the ten thirty one
exchange works really well.
They can sell their property.They can defer all of their
(06:21):
capital gain, redeploy that intodifferent assets, and still get
mailbox money and not give, youknow, anywhere from 10 to 40% to
the to the government. So theten thirty one exchange is
really, really popular. Youdon't have to be a full time
real estate investor. Anyonecould do the ten thirty one
exchange.
There are obviously and I'vedone it done a ten thirty one
(06:44):
exchange myself. There areobviously rules and regulations.
You can't have the the money hityour bank account. You have to
use something called a qualifiedintermediary. There are rules as
far as identifying a replacementproperty and being able to close
on that replacement property.
John, we just, in the last fewmonths, did a podcast on
Delaware statutory trust, whichis a type of ten thirty one
(07:06):
exchange. Ultimately, if you'rein a situation where you are
selling a property and you'regonna have a large capital gain
and you don't necessarily needthat cash and you don't wanna
give a bunch to the government,let us know. We could get you in
contact with a qualifiedintermediary, and then you could
start looking at what's calledreplacement property. Now one
thing to consider on 10:31exchange, this is a this is a
(07:28):
commonly asked question. If I ifI were to sell a a residential
property, right, if I was tosell a residential property, do
I have to buy anotherresidential property?
No. You don't. It just has to belike kind. It has to be
investment property. So we haveseveral people that sell a
residential property and buyinto maybe, like I said, a
(07:51):
syndication where they wantapartment complexes or
commercial property or, youknow, it could be any type of
real estate that's investmentthat's an investment.
So that gives you a lot offlexibility. You can sell one
property. I've had clients thathave sold one property and
bought several other propertiesbecause they just wanted more be
be more diversified in inespecially not only in asset
(08:13):
class, but in geographiclocation.
John Tripolsky (08:16):
Yeah. And and anybody that's interested in
this, Chris, you mentioned youmentioned a great point. You
know, you have to go through aQI. So it's a qualified
intermediary. If it hits yourbank account, sorry.
Too late. You're out of luckkinda deal. And if anybody's
interested in the podcast thatwe've mentioned this on, which
has been many, in some way,shape, or form, and also content
on our website, YouTube,etcetera, wherever you see
(08:37):
something teaching tax flow,just do a search and type in
1031. That's only, like, thenumber 1031, and you'll get a
handful of stuff. It searcheseverything we have, and it's a
it's great.
So you can dork out on it. Butthe I I'll say the one piece of
advice I feel like I said on thelast time we talked about it is,
literally, you have to plan forit. I feel like I'm I'm arping
(09:00):
that like crazy now, but youdon't wanna have to make that
call at the witching hoursaying, oh, crap. I'm I'm
sitting at the closing tablesipping on my sparkling water
about to be a happy camper, but,oh, boy, I forgot something. So
not that I know anybody that'sdone that or anything.
But
Chris Picciurro (09:16):
Exactly. You've gotta take care of it before
closing. And, John, you knowwhat? I'm gonna challenge you on
something. Oh.
John Tripolsky (09:22):
I'm gonna
Chris Picciurro (09:22):
challenge you to come up with a cool drop for
this podcast every time we use atext related acronym. And you
you said QI. So we gotta come upwith some type of jingle. We
gotta have something. I thinkthat would be fun.
Yeah. And, you know, I'mimpressed, John. You dropped a
QI on us. This is yeah. I feellike you've really learned a lot
(09:43):
through the podcast.
John Tripolsky (09:44):
I think so. I think so. Well, what's that line
that you always say you don'tknow it until you teach it?
Well, I feel like, I've I'vetaught it to myself on this
from, you know, osmosis fromworking with you on these. But,
yeah, it's you know, it's a it'sa great hack.
It's a great strategy, andthere's so much power to that
one specifically. And, you know,it's, we'll have fun with some
noises. If anything, ifanybody's, you know, really
(10:05):
wants to geek out, just have tolisten to our podcast and make a
drinking game out of it everytime we drop an acronym. And, I
mean, you'll you'll be in goodshape by the end of every every
episode.
Chris Picciurro (10:14):
So, yeah, don't don't listen in the car then.
Right? Make sure you're takingyour dog for a walk or to go in
for a jog.
John Tripolsky (10:20):
Now somebody's gonna get a public intoxication
citation. Oh,
Chris Picciurro (10:24):
man. Well, another one is gonna be numb is
the now before I say this, John,you know this is a hot button
issue for me, and this is thethis is a strategy that is often
used too early, prematurely inthe in in the life cycle of a
business. But for the rightsituation, it could save a
significant amount of payrolltaxes. That's s corp election.
(10:46):
So if you're in the real estatebusiness, let's say you're a
broker and you can have youryour commissions paid to an
entity or you are a full timehouse flipper or a wholesaler
and you have a profit of ahundred and $50,000 or more and
you're self employed, the scorporation election can make a
really, really big difference inyour tax bill.
It is not a good option if youhave buy and hold real estate.
(11:09):
So s corp election is numbertwo, often overused. But real
story, John, we just in ourprivate CPA practice we worked
on a case where we had ataxpayer who has a significant
amount of income, well over$200,000 of self employment
income in the real estatebusiness. His spouse helps him
out with the business, and theyhave well over $20,000 a year
(11:31):
medical expenses that they aregetting no deduction for. In
that case, we did an s corpelection for the business.
We put, we're paying the the theoperator, and we're gonna pay
his spouse a fair wage based onwhat we call reasonable
compensation study. Yes. We havean episode just on s corps that
John made me do.
John Tripolsky (11:51):
Episode 120, by the way, if anybody's
interested.
Chris Picciurro (11:54):
And, also, we implemented what's called a
section one zero five plan sothat the business can reimburse
employees for out of pocketmedical expenses, and now this
whole thing is gonna save them,we think, between 18 and $20,000
a year. So in that case, hugesavings.
John Tripolsky (12:13):
Absolutely. And and, Chris, I would say or or
you tell me, am I wrong insaying that the s corp election
is definitely one of thosestrategies that's kind of out
there, probably the most onsocial media reels? And I feel
like they're almost like hypevideos. Like, they get people
very excited about it. But, youknow, as we discussed in that
(12:34):
podcast one twenty, it it itcould be a sticky situation, if
not really.
Chris Picciurro (12:39):
Way I'm looking at this, John. You've ever been
to one of the I haven't been ina while. But in my younger days,
we used to go to all you can eatpizza buffets. Very dangerous
place to go if you're China.
John Tripolsky (12:53):
Wasn't it like a Pizza Hut that used to do those
way back in the day?
Chris Picciurro (12:57):
They had lunch ones, but there was other ones.
Most of them have been out ofbusiness, actually. But these
all you can eat piece I think,is it Cici's Pizza one whatever.
You're not a sponsor, so I'm notgonna mention your darn pizza.
But here's the thing.
John, you and I going to the allyou can eat pizza buffet for
$10, you and I are gonna pounddown about $30 worth of pizza.
(13:18):
Right?
John Tripolsky (13:20):
Oh, yeah.
Chris Picciurro (13:21):
Right. You take your daughter, who might is
about four years old. Is shegonna eat $10 worth of pizza
probably? Probably.
John Tripolsky (13:29):
Probably $2.50 and a dollar 25 that's gonna be
on the floor.
Chris Picciurro (13:35):
Or, you know, some you know, let's say you
bring in someone that just wantssome salad in one little slice.
My point is, the s corp is likethe buffet. If you're gonna if
you're gonna eat a lot, it'sworth it. If you have a lot of
profit, it's worth it. If youdon't have a lot of profit, it's
not worth it.
John Tripolsky (13:53):
Great analogy. It's the pizza strategy.
Chris Picciurro (13:56):
The s corp, all you can eat pizza buffet. I'm
gonna I'm gonna use that in thefuture.
John Tripolsky (14:01):
Yeah. Number three. A way to make, like, the
s stand for saucy or something.Yeah. We'll come up with that.
Chris Picciurro (14:07):
I like it. Number three is gonna be and we
have an entire episode on this,cost segregation study. So what
this is doing is it is allowingyou to front load the deductions
for your real estate that youbuy and hold. Okay? I'm not
gonna worry about too much aboutthe mechanics of it here, but if
you have buy and hold realestate, you might wanna consider
(14:28):
a cost segregation study becauseyou're able to take out the
personal property portion.
Now that's a that's a mouthfulof the real estate and take
immediate deductions for it.When does this make sense?
You've got three situations.One, if you are a real estate
professional status with IRS andyou want to offset your active
income. Two, if you own andoperate a short term rental
(14:51):
property and you meet the shortterm rental loophole.
Oh, but what's that? Well, guesswhat? You better go back to that
episode and listen to it becauseit's pretty darn good.
John Tripolsky (15:03):
And that's another one that we've talked
about a couple times too. And,yeah, there's some there's some
real meat to that one. Huge,huge benefits.
Chris Picciurro (15:09):
Oh, you're you're staying on the meat
lovers pizza? Yes. Thick. Numberthree. You are trying let's say
you are a passive investor, butyou wanna generate passive
losses, losses.
You could do the cost seg study.Why? Well, not every tax
advantaged or tax strategy meansthat we need deductions today.
(15:29):
Creating passive losses couldcreate tax free cash flow in the
future, Or let's say you soldwhen you're when you're passive
rentals and you have a big gain,you wanna pair that with a
passive loss, and you could hitthat cost segregation study on
it. So cost segregation studynumber three, It's pretty much
the best bang for your dollarwhen it comes to tax strategies
(15:52):
in real estate.
Now I'm gonna mention this.Maybe I did mention it. I don't
know. I've been on a roll today.Tax strategies.
John, they're not they don'tlike being lonely. You know?
They're not they're not HanSolo's. They're they're they
want a they want a friend. Sowhen you're talking
John Tripolsky (16:09):
about tax mustard and ketchup or peanut
butter jelly.
Chris Picciurro (16:12):
Peanut butter jelly. Right?
John Tripolsky (16:13):
Like water the other way.
Chris Picciurro (16:15):
Yeah. The the so tax strategy should be
blended or stacked together.They don't live on an island. So
when I talk about the next one,it's typically blended with the
strata the second one Imentioned, which is your s corp
election, income shifting. Soincome shifting to family
(16:35):
members, such as a spouse orchildren, can significantly
reduce your overall tax burden.
It could also allow you toprovide employee benefits and
group benefits to your family,especially if you're income
shifting to children. It couldbe paired with, hey. Let's pay
our kids. You know? We've had wehave content on this.
(16:56):
Right? It's gotta be a fair wagefor the work that they're doing
for the business. Okay? Butlet's say you could pay your
children $15,000 a year. They'reto but they're not gonna pay
much tax on that at all, butthen they can contribute to a
Roth IRA.
So you're pairing maybe a RothIRA contribution with income
shifting. So if you're operatinga a real estate business,
(17:17):
shifting income to your spouseor shifting income to your
children can make a lot ofsense. If you're if you don't
have a spouse and you don't havechildren and you still have a
significant amount of netrevenue, income shifting to a
related entity like the eightthirty one b strategy, which we
have an entire podcast on that,could make sense. And if you
(17:37):
don't have a spouse andchildren, you probably have a
lot more profit than you'reprobably the same, but you
John Tripolsky (17:43):
have a
Chris Picciurro (17:43):
lot more disposable cash.
John Tripolsky (17:45):
Yeah. And I think it was episode one
thirteen. Again, kind of ashameless plug. I think that was
the one thirteen or 14 that wecalled it or titled it, it
should say, should I pay myspouse, where we dive into that
specifically. And that wasanother good one.
Chris Picciurro (17:58):
So income shifting both to related
entities. And if don't have arelated entity, does it make
sense for you to create one, orto family members? So that's my
fourth one. The final one is onethat I love to pair with cost
segregation studies, Rothconversions. Okay, John.
I'm gonna paint a picture foryou.
John Tripolsky (18:19):
Bob Ross style, heavy treats.
Chris Picciurro (18:21):
I I don't think it's pizza, but I I can't
remember.
John Tripolsky (18:23):
Let's see. Believe it or not, tuna fish
salads. Oh, that's kinda weird.You don't know what we might we
won't make me sound like somecrunchy person here. We're,
let's say let's say steak.
Chris Picciurro (18:40):
Okay. Here's what we're gonna do, John. We're
you you and I are gonna go outto dinner. We're gonna go to a
beautiful steak place. You'regonna have a nice steak, and
when you go to pay for thesteak, they're gonna say, no,
John.
I'm you don't have to pay forthe steak. Okay. You consumed
it. You enjoy it. Yep.
Actually, John, in thirty years,we're you're gonna pay for that
(19:02):
steak, but you're gonna paywhatever that steak's price is
in thirty years from now. Whichwe have no clue.
John Tripolsky (19:11):
That's like filling up your tank and with
gasoline thirty years ago. Well,let's say twenty five years ago.
Right?
Chris Picciurro (19:17):
Well, that's what people do.
John Tripolsky (19:19):
To do it at the pump then than now.
Chris Picciurro (19:21):
Well, and that's where the argument for
maybe putting money away into aRoth or doing a Roth conversion
today, paying the tax on yourRoth conversion today instead of
whatever that's gonna be in thefuture plus its growth. And we
do that all the time. Right? SoRoth conversions are great to
pair with cost segregationstudies. So if you are in a
situation where I mean, I've hadreal situations where we have
(19:42):
people making $3,400,000 ofincome.
They buy an apartment building,etcetera. They get a cost
segregation study to come in ata $500,000 loss this year. We've
got a bad situation now. Nowwe've got $500,000 worth of loss
and $400,000 worth of income.We're wipe we're we're we're
using deductions to wipe out 12%marginal tax rate, and we have
(20:03):
$100,000 of deductions that wehave to carry forward to the
next year, and we only get tocarry forward 80% of them.
The point is the costsegregation study created a loss
that's now inefficient. What dowe do? The first thing I'm gonna
do is talk to that taxpayer andsay, do you have money sending
in your four zero one k, oldIRA? Yeah. Well, guess what?
Why don't you convert that toRoth this year, ultimately pay
(20:24):
almost no tax on that, and nowthat money's gonna grow tax free
the rest of That's anotherthat's another example of
blending the strategies. So Rothconversions, you might not think
about real estate investors whenit comes to Roth conversions
right away, but a lot of times,Roth conversions make sense,
especially for people leavingcorporate America. Maybe they
had those higher w two wages.They get into real estate. Maybe
(20:44):
they could be that first year,they're not making as much
money.
You wanna do the Rothconversions when you have a
lower marginal tax rate.
John Tripolsky (20:51):
Right. And and everything we talked about here,
Christy, I think it's superimportant, you know, for
somebody who is not in thisworld yet, or maybe is thinking
about it, it is a business. It'snot just a, you know, like,
selling things on eBay here andthere. Like, you are forming an
entity most likely, and then alot of these strategies, right,
you have to be aware of them.Again, because you it's almost
(21:12):
like if you take one leg off ofa of a three legged table.
Right? It's still a table. It'sjust, you know, head over heels.
It it didn't go the way you wantit to, or, you know, you went to
the pizza buffet, and all thepizza was gone. Either way,
there's a lot of lot of badexamples.
But I say that with it being abusiness because treating it as
such really does kinda set theprecedence for success. Right?
(21:35):
And and knowing what you havegoing on, and I think kind of a
twofold. Right? It helps youkind of plan for ways to
obviously implement taxadvantaged strategies, but then
also, it helps you just franklygrow and manage your business
because you treat it like that.
Right?
Chris Picciurro (21:52):
Absolutely. Remember, you ought to pick your
tax. If you don't pick your tax,the IRS will for you. So those
are my top five. There areseveral other ones.
We pretty much have a podcastepisode on all this. We have
YouTube episode YouTubeinformation. But, yeah, if if
any of this, you know, piquesyour interest or if you just
wanna be a friend, bring afriend into the Teaching Tax
(22:14):
Flow community. Just check outteachingtaxflow.com or jump into
the Defeating Taxes privateFacebook group. And and, John,
selfishly, we get a bunch of ourcontent ideas from our
community.
So
John Tripolsky (22:25):
thank you. Absolutely. In some way, shape,
or form. Right? It's eitherconversations, questions asked.
Sometimes it's answers to otherquestions that were asked. It's
really interesting seeing howthey come up. So as always, this
is a great topic that we doveinto. If it wasn't great, we'd
kick it to the curb and deleteit from our spreadsheet, our
little roster that we keep. But,we do have some great guests
(22:45):
coming up, and obviously, somegreat topics still on the on the
radar here.
And then, you know, here we arekind of that time of year. We're
not gonna say that thing thatwe'd call tax day because it
really doesn't exist in ourworld, but keep planning, keep
yourself educated on all thestrategies that are out there
and all of the really industrytax fed news that's coming down.
(23:07):
Be the smartest guy in the room.Anything we can do to assist you
by doing that, feel free toreach out. We are here.
Anywhere you can search teachingtax flow, you will find us
everywhere. Shoot us a message.Shoot us those comments, and
we'll see you back here againnext week on the teaching tax
flow podcast. And I almostforgot. Different time, roughly,
different date, completelydifferent topic.
(23:29):
Have a good week, everybody.
Disclaimer (23:34):
The content provided is for educational purposes
only. We encourage you to seekpersonalized investment advice
from your financialprofessional. For all tax and
legal advice, please consultyour CPA or attorney. Investment
advisory services are offeredthrough Cabin Advisors, a
registered investment advisor.Securities are offered through
Cabin Securities, a registeredbroker dealer.
The content of this podcast doesnot constitute an offer of
(23:55):
securities. Offerings can onlybe made through an offering
memorandum, and you shouldcarefully examine the risk
factors and other informationcontained in the memorandum.
Welcome back to the Teaching Tax Flow podcast
today, episode 128. We arelooking at those top five tax
hacks for real estate investors.Before we get into this one, of
course, let's take a briefmoment and thank our episode
sponsor.
Ad Read (00:23):
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John Tripolsky (01:23):
Hey, everybody. Welcome back to the podcast. If
you read the title here, we'regonna talk about some tax hacks
for real estate investors. Sowhy bring that up and why make a
point of that? Even if you'renot a real estate investor yet
or even if you have no intentionof ever doing it, I promise you
by the end of this, you're gonnalearn something.
Because even though the contentin this is really geared around
(01:44):
REIs, that real estate investor,a lot of it is actually gonna be
somewhat applicable to you atsome point your life. And heck,
even if it's not, you can atleast bring up some, knowledge
bombs, drop them at theThanksgiving table, and sound
like a genius. So let's stop BSing around it. Let's jump into
it. Chris Pacquero, welcomeback, sir.
Are you ready for this one?
Chris Picciurro (02:02):
Oh, I'm ready. You know that we, spend a lot of
time with real estate investorsand truly enjoy doing it, on our
in our personal lives. And andyou're you're right, John. I
mean, even if you're not a realestate investor, being aware of
this is is very important. Wehave a lot of content on the tax
advantages of primary homestead,ownership, but this is we're
(02:24):
talking about people that gobeyond investing in their
primary homestead as as realestate.
And and the other thing toconsider is you might not be in
a position or that you want tomaybe buy a single family home
or short term rental property,but some of these ideas might
spur some thoughts about maybepartnering with other people or
going into a syndication whereyou own like, I could say
(02:46):
personally, you know, I'veinvested in syndications where
we own mobile home parks, andwe've owned, multifamily and
apartment buildings. Like, Idon't personally wanna buy an 80
unit apartment building and andbe worried about the management
of it, but it's nice tounderstand those tax benefits
that come along with it. So,yeah, let's jump in on REIs, as
you said. You know, we like ouracronyms here at Teaching Tax
(03:07):
Flow.
John Tripolsky (03:07):
Oh, yeah. Oh, yeah. It's you know, I mean,
heck, you're basing off of, youknow, CPA, ARA, all I mean, you
got you have half the alphabetat the end of your name on your
LinkedIn page. But this one, Iremember specifically that we've
done a few no. We you've done acouple presentations on this
specifically.
So, again, if anybody'slistening or watching this and
you were at one of thosepresentations, I know one of
(03:27):
them, I think, was down inFlorida not too too long ago. It
might sound a little familiar toyou, obviously, but I can
definitely say this, that Iremember very vividly doing this
presentation or, again, being inthe audience for it, and there
were so many questions around itbecause people may have heard of
these concepts or these hacks,but they really didn't know kind
(03:47):
of the the full breadths of itall. Right? Like, they they
might know this much, and,again, those are watching. I'm
kinda holding my finger up justa little bit, but then how they
kinda play into each other aswell too.
So and which is really taxplanning. Right? If you don't
plan, then, you know, a lot ofthis, you can't take advantage
of, or you might miss the boat.
Chris Picciurro (04:05):
Absolutely. It's proactive planning. Either
you pick your tax or the IRSpicks your tax. It's up to you.
So these are our top five taxhacks.
There are I mean, there are tonsof hacks, and a lot of these
things, these strategies, can beblended or stacked together.
Well, I'm gonna just talk aboutour top five, Paint a picture.
Remember, in teaching tax law,we have a proprietary process
(04:28):
for tax planning and strategy,which means diagnose your
situation, prescribe differentstrategies, run through the IQ
test. Does it make sense for youfinancially and nonfinancially?
And then implement.
TikTok, Instagram, they arereally great resources for
ideas, but ideas are cheap.Implementation is valuable.
(04:51):
That's where the teaching taxtool community comes in, helping
you with these implementations.But let's just talk about our
top five tax hacks. I'll giveyou a 30,000 foot view on each
one, and we're gonna jump inwith with both feet.
John Tripolsky (05:04):
Sounds good. Let's do it, man. I got my
swimsuit on.
Chris Picciurro (05:07):
Oh, good. Well, John, I appreciate that you wore
your your normal shorts and notyour banana hammock this time,
as a swimsuit. You know, I knowyou've you've donned that many
times when we're on the road andwe go to the pool, you know, you
like to strut your stuff around.So
John Tripolsky (05:23):
Oh, well, how do you know that? You know, these
these webcams, they're they'revery good at, you know, cutting
off half of the body. I couldhave one that says TTF on it in
places that we do not mention.So
Chris Picciurro (05:35):
Well
John Tripolsky (05:36):
Talk about hacks. So
Chris Picciurro (05:38):
We'll we'll take that branding. And, anyway
There you go. So, like, numberand, again, these are in no
particular order. These are justthe ones we're seeing most
popular. First one's gonna bethe 10:31 exchange.
So remember, one of the threelaws of teaching tax flow. Tax
agencies are your involuntarybusiness partner. Tax laws are
in to encourage and discouragecertain behavior. So if you're
(05:58):
in a situation where you wannasell a piece of real estate,
maybe you're repositioning, andyou don't need the cash in your
pocket, you want to have anotherpiece of productive asset. A lot
of times, we find people thatare landlords, or rental
property owners, and they wantto be more passive, they wanna
shift their portfolio somewhereelse, the ten thirty one
exchange works really well.
They can sell their property.They can defer all of their
(06:21):
capital gain, redeploy that intodifferent assets, and still get
mailbox money and not give, youknow, anywhere from 10 to 40% to
the to the government. So theten thirty one exchange is
really, really popular. Youdon't have to be a full time
real estate investor. Anyonecould do the ten thirty one
exchange.
There are obviously and I'vedone it done a ten thirty one
(06:44):
exchange myself. There areobviously rules and regulations.
You can't have the the money hityour bank account. You have to
use something called a qualifiedintermediary. There are rules as
far as identifying a replacementproperty and being able to close
on that replacement property.
John, we just, in the last fewmonths, did a podcast on
Delaware statutory trust, whichis a type of ten thirty one
(07:06):
exchange. Ultimately, if you'rein a situation where you are
selling a property and you'regonna have a large capital gain
and you don't necessarily needthat cash and you don't wanna
give a bunch to the government,let us know. We could get you in
contact with a qualifiedintermediary, and then you could
start looking at what's calledreplacement property. Now one
thing to consider on 10:31exchange, this is a this is a
(07:28):
commonly asked question. If I ifI were to sell a a residential
property, right, if I was tosell a residential property, do
I have to buy anotherresidential property?
No. You don't. It just has to belike kind. It has to be
investment property. So we haveseveral people that sell a
residential property and buyinto maybe, like I said, a
(07:51):
syndication where they wantapartment complexes or
commercial property or, youknow, it could be any type of
real estate that's investmentthat's an investment.
So that gives you a lot offlexibility. You can sell one
property. I've had clients thathave sold one property and
bought several other propertiesbecause they just wanted more be
be more diversified in inespecially not only in asset
(08:13):
class, but in geographiclocation.
John Tripolsky (08:16):
Yeah. And and anybody that's interested in
this, Chris, you mentioned youmentioned a great point. You
know, you have to go through aQI. So it's a qualified
intermediary. If it hits yourbank account, sorry.
Too late. You're out of luckkinda deal. And if anybody's
interested in the podcast thatwe've mentioned this on, which
has been many, in some way,shape, or form, and also content
on our website, YouTube,etcetera, wherever you see
(08:37):
something teaching tax flow,just do a search and type in
1031. That's only, like, thenumber 1031, and you'll get a
handful of stuff. It searcheseverything we have, and it's a
it's great.
So you can dork out on it. Butthe I I'll say the one piece of
advice I feel like I said on thelast time we talked about it is,
literally, you have to plan forit. I feel like I'm I'm arping
(09:00):
that like crazy now, but youdon't wanna have to make that
call at the witching hoursaying, oh, crap. I'm I'm
sitting at the closing tablesipping on my sparkling water
about to be a happy camper, but,oh, boy, I forgot something. So
not that I know anybody that'sdone that or anything.
But
Chris Picciurro (09:16):
Exactly. You've gotta take care of it before
closing. And, John, you knowwhat? I'm gonna challenge you on
something. Oh.
John Tripolsky (09:22):
I'm gonna
Chris Picciurro (09:22):
challenge you to come up with a cool drop for
this podcast every time we use atext related acronym. And you
you said QI. So we gotta come upwith some type of jingle. We
gotta have something. I thinkthat would be fun.
Yeah. And, you know, I'mimpressed, John. You dropped a
QI on us. This is yeah. I feellike you've really learned a lot
(09:43):
through the podcast.
John Tripolsky (09:44):
I think so. I think so. Well, what's that line
that you always say you don'tknow it until you teach it?
Well, I feel like, I've I'vetaught it to myself on this
from, you know, osmosis fromworking with you on these. But,
yeah, it's you know, it's a it'sa great hack.
It's a great strategy, andthere's so much power to that
one specifically. And, you know,it's, we'll have fun with some
noises. If anything, ifanybody's, you know, really
(10:05):
wants to geek out, just have tolisten to our podcast and make a
drinking game out of it everytime we drop an acronym. And, I
mean, you'll you'll be in goodshape by the end of every every
episode.
Chris Picciurro (10:14):
So, yeah, don't don't listen in the car then.
Right? Make sure you're takingyour dog for a walk or to go in
for a jog.
John Tripolsky (10:20):
Now somebody's gonna get a public intoxication
citation. Oh,
Chris Picciurro (10:24):
man. Well, another one is gonna be numb is
the now before I say this, John,you know this is a hot button
issue for me, and this is thethis is a strategy that is often
used too early, prematurely inthe in in the life cycle of a
business. But for the rightsituation, it could save a
significant amount of payrolltaxes. That's s corp election.
(10:46):
So if you're in the real estatebusiness, let's say you're a
broker and you can have youryour commissions paid to an
entity or you are a full timehouse flipper or a wholesaler
and you have a profit of ahundred and $50,000 or more and
you're self employed, the scorporation election can make a
really, really big difference inyour tax bill.
It is not a good option if youhave buy and hold real estate.
(11:09):
So s corp election is numbertwo, often overused. But real
story, John, we just in ourprivate CPA practice we worked
on a case where we had ataxpayer who has a significant
amount of income, well over$200,000 of self employment
income in the real estatebusiness. His spouse helps him
out with the business, and theyhave well over $20,000 a year
(11:31):
medical expenses that they aregetting no deduction for. In
that case, we did an s corpelection for the business.
We put, we're paying the the theoperator, and we're gonna pay
his spouse a fair wage based onwhat we call reasonable
compensation study. Yes. We havean episode just on s corps that
John made me do.
John Tripolsky (11:51):
Episode 120, by the way, if anybody's
interested.
Chris Picciurro (11:54):
And, also, we implemented what's called a
section one zero five plan sothat the business can reimburse
employees for out of pocketmedical expenses, and now this
whole thing is gonna save them,we think, between 18 and $20,000
a year. So in that case, hugesavings.
John Tripolsky (12:13):
Absolutely. And and, Chris, I would say or or
you tell me, am I wrong insaying that the s corp election
is definitely one of thosestrategies that's kind of out
there, probably the most onsocial media reels? And I feel
like they're almost like hypevideos. Like, they get people
very excited about it. But, youknow, as we discussed in that
(12:34):
podcast one twenty, it it itcould be a sticky situation, if
not really.
Chris Picciurro (12:39):
Way I'm looking at this, John. You've ever been
to one of the I haven't been ina while. But in my younger days,
we used to go to all you can eatpizza buffets. Very dangerous
place to go if you're China.
John Tripolsky (12:53):
Wasn't it like a Pizza Hut that used to do those
way back in the day?
Chris Picciurro (12:57):
They had lunch ones, but there was other ones.
Most of them have been out ofbusiness, actually. But these
all you can eat piece I think,is it Cici's Pizza one whatever.
You're not a sponsor, so I'm notgonna mention your darn pizza.
But here's the thing.
John, you and I going to the allyou can eat pizza buffet for
$10, you and I are gonna pounddown about $30 worth of pizza.
(13:18):
Right?
John Tripolsky (13:20):
Oh, yeah.
Chris Picciurro (13:21):
Right. You take your daughter, who might is
about four years old. Is shegonna eat $10 worth of pizza
probably? Probably.
John Tripolsky (13:29):
Probably $2.50 and a dollar 25 that's gonna be
on the floor.
Chris Picciurro (13:35):
Or, you know, some you know, let's say you
bring in someone that just wantssome salad in one little slice.
My point is, the s corp is likethe buffet. If you're gonna if
you're gonna eat a lot, it'sworth it. If you have a lot of
profit, it's worth it. If youdon't have a lot of profit, it's
not worth it.
John Tripolsky (13:53):
Great analogy. It's the pizza strategy.
Chris Picciurro (13:56):
The s corp, all you can eat pizza buffet. I'm
gonna I'm gonna use that in thefuture.
John Tripolsky (14:01):
Yeah. Number three. A way to make, like, the
s stand for saucy or something.Yeah. We'll come up with that.
Chris Picciurro (14:07):
I like it. Number three is gonna be and we
have an entire episode on this,cost segregation study. So what
this is doing is it is allowingyou to front load the deductions
for your real estate that youbuy and hold. Okay? I'm not
gonna worry about too much aboutthe mechanics of it here, but if
you have buy and hold realestate, you might wanna consider
(14:28):
a cost segregation study becauseyou're able to take out the
personal property portion.
Now that's a that's a mouthfulof the real estate and take
immediate deductions for it.When does this make sense?
You've got three situations.One, if you are a real estate
professional status with IRS andyou want to offset your active
income. Two, if you own andoperate a short term rental
(14:51):
property and you meet the shortterm rental loophole.
Oh, but what's that? Well, guesswhat? You better go back to that
episode and listen to it becauseit's pretty darn good.
John Tripolsky (15:03):
And that's another one that we've talked
about a couple times too. And,yeah, there's some there's some
real meat to that one. Huge,huge benefits.
Chris Picciurro (15:09):
Oh, you're you're staying on the meat
lovers pizza? Yes. Thick. Numberthree. You are trying let's say
you are a passive investor, butyou wanna generate passive
losses, losses.
You could do the cost seg study.Why? Well, not every tax
advantaged or tax strategy meansthat we need deductions today.
(15:29):
Creating passive losses couldcreate tax free cash flow in the
future, Or let's say you soldwhen you're when you're passive
rentals and you have a big gain,you wanna pair that with a
passive loss, and you could hitthat cost segregation study on
it. So cost segregation studynumber three, It's pretty much
the best bang for your dollarwhen it comes to tax strategies
(15:52):
in real estate.
Now I'm gonna mention this.Maybe I did mention it. I don't
know. I've been on a roll today.Tax strategies.
John, they're not they don'tlike being lonely. You know?
They're not they're not HanSolo's. They're they're they
want a they want a friend. Sowhen you're talking
John Tripolsky (16:09):
about tax mustard and ketchup or peanut
butter jelly.
Chris Picciurro (16:12):
Peanut butter jelly. Right?
John Tripolsky (16:13):
Like water the other way.
Chris Picciurro (16:15):
Yeah. The the so tax strategy should be
blended or stacked together.They don't live on an island. So
when I talk about the next one,it's typically blended with the
strata the second one Imentioned, which is your s corp
election, income shifting. Soincome shifting to family
(16:35):
members, such as a spouse orchildren, can significantly
reduce your overall tax burden.
It could also allow you toprovide employee benefits and
group benefits to your family,especially if you're income
shifting to children. It couldbe paired with, hey. Let's pay
our kids. You know? We've had wehave content on this.
(16:56):
Right? It's gotta be a fair wagefor the work that they're doing
for the business. Okay? Butlet's say you could pay your
children $15,000 a year. They'reto but they're not gonna pay
much tax on that at all, butthen they can contribute to a
Roth IRA.
So you're pairing maybe a RothIRA contribution with income
shifting. So if you're operatinga a real estate business,
(17:17):
shifting income to your spouseor shifting income to your
children can make a lot ofsense. If you're if you don't
have a spouse and you don't havechildren and you still have a
significant amount of netrevenue, income shifting to a
related entity like the eightthirty one b strategy, which we
have an entire podcast on that,could make sense. And if you
(17:37):
don't have a spouse andchildren, you probably have a
lot more profit than you'reprobably the same, but you
John Tripolsky (17:43):
have a
Chris Picciurro (17:43):
lot more disposable cash.
John Tripolsky (17:45):
Yeah. And I think it was episode one
thirteen. Again, kind of ashameless plug. I think that was
the one thirteen or 14 that wecalled it or titled it, it
should say, should I pay myspouse, where we dive into that
specifically. And that wasanother good one.
Chris Picciurro (17:58):
So income shifting both to related
entities. And if don't have arelated entity, does it make
sense for you to create one, orto family members? So that's my
fourth one. The final one is onethat I love to pair with cost
segregation studies, Rothconversions. Okay, John.
I'm gonna paint a picture foryou.
John Tripolsky (18:19):
Bob Ross style, heavy treats.
Chris Picciurro (18:21):
I I don't think it's pizza, but I I can't
remember.
John Tripolsky (18:23):
Let's see. Believe it or not, tuna fish
salads. Oh, that's kinda weird.You don't know what we might we
won't make me sound like somecrunchy person here. We're,
let's say let's say steak.
Chris Picciurro (18:40):
Okay. Here's what we're gonna do, John. We're
you you and I are gonna go outto dinner. We're gonna go to a
beautiful steak place. You'regonna have a nice steak, and
when you go to pay for thesteak, they're gonna say, no,
John.
I'm you don't have to pay forthe steak. Okay. You consumed
it. You enjoy it. Yep.
Actually, John, in thirty years,we're you're gonna pay for that
(19:02):
steak, but you're gonna paywhatever that steak's price is
in thirty years from now. Whichwe have no clue.
John Tripolsky (19:11):
That's like filling up your tank and with
gasoline thirty years ago. Well,let's say twenty five years ago.
Right?
Chris Picciurro (19:17):
Well, that's what people do.
John Tripolsky (19:19):
To do it at the pump then than now.
Chris Picciurro (19:21):
Well, and that's where the argument for
maybe putting money away into aRoth or doing a Roth conversion
today, paying the tax on yourRoth conversion today instead of
whatever that's gonna be in thefuture plus its growth. And we
do that all the time. Right? SoRoth conversions are great to
pair with cost segregationstudies. So if you are in a
situation where I mean, I've hadreal situations where we have
(19:42):
people making $3,400,000 ofincome.
They buy an apartment building,etcetera. They get a cost
segregation study to come in ata $500,000 loss this year. We've
got a bad situation now. Nowwe've got $500,000 worth of loss
and $400,000 worth of income.We're wipe we're we're we're
using deductions to wipe out 12%marginal tax rate, and we have
(20:03):
$100,000 of deductions that wehave to carry forward to the
next year, and we only get tocarry forward 80% of them.
The point is the costsegregation study created a loss
that's now inefficient. What dowe do? The first thing I'm gonna
do is talk to that taxpayer andsay, do you have money sending
in your four zero one k, oldIRA? Yeah. Well, guess what?
Why don't you convert that toRoth this year, ultimately pay
(20:24):
almost no tax on that, and nowthat money's gonna grow tax free
the rest of That's anotherthat's another example of
blending the strategies. So Rothconversions, you might not think
about real estate investors whenit comes to Roth conversions
right away, but a lot of times,Roth conversions make sense,
especially for people leavingcorporate America. Maybe they
had those higher w two wages.They get into real estate. Maybe
(20:44):
they could be that first year,they're not making as much
money.
You wanna do the Rothconversions when you have a
lower marginal tax rate.
John Tripolsky (20:51):
Right. And and everything we talked about here,
Christy, I think it's superimportant, you know, for
somebody who is not in thisworld yet, or maybe is thinking
about it, it is a business. It'snot just a, you know, like,
selling things on eBay here andthere. Like, you are forming an
entity most likely, and then alot of these strategies, right,
you have to be aware of them.Again, because you it's almost
(21:12):
like if you take one leg off ofa of a three legged table.
Right? It's still a table. It'sjust, you know, head over heels.
It it didn't go the way you wantit to, or, you know, you went to
the pizza buffet, and all thepizza was gone. Either way,
there's a lot of lot of badexamples.
But I say that with it being abusiness because treating it as
such really does kinda set theprecedence for success. Right?
(21:35):
And and knowing what you havegoing on, and I think kind of a
twofold. Right? It helps youkind of plan for ways to
obviously implement taxadvantaged strategies, but then
also, it helps you just franklygrow and manage your business
because you treat it like that.
Right?
Chris Picciurro (21:52):
Absolutely. Remember, you ought to pick your
tax. If you don't pick your tax,the IRS will for you. So those
are my top five. There areseveral other ones.
We pretty much have a podcastepisode on all this. We have
YouTube episode YouTubeinformation. But, yeah, if if
any of this, you know, piquesyour interest or if you just
wanna be a friend, bring afriend into the Teaching Tax
(22:14):
Flow community. Just check outteachingtaxflow.com or jump into
the Defeating Taxes privateFacebook group. And and, John,
selfishly, we get a bunch of ourcontent ideas from our
community.
So
John Tripolsky (22:25):
thank you. Absolutely. In some way, shape,
or form. Right? It's eitherconversations, questions asked.
Sometimes it's answers to otherquestions that were asked. It's
really interesting seeing howthey come up. So as always, this
is a great topic that we doveinto. If it wasn't great, we'd
kick it to the curb and deleteit from our spreadsheet, our
little roster that we keep. But,we do have some great guests
(22:45):
coming up, and obviously, somegreat topics still on the on the
radar here.
And then, you know, here we arekind of that time of year. We're
not gonna say that thing thatwe'd call tax day because it
really doesn't exist in ourworld, but keep planning, keep
yourself educated on all thestrategies that are out there
and all of the really industrytax fed news that's coming down.
(23:07):
Be the smartest guy in the room.Anything we can do to assist you
by doing that, feel free toreach out. We are here.
Anywhere you can search teachingtax flow, you will find us
everywhere. Shoot us a message.Shoot us those comments, and
we'll see you back here againnext week on the teaching tax
flow podcast. And I almostforgot. Different time, roughly,
different date, completelydifferent topic.
(23:29):
Have a good week, everybody.
Disclaimer (23:34):
The content provided is for educational purposes
only. We encourage you to seekpersonalized investment advice
from your financialprofessional. For all tax and
legal advice, please consultyour CPA or attorney. Investment
advisory services are offeredthrough Cabin Advisors, a
registered investment advisor.Securities are offered through
Cabin Securities, a registeredbroker dealer.
The content of this podcast doesnot constitute an offer of
(23:55):
securities. Offerings can onlybe made through an offering
memorandum, and you shouldcarefully examine the risk
factors and other informationcontained in the memorandum.
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