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Welcome back to the Clappy and Frank
Show, episode 23. We're about a half a
year in. The feedback is tremendous.
Last week we had on our great friend
Mickey. Mickey told us what not to do.
But one of the most intriguing, amazing
conversations that we're going to be
having today is about a topic that's
extremely taboo. Nobody wants to talk
about the IRS. It's on your mind 247.
Tax season is upon us. 2025 has to be
filed. Deadlines are approaching. We
have with us somebody that worked for
the IRS, the scary IRS, the Internal
Revenue Service, my good friend, Yall
Israel Astra. Uh, it's an honor and
pleasure. Thank you so much for agreeing
to come on
>> here for 17 years.
>> 17 years.
>> Wow.
>> Close to 20. Close to 20. [laughter]
>> Israel, tell us a little bit about
yourself.
>> Well, thanks for having me on.
Like I like you said, I've worked close
to 20 years at the IRS. I was a revenue
agent for 10 years auditing people,
individuals, companies,
offshore accounts, special issues, and
then I worked seven plus years as an
appeals officer and there I was dealing
with the litigation, meaning if you
protest or you're you you protest, you
have a tax petition, the tax court can't
take every case. So it goes on the
appeals officer's desk and they try to
resolve it
>> before it goes to court.
>> Yeah. And a good percentage like 80 plus
percent doesn't go to court.
>> You said 80% doesn't go to court when
somebody appeals the IRS bill. Last week
we had somebody that sat in prison over
12 and a half years, two stints in
prison, our good friend, our Chevan
friend. So he was saying that when the
uh prosecutors when the government the
US district attorneys come after you
their prosecution rate of success of
getting you you know tossed in jail is
over 97% success rate. So it's
interesting that when the government
does something they do it with such a
strong
hand with a mighty power of the US
government that when you appeal it 80%
of the people just settle and they don't
even actually want to go to trial.
You're saying
>> no. No. Both. The government can't take
every single case in front of a judge.
And a lot of these cases, you could
resolve it relatively easily by just
sitting with an appeals officer and
resolving the case. What you're saying
is something completely different.
Now, in terms of prosecuting and civily
going after people for doing something
with fraud, if the government's going to
go after you, a they're going to go
after you because you either have money
or you're a name, you have a big name,
and then their success rate is very
high.
>> What triggers a audit from the IRS?
>> So, these are
>> Do poor people get audited?
>> All the time.
>> Poor people really
>> all the time. All the time.
>> For what? Well, there's something called
earn income credit, child tax credit.
This is basically money the government
gives you if you have kids, if you have
dependent. And a lot of poor people, I
say poor like this, or people that are
in poverty or make less money. Sometimes
they go to a tax preparer that's not
really a CPA, they're just very good at
giving you your earned income income
credit. So, if you get a refund and you
make very little money from earned
income credit, child tax credit, you can
be getting back seven, eight, nine,
$10,000 back.
And a a lot of times these preparers,
they don't know what they're doing or
they don't care or they're not following
the due diligent laws. And so when
somebody comes to them, they're going,
"Oh, we can give them an $8,000 refund,
earn income credit. They can claim their
brothers. They can claim their aunts.
they can claim their uncles and then
they get a $8,000
refund and sometimes they get audited
and they have to pay that money back two
three years later.
>> Why weren't they entitled to that $8,000
that the tax preparer thought that they
were entitled to? Give me an example if
you don't mind.
>> The example maybe their uncles
maybe their uncle aunt are could an
uncle and aunt ever be a dependent of
yours or it's never possible. an an
uncle and aunt could claim their niece
and nephew if they're supplying half of
the half of their support. They're
actually they live by that.
>> So they they just check the box to help
their client get the extra $3,000 that
they weren't really entitled to. So even
a poor person like wink wink poor could
get audited because it doesn't make
sense why they're claiming their uncle
and aunt don't even live in the same
house.
>> And and also you have to be making money
>> to get earn income credit to get tax
refunds. I mean, uh, not tax refunds,
child tax credit. So, a lot of times
they'll go to these preparers. They'll
say, "Okay, you're a barber in your
house. You made $30,000. You have zero
expenses
and and we're going to claim your little
sister or niece or nephew." And then
they get back a refund when they never
made $30,000. They never were a barber.
[laughter]
>> And they That's very common.
>> There's a barber shop next door to here
in this office. Typically what do you do
with those kids? You just tell them give
the money back or you go after them, you
throw them in jail or what's usually the
process?
>> Usually they go after these preparers
for not following the due diligent
requirements
which is a lot of documentation, a lot
of form filing, a lot of recordkeeping.
They go after the preparer themselves,
but a lot of times before they go after
the preparer or as they're going after
the preparer, they're auditing a lot of
the uh their clients. So if you file
this fraudulent return with a tax
prepareer then it's not your who's who's
liable the person who's filing to get
the money or the person who's preparing
doing the tax preparing.
>> It's a great question.
>> It's a very good question
>> because you just mentioned how they
usually go after the preparing.
>> I'm actually curious who's in trouble.
>> They So what happens is imagine this
taxpayer in my opinion I feel bad for
the taxpayer. They're just doing what
their friends are telling them to do.
They're getting back in a period of
three years, let's just say anywhere
from 5,000 to 10,000. And that equals
after 3 years,
$30,000.
So imagine after these three years, they
got that all that money back. They
bought a TV. [laughter]
They're uh they bought a new car. They
have nice clothing. They got the Jordans
with all that money. And now the IRS, me
as an auditor is coming after them and
we usually open up all three years. Now
they have to pay back all that money
interest.
>> Oh my god.
>> And penalties.
>> So
>> how much is the interest?
Sure. Yeah. Um
>> it's not 2 3%. It's higher. It's real.
It's real money.
>> I don't remember. I got to be honest.
[laughter]
But it's uh it's probably around that.
So that's on the personal end.
Businesses. What are the red flags for
businesses? And are they algorithm
algorithmic in um notified or it's every
little tax return that comes into the
IRS is reviewed by a human being?
>> No, the computer picks up on most. So
the most perfect thing I've seen it so
many times. You look at the schedule C.
Schedule C is the business portion of
someone who's self-employed. It shows
gross receipts. It shows the expenses,
car and truck, cost of goods sold, and
how many times have I looked at it and
you see car and truck expense $20,000
and other deductions. You'll see other
deductions $10,000.
So these are round numbers. It's not
likely
the computer will pick up on it. And
even if the computer doesn't pick up on
it, me as the auditor when I see that
return will pick up on it. It's a
common. It's called an LUQ. Large unique
quantitative thing on the return. What
is the the the likelihood that there's
three things that equal zeros on the
return and high numbers, you know? So, a
lot of
adjustments come from that. And if
you're already being audited,
let's just say you don't keep good
records. You're already being audited.
You already have three things on the
return that equal 10,000 25,000. Now,
the auditor is looking at the general
ledger, which is the books that go on
paper.
>> PNL PNL PNL as well. And now on there
we're also finding things that end with
0 0.
Doesn't mean it could be likelihood that
some things is legit, but you're seeing
a lot of things that equal $10,000.
So when you have your own business and
you have your own expenses, how many
things equal exactly on the dot with
taxes?
>> Zero is suspicious.
>> Yes.
>> Perfect numbers are suspicious.
>> Yeah.
>> What about social media posts? Someone's
flashing Rolls-Royce private jets. Is
that something that IRS has their uh AI
or whatever searches or Google alerts?
>> Uh not that I'm aware of. Not that I'm
aware of. A lot of people on social
media like to go in front of a nice car
and pretend it's theirs. Uh that's not
what they do. But what happens is if
you're getting audited or investigated,
they are going to look at your assets
and they're going to go, "Wow, this guy
Mosha Frank has a Mercedes. I wish.
>> But he only makes
$60,000, has five kids, you know. Maybe
you make 90,000, but how does he have a
Mercedes,
you know? So that's when they look and
they may go, you have to show me how you
paid for this Mercedes. I want to say
it's very interesting because I know
doctors, I know lawyers, I even know a
judge, police officers, there's even a
few a few from Crown Heights police
officers, firefighters, I know less, but
there are guys I know that are on Fidney
as medics. You're the only um Labavich
and you grew up in Crown Heights.
Labavicher um guy that I know ever in my
life that worked for the IRS and I think
it's very intriguing because the
likelihood of I know guys that in my
class are in the American army and the
Israeli army. Never met another IRS guy.
now with your ex IRS. But tell me a
little bit about your upbringing and how
in the world did you end up working for
the IRS for so many years.
>> So before I say that, I was six months
into the IRS and there was a new hiring
group and I see a guy with a beard. I
was a little bit upset because I wanted
to be the only Kabad guy at the time and
I became good friends with him. He now
lives in Israel. His name is Mendy. Uh
so I wasn't the only one. And I have a
my friend's father also worked for the
IRS in a different department.
So what was the question? H
>> your a little bit of your upbringing and
how you landed at the IRS.
>> So I grew up with nine siblings, Crown
Heights, Montgomery Street. I went to
Kabat schools.
And uh after I
after I uh finished high school, I was
like, I got to go to college. I didn't
know what I wanted to do. But I was
like, if I go for social work and I
don't want to be a therapist, screwed.
If I go for something that's very niche,
I'm screwed. So, I was like, accounting,
I can always transfer that. After I went
to school for accounting, a few years
later, I applied for the IRS. I
completely forgot I applied for the IRS.
They called me and they go, "Is this Yra
Astrav?" Like, "Yeah, this is Joy from
the IRS." Like, holy crap. [laughter]
>> By the way, when this joy calls people
and says, "I want to bring some real joy
into your life. I'm calling from the
IRS. How are you doing?"
>> Yeah. Yeah.
>> Her name was Joy.
>> Joy Dellis. She actually was my manager
for years. A sweet lady. Really a sweet
lady.
>> She did bring She did bring him joy.
[laughter]
>> Sweet lady. And uh
>> out of the blue, they call you up years
later.
>> No, it was like uh it was could have
been four months later. Okay.
>> I don't remember cuz I applied for
>> you graduated with a degree in in in
accounting. You applied. You forgot that
you even applied and then you get a call
one day. Okay.
>> Yeah. And like would you like to come in
for an interview and I was like yes and
uh I had the interview and then uh I was
studying for the series 6 and seven. I
really hated it but I needed I needed a
job. I couldn't I was working
>> series 67 for what type of job? That's
dealing with insurance, securities, you
know,
>> banking.
>> Yeah. I hated it. And then I got a call
on the way. I'm walking to the library
to and they're like, "You got the job?"
And like, "Are you do you want it?" I'm
like, "Yeah." Coming from where I was at
that time, getting the IRS job, the way
how I felt is probably like someone
winning a billion dollar account. You
know, I was so happy. I quickly took the
series six stuff and seven stuff, threw
it in the garbage. [laughter]
>> You don't need it to work for the IRS.
>> No. No. And it was uh it was very good
experience working for the IRS. Very
good.
>> What is just off starting salary IRS?
60K
>> that time. It depends depends what
series and grade that time it was 40
something,000
to start.
>> Gotcha. I remember I was single and uh
I'm at a singles party and my friend
some girl asked what do you do and I
said oh I work for the IRS and then my
friend goes he makes 42,000 [laughter]
I was like
[laughter]
>> date ended whatever was like what are
you doing man
>> didn't even have a follow-up he said it
was at an event
Yeah, but you get you get promoted um if
you work hard and smart. Uh that you go
up relatively quick compared to other
>> you get commission depending on how
[laughter]
how hard you audit somebody. No
commission.
>> You get bonuses if you catch big fish.
>> No.
>> No, you don't get recognized.
>> Do that cuz it's illegal. And if
somebody offers me a a bribe,
>> you was wondering how you got that Ublau
watch. I was I'm I was assuming one of
the people you ordered gave you as a
gift. That's what it was about.
>> He declared he declared it on his
return. [laughter]
>> It's fake. It's fake.
>> Got in the street on 42nd Street.
[laughter]
40 seconds.
>> So, you get this job. Now, I'm guessing
whatever you study in college doesn't
prep you for being an IRS auditor.
>> No.
>> So, they tell you that you're hired for
the IRS. They give you your assignment
right away or like what your division is
going to be.
>> They put you on training. You go away
for a month. Classroom training.
>> Where's that?
>> Every time it's somewhere else, but
Covington, Kentucky. Wow. Near
Cincinnati.
>> Yeah. Yeah.
>> Cross across the river.
>> Is it like the military do big
background checks? Like
>> they do a background check on you, too.
They came knocking on my neighbor's
door, asking questions about me.
>> Yeah. Yeah. Yeah. They came knocking.
>> Yeah. This is right block knocked on the
door. [laughter]
>> They had some great war stories of you
uh visiting businesses. The IRS.
>> Wait a second. You got a sign. So they
hired you, sent you for a month training
to just a general idea of what to teach
you how to use an IRA.
>> They started No, no. That you learn
relatively quick, but month train 1040
schedule C training. That's simple uh
self-employment.
>> People that work for themselves, small
business owners,
>> small business owners
>> have to do a what is it called? A 10,
>> they do a schedule C usually.
>> What's a schedule C? It's a it's a
>> it's on the tax return, right?
>> That's self-employment. So imagine
you're a barber.
You make, you don't get a W2. You make
38,000, right?
>> You put it on schedule C, gross
receipts, line one. Then you put your
expenses on there as well, the
materials, and minus all the expenses.
>> We're talking about a guy that has a
barber shop in his basement. He didn't
file. He didn't open up a corporation.
He didn't open up a an LLC. He didn't
open up an S.
>> You don't need to open that up.
>> You don't have to. So, if you if you're
saying a lot of people just they do uh
three haircuts a day at $34. They t
calculate it. They have to tell the IRS
how much money they made, what was an
expense, and then just have to send in a
yearly thing on how much money they
made.
>> Hold on. Speaking of the barber, I don't
think it's one.
>> He doesn't need a barber. [laughter]
>> How long you don't need a barber for?
>> I need a barber for the beard.
>> Oh, you have to you have to pay tax on
how much it would have costed you to
have a barber. [laughter]
IRS still needs to get their cut. You
know, they're cut their will cut.
[laughter]
I heard in Israel there was a story
because I heard their IRS is has doesn't
have a good name either. They went into
a shawarma store and they were counting
all of the cut up parts of the pita
bread to see how much they sold how much
they sold and to confirm it with the
amount that they're saying they sold.
>> But it does have a military tough look.
You know,
>> if this guy knocked on my door from the
IRS, [laughter]
I would run from my one. Usually people
were very uh were uh were not
>> when you go to show up to business
>> people were what? People were not afraid
of me.
>> When you show up, you show up with guns
like here in IRS.
>> That's a special agent.
>> So you don't you didn't never show up at
all with guns drawn. Let me check your
books. So you just knock on the door un
unannounced.
>> Send a letter. You send a letter.
>> You send a letter. Oh, so they know
you're coming.
>> Yeah.
>> You're not unannounced with guns drawn.
>> When they get the letter, they hard the
schwarma rapper. [laughter] They hard
the pizzas
>> and they know when you're coming. It's
scheduled. Usually they get a if it if
it's an audit, they get a letter, they
have to call the revenue agents at at a
certain time. Maybe the re if the person
doesn't call the revenue agent.
>> Uh maybe they'll try a few more things.
Then the revenue agent may go to their
house or place of business to knock on
their door saying you didn't respond to
our letter. Here's they give them some
documentation and call.
>> You used to do that. I used to show
people's houses.
>> Yeah.
>> Were you afraid?
>> No.
>> Never. I mean there might have been if I
felt uncomfortable I wouldn't do it but
usually it's you just put something in a
mailbox if they don't answer.
>> So you're never afraid to walk in the
business as IRS agent.
>> You ever thought your safety was
>> compromised?
>> No. Never.
>> I felt uncomfortable but never uh
>> I mean no one no one's like oh the IRS
oh we'd love to have you here.
>> Usually when you go
>> they want you some coffee. You probably
>> usually when they're being audited
people are so excited to talk about
their business.
>> Interesting. They're so excited and I'm
asking open-ended questions. Think about
it this way. Most people like to talk
about themselves. Right or wrong?
>> Me do. But
>> even if it's the IRS,
>> Wow.
>> and they're sitting there and you're
asking open-ended questions.
Most people
want to talk about their business.
They're excited.
You know, a lot of people have hire
representatives and tell them to shut
their mouth.
You know,
>> I think people get in trouble for
talking too much to the IRS visit.
>> Sometimes you don't want to give off too
much information. In anything, any
business, you just want to talk about
the facts. You don't want things to go
get off course, you know.
>> And if you come to business and they
don't want to talk to you, what do you
do? What was like the procedures?
>> Usually they talk or they have a
representative.
>> Then you you can summon bank accounts.
Uh
>> you come to place and they just say,
"I'm pleading the fifth. I don't talk to
you." Like you have those responses
>> in those situations. They everything
gets summoned. You summon the bank
account. It's not a pleasant experience.
>> Oh, so they rather talk to you.
>> Yeah.
>> Start the conversation.
>> You rather
>> you find out where they're making issues
and you bill them and then if they pay
then
>> Well, if they're not, you you uh go a
lot of times they
>> summons the bank accounts. They'll
create their own bank deposit analysis
which is the revenue agent's going to
add up all the gross receipts uh
negative take out all the transfers if
if if there is and then it goes oh here
you have unreported income they're not
responding and so they create a uh uh
the IRS will sometimes do that.
>> So if IRS shows up
>> you suggest people to talk to the IRS or
just you know hire a lawyer and just zip
up. What do you recommend? You you speak
to a professional before you you speak
you
>> if if you own a business and someone
like you showed up to audit them.
>> Yeah.
>> Would you tell them would you tell
yourself to talk to the IRS?
>> I heard the question.
>> Okay.
>> So, not everyone has money to pay for a
representative,
right? Then the smartest thing to do
would be to call people.
I don't know if you go to synagogue, go
speak to the main rabbi. I'm being
audited. Could Can I need some guidance?
uh if you if you can't pay for a
representative, so you don't put your
foot in your mouth and it's a very scary
process. You want support going through
something like this. If someone were be
were to go through anything scary in
life, a divorce, a bankruptcy, you don't
want to sit by yourself and think figure
it out on your own. You want to talk to
people. There are plenty of people out
there that will it would be their
pleasure to guide you or help you if
>> or call you. They could also call you if
they have an audit, right? Who called
me?
>> You deal with audits?
>> Yeah, currently.
>> Oh, now yeah. Or call someone like me.
>> Now your business is when somebody gets
audited, you walk them through the
process that when an IRS knocks on for
the appointment, you're sitting there
representing them.
>> Like, oh, John, how's it going? We
haven't seen each other. You have those
relationships, right?
>> I keep the I have a lot of relationships
at the IRS that I still keep and a lot
of connections there. But yes, I help
people that are being audited. I also
help people that are going through the
appeals process. And I also help people
that have a big bill from the IRS and
their account is being levied and it's a
very scary thing.
>> You can negotiate, right? You can
negotiate with them.
>> There's ways of
putting in offers to the IRS called
offer and compromise certain installment
agreements that could work in the uh tax
where the taxpayer can pay much less.
>> How common is it for former IRS people
to open their own business? Is it a
common or uncommon practice? Well, let's
ask the question this way. How common it
is for people to open their own
business, period. [laughter] It's a very
small percentage. Uh I know I have a few
former co-work in particular, she has
her own tax resolution business,
>> but it's not so common. No.
>> What's the craziest story you had or I'm
sure you have a lot of them. Did it for
17 years. What was the craziest story
you walked in some business? Can you
tell us share some funny stories?
>> I have so many stories that like I don't
know where to start. tell us a crazy
story that like you like you walked
around shaking or laughing for days like
somebody made an expense sheet that like
made no how you caught them like lying
or something crazy.
>> So uh so the way how it works when if
you have a business and you're getting
audited the revenue agent does something
called a tour of business. So they'll
walk in the business and they basically
want to see when a customer comes
to when the customer leaves how does
that transaction enter the books. So I
did a bad
>> So you come in as a as a spy kind of.
>> No, no. They know I'm coming there.
>> Are you allowed to go to the store
without the let them know you're there
and stay?
>> No. No.
>> Wouldn't it be better that you walk in
on a Monday afternoon pretending you're
a customer and see what really goes on?
You're not allowed to do that.
>> Uh I'm not so sure.
>> But you didn't do that.
>> No. No.
>> It was always scheduled.
>> Maybe I if the someone didn't respond to
a letter. Uh that's to me that to me
that sounds like a little bit like
harassment.
>> Okay.
>> Uh no. I never did that.
>> Okay. So, you show up to a bedga.
>> No. What's the story?
>> They're saying a story.
>> I said I showed up to a bed.
>> Where was it? In Brooklyn.
>> I don't remember.
>> Okay.
>> And
I'm like, can I see your books and
records? Like, how does Basically, I ask
him the question, how do you keep how do
you know how much money you make at the
end of the day? By the way, every
business has something that's telling
them how how much money they're making
each day or month or week. And the guy's
like, I don't know.
And I'm like I point to the cash
register. He's not there. And I go, "How
do you know that that guy is not
stealing your money?"
And he goes, "Oh." And then he was
showed me the uh that usually people
that have cash registers in like bedas
or near gas stations, they write at the
end of the day how much money came in
cash, how much money came in credit
card.
>> They keep records.
>> They keep records. But that's not the
funniest story. It's just that was like
a uh one of them. I've been through a
lot.
>> Can you tell us some good ones?
>> I can tell you some sad ones.
>> I love the sad
>> ones.
>> The sad the cases I did not like working
the most at the IRS was the offshore
activity ones. Now imagine someone's
grandfather has an account, a Lud
account in Israel. Doesn't even have to
be Jewish. It can be an account on uh an
account offshore and they're older
already. They don't remember or they
don't know. Technically, you're supposed
to report all offshore activity.
>> Just to be clear, if I have an account
in Dominican Republic with $2 million
US,
>> I'm supposed to let the IRS occasionally
know that I have $2 million sitting in
Dominican every year.
>> Yeah.
>> And and also and let them know what's
going on over there. Is it sitting there
just collecting interest or not
collecting or if I'm investing in it?
They should know what's going on. They
should know that where your the foreign
assets that you
>> so an American all 300
>> tax is it tax foreign
>> it has to be I'm not 100% sure I don't
remember fully but it is no it has to be
reported
>> basically if every one of the 340
million American citizens when they file
their tax returns every year they have
to let them the government know the IRS
know how much money they have in foreign
accounts
>> correct
>> I don't have this problem that I I don't
have any money in any I barely have any
money in American accounts so but I'm
just saying but just interesting my my
audience should know that this has to be
reported yearly
>> this has to reported
>> and if let's say for 20 years you never
reported it and now you want to like
snitch on yourself to
>> what happened was a lot of these
accounts they called whistleblowers they
let the the United States know that
there's a bunch of US citizens that have
money in X Y and Z account so the IRS
came and said we're giving you a certain
time to if you disclose that you uh make
this that you have this money we will
penalize you much less and it's called
voluntary disclosure not everybody
uh took advantage the voluntary
disclosure because they didn't know.
Imagine you have a grandfather that has
an account in a different country. They
passed away. You don't know about it or
and now the living children now get a
letter from the IRS saying there's
there's this account offshore and the
penalties were a lot.
>> Like how much? A $10 million account
they could get penalized how much?
>> Big number big money.
>> Hundreds of thousands. I don't remember
exactly. Even though they never, it
wasn't their fault. It was their
grandfather's fault.
>> They did it. No. Yeah.
>> So, you said the sets or this is a set.
>> Poor families.
>> Poor families with $10 million accounts.
Sometimes it's not 10 million. Sometimes
it's uh it's a million or a hundred
thousand or whatever. It's still a uh
>> And they became the liable became
they're on the hook.
>> They're on the hook.
Yeah. So, what do you advise somebody
that's grandfather dies, leaves them $2
million in the Cayman Islands, and they
want to do a voluntary disclosure? They
should
>> right now voluntary disclosure is over.
But you always when it comes to taxes
and you talking that that big money, you
want to be talking to CPAs, accountants
that know what they're doing.
>> It's not going away and you got to work
on it.
>> Yeah.
>> Which industries get the most audited?
>> I don't know.
A lot of small businesses get audited.
>> A lot.
>> Do you guys in the IRS office, every
time you get someone, you all like
high-fiving each other? Oh, he just got
this guy. You try to rip off 10. Like,
what's the environment in the office?
They're all high-fiving each other.
>> No. No. Most people are
>> What's the energy in the room there?
>> They're doing their job. You know, they
want to close the cases. You know,
>> they want to finish them.
>> They want to close the cases.
>> When you say, "Oh, I just got this guy.
He's whipped us off $20 million." They
they don't look at it that way. They're
looking they look at it as almost like
someone at the IRS has inventory. They
have a bunch of cases.
>> They want to close their cases because
they want their manager off their back.
>> What are some of what are some of the
biggest because I want to educate the
audience. What are the biggest mistakes
that small business owners are making?
Easy, simple mistakes that if they're
watching the show right now, they could
start making little habits to change
some mistakes they're going to make to
help them with the IRS. Maybe five even.
As many as you could think of.
>> Keep your records.
bad, inadequate recordkeeping, literally
hire a bookkeeping company if you can't
do it yourself. But being able to
understand how to read a general ledger,
a P&L, these things are not small
things. Uh, you have to be able to look
at the P&L, the general ledger, and
understand it without getting your
accountant to explain it to you. And a
lot of times people are like, "Here's
the shoe box. Let my accountant deal
with it." You got to understand what's
on your return.
>> So, you should probably know if you're
making money, it's a good idea.
>> Yeah. Even if you're not making money,
it's a good idea. No,
>> I'm saying it's good to know if your
business makes money.
>> Yeah. Yeah. You're saying even a small
business owner should hire a bookkeeper,
had a profit on Wall Street, have all
their invoices, everything should be in
order,
>> especially if they're not bookkeeping
style like like me. Like I I as poor or
rich as I ever was, I always
>> found a bookkeeper to run cuz it's just
I'm the worst at it. But it's not just
hiring a bookkeeper. It's hiring a
bookkeeper
or an accountant that can teach you how
to read the statements and teach you how
to read the general ledger, the P&L, the
balance sheet, you know,
>> what was the most arrogant
>> a bookkeeper knowing how to learn how to
read your profit on lo sheet. Yeah.
Keeping receipts, not just dumping
things into shoe boxes. Correct. What
what three
>> other mistakes that small business
owners are making?
or things they could do to make life
easier for themselves.
>> What What was the most arrogant thing
someone told you while that you're doing
audit?
>> Well, I had a uh a lawyer who was
representing their client and I asked a
question and the lawyer started
screaming at me saying how smart his son
is. [laughter]
My son is smarter than you and
that it didn't do well for him.
>> I I don't remember. I [laughter] don't
remember. Uh to to be honest, I a lot of
times I understood representatives,
taxpayers, it's very scary. Imagine you
prepared the tax return and here comes
someone from the IRS
and this same tax preparer or
representative tells their client, "I'm
going to be able to get you out of
this." [laughter] And then they're not
able to get it for whatever reason.
Maybe they misunderstood
>> and now they're going to be getting they
have to go they have to go to their
client and say I couldn't do I couldn't
I couldn't succeed. I had a CPA doing my
wife and I's accounting every year
>> and one year in middle of the year my
wife's company that she worked for they
changed their payroll company. So when
they sent her the the taxpayer what's it
called? The W2.
>> Yeah.
>> So she got the W2 I got my W2. We did
all the expenses. Any other businesses
we did we gave it to him. He filed. He
took his fee. We sent it in. We got a
state and federal returns and then a few
months later we get a few thousand bill
from the IRS because the payroll company
that changed in the middle of the year
didn't send us that W2 and the IRS right
away picked up on it based on the social
or whatever and they sent us let's say a
$7,000 $8,000 bill plus and I remember
it being high tax penalty and like 89
10% whatever and this is a very
competent CPA and he was not in he like
he's like yeah I didn't have that paper
I said what should I do he says YOU
SHOULD PAY THE BILL QUICKLY
like just pay the bill and move on. Like
the IRS is asking for money. Just shove
it shove it at them. So that guy got
arrogant, but really he should have just
sat down, figured it out, and came to a
number. You're not going to win. I'm
saying.
>> Yeah.
>> Have you ever seen someone completely
ruin their life from taxes problems?
>> Uh so one of the reasons why I do what I
do, why I left the IRS is because I see
what it does to the average person.
you're getting audited, you now owe a
lot of money. And sometimes these things
are open, could be open for two, three
years if you don't have adequate good
representation. And I've seen good
representation and I've seen not so good
represent people not representing their
clients properly. And I see what it does
to a lot of people, what it does to
their lives. Can imagine it ruins their
marriage. You can imagine if you're a
parent, the anxiety that the kids are
living with. So, it's it's a very
stressful. I believe most people that
get audited, whether they're aware or
not aware or they're with the IRS,
they're being affected negatively. And
that's why I do what I do. That's why I
left the IRS because I believe I can do
it much quicker than the average
representative and get better results.
And the main thing is the client, the
taxpayer to get on with their life.
>> Is IRS political?
>> Not within
the uh not with the regular people
working there. The people that are in
Washington DC, you can make a case they
are.
>> And how does that play out?
>> Well, the pe I wouldn't use the word
political. They have agendas.
They'll come out of nowhere and say,
"All right, we're now going to be
auditing
companies that are in their final year."
You're able to put final year on your uh
if you're a business.
>> What does that mean, final year?
>> If you know it's your final year, you
you have to disclose that it's your
final year.
>> Oh, I don't know. There's a lot of tax
companies going out of business after 53
years. Let's say Macy's decides to
close,
>> they have to write down that it's their
final year
>> within the B within the Yeah, there's
certain tax. Yeah,
>> private. I don't want anybody to know.
certain things that have have to happen
with their assets that certain things
get taxed on their balance sheet
>> and uh but I'm just giving that as an
example. So they'll say we're auditing
these returns. So out of nowhere you
have a big case load and the people that
are work that are from the top now say
we have to work these cases and it goes
down to the manager and then it goes
down to the employees and now we're told
after we were told them uh 3 months
before to work partnership returns and
to work shareholders. Now we have to add
this as well. So there's a lot of
bureaucracy. So I call I call it more
more bureaucracy than I would call
political.
>> Most people are not
>> political in that aspect.
>> How aggressive are they would you say
from when you started until you left?
>> What do you mean by aggressive?
>> Like chasing, hunting, witch hunting?
>> Well CI, which is criminal
investigations, which I didn't work for,
is aggressive.
uh they're aggressive in the sense if
you're audited to follow the laws or to
follow the procedures in that if you're
getting audited, you're getting a bank
deposit analysis. If you have a
business, you're going to be looking at
your bank account. So, if you say
aggressive in that aspect, it's
aggressive. And if you're
putting in an appeal or going in a tax
petition, they're aggressive in this in
keeping the tax law or the uh the tax
law, the court law. I'm getting confused
right now. There's tax law, case law,
you know, and then there's uh the tax
law.
>> Didn't Trump fire a bunch of IRS agents?
>> Was it recent? A year ago?
>> That was about a little over a year ago.
Not too many got fired. A lot retired.
>> Oh, you like he encouraged retirement.
>> Yeah, a lot of people left.
>> Does that mean it's a better time to
commit fraud or
>> No.
>> What does it mean practically?
>> Well, software take over a lot.
>> It's never a good time to commit fraud
because if you commit fraud
and you get caught, it's not pleasant.
uh even in that even if you don't get
caught, even if you're audited for for
potential fraud and you did nothing
wrong, it's not pleasant. Let me just
say this because I know that question
was a joke in a way, but when it comes
to taxes and it comes to money and it
comes to business, it's really not worth
it. Do things kosher, do things legal. I
want to say a story. I had a friend that
came to me when I first was working at
the IRS. He's like, "Israel,
if I just add these expenses on my
return, I'll get back more money. What
do you think?"
You know, and I said, "What I think is
you'll put in more expenses, you'll get
a bigger refund 3 years from now after
you bought the TV or after you pay for
your kids tuition,
you'll get audited.
And not just will you pay the money that
you have to pay back, you'll also pay
interest and penalties. let alone the
stress of not being honest and the
stress of being audited and what that
does to somebody. It's literally it's
like having a clean room. You have a
clean room, you're more at peace. You
want to be ethical.
>> What happens internally if an agent
messes up? Like is there what the
repercussions?
>> Depends what you mean by messing up.
If let's say you audit somebody and you
at when you finish doing the audit, you
sign off on it and say he owed let's say
$12,000
>> and we did this in this balance sheet
and he paid $11,000. The at some point
the case is closed, right?
>> Mhm.
>> Now that guy now goes to sleep at night.
He's starting fresh. The IRS cleared
him. He gets like a letter that he's
pardoned like jury duty. You get a
letter of release. You're done. You come
back to your office. You file the case
and your supervisor in the IRS says, "By
the way, you made a major mess up. This
guy owes another $22,000. Could you
reopen the case and say, "Hey, we want
to now get 22 grand." Or because you
already said, "Oh, you're off the hook
and you made a mistake internally with
the paperwork."
>> So, it all go when it comes to something
like that. Let's say I audited somebody
or [clears throat]
there was an appeals case and let's say
I made a mistake. By the way, I've
worked
uh thousands of cases. I don't think I
made one mistake.
>> Wow.
>> By the way, when I say that, there's I'm
just saying
>> statistically we make mistakes. We're
human beings. Okay. You don't.
>> But I don't.
>> I'm not human, man. [laughter]
Uh, but
what happens is as soon the manager has
to sign off on the case, the manager
notices that Israel forgot something or
made an error, she or he will give the
case back to me or back to the agent to
now go back to the taxpayer and say,
"I'm sorry, I made a mistake."
>> Oh, so you it's not it's not it's not
forgiven because you made a mistake. you
make a mistake, you have to go back to
the customer and say, "We made a
mistake. There's more money owed."
>> Well, what happens is is first thing
first, whenever I were to do an audit, I
always would let them know subject to
manager review. And a manager can look
at it, look at a case, and just can just
say, "hm, you didn't look at this issue.
I feel like you should have looked at
this issue. Go back to the taxpayer."
Uh, and then I I'd have to listen to my
supervisor. But that doesn't mean I made
a mistake. It's just part of she's doing
her checks and balances.
And yeah,
>> so far the thing that I'm the most
intrigued about, which is so simple, but
I didn't realize, is that let's say you
could do a maximum amount of deductions
for certain things, people write the
zero amount. So if it's 10,000, they
write exactly$10,000,
>> which flags, because usually when you
pay up your 12-month expenses on your
car or truck, the bill might come out to
be $9,326.14,
just the way the numbers are. So you
right away know the guy's just playing
games and seeing what the maximum amount
is and doing that. So that subjects to
an audit. What other things that a small
business um account does that will
trigger major alarms besides the numbers
all being the maximum?
>> How do you lower how do you you lower
your audit risk?
>> Yeah. What other things are very popular
that cause alarms?
>> Well, we let me just go back to the
round numbers. Sometimes the person's
not doing anything wrong. they lost
their records and they're just
estimating expenses and that's what
they're doing. It's not always that the
person is trying to do something wrong.
They just don't have their record so
they put round numbers. Uh
so when it comes to a lot of other
things, income is a big one. You want to
make sure that you account for all
income. Uh you want to make sure you
account for it all. Uh another thing
when it comes to the balance sheet
there's a lot of times there's something
called loans from shareholders a lot or
loans to shareholders. So a lot of times
within these loans there can be a mixup
that there's loans to the shareholder
which is the partner or the business
owner and sometimes they're taking those
lo those loans and they're not paying
the loans back and
>> and loans are taxree so it would be
right. Well, they have to pay it back,
you know?
>> Right. But theoretically, a loan is not
>> income. Yeah. Yeah. You know, imagine
you start your own business. You're
putting your own money into your
business. So, it's loans to
shareholders. Then there's also loans
from shareholders.
>> I mean, how crazy are people supposed to
be? Let's talk the letter of the law. A
guy got for a bar mitzvah gift from his
uncle. His uncle Rob Robert gave him
five uh silver dollars for his bar
mitzvah gift. He gave him five silver
dollars. At the time, silver was a 123
an ounce. and silver hits $130. He takes
the five silver coins, runs to the
diamond district last week. Now it's
back to like 70. But he runs and they
take whatever bullion, whatever the
number is. They round it off. I heard
they're paying a lot less now to
refineries backed up. They give him
$9825
an ounce. So he gets $500. The guy takes
out from the register $500. Gives him
$500. He just made $500 because he got
it when it was worth zero. He's supposed
to fill out a form in his tax return
that says, "I got $500 se on um on
November 16th. I got $500 and then he's
supposed to declare it and see what the
tax rate is and pay the full tax. That's
the letter of the law. Correct.
>> So, it's not a simple it's not an easy
thing for me to answer cuz I would
imagine there are certain laws and rules
regarding what's like the silver store.
What's it called?
>> Bullion.
>> These places that they themselves have
to fill out a form. Not
>> ask for ID and fill out a form
>> if it's a certain amount of money. I'm
sure it's similar to casinos. You make a
certain amount of you coming in. If it's
more than 10,000, I don't know what the
law is. They have to give you a form and
then you have to file that on your tax
return. So, I'm sure it's pretty similar
to that as well. So, when it comes to
something like that, technically
technically you're supposed to report
that as income, right? But if you didn't
get anything from the place that gives
you the money, and I'm like, I'm not
familiar with the laws, but I'm pretty
sure they have to fill out something if
it's more than 500 or more than 5,000.
I'm sure there's some listeners know
this. I don't. Uh, but the IRS will know
in that case. You ever go to the horse
the horse betting, horse racing, if
people a lot of times they the horse
wins, they win a lot of money and then
they give them a paper showing them the
$5,000 or 10,000 that they won and now
they have to report that.
>> You familiar with the cash appela rules
now or no?
>> No.
>> Okay. I know they changed it recently to
lower the higher. If someone knows,
please comment below. Somebody told me
that if you It used to be that if you
gave somebody over I think500 $600, you
had to fill out a form that you gave
them like it was at the 109. It was a
10. You have to fill out
>> Trump change it.
>> I I I recently Googled it for somebody.
I think it went up to I think 2026 I
think it's going to like $2,100. You
have to report I think over $2,100 and
it would make no difference. Whatever
the minimal reporting is, no matter how
it is, cash, zel, cash app, you if you
the law is you have to give somebody a
certain amount, then you have to f you
have to have them fill out the W2 or
whatever the paperwork is, you have to
fill it out because it's subject that
that would be the law would be subject
to um reporting.
>> What is it 500 now? What's the
>> I think it's going up in 2026 to like
$2,000 or something.
>> Do religious communities tend to be more
uh tax compliant or less less compliant?
I wouldn't have the statistics on that,
but a lot of times within the religious
community, a lot of times they're
flagged because they make X, Y, and Z.
They have five to seven kids. And a lot
of times that by itself is like, how are
you living? So the computers sometimes
pick that up as there has to be more
income here. So that happens
often that but that's nobody going after
anybody. to computers.
>> What are some of the task risks about
cash heavy businesses
like jewelry or I don't know barber shop
or
>> barber [clears throat] shop to jewelry.
>> Yeah, the old cash, right?
>> Well, these days most people are
accepting credit card,
>> right?
>> Uh
that's what I would say.
>> There's a famous store that doesn't
accept any a famous food establishment
in Brooklyn. And I don't want to get any
more specific. Till today, till today,
the only thing they will take is cash.
>> Okay.
>> So annoying. Like you have to double
park and run to an ATM machine and it's
like whatever.
>> And I always wonder like if they're
doing it to try to save money on taxes.
If I work for the IRS, that's the first
store I would audit. Why would somebody
only take cash? It makes no sense to me.
>> Well, they don't want to pay the fees.
>> What fees?
>> Credit cards charge 3 4%.
>> So charge a lot of stores charge the 3%.
I think I'm not sure legal out of
charge.
>> Everybody does. It's 100% legal.
Everybody charges comment below if it's
legal or not.
>> Everybody charges the 3% fee.
>> So if you're a cash,
>> but let me answer that question
[laughter] cuz that's a good one. A lot
of times there are people that own their
business. They're 70, 80 years old. They
don't want to accept the credit card
machines. They're annoyed by it and they
say just cash. You
>> just go tap today. It's easy. Also, when
it comes to industries that with cash,
the IRS, the government has the the
statistics on what the income should be.
If, for instance, if you're a a food
store,
>> there the odds are you're making income
of 0. When I say food store, restaurant,
one of the toughest business to make
money in, the statistics show you're not
making too much money. Uh but there are
certain businesses
the gross receipts the money coming into
cost of goods sold is a certain
percentage. The materials cost of goods
sold are the materials that are for the
goods. And if the cost of goods sold is
very high and the income is very low
that would trigger something that would
trigger an audit that would trigger a
question mark. And from there they would
uh they could go after them.
>> CL you wanted to talk to about sponsors.
Oh, of course. The most favorite
favorite fa the most favorite part of
our show.
>> We have some breaking news today. We
have two top corporate sponsors that are
joining the Clappy and Frank show as
advertising sponsors.
>> The first one is A1 Party Rentals. It's
a top top top party rental company. So
if we want to look as good as
>> when you put into when you put into
Google corporate sponsored parties,
table rentals, chairs, high-end, I mean
they build a they build buildings like
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>> A1 A1 [clears throat]
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>> And the legendary
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>> Here we go.
>> Chocolates. The Reb, the Reb used to eat
swirling chocolate. Everybody know.
Yeah. Yeah. The rebre the reb.
[laughter]
>> Now, the minor chocolate. What I love
about the minor chocolates, everybody's
eating this. It's not only minors. The
adults love the minor chocolates. The
minor chocolates
>> small
>> are great for the shalah. Also, when
your three-year-old says he wants a
chocolate bar, you don't want him eating
an entire chocolate bar. Portion
control. Portion control.
>> Over here, you get the entire bar in one
serving. Delicious. Delicious chocolate.
Troy, I want you to taste this
chocolate. And I'm going to have to
you're going to have to report income on
$1.79 [laughter]
>> that you were gifted on the Clappy F
show.
>> I grew up with these chocolates.
>> Oh, there you go.
>> Can never get bored of these chocolates.
Oh my god.
>> Clappy assh.
>> I'm as newly minted gym rats. Portion
control. You don't eat the whole bar.
>> Portion control.
>> It's only 130 calories.
>> Perfect for
>> Oh, these go perfect in shakmanes. So a
lot of people that give their friends a
shakman it's like a negleis or a shabas
or a head or whatever
>> but you still need to do the mitzvah. So
you do is you buy a minor, two of them,
you tape it to the box together with a
hamage and you have the two mitzvah of
these minors come in so handy,
sneak them into your jackets while
you're [laughter]
easy enough. It's very good. The minor
chocolates, they're known the smurlings.
Is this one kosh?
>> I think they're always
>> all year round.
>> Whatever's left over from you.
>> Yes.
>> And the rebabing
chocolate. So, you don't get it better
than that. Then we got
>> Butcher,
>> the CH Butcher restaurant on Troy and
their deli on Albany Avenue in Brooklyn.
Now, they all have a full line of meat
product takeouts where all quality
frozen foods are sold. Here we have the
Laim.
>> Last week, we tipped the parking lot
agent, the empanady. He was so happy.
>> He loved it. He loved it.
>> He was happier than he got cash. I was
like I was like I felt I felt bad no
cash on me, you you know, I want to make
sure I'm all legal, so I never carry
cash. And we were felt bad, you know. I
said, "Oh, here's a little impanada from
the show." He's like, "What? Beef?
Really? Is there beef in here?" He's
like, "Yeah, there's beef in [laughter]
here." Rascins classic tuna. Their
classic tuna I buy for Shabas because
Sunday morning we have it with bagels.
My wife goes shopping at Rascins every
Friday. We have the alapino schmaltz
herring today.
>> Jalapo.
>> Jalapo. We have the Danish style herring
and cream sauce. And we brought the
schmaltzy salmon. The schmaltzy salmon
with the onions. M and then the only
place in the world that makes a herring
kickle exclusively to eat with herring
is rasins.
This was not gifted. I paid for
everything. I don't want to get audited.
[laughter]
>> I got a lot of comments last week the
>> comments like this.
>> What said I would get a lot of auditing
comments like this.
>> You said you're not a big herring guy,
but I want you to give you Israel. I
want you to taste the tuna. M I can see
the scallions. M
>> Israel, I know you you you married
Syrian. Have your taste buds changed
since you married into the
>> Oh, definitely delicious food.
>> Yeah.
>> Delicious food.
>> Kubet, what what's the Syrians eat?
>> K.
They eat a lot of lamb.
>> A lot of lamb.
>> Yeah. Yeah.
>> What's the biggest difference between
Syrians and Kabad people? Top three.
>> You went top three. top three different
like major like eye openers like huh
>> truly you're the second person in your
family to marry Syrian your sister
Shashana also married David cameo David
cameo when he coming on the show tell us
about the rich Syrians
[laughter]
>> I think they're it's different different
like kabad is more lively
>> Syrians are more analytical
>> you know but uh
>> oh my god
>> we're analytical
What? You have a dial in your mind?
>> That's all right.
>> But they're all good. They're good
people. I mean, good people are
everywhere. It's like,
>> do you have to drive Mercedes to be a
luxury car to be Syrian or is it
mandatory or
>> Well,
>> they let you in chill without it. What's
the deal?
>> No, don't let you went to show without a
fancy car.
>> I have a Nissan Central.
>> You have A NISSAN CENTRAL.
>> OH MY GOD. [laughter]
>> YOU ALWAYS HAD IT.
>> WHEELS TO LEASE. MY FRIEND SAUL IS FROM
WHEELS TO LEASE. CORPORATE SPONSOR.
>> NISSAN SENTRA. WHAT DID he write? Nissan
Sentra.
>> We just got off the phone on the way to
the show with Saul. He said, "Last week,
I said for 200 bucks you could get into
a Nissan Sentra
>> a month."
>> A month. Now he tells me, Izzy, you
could tell your customers at wheels to
lease a Nissan Sentra under 200 a month.
>> Wow.
>> Under 200 a month.
>> When are they going to pay you to drive
a Nissan? That's That's
>> The pricing is so crazy. It's the only
thing affordable. IT'S THE ONLY THING
THAT WENT down in price when Donnie got
out of office. [laughter]
The Nissan Sentra. The roads the roads
are not shoveled. BUT IF YOU HAVE A
PLACE TO PUT A CAR, you could have a
Sentra.
>> You recommend Nissan Sentra in the snow.
[laughter]
>> I don't know. I'm used to going in
Escalades lately. But um Nissan Central.
And I asked him what other good deals.
He says that the Honda
>> Odyssey
>> Odyssey is the cheapest he's seen in
years. And this is what he told me.
Don't wait till Pesak comes and your car
is so dirty and you want to get rid of
it. Instead of cleaning your car for
Pesak, get a new car for Pesak.
And by the way, when you call Wheels to
Lease, you call Soul or Izzy, the car is
in your driveway within a few hours.
There's no waiting around.
>> Some people tell me that they only want
a car just for the summer. Do you think
they should rent or they just have a car
all year round? I
>> think for 200 bucks a month, just keep
it around whenever you have an extra
car,
>> right? Where you going to park it?
>> Wheels to the only way. It's the only
way to go is wheels to lease. Anyhow,
so you're saying keep a clean good keep
a clean book. Let me ask you a question,
Izzy. When the IRS comes after you at
the end of the day, are they looking to
throw you in jail or they're just
looking for you to pay your bill and
move on with life? No, they're not
looking to throw you in jail. Only if
you don't report income, a lot of
income. Um because uh jail is criminal
investigation.
They usually only go after people in
terms of jail wise that didn't report. I
don't know what the amount is, but
>> it's in the millions
>> probably.
>> A guy making $200,000 a year. He sends
in his tax return every year. He's off
by a few thousand. He gets audited.
You're saying get a preparer, sit down
at the table, pay a few thousand bucks,
move on with life. They're not arresting
you. They're not putting you in jail.
Just Just
>> It depends.
>> Do Chuva. You're saying you could
>> Are there times where you cross a
certain line even if it's a small amount
and that's where they go criminal on you
or
>> No, it has to be a lot and it has to you
have to show intent to
>> to not report.
>> Nobody ever has intent but not pay tax.
>> So you have to prove you didn't have the
intent and a lot of times you can prove
it.
>> Yeah.
>> What are common mistakes people make
about deducting for charitable
donations?
that it's sometimes it's not a
charitable organization that they're
donating the money to.
>> It's not a 501c3. Is that that what it's
called? It's a
>> and they give money to an organization
that is not a charitable organization
and they can't deduct that. Sometimes
people go, I gave I gave my uh
>> my friend to go who's who's struggling
financially, I gave them money. You
can't deduct that. has to be a
charitable organization.
>> You should give the money to a 501c3 to
then give it to that guy.
>> That would be a better idea. No,
>> if you can. Yeah.
>> Have you seen uh non forprofits abusing
their status?
>> I've seen that. But I didn't do non
forprofits, but I've seen it. I've seen
uh I've seen that. Yeah.
>> What are common mistakes um
landlords make with taxes?
Can you be specific?
>> They they pay they have three tenants in
their house, a basement, a first floor,
a second floor, and they just live on
the top floor. They charge all their
tenants two grand a month. They're
bringing in six grand a month. So, what
does that tend to be? Like 80 grand a
year in taxes. What's the proper way for
them to report the 80 grand? And what's
the not proper way for them to report
the 80 grand?
>> So, I have [snorts] a challenge. I
started eating this stuff and now the
food's in my mouth. [laughter]
>> Okay. So, when it comes to rental
properties, that could be very, very
gray. and you're saying a little area a
lot of times with rental properties it
can get very complex the tax law and
that that there you would want to get
real advice on what you should do and
how to report. So when it comes to like
a simple landlord, maybe they they don't
or simple property owner, maybe they're
not depreciated depreciating their
property properly.
And uh I've seen cases where they charge
less if you're not charging you you
can't you you have to charge fair market
value. If rent goes for $3,000 in Crown
Heights for a onebedroom and you're
charging $1,500 cuz it's your cousin or
nephew, you can't then deduct a loss.
>> You're not allowed to deduct a loss. It
has to be fair market value. There's a
lot of laws regarding rental property if
if no one's living in it. And it's very
important to know what you're doing.
Here again, we want to go know what
you're doing. Hire an accountant. Speak
to the speak to people in sh so to speak
that know this stuff if you can't afford
an accountant to make sure you're doing
things correctly.
>> If someone's been messing around
for the past, let's say 5 years and they
hear this show and they want to do
chuva, how do they go about it? What's
the steps they take?
>> Chuva. What do you mean by chuva?
>> They want to start.
>> So I come across people like that all
the time. And a lot of times it's very
similar to somebody that wants to eat
healthy.
They say they want to eat healthy and a
month later, a year later, it's the same
complaint. And usually what happens is
by the time they want to make so-called
chuva, that's when the IRS is after them
or that's when they have to file
bankruptcy, that's when their business
collapses because they weren't on top of
their books and records.
So, first thing first, get your books in
order and get everything in order. Hire,
if you can't do it, hire the right
bookkeeper/acountant.
Don't be cheap.
Don't be cheap. And from there, have the
accountant, if you have issues, if you
have issues with the IRS, come to me.
I'm going to do a whole investigation.
I'm going to look at your history. I'm
going to see where you owe money, where
you potentially your accounts could be
levied, where maybe we can get rid of
some penalties, penalty abatement. Come
to me. If you're if you're having issues
already with the IRS, come to somebody
like me who will work the case and will
work it much quicker than the average
person and get the best results as
possible.
>> You're going to tell them the real
honest truth as is. No filters.
>> No, no. Everything is truth.
>> You don't seem like a filter guy.
>> No. No. everything. You got to deal with
reality here. It's very similar.
Somebody's coming to the dentist and now
they have to get their tooth extracted.
>> The guy the dentist is not going to try
to make it sound nice. Here's what's
happening. You need an implant and it's
going to be hell, you know, and here are
the three appointments and here's what
the what it's going to feel like. So,
when you're already in this situation,
you need the truth, but you want to deal
with it in the quickest, best efficient
way as possible. Does that answer the
question?
>> Yeah, it sounds good.
>> Yeah. Does it respond?
>> What are we What are we talking about? A
guy like you because you have 17 years
of working for the IRS. You know all the
secrets. You're going to get them out of
their pain and misery really quickly and
chitchat open. You're charging 500 an
hour or a,000 an hour. You take on a
case no matter how long.
>> I charge the compet what the competitive
rates are. I don't go higher than the
competitive rates for tax resolution.
>> What do we What What does it look like?
>> It depends.
>> Call him for rates.
>> Call for rates.
>> Call for rates. It depends.
>> Does response Everyone does this. Does
the IRS buy that response? If someone
says, "Oh, why are you doing this?" He's
like, "Oh, everyone does it." Does that
fly at all in the IRS?
>> Yeah, that that works very well.
[laughter]
>> I've gotten a lot of those.
>> Don't let anybody do that. I've gotten a
lot of those. Uh yeah. No, that doesn't
fly. You need It's very clear in terms
of what is an The law is what is an
ordinary and ne what is a what an
ordinary my brain? What is an or what is
ordinary and necessary for the average
business? What are what are they
supposed to do according to the Internal
Revenue Code 162? They have to keep
records. It's the law. If you say, "I
know a friend that doesn't keep records.
Everyone doesn't."
Doesn't fly. Where's your records? You
know, they have it a lot with, like I
said, earn income credit. My uh my
friends, they claim their nieces and
nephews and their brothers and sisters.
Why can't I? They all do it because
you're not allowed to unless you're
following the law.
>> If they ask you to speak in Shan Chabas,
what would you tell the community about
taxes? What would be your your your
statement to them?
I got to be honest. I hate talking about
taxes [laughter]
on Shabbat. I was asking I used to say
Shabas.
>> You switched.
>> Now I say Shabbat and sometimes I say
Shabbat. It's it's a mixture of it all.
I have everything in me right now.
>> Who do you prefer? The Kabat or the
Syrians?
>> I love everybody. You
>> love everybody.
>> Everybody. Especially if there's you
know [laughter]
>> there's a different
>> preference.
>> There isn't. Everyone has their own
uniqueness. I know the Syrian community
sometimes it gets a bad rap
>> for what?
>> Like sometimes kabad gets a bad rap.
>> What if Syrians get bad rap using for?
>> Um
what do you think?
>> I don't know.
>> It's like stereotypes.
>> What's the stereotype?
>> Being rich, being arrogant, flexing,
going to deal, buying $10 million homes,
the usual stuff,
>> you know. Yeah. I mean and you know
people can be known
>> saying Rabbi Mansur is the only rabbi in
the worlds [laughter]
>> but mansurans
>> I don't even know the guy
>> but there's a great
>> my point is is that there's the Jewish
people in general as I'm getting older
I'm in my 40s now the black and white
way of thinking is gone remember in kids
misnom are bad [laughter] you know it's
like no
>> snag them are not bad
>> when we were kids you know we would
fight with them in camp when we went on
the same trips. The reality is is that
everybody is is good. There is like an
Amnus Khai type thing and plenty of
Syrian Jews out there, they would take
their shirt off their back to help
another Jew. And uh that doesn't matter
if they're kabad or lipish or anything.
And I think it's as as I'm getting
older, maybe it could be I'm older,
maybe it could just be with the with the
times, there's a certain unity and
there's good with everybody and there's
rotten apples on trees everywhere that
doesn't make anybody or any group bad or
not bad.
>> Could you claim mental health or illness
with the IRS? Does that how much weight
does it have or what's how does that
work?
Well, you could claim it if you're able
to prove it in a sense of why you didn't
file your tax returns and why you
shouldn't uh why you shouldn't be
penalized penalized uh for not filing on
time and for not paying on time. So, you
could if you're able to prove that
there's a real mental health issue or a
real health issue, but it's you got to
be able to prove it in a sense. You
can't say I have a health issue, but I
was paying my light bill but not paying
the the IRS. You would have also have to
show I wasn't even paying my light bill.
>> Stop. People should stop paying all
their phones.
>> Is ADD consider?
>> I don't pay any bills.
>> Is ADHD considered a mental illness with
IRS? I know.
>> But like I said, if they have ADHD and
they're paying their light bill, but not
>> paying a light bill is more is more
simple click pay than filing taxes and
freeing your law statement. If you're
able to pay with your a ADHD, your
leased vehicle payment and your
insurance payment, you could pay the IRS
as well. So, it's not impacting your
capabilities or your capacity to
function in life. So, the same should is
true. The IRS will look at it in that
way as well.
>> So, it doesn't you're saying
>> he's trying to say there's a mental
health issue going on and everybody
could claim in something.
>> Yes. [clears throat] Do you think
everyone has mental illness? What
>> do you think everyone has mental
illness?
Everyone ch has challenges with it.
Isn't the whole Tanya on that? The nepha
Bahamas, the nephis, the godly soul, the
anim animalistic soul. And when the
animalistic soul takes control and the
godly soul,
>> the animalistic soul doesn't want to pay
taxes. And the and the godly soul wants
to pay the IRS all their money. They
want to give them everything.
>> He's asking uh
>> here's when you join community, did they
welcome what was the welcome package
like?
We're saying like who's this kaban guy
intruding or what's it's very is it very
tight-knit.
>> I only had good beautiful experience.
>> Wait a minute. They wanted an insider
from the IRS.
>> I [laughter] I only had be I only had
beautiful experiences with uh not just
with the SI community
with with most communities. I only have
you attract what's inside. If you think
everybody is bad or then you're going to
see it everywhere. It's uh
Yeah.
>> Well, powerful stuff. Powerfully good.
>> What's worse?
>> Yeah.
>> To be ignorant for the IRS or being in
malicious. Does it make a difference?
>> Malicious is worse.
>> Intentional avoidance.
>> Oh, that's worse. Yeah.
>> So, if you claim just you're messy, you
know what you're doing, then?
>> Yeah. It's different. intent is uh can
get you in can get you in prison or if
not in prison will give you a fraud
penalty and a lot of penalties if you're
saying that you I didn't know or I'm my
accountant did it for me you can
potentially depending on the situation
>> uh get out of some penalties
>> you want one or two bites and you're
eating chocolate the whole time you're
not saving any for anybody [laughter]
eating the chocolates are so good you
just just can't stop justing [snorts]
chocolates are crazy so
When you're uh let's say you're helping
a friend, you're giving him some money,
lending him money, giving him money. At
what point do you have to start 1090,
like how does that work? You just give
him money. Like
>> so you're talking about
>> a friend calls you, oh, I need some
money. I need help paying the rent, blah
blah blah. So he's not he's not a non
forprofit, right?
>> Right. So that that we're talking about
the potentially a complex tax issue. So
if you're let's say a business and
you're lending money let's use a
business you're you as a as a person
you're lending money to as a business so
there are certain laws you have to
called bad business bad debt business
bad debt expense I believe I'm not 100%
sure you have to follow certain
guidelines right so if this person lends
money let's say I lend you money and
I need the money back and you're not
paying me back. So legally, what I have
to do is just like a business, I have to
send you letters
saying
almost like collection letters, you owe
me the money, please respond. If you
don't do it, as time goes on, then you
could potentially claim a loss if it's
done in that aspect. But if I lend you
money and it's just one friend to
another friend and you don't pay me
back, for the most part, there's nothing
you can do. I think you have to really
send the guy a debt collection letter
like like you're running like a
>> and you have to have a real loan
agreement and everything.
>> Oh my god, we almost forgot the uh the
500 pound elephant in the room.
Everybody jokes around about this. Oh, I
could swipe my credit card. It's a
business expense. I could pay for
dinner. It's a business. You want to buy
a new MacBook? $8,000 with 50 gigabytes
of RAM and terabytes and hard drive. I
don't even know this stuff. Business
expense. What's a real business expense?
What's not a business expense? What's
realistic? because everybody's talking
about now like, "Oh, before I file for
last year, let me see all these things
are business expenses."
>> So,
>> could you how about this? Could you go
to if you only needed a $1,100 MacBook
for your business, could you go and say,
"I'm going to get a $5,000 MacBook with
every add-on with Apple Care," which I
would never pay if it was out of my
pocket, and say it's a business expense.
If you're using it for business,
>> you're using it, but you really you need
a a $200 computer from
>> Now, let me ask you, how smart is that?
You, the business owner, that's spending
instead of a $500 computer, you're
spending a $5,000 computer. So, you
could save a few bucks on taxes, but
you're really spending $4,000 extra on
the computer.
>> Just the terms I hear people saying
about it's a business expense. It's a
It's an overused. It's an overused.
>> Me and Israel are content creators. We
could really say everything is we're
going we're making a wedding and you
document the whole wedding. It's like
it's all business expense. It's all
content. So where do you draw the line?
>> Okay. So let's go let's go through that.
>> Yeah. So we're influencers.
>> It has to be an ordinary and necessary
business expense for the industry that
you're in.
So you in your industry, let's say
you're going to a wedding and you're
actually going to take videos there,
right? You can make the case that it's a
business expense. You needed the plane
ticket. You needed the Uber to get to
the plane.
>> No, like
>> No, I'm saying that's a business
expense.
>> As an influencer, you're basically a
news company. A news company, just like
a news company flies to, I don't know,
to Iran. And
>> but you also have to follow certain
laws, rules. You have to have good
recordeping. Who did you meet with when
you flew to uh you going to your
friend's wedding or you actually going
there for uh
>> content?
>> For content creation, that's where you
would need a
>> guy pulling out his phone documenting
anybody in the world. It's always
content creation. you you is it the
question you would have to ask your
accountant is this an ordinary and
necessary expense are you is it and you
can make a case yes
>> if I go to steam with my kids and I
document the whole thing
>> no that's different you
>> but it's content
>> well you can't you certainly can't
deduct your uh your wife's plane ticket
your kids's plane ticket the hotel
ticket the hotel ticket cuz you there's
a certain recreation there
>> again you would want speak. You would
want to speak to your accountant and
hopefully they they're wellversed in
your industry. However,
someone has a business and they're going
with their wife and kids to a restaurant
and they go, "Yeah, this is a business
expense." No, it's not. [snorts] They're
ordering all taking all their Amazon's
Amazon receipts and going a business.
No, it's not. Your situation is gray.
It's a gray situation. It's different
than what many people do where they're
just going business expense, business
expense, business expense
>> and then they win a $10,000 even number.
>> You I would look at the I remember
looking at the general ledger and you
see Costco, Wegman's.
It could be that they're going to
Wegman's to buy food for their business
every day. You know, Shopright, it could
be, but and also there's certain, like I
said, record keeping laws.
>> Office pantries is deductible.
If you're feeding all your employees, is
that considered a do you familiar with
that?
>> I I'm not 100% familiar. It's certainly
deductible. I don't remember the exact
laws around it, but you could look it up
on Google.
>> Yeah,
certainly. There is deduction for that.
Yes.
>> Did anyone ever punch you in the face as
IRS agent when you were ordering them?
>> No. No.
>> Do they ever smack you, kick you?
>> Never. No.
>> Curse you out?
>> Curse me out. Yeah.
>> Do they say you dirty Jew IRS? They
never They never did play the the race
card.
>> No. Never.
>> Never.
>> I have had people scream at me about
Barney Frank getting away with taxes.
Why is he not sitting here? [laughter]
And uh talking about how unfair it is or
and I've had a lot of that. But usually
people are for the most part civil and
there are people that are very emotional
and you learn to handle it. You know,
like I said, it's a very scary thing to
be dealing with the IRS. People don't
realize how scary it is until they go
through it. Your life is upside down.
All your childhood traumas come up in
that in that thing. And your whole life
can be turned upside down. And uh you
deal with a lot of people with fears
with a lot of big heavy emotions. And my
heart always went out for them because
my god their lives are upside down
>> with with audit
>> with with the audit. It's open for three
years. There's anxiety. the wife is
unhappy or the husband's unhappy, you
know, and uh
>> have you seen people get divorced over
these audits?
>> Uh I've heard stories. I mean, they're
not I don't see the divorce ceremony in
the audit, but [laughter]
yeah,
>> from people you visited, it's suddenly
the end of
>> I know people in personally that come
talk to me in the from the Jewish
community. They come to me over the
years and their lives are upside down.
Their marriage is not good. Their kids,
they're stressed out
>> because of the audits. Yeah, it could be
very scary. Can be very, very scary.
>> So, I think my takeaway is Iris is
pretty reasonable. They're not looking
to go after everybody. If your numbers
are totally off and doesn't make sense,
you know, if you're a barber shop and
you have and you're driving a
Rolls-Royce, [laughter]
it's probably not deductible, right?
>> Yes.
>> I mean, if you're running a private
wealth management firm in the Hamptons,
you're driving a Rolls-Royce, it makes
more sense, right?
>> Yes. So, if things are totally out of
whack, they probably don't make sense
and IRS will be concerned and will go
after you.
Takeaway is pay your taxes,
make the deductions be half normal. And
any time you're being audited or you
have major problems with the IRS, you
call my buddy Israel Ostrov.
He knows the tricks. He'll calm you
down. He'll say, "You know what? Instead
of being having anxiety and fear, just
pay me. I'll take care of it all. I'll
represent you." We'll get a number.
You'll write out a check or whatever it
is.
>> Pretend you're a veteran.
>> Sad. That's it.
>> You get a pension. Hold on. Israel.
>> Think they pay you. They don't have to
have the stress. You just take care of
it and it's over.
>> Israel, what's a pension thing? Two
different questions at me.
>> Oh, I'm sorry. You got a good pension
after
>> I I left. I left. It would have served
me better to stay at the IRS
>> for 20 or 25 years.
>> The 25 until retirement age in terms of
pension. My pension is not that good cuz
I left early. Uh, I like I said, the
reason why I left the IRS is to help
people. Uh, I I just want to say that
when it comes to representing people
that are dealing with this, because I've
seen a lot of representatives, sometimes
the best representatives were the ones
that had no name, no no letters to their
name, and sometimes the worst were the
ones that had ESQ or CPA. Uh, that
doesn't mean all were bad. I'm just
saying when it comes to someone
representing you, do you want the case
open for 3 years or do you want a
representative that's proactive that
understands what the IRS is looking for
and that instead of this case being open
for 2 3 years, it will be open a quarter
of that amount of time or half, depends
on the situation.
And uh my takeaway to you is if you're
dealing with the IRS, you want somebody
that's going to give you good results
and you want to get back to your life.
Now, I don't know which one of you asked
the question, uh if you're being audited
by the IRS,
what you should look for, you want you
want to make sure that this thing is not
open for three years.
>> What does that mean open for three
years? You said the case is open.
Sometimes it's audited after the audit
that can it can sometimes be open for a
year plus and then crazy for three
years. Then you file an appeal and then
uh and then and then by the time it it
gets to the appeals officer's desk and
it gets resolved it's already three
years later and let alone the headache
of everything.
So you when you get involved with quick
>> quicker as efficient as possible and to
get the best results.
>> What do you miss the most about Kates
living in the Syrian town for all this
time?
>> I live in New Jersey.
>> New Jersey.
>> Let's get it straight. I live with
Ashkanaz Syrians all mixer.
>> What do you miss the most about Crown
Heights or nothing?
>> I don't know. When I go to Crown Heights
now, there's more establishments,
you know. Uh I think what I miss most
about Crown Heights are the people, the
friends. I have good cousins there. I
have uh aunt and uncle there. My parents
are there. There are these old uh
teachers. You know, when I was younger,
there wasn't an appreciation for all the
connections I've had. And now that I'm
like in my 40s, low 40s, there is a an
appreciation for all of the contacts
I've had when I was younger. So whenever
I go to Crown Heights, it's it's like
feeding the soul of seeing all the
cousins I've taken for granted, you
know, cuz you're young, you take
everything for granted. My parents are
still alive, so it's a blessing to see
them. My aunt and uncle, it's a blessing
to see them and to see friends. So I
miss that. One thing about Crown
Heights,
>> the connection, the livelihood, which
can be viewed upon it, it can be viewed
from the outside as chaotic, right?
>> But there's a something very beautiful
about it when you're not in it.
When you're not in it and you're away
from Crown Heights and you're not in
that socalled chaos, which by the way, I
don't think is chaos,
there's an appreciation for it. M
>> thank you very much Israel for your
time.
>> Thank you so much for coming. Again,
we're going to have his information how
to reach out to Israel for all your
issues with the IRS or preemptive
resolving your your taxes and your
bookkeeping. You're going to reach out
to Israel and he's going to take care of
you. Thank you so much for coming on the
show.
>> Pay your taxes, keep organized, and you
won't have to use Israel or you want him
as a consultant.
>> Thanks so much. Thank you.