March 19, 2024 • 27 mins
In this episode of the Teaching Tax Flow podcast, hosts Chris and John dive deeply into the intricacies of 1099 forms with the help of guest expert Kaitlyn Rummel from EH Business Services. Kaitlyn brings her experience to the table, discussing how 1099 forms work, their significance in tax documentation, and strategic tips for businesses to manage them efficiently.
Opening with an introduction to the topic, Kaitlyn sheds light on different types of 1099 forms, emphasizing the infamous 1099-NEC. With a focus on how businesses can minimize tax burdens legally and ethically, the episode uncovers best practices, common misconceptions, and the dos and don'ts of 1099s. The conversation explores the close interplay between professional bookkeeping and foolproof tax planning, presenting guidance that listeners can implement immediately.
Key Takeaways:
- 1099-NEC forms are essential for businesses to report non-employee compensation, and they must be filed by January 31 each year.
- Businesses should collect a W-9 form from contractors before commencing financial transactions to facilitate accurate 1099 documentation.
- Payments made via credit card do not require a 1099-NEC because they are reported on a 1099-K by the card processor.
- Penalties for not filing 1099s can range from minor fees to substantial charges, depending on the delay and the nature of non-compliance.
- Keeping organized records and leveraging bookkeeping software like QuickBooks can significantly ease the process of issuing 1099s.
Notable Quotes:
- "It's better to have [a W-9] and then find out that you don't need it." - Kaitlyn Rummel
- "Just because you have a contractor doesn't always mean that you will file a 1099 for them." - Kaitlyn Rummel
- "Quickbooks will automatically take out those transactions made with a credit card and just give you the transactions that count towards the 1099." - Kaitlyn Rummel
Episode Sponsor:
REPStracker
www.repstracker.com/affiliate/teachingtaxflow (CODE: IFG)
EH Business Services
www.ehbusiness.net
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
John Tripolsky (00:04):
Welcome to the Teaching Tax Flow podcast, where
the goal is to empower andeducate you to legally and
ethically minimize taxes paidover your lifetime.
Disclaimer (00:15):
Hey, everyone, and welcome back to the podcast here
today. We are gonna dive intoepisode 75. It's got a little
bit of a ring there. Those 10 90nines, the what, when, and how
they are issued.
John Tripolsky (00:27):
But before that as always, let's take a brief
moment, and thank our sponsor onthis episode.
Disclaimer (00:34):
This podcast is sponsored by Repstracker. Are
you a real estate investor whois bogged down with the huge tax
burden? Real estate investingcan open the door to powerful
tax benefits. Reps tracker canstreamline the process of
accelerating these tax benefits.To take advantage of a special
TTF community discount, go towww.repstracker.com/affiliate/teachingtaxflow
(00:56):
and use the code ifg.
You can look in our show notesor email us at hello @
teachingtaxflow.com.
John Tripolsky (01:07):
Hey, everybody, and welcome back to Teaching Tax
Flow, the podcast. We have got agreat topic today. I know some
of you were waiting for. We aregonna talk about those 10 90
nines. So as I always like topoke fun at, if you took the all
of 13 seconds or so, listen tothe intro of this show, or if
you know how to read, youprobably read the show notes
already.
Kinda like the cliff notes. Butwithout giving away too much
(01:29):
information on these 10 90nines, Chris, welcome back to,
well, let's call it what it is.It's your own show. How's it
going, man?
Chris Picciurro (01:37):
It is going wonderfully, John. It's it's our
show. It's our little baby. Oh,my goodness. Social Security
number.
Maybe we can put it on our taxreturn. We'll have a custody
we'll have a custody agreement.
John Tripolsky (01:49):
Oh, boy. See where see where this is going?
Oh, man. Well, well, Ian, let'stake let's take the fun out of
you wanting to, formalize ourchild here. I guess we can call
this podcast.
But we brought on somebody thatknows a lot more about this than
I do, which is Chris likes topoke fun at me with. It doesn't
take a whole lot to do that. SoCaitlin Rummel from Business
(02:12):
Services is gonna run us throughwhat these 10 90 nines actually
are and maybe even moreimportantly what they aren't.
So, Caitlin, how are you doingtoday?
Kaitlyn Rummel (02:21):
I'm doing good. How are you?
John Tripolsky (02:22):
Well, we're doing pretty good. Obviously,
you can tell by, me and misterPecuro poking fun at each other.
So, hopefully, you know what yousigned up for.
Kaitlyn Rummel (02:30):
Yeah. Sounds like it's gonna be a good time.
John Tripolsky (02:33):
Well, we well, I apologize for anything that
Chris may say. So we,
Chris Picciurro (02:36):
Right. Yeah. That that goes without saying.
Well, Caitlin, welcome. I knowwe've worked a lot on some
mutual clients together.
Thanks for joining the podcast.Before we dive into the 10/99
issue or issues, tell us alittle bit about yourself and
how you got into bookkeeping andand what kind of kind of clients
(02:57):
that you typically work with.
Kaitlyn Rummel (03:00):
So I got into bookkeeping because of my mom.
She was a bookkeeper. And justgrowing up seeing that kind of
got me interested. And where Ilearned most of my stuff from
was her. I'm sorry.
Somebody just walked in.
John Tripolsky (03:19):
Hey. You know what? It's kinda like a 10.99
when they randomly show up inthe mail, you know, unexpected.
You need to know what to do withthese things. Right?
So as is life. It's totallyfine. Yeah. Exactly. Totally
fine.
Exactly fine.
Chris Picciurro (03:31):
So, Caitlin, man, where do you do do you
where where did you grow up?And, I mean, what what you know,
did you work with clients in aspecific area or or all over the
country?
Kaitlyn Rummel (03:43):
So I grew up in Pennsylvania. I still live here,
and mostly I've worked remotely,with clients all over the United
States.
John Tripolsky (03:54):
And then to Caitlin, so here here's a
question for you. So, obviously,Chris knows more about this than
I do. You know more about itthan all of us. So a lot of our
listeners being self employed.Right?
So I'll I'll kinda use myself asan example to kinda get into
this. So first question. Right?I always used to call Chris and
other people like him, you know,oh, well, they're they're my
(04:15):
bookkeeper. They're myaccountant.
In your eyes, they're different.Right?
Kaitlyn Rummel (04:21):
Correct. Yeah.
John Tripolsky (04:23):
Obviously. So and I know we talked about this
in a previous episode, but Ireally want people to kinda get
their get the grasp on this.Right? So give us kind of your
your comparison really betweenthe 2 of those, and then I'll
get into a 10/99 specificquestion for you.
Kaitlyn Rummel (04:36):
So I work throughout the year, with their
transactions, their dailytransactions with their bank
account, categorizing theirexpenses, looking at their
income, if they do, like,accounts receivable, that kind
(04:57):
of stuff, just making sure thattheir invoices are all being
paid, and sending reports, thatkind of stuff. I kind of prepare
their books so that Chris can,at the end of the year, do his
thing.
John Tripolsky (05:13):
Makes sense. Makes sense. So so here's the
the 10.99 question. Right? So,again, kind of using myself as
an example, had a marketingagency for a number of years.
We had a couple employees, a lotof contractors. Right? And when
I first started off, I justassumed that, you know, we just
kinda paid these people ad hocas the projects came in and
projects were delivered, and andthat was kind of the end of it.
(05:36):
And then this thing, you know,1099 rolled around in my mind.
And it kind of takes you alittle bit by surprise.
Right? So I know they're kind ofwalk us through, you know, what
exactly these are, But then, youknow, we'll get into it a little
bit later in the show or feelfree to to talk about them at
your will. But so let's talkabout what they are, but then
also if somebody doesn't issuethem. You know, what what are
(05:59):
the potential issues with thatas well as anything else really
around it? Kind of approachingthis as if nobody knows anything
about what a 1099 is.
Kaitlyn Rummel (06:08):
Okay. So a 1099, the most common one is the 1099
NEC. So that's what I will bereferencing here. It's just a
way for businesses, to reportincome, or stuff that they money
they paid to either a contractoror another small business for
(06:33):
services. There is a tax gap in,income that is reported to the
IRS, and this is kind of theIRS's way to capture that
income.
Of course they want their money,so they want everyone to pay
taxes on the money that theymake. So, you want to businesses
(06:55):
wanna make sure that they'regiving 10.90 nines to, people
that perform services for theirbusiness. So if they have, like,
a graphic design design companythey work for, they work with or
if they have, like, alandscaper. Both of those are
(07:16):
gonna be, issued a 10.99. Thereare penalties.
All 10 90 nines, whether we'retalking about the NEC or any of
the other 10 90 nines, they areall due, to be filed by January
31st every year. And if theyaren't, there are some penalties
(07:39):
in place that you could get.
John Tripolsky (07:42):
Makes sense. And what are what are those
penalties actually? Are theypretty substantial, or are they,
you know, just kind of anuisance? Chris, you probably
know that one.
Chris Picciurro (07:48):
Right. No. They're both John. So yeah. No.
They're both John. They could bethey are a nuisance, but they
could pile up. You know? And Ithink that, you know, one of the
things excuse me. One of thethings that Caitlin pointed out
first is that there are severaltypes of 10.90 nines.
Right? We we get them all thetime. We get 10.99 INT for your
interest, 10.99 DIV dividend,10.99 b, 10.99 r's for
(08:13):
retirement distributions. Butit's the the 10.90 nines that
caused the most confusion by farare the 1099 NEC. So Caitlin
nailed the nailed the nail ah,hit the nail on the head.
That used to and there are 1099MISC for miscellaneous income,
but really that changed a littlebit ago where that NEC, so non
(08:35):
employee compensation. Thepenalties are can be
significant. There's there's acouple different issues. There
are, first of all, there's thethe worst penalty would be
backup withholding. Right?
So if let's say you paidsomeone, $10,000 and you didn't
issue them a 10.99, well, youcan get charged 28% backup
(09:00):
withholding. Because essentiallythe government's saying, well,
that's the that's the tax ratewe would assume that someone
would pay on this, so you'rejust gonna pay the tax because
you're you bozoed around and youdidn't get the required
information. The the late filingpenalties, they range from $50
to $280, per form, depending onyou know, it's kinda like
(09:22):
speeding ticket, John. If you'regoing 5 over, it's probably a
little less. The way you drive,John, you might be going 50.
No. Actually, very
John Tripolsky (09:30):
Depends what we're driving here.
Chris Picciurro (09:31):
You're very safe, strong ever, John. You've
got that big diesel so you can'tget going too much. But but if
you're very negligent, it couldbe higher. Same thing with, you
know, if a business fails tofile, those penalties can range,
you know, range not only sothere's a late filing penalty
(09:53):
and then there's a failure tofile penalty. So just like in
the income tax, there's a latepayment or tax penalty and then
there's a failure to file.
Those are 50 to $560 per formwith the intentional disregard
being up to $560 per form. It'svery rare that someone have has
an intentional disregard.Usually, what we see is there's
a they might not understand,but, hence, why we're doing this
(10:16):
podcast. Right? They might notunderstand the reporting
requirements.
So there are always, you know,reasonable cause exceptions or
there there there might be,yeah, there might be a good
reason you didn't issue a 10.99,but that's where bookkeeping and
Caitlin and the team at Businessand other bookkeepers really
come into play. It's it's a goodquestion about penalties, but we
(10:39):
wanna do is we wanna prevent thepenalties before they happen.
So, Caitlin, I'm gonna throw itback to you. What are some of
the things that you recommendthat you guys implement within
your guys your bookkeepingbusiness to identify a problem
before it's a problem? Meaning,oh, gosh.
I'm I see a contractor poppingup in someone's books. What
should someone do to make surethat they could they they
(11:01):
collect you know, what do theyneed, first of all? What kind of
information do they need fromthat contractor? And second of
all, what what's best practicesfor tracking?
Kaitlyn Rummel (11:09):
So first thing that you wanna do when you start
any relationship with acontractor is get a w nine. This
is going to give you theinformation that you need to
collect, to file your 10.99 atthe end of the year. You wanna
make sure that you're gettingthis from the start so that in
(11:31):
January you're not scramblingaround trying to get all of the
w nines that you need. It'sbetter to have it and then find
out that you don't need it.
Chris Picciurro (11:41):
Well, what are, you know, what are best
practices in in how, you know,for tracking how much someone's
been paid. So for instance, mostbusiness small businesses use
QuickBooks online at all ofthem. You don't you're not
required to, obviously. It's aprivate organization that has
that software. But what what aresome of the practical tips,
especially for someone juststarting out?
(12:02):
I mean, let's say someone juststarts a you know, starts an ice
cream stand, scoops in in at acounty fair, and they hire some
labor ad hoc. Obviously, we haveanother podcast episode that
talks about laborclassification, but let's assume
they hire an, a a, a contractor.Best yeah. Best practice for
(12:25):
making sure that the amount paidto that person is kept track of?
Kaitlyn Rummel (12:29):
So I would recommend getting some sort of
software. We like to useQuickBooks online. But if your
business isn't quite there yet,you could do it manually. Just
make sure that you're trackingall of the payments that you're
paying to your contractor, andkeep on file their w nine so
(12:50):
that you have that to referenceat the end of the year. Just
because you have a contractordoesn't always mean that you
will get, file a 1099 for them.
If you pay them under $600 ayear, they won't need a 10.99.
(13:11):
If they are a corporation,either an s corp or a c corp,
they won't need 1. And how youfind that out is on that w nine.
It will have, a little boxchecked if they are a
corporation, and then you won'thave to send them a 10.99. Also
(13:33):
go ahead.
No. Also, if you are paying themwith a credit card, you won't
have to include that, in theamount towards the 10.99. So if
you pay them, through your bankor ACH or checks, you will
include that, in thosetransactions. But with a credit
(13:57):
card, those are reported on a10.99 k, so those won't need to
be included for the 1099 and cNEC.
Chris Picciurro (14:06):
Then that is a great point. So if you're and
and that's a question we get alot, you know, in the teaching
tax flow community. So asCaitlin said, let's say I paid,
you know, John no. I had abirthday party for my for my,
son. I hired John to jump out ofthe cake.
Wouldn't have too many peoplethrilled about that. Well, let's
say we did that.
John Tripolsky (14:26):
No. They they'd think I was a pinata, and they
just try to hit me with abaseball bat
Chris Picciurro (14:30):
or something. And for some sort of broken I
paid John more than $600 to jumpout of this cake. Right? That
that would be an awful, awfulway to spend my money, but let's
say I did. I would wanna getJohn's w nine information.
Well, I guess if it's my kid'sbirthday party, I wouldn't
really issue him with that.Well, let's let's assume it's a
corporate event and I'm tryingto impress my clients and and
John jumps out of the cake. Iwould want, like Caitlin said,
(14:53):
that w nine information, so soimportant. That's a withholding
certification. Just like anemployee fills out a w four that
tells its employer how much taxto withhold, that w nine is
telling the payee or payorrather how much money you know,
what are they classified as forbusiness tax business purposes?
(15:14):
So, Kayla and Eilich, you couldhave an LLC that's taxed as an s
or c corp, hence you wouldn'tissue a 10.99. Now,
unfortunately, the $600threshold is extremely low.
There's some legislation outthere to increase that. I think
we'd all be happy if that wentup. But so but if you meet the
$600 threshold, then you then Iwould have to issue John that
10.99, but if I wanted to makesure I got my Southwest Airline
(15:38):
points or Marriott points, oh, Ishouldn't have said those 2
because they are not sponsors ofthis podcast yet, although they
should deeply consider that, andI pay with a credit card, then
the credit card company actuallytakes care of that 10.99 with,
requirement issues, John, that10.99 k.
So, Caitlin, that was veryhelpful, and and good for people
to know. You know, it does getkind of tricky when you're
(16:01):
paying people with, like, aVenmo or a Stripe app. You know,
you've gotta really look atmaking sure, you know, in
general and, Caitlin, you youcould speak to this a little
more than I can, I'm sure, butthat if you know, to determine
if if the the third party isgoing to issue that 10.99 k to
the person ultimately gettingthe payment. So
Kaitlyn Rummel (16:23):
That's where having those software the
bookkeeping software in placereally helps out. QuickBooks
will automatically, take outthose transactions that are made
with a credit card and just giveyou the transactions that count
towards the 10.99. So you caneasily see how much you're
supposed to file that 1099, andQuickBooks will do that for you.
(16:47):
With a push of of a button, yougotta go through the steps.
Chris Picciurro (16:50):
Nice. Well, I want and I wanna clarify some
backup withholding's 24% and at28%. So I apologize. You know, I
just wanna give the governmentmore money, I guess. Usually
usually, the opposite is whatwe're trying to accomplish in in
teaching tax flow.
But, yeah, I mean, there are Imean, there could be challenges.
I I mean, Caitlin, you know,maybe you could speak to some of
(17:11):
the challenges common challengesthat you see out there with 10
90 nines, but I'll give you anexample. What if you had a corp
company that was only open 8months of the year, they
close-up shop, they're stillobligated to to issue 10.90
nines to people that they paid.And who knows? They may have
closed their bank account.
They may have gone, you know,bye bye. We don't know what you
(17:32):
know, who knows? So that's anyany other things that could be a
challenge that, or or tips thatyou can give people to prevent
those challenges?
Kaitlyn Rummel (17:41):
I think the the best thing is just staying
organized throughout the year,and knowing when you're starting
that relationship, oh thislandscaper I know I'm gonna have
to give him a 10.99 at the endof the year. Or, whoever it is,
just knowing who they are andhaving your books in order is,
(18:03):
gonna set you up for Januarybeing able to do those 10.90
nines. And if you haven't, justgo back to your your bank
records, your statements. Lookat your statements and look at
your transactions and do itmanually. Make a spreadsheet of
each of the contractors' names,and look for the transactions in
(18:24):
your statements to find out thenumbers.
Chris Picciurro (18:27):
Well, we've talked about that 1099 NEC.
That's the really the focus ofthis specific, episode. We've
talked about when when you issueit. Galen, you know, said that
these are due on January 31st,for unincorporated payees that
are paid $600 or more. Finalthing we we wanted to talk about
(18:48):
was the how.
So, you know, do these getmailed in? Do they get submitted
electronically? What are thebest, you know, best practices?
I mean, I'm I'm and, John, youknow, in our pre show meeting,
made made some cracks about myage. Yes.
I'm a little more mature agethan you 2. So back when I first
started, we we would have a rentcopy, I think, that went to the
(19:11):
IRS, and we'd have to mailcopies to the to the to the
person getting paid and thenanother copy to the state. So,
Caitlin, is there are thereoptions for people to do this
electronically versus mail itin? Are there you know, what are
Kaitlyn Rummel (19:24):
There are. There's many different softwares
out there that you can use. Someare mixed in with your
bookkeeping software. Like Isaid, QuickBooks online, you can
go through easily. But there'sother softwares that you can use
outside of QuickBooks, just for10.99 processing.
(19:47):
And then you pay per per 1010.99 that you file.
Chris Picciurro (19:52):
No. I appreciate that. So we've hit
the who, rather the what, thewhen, and how. I mean, we also,
I guess maybe one more questionfor for Caitlin and and then,
see if John has anythinganything to throw in the mix.
But we've got, you know,sometimes you see taxpayers get
a notice from the IRS thatthere's a matching issue.
(20:14):
And sometimes people eithercould be could be on purpose or
could be on accident, givesomeone the wrong information,
wrong Social Security number,and and what happens is a 1099
gets filed with IRS and itdoesn't match the records that
the IRS has. In that case, yes,Caitlin, have you ever run into
a client that has had thatsituation?
Kaitlyn Rummel (20:37):
Yes. We have. You're gonna wanna go back to
whatever side you're on. You'regonna wanna go back to whoever
filed that 10.99. Also, look atyour records, and see if there
was something, that was missedand if you can narrow down what
(20:57):
the difference is.
Go back to who filed it, andonce it's resolved, you can do a
correction through that same,software that you used to file
the first 10.99, and issue thecorrect amount for the 1099.
John Tripolsky (21:17):
And that's actually a great point to kinda
wrap up with this, right, issometimes it's not done
malicious, neglectful, or peoplejust forgot sometimes, you know,
the, the 8 turned into a 0, andthen, you know, all the, the
chain links don't go together.So I appreciate both of you
kinda running through this. So Ikinda feel like I was sitting
here taking notes. You know,like, I'm in a I'm in a lecture
(21:38):
session because it's interestingbecause Caitlin really, you
know, knowing the relationshipthat you guys have had working
with Chris so much in the past,and it's like a, we'll call it a
harmonious process. Right?
Because, Chris, you guys, youknow, you're you're not the ones
on the tax side filing 10 90nines. And, Caitlin, you know,
you guys and your team do afantastic job of of really
preparing them. And I wouldn'tsay out of sight, out of mind,
(22:01):
but you guys handle it so wellfor clients that when it comes
time, then, you know, we wewon't call it tax season because
we don't want Chris's head to,you know, explode on us. We'll
call it tax time. When it comestime to collect all those, you
guys obviously preparing a wellahead of time.
Chris, you're you and your teamor your team specifically, you
know, you guys have them inplace. So there's not really,
(22:24):
oh, I wonder if they were doneor what are these things. And
Caitlin, you went into somereally, really good points. I
think that a lot of people don'tmaybe they don't think about. I
mean, to be honest, I didn'teven know that with the credit
card payments, you know, notrequiring filings.
That was I appreciate thatpersonally. But then also, you
know, kind of reiterate what youhad mentioned, really just the
importance of getting that wnine as early as you possibly
(22:47):
can, even if you don't need it.Right? So case in point, you
might have somebody that you'rebringing on, say you hire them
$100 an hour. You got them 2,you know, 2 hours.
You know, you're well under that$600 threshold. You're at $200,
say. But who knows? You may rampup and kick into another,
contracted project with themlater in the year. So it's nice
to get that, from the beginning.
(23:09):
But then also too from theemployee or I shouldn't say the
employee, from the company sideof things. We don't wanna get
into employee classificationissues, which is a whole
previous podcast, but it almostI would say it puts your best
foot forward. Right? Say youbegin working with a contractor.
You request that w nine from aright out of the gate.
It kinda shows that you got youract together. You respect the
(23:30):
relationship, and, obviously, itmakes your life easier on the on
your side, Caitlin. So thank youfor thank you for joining us. I
I really appreciate it, and IThanks
Kaitlyn Rummel (23:40):
for having me.
John Tripolsky (23:40):
You know, we it's nice to get another voice
on here than just me and Chris.You know, he's referencing all
the old way of doing things andfiling these forms. They
probably you know, he probablyhad a stack of these forms right
next to his abacus sitting onhis desk too is the way he used
to do things. So Well,
Chris Picciurro (23:56):
I guess but we'll make a bond we'll make a
bonfire out of them and makesure that Avis get filed
electronically. And and if youhave any questions, definitely
reach out to us. We can get youconnected with Kate Caitlin's
all all her information, andbusiness will be in this in this
podcast, link and show notes, Ishould say.
John Tripolsky (24:15):
Absolutely. Absolutely. Well, thank you both
for joining us, and thank youeverybody for joining us here as
well on the listening side ofthe podcast. Hopefully, you took
some notes from this. And, youknow, as mentioned, myself
included, we covered a couplethings here that you probably
didn't know before.
But really just harping home, asI always say harping home
because it makes absolutely nosense when I say that. I did it
about 15 episodes ago, and theycalled me out on it. So I just
(24:39):
make up my own terms here.Obviously, you can't do that
figures out of 10.99. So alljoking aside, we will see
everybody back here next week,same place, different time on
the Teaching Tax Flow podcast.
Hey, everybody. Thanks forhanging out with us here on this
(25:00):
episode as we dove into those 1090 nines, those pesky little 10
90 nines sometimes, butnevertheless, very important. So
Caitlin, thank you again forjoining us on this show. Go into
some great, great topics, somelittle components as we could
say of those 10.99s that a lotof us maybe not have knew about,
I should say, and actually againkind of throwing myself in front
(25:23):
of her under the bus, I shouldsay I really didn't know about
that with the credit cards. Sonow I do and hopefully you do as
well, but as always, anyquestions you guys have for us
or if you want an introductionto Caitlin and her team, please
drop us a line.
You can even email us at helloat teaching tax flow dot com or
better yet, connect with us onsocial media on pretty much
(25:44):
every platform out there or eveneasier. Just go to defeating
taxes.com. It'll send youdirectly to our private Facebook
group. Go ahead. Join that.
This is your invite. Drop us aline through there or just ask
any tax questions. Either myselfwon't be giving any real tax
advice. Let's be honest withthat. I'm just the marketing
guy.
But Chris or other thoughtleaders in that group will will
(26:05):
be more than happy to answeryour question or connect you
with somebody who does. And Iguarantee if you have that
question, like you always heardback in school, if you have the
question, we almost bet thatother people have the same one,
so don't wait to ask it. Feelcomfortable. Ask those
questions. Let's do it together.
Let's defeat taxes. Sounds very,Viking ish of us, but, anyways,
(26:28):
we'll see everybody back herevery soon. Keep dropping us
those questions, comments,feedback, anything you have. We
are here for it, and hopefullyy'all are ready for, for tax
prep time. So creeping up soonerthan you things.
See everybody back here verysoon.
Disclaimer (26:52):
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 adviser.Securities are offered through
Cabin Securities, a registeredbroker dealer.
The content of this podcast doesnot constitute an offer of
(27:14):
securities. Offerings can onlybe made through an offering
memorandum, and you shouldcarefully examine, Offerings can
only be made through an offeringmemorandum, and you should
carefully examine the riskfactors and other information
contained in the memorandum.
Welcome to the Teaching Tax Flow podcast, where
the goal is to empower andeducate you to legally and
ethically minimize taxes paidover your lifetime.
Disclaimer (00:15):
Hey, everyone, and welcome back to the podcast here
today. We are gonna dive intoepisode 75. It's got a little
bit of a ring there. Those 10 90nines, the what, when, and how
they are issued.
John Tripolsky (00:27):
But before that as always, let's take a brief
moment, and thank our sponsor onthis episode.
Disclaimer (00:34):
This podcast is sponsored by Repstracker. Are
you a real estate investor whois bogged down with the huge tax
burden? Real estate investingcan open the door to powerful
tax benefits. Reps tracker canstreamline the process of
accelerating these tax benefits.To take advantage of a special
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(00:56):
and use the code ifg.
You can look in our show notesor email us at hello @
teachingtaxflow.com.
John Tripolsky (01:07):
Hey, everybody, and welcome back to Teaching Tax
Flow, the podcast. We have got agreat topic today. I know some
of you were waiting for. We aregonna talk about those 10 90
nines. So as I always like topoke fun at, if you took the all
of 13 seconds or so, listen tothe intro of this show, or if
you know how to read, youprobably read the show notes
already.
Kinda like the cliff notes. Butwithout giving away too much
(01:29):
information on these 10 90nines, Chris, welcome back to,
well, let's call it what it is.It's your own show. How's it
going, man?
Chris Picciurro (01:37):
It is going wonderfully, John. It's it's our
show. It's our little baby. Oh,my goodness. Social Security
number.
Maybe we can put it on our taxreturn. We'll have a custody
we'll have a custody agreement.
John Tripolsky (01:49):
Oh, boy. See where see where this is going?
Oh, man. Well, well, Ian, let'stake let's take the fun out of
you wanting to, formalize ourchild here. I guess we can call
this podcast.
But we brought on somebody thatknows a lot more about this than
I do, which is Chris likes topoke fun at me with. It doesn't
take a whole lot to do that. SoCaitlin Rummel from Business
(02:12):
Services is gonna run us throughwhat these 10 90 nines actually
are and maybe even moreimportantly what they aren't.
So, Caitlin, how are you doingtoday?
Kaitlyn Rummel (02:21):
I'm doing good. How are you?
John Tripolsky (02:22):
Well, we're doing pretty good. Obviously,
you can tell by, me and misterPecuro poking fun at each other.
So, hopefully, you know what yousigned up for.
Kaitlyn Rummel (02:30):
Yeah. Sounds like it's gonna be a good time.
John Tripolsky (02:33):
Well, we well, I apologize for anything that
Chris may say. So we,
Chris Picciurro (02:36):
Right. Yeah. That that goes without saying.
Well, Caitlin, welcome. I knowwe've worked a lot on some
mutual clients together.
Thanks for joining the podcast.Before we dive into the 10/99
issue or issues, tell us alittle bit about yourself and
how you got into bookkeeping andand what kind of kind of clients
(02:57):
that you typically work with.
Kaitlyn Rummel (03:00):
So I got into bookkeeping because of my mom.
She was a bookkeeper. And justgrowing up seeing that kind of
got me interested. And where Ilearned most of my stuff from
was her. I'm sorry.
Somebody just walked in.
John Tripolsky (03:19):
Hey. You know what? It's kinda like a 10.99
when they randomly show up inthe mail, you know, unexpected.
You need to know what to do withthese things. Right?
So as is life. It's totallyfine. Yeah. Exactly. Totally
fine.
Exactly fine.
Chris Picciurro (03:31):
So, Caitlin, man, where do you do do you
where where did you grow up?And, I mean, what what you know,
did you work with clients in aspecific area or or all over the
country?
Kaitlyn Rummel (03:43):
So I grew up in Pennsylvania. I still live here,
and mostly I've worked remotely,with clients all over the United
States.
John Tripolsky (03:54):
And then to Caitlin, so here here's a
question for you. So, obviously,Chris knows more about this than
I do. You know more about itthan all of us. So a lot of our
listeners being self employed.Right?
So I'll I'll kinda use myself asan example to kinda get into
this. So first question. Right?I always used to call Chris and
other people like him, you know,oh, well, they're they're my
(04:15):
bookkeeper. They're myaccountant.
In your eyes, they're different.Right?
Kaitlyn Rummel (04:21):
Correct. Yeah.
John Tripolsky (04:23):
Obviously. So and I know we talked about this
in a previous episode, but Ireally want people to kinda get
their get the grasp on this.Right? So give us kind of your
your comparison really betweenthe 2 of those, and then I'll
get into a 10/99 specificquestion for you.
Kaitlyn Rummel (04:36):
So I work throughout the year, with their
transactions, their dailytransactions with their bank
account, categorizing theirexpenses, looking at their
income, if they do, like,accounts receivable, that kind
(04:57):
of stuff, just making sure thattheir invoices are all being
paid, and sending reports, thatkind of stuff. I kind of prepare
their books so that Chris can,at the end of the year, do his
thing.
John Tripolsky (05:13):
Makes sense. Makes sense. So so here's the
the 10.99 question. Right? So,again, kind of using myself as
an example, had a marketingagency for a number of years.
We had a couple employees, a lotof contractors. Right? And when
I first started off, I justassumed that, you know, we just
kinda paid these people ad hocas the projects came in and
projects were delivered, and andthat was kind of the end of it.
(05:36):
And then this thing, you know,1099 rolled around in my mind.
And it kind of takes you alittle bit by surprise.
Right? So I know they're kind ofwalk us through, you know, what
exactly these are, But then, youknow, we'll get into it a little
bit later in the show or feelfree to to talk about them at
your will. But so let's talkabout what they are, but then
also if somebody doesn't issuethem. You know, what what are
(05:59):
the potential issues with thatas well as anything else really
around it? Kind of approachingthis as if nobody knows anything
about what a 1099 is.
Kaitlyn Rummel (06:08):
Okay. So a 1099, the most common one is the 1099
NEC. So that's what I will bereferencing here. It's just a
way for businesses, to reportincome, or stuff that they money
they paid to either a contractoror another small business for
(06:33):
services. There is a tax gap in,income that is reported to the
IRS, and this is kind of theIRS's way to capture that
income.
Of course they want their money,so they want everyone to pay
taxes on the money that theymake. So, you want to businesses
(06:55):
wanna make sure that they'regiving 10.90 nines to, people
that perform services for theirbusiness. So if they have, like,
a graphic design design companythey work for, they work with or
if they have, like, alandscaper. Both of those are
(07:16):
gonna be, issued a 10.99. Thereare penalties.
All 10 90 nines, whether we'retalking about the NEC or any of
the other 10 90 nines, they areall due, to be filed by January
31st every year. And if theyaren't, there are some penalties
(07:39):
in place that you could get.
John Tripolsky (07:42):
Makes sense. And what are what are those
penalties actually? Are theypretty substantial, or are they,
you know, just kind of anuisance? Chris, you probably
know that one.
Chris Picciurro (07:48):
Right. No. They're both John. So yeah. No.
They're both John. They could bethey are a nuisance, but they
could pile up. You know? And Ithink that, you know, one of the
things excuse me. One of thethings that Caitlin pointed out
first is that there are severaltypes of 10.90 nines.
Right? We we get them all thetime. We get 10.99 INT for your
interest, 10.99 DIV dividend,10.99 b, 10.99 r's for
(08:13):
retirement distributions. Butit's the the 10.90 nines that
caused the most confusion by farare the 1099 NEC. So Caitlin
nailed the nailed the nail ah,hit the nail on the head.
That used to and there are 1099MISC for miscellaneous income,
but really that changed a littlebit ago where that NEC, so non
(08:35):
employee compensation. Thepenalties are can be
significant. There's there's acouple different issues. There
are, first of all, there's thethe worst penalty would be
backup withholding. Right?
So if let's say you paidsomeone, $10,000 and you didn't
issue them a 10.99, well, youcan get charged 28% backup
(09:00):
withholding. Because essentiallythe government's saying, well,
that's the that's the tax ratewe would assume that someone
would pay on this, so you'rejust gonna pay the tax because
you're you bozoed around and youdidn't get the required
information. The the late filingpenalties, they range from $50
to $280, per form, depending onyou know, it's kinda like
(09:22):
speeding ticket, John. If you'regoing 5 over, it's probably a
little less. The way you drive,John, you might be going 50.
No. Actually, very
John Tripolsky (09:30):
Depends what we're driving here.
Chris Picciurro (09:31):
You're very safe, strong ever, John. You've
got that big diesel so you can'tget going too much. But but if
you're very negligent, it couldbe higher. Same thing with, you
know, if a business fails tofile, those penalties can range,
you know, range not only sothere's a late filing penalty
(09:53):
and then there's a failure tofile penalty. So just like in
the income tax, there's a latepayment or tax penalty and then
there's a failure to file.
Those are 50 to $560 per formwith the intentional disregard
being up to $560 per form. It'svery rare that someone have has
an intentional disregard.Usually, what we see is there's
a they might not understand,but, hence, why we're doing this
(10:16):
podcast. Right? They might notunderstand the reporting
requirements.
So there are always, you know,reasonable cause exceptions or
there there there might be,yeah, there might be a good
reason you didn't issue a 10.99,but that's where bookkeeping and
Caitlin and the team at Businessand other bookkeepers really
come into play. It's it's a goodquestion about penalties, but we
(10:39):
wanna do is we wanna prevent thepenalties before they happen.
So, Caitlin, I'm gonna throw itback to you. What are some of
the things that you recommendthat you guys implement within
your guys your bookkeepingbusiness to identify a problem
before it's a problem? Meaning,oh, gosh.
I'm I see a contractor poppingup in someone's books. What
should someone do to make surethat they could they they
(11:01):
collect you know, what do theyneed, first of all? What kind of
information do they need fromthat contractor? And second of
all, what what's best practicesfor tracking?
Kaitlyn Rummel (11:09):
So first thing that you wanna do when you start
any relationship with acontractor is get a w nine. This
is going to give you theinformation that you need to
collect, to file your 10.99 atthe end of the year. You wanna
make sure that you're gettingthis from the start so that in
(11:31):
January you're not scramblingaround trying to get all of the
w nines that you need. It'sbetter to have it and then find
out that you don't need it.
Chris Picciurro (11:41):
Well, what are, you know, what are best
practices in in how, you know,for tracking how much someone's
been paid. So for instance, mostbusiness small businesses use
QuickBooks online at all ofthem. You don't you're not
required to, obviously. It's aprivate organization that has
that software. But what what aresome of the practical tips,
especially for someone juststarting out?
(12:02):
I mean, let's say someone juststarts a you know, starts an ice
cream stand, scoops in in at acounty fair, and they hire some
labor ad hoc. Obviously, we haveanother podcast episode that
talks about laborclassification, but let's assume
they hire an, a a, a contractor.Best yeah. Best practice for
(12:25):
making sure that the amount paidto that person is kept track of?
Kaitlyn Rummel (12:29):
So I would recommend getting some sort of
software. We like to useQuickBooks online. But if your
business isn't quite there yet,you could do it manually. Just
make sure that you're trackingall of the payments that you're
paying to your contractor, andkeep on file their w nine so
(12:50):
that you have that to referenceat the end of the year. Just
because you have a contractordoesn't always mean that you
will get, file a 1099 for them.
If you pay them under $600 ayear, they won't need a 10.99.
(13:11):
If they are a corporation,either an s corp or a c corp,
they won't need 1. And how youfind that out is on that w nine.
It will have, a little boxchecked if they are a
corporation, and then you won'thave to send them a 10.99. Also
(13:33):
go ahead.
No. Also, if you are paying themwith a credit card, you won't
have to include that, in theamount towards the 10.99. So if
you pay them, through your bankor ACH or checks, you will
include that, in thosetransactions. But with a credit
(13:57):
card, those are reported on a10.99 k, so those won't need to
be included for the 1099 and cNEC.
Chris Picciurro (14:06):
Then that is a great point. So if you're and
and that's a question we get alot, you know, in the teaching
tax flow community. So asCaitlin said, let's say I paid,
you know, John no. I had abirthday party for my for my,
son. I hired John to jump out ofthe cake.
Wouldn't have too many peoplethrilled about that. Well, let's
say we did that.
John Tripolsky (14:26):
No. They they'd think I was a pinata, and they
just try to hit me with abaseball bat
Chris Picciurro (14:30):
or something. And for some sort of broken I
paid John more than $600 to jumpout of this cake. Right? That
that would be an awful, awfulway to spend my money, but let's
say I did. I would wanna getJohn's w nine information.
Well, I guess if it's my kid'sbirthday party, I wouldn't
really issue him with that.Well, let's let's assume it's a
corporate event and I'm tryingto impress my clients and and
John jumps out of the cake. Iwould want, like Caitlin said,
(14:53):
that w nine information, so soimportant. That's a withholding
certification. Just like anemployee fills out a w four that
tells its employer how much taxto withhold, that w nine is
telling the payee or payorrather how much money you know,
what are they classified as forbusiness tax business purposes?
(15:14):
So, Kayla and Eilich, you couldhave an LLC that's taxed as an s
or c corp, hence you wouldn'tissue a 10.99. Now,
unfortunately, the $600threshold is extremely low.
There's some legislation outthere to increase that. I think
we'd all be happy if that wentup. But so but if you meet the
$600 threshold, then you then Iwould have to issue John that
10.99, but if I wanted to makesure I got my Southwest Airline
(15:38):
points or Marriott points, oh, Ishouldn't have said those 2
because they are not sponsors ofthis podcast yet, although they
should deeply consider that, andI pay with a credit card, then
the credit card company actuallytakes care of that 10.99 with,
requirement issues, John, that10.99 k.
So, Caitlin, that was veryhelpful, and and good for people
to know. You know, it does getkind of tricky when you're
(16:01):
paying people with, like, aVenmo or a Stripe app. You know,
you've gotta really look atmaking sure, you know, in
general and, Caitlin, you youcould speak to this a little
more than I can, I'm sure, butthat if you know, to determine
if if the the third party isgoing to issue that 10.99 k to
the person ultimately gettingthe payment. So
Kaitlyn Rummel (16:23):
That's where having those software the
bookkeeping software in placereally helps out. QuickBooks
will automatically, take outthose transactions that are made
with a credit card and just giveyou the transactions that count
towards the 10.99. So you caneasily see how much you're
supposed to file that 1099, andQuickBooks will do that for you.
(16:47):
With a push of of a button, yougotta go through the steps.
Chris Picciurro (16:50):
Nice. Well, I want and I wanna clarify some
backup withholding's 24% and at28%. So I apologize. You know, I
just wanna give the governmentmore money, I guess. Usually
usually, the opposite is whatwe're trying to accomplish in in
teaching tax flow.
But, yeah, I mean, there are Imean, there could be challenges.
I I mean, Caitlin, you know,maybe you could speak to some of
(17:11):
the challenges common challengesthat you see out there with 10
90 nines, but I'll give you anexample. What if you had a corp
company that was only open 8months of the year, they
close-up shop, they're stillobligated to to issue 10.90
nines to people that they paid.And who knows? They may have
closed their bank account.
They may have gone, you know,bye bye. We don't know what you
(17:32):
know, who knows? So that's anyany other things that could be a
challenge that, or or tips thatyou can give people to prevent
those challenges?
Kaitlyn Rummel (17:41):
I think the the best thing is just staying
organized throughout the year,and knowing when you're starting
that relationship, oh thislandscaper I know I'm gonna have
to give him a 10.99 at the endof the year. Or, whoever it is,
just knowing who they are andhaving your books in order is,
(18:03):
gonna set you up for Januarybeing able to do those 10.90
nines. And if you haven't, justgo back to your your bank
records, your statements. Lookat your statements and look at
your transactions and do itmanually. Make a spreadsheet of
each of the contractors' names,and look for the transactions in
(18:24):
your statements to find out thenumbers.
Chris Picciurro (18:27):
Well, we've talked about that 1099 NEC.
That's the really the focus ofthis specific, episode. We've
talked about when when you issueit. Galen, you know, said that
these are due on January 31st,for unincorporated payees that
are paid $600 or more. Finalthing we we wanted to talk about
(18:48):
was the how.
So, you know, do these getmailed in? Do they get submitted
electronically? What are thebest, you know, best practices?
I mean, I'm I'm and, John, youknow, in our pre show meeting,
made made some cracks about myage. Yes.
I'm a little more mature agethan you 2. So back when I first
started, we we would have a rentcopy, I think, that went to the
(19:11):
IRS, and we'd have to mailcopies to the to the to the
person getting paid and thenanother copy to the state. So,
Caitlin, is there are thereoptions for people to do this
electronically versus mail itin? Are there you know, what are
Kaitlyn Rummel (19:24):
There are. There's many different softwares
out there that you can use. Someare mixed in with your
bookkeeping software. Like Isaid, QuickBooks online, you can
go through easily. But there'sother softwares that you can use
outside of QuickBooks, just for10.99 processing.
(19:47):
And then you pay per per 1010.99 that you file.
Chris Picciurro (19:52):
No. I appreciate that. So we've hit
the who, rather the what, thewhen, and how. I mean, we also,
I guess maybe one more questionfor for Caitlin and and then,
see if John has anythinganything to throw in the mix.
But we've got, you know,sometimes you see taxpayers get
a notice from the IRS thatthere's a matching issue.
(20:14):
And sometimes people eithercould be could be on purpose or
could be on accident, givesomeone the wrong information,
wrong Social Security number,and and what happens is a 1099
gets filed with IRS and itdoesn't match the records that
the IRS has. In that case, yes,Caitlin, have you ever run into
a client that has had thatsituation?
Kaitlyn Rummel (20:37):
Yes. We have. You're gonna wanna go back to
whatever side you're on. You'regonna wanna go back to whoever
filed that 10.99. Also, look atyour records, and see if there
was something, that was missedand if you can narrow down what
(20:57):
the difference is.
Go back to who filed it, andonce it's resolved, you can do a
correction through that same,software that you used to file
the first 10.99, and issue thecorrect amount for the 1099.
John Tripolsky (21:17):
And that's actually a great point to kinda
wrap up with this, right, issometimes it's not done
malicious, neglectful, or peoplejust forgot sometimes, you know,
the, the 8 turned into a 0, andthen, you know, all the, the
chain links don't go together.So I appreciate both of you
kinda running through this. So Ikinda feel like I was sitting
here taking notes. You know,like, I'm in a I'm in a lecture
(21:38):
session because it's interestingbecause Caitlin really, you
know, knowing the relationshipthat you guys have had working
with Chris so much in the past,and it's like a, we'll call it a
harmonious process. Right?
Because, Chris, you guys, youknow, you're you're not the ones
on the tax side filing 10 90nines. And, Caitlin, you know,
you guys and your team do afantastic job of of really
preparing them. And I wouldn'tsay out of sight, out of mind,
(22:01):
but you guys handle it so wellfor clients that when it comes
time, then, you know, we wewon't call it tax season because
we don't want Chris's head to,you know, explode on us. We'll
call it tax time. When it comestime to collect all those, you
guys obviously preparing a wellahead of time.
Chris, you're you and your teamor your team specifically, you
know, you guys have them inplace. So there's not really,
(22:24):
oh, I wonder if they were doneor what are these things. And
Caitlin, you went into somereally, really good points. I
think that a lot of people don'tmaybe they don't think about. I
mean, to be honest, I didn'teven know that with the credit
card payments, you know, notrequiring filings.
That was I appreciate thatpersonally. But then also, you
know, kind of reiterate what youhad mentioned, really just the
importance of getting that wnine as early as you possibly
(22:47):
can, even if you don't need it.Right? So case in point, you
might have somebody that you'rebringing on, say you hire them
$100 an hour. You got them 2,you know, 2 hours.
You know, you're well under that$600 threshold. You're at $200,
say. But who knows? You may rampup and kick into another,
contracted project with themlater in the year. So it's nice
to get that, from the beginning.
(23:09):
But then also too from theemployee or I shouldn't say the
employee, from the company sideof things. We don't wanna get
into employee classificationissues, which is a whole
previous podcast, but it almostI would say it puts your best
foot forward. Right? Say youbegin working with a contractor.
You request that w nine from aright out of the gate.
It kinda shows that you got youract together. You respect the
(23:30):
relationship, and, obviously, itmakes your life easier on the on
your side, Caitlin. So thank youfor thank you for joining us. I
I really appreciate it, and IThanks
Kaitlyn Rummel (23:40):
for having me.
John Tripolsky (23:40):
You know, we it's nice to get another voice
on here than just me and Chris.You know, he's referencing all
the old way of doing things andfiling these forms. They
probably you know, he probablyhad a stack of these forms right
next to his abacus sitting onhis desk too is the way he used
to do things. So Well,
Chris Picciurro (23:56):
I guess but we'll make a bond we'll make a
bonfire out of them and makesure that Avis get filed
electronically. And and if youhave any questions, definitely
reach out to us. We can get youconnected with Kate Caitlin's
all all her information, andbusiness will be in this in this
podcast, link and show notes, Ishould say.
John Tripolsky (24:15):
Absolutely. Absolutely. Well, thank you both
for joining us, and thank youeverybody for joining us here as
well on the listening side ofthe podcast. Hopefully, you took
some notes from this. And, youknow, as mentioned, myself
included, we covered a couplethings here that you probably
didn't know before.
But really just harping home, asI always say harping home
because it makes absolutely nosense when I say that. I did it
about 15 episodes ago, and theycalled me out on it. So I just
(24:39):
make up my own terms here.Obviously, you can't do that
figures out of 10.99. So alljoking aside, we will see
everybody back here next week,same place, different time on
the Teaching Tax Flow podcast.
Hey, everybody. Thanks forhanging out with us here on this
(25:00):
episode as we dove into those 1090 nines, those pesky little 10
90 nines sometimes, butnevertheless, very important. So
Caitlin, thank you again forjoining us on this show. Go into
some great, great topics, somelittle components as we could
say of those 10.99s that a lotof us maybe not have knew about,
I should say, and actually againkind of throwing myself in front
(25:23):
of her under the bus, I shouldsay I really didn't know about
that with the credit cards. Sonow I do and hopefully you do as
well, but as always, anyquestions you guys have for us
or if you want an introductionto Caitlin and her team, please
drop us a line.
You can even email us at helloat teaching tax flow dot com or
better yet, connect with us onsocial media on pretty much
(25:44):
every platform out there or eveneasier. Just go to defeating
taxes.com. It'll send youdirectly to our private Facebook
group. Go ahead. Join that.
This is your invite. Drop us aline through there or just ask
any tax questions. Either myselfwon't be giving any real tax
advice. Let's be honest withthat. I'm just the marketing
guy.
But Chris or other thoughtleaders in that group will will
(26:05):
be more than happy to answeryour question or connect you
with somebody who does. And Iguarantee if you have that
question, like you always heardback in school, if you have the
question, we almost bet thatother people have the same one,
so don't wait to ask it. Feelcomfortable. Ask those
questions. Let's do it together.
Let's defeat taxes. Sounds very,Viking ish of us, but, anyways,
(26:28):
we'll see everybody back herevery soon. Keep dropping us
those questions, comments,feedback, anything you have. We
are here for it, and hopefullyy'all are ready for, for tax
prep time. So creeping up soonerthan you things.
See everybody back here verysoon.
Disclaimer (26:52):
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 adviser.Securities are offered through
Cabin Securities, a registeredbroker dealer.
The content of this podcast doesnot constitute an offer of
(27:14):
securities. Offerings can onlybe made through an offering
memorandum, and you shouldcarefully examine, Offerings can
only be made through an offeringmemorandum, and you should
carefully examine the riskfactors and other information
contained in the memorandum.
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