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June 11, 2024 36 mins

In this episode of the Teaching Tax Flow Podcast, hosts Chris and John are joined by guest, Jim Cunningham, and jump deep into the intricacies of selling a business. With a focus on empowering listeners to minimize tax liabilities while navigating significant legal considerations, this episode is a must-listen for business owners considering a transition. Brought to you by Legacy Lock, the episode provides a roadmap to understanding essential components of business sales, including asset vs. stock sales, the timing of business transitions, and the legal and tax advantages of different transaction structures.

The conversation kicks off with the importance of planning when selling a business and dives into the differences between asset and stock sales. Jim emphasizes how critical it is to prepare well in advance by consulting with financial and legal advisors. The episode also explores the pros and cons of seller financing, the impact of goodwill and enterprise value, and strategic considerations for both buyers and sellers to ensure a smooth transition. With real-world anecdotes and expert advice, this episode provides actionable insights for turning business transitions into lucrative opportunities.

Key Takeaways:

  • Importance of Early Planning: Engaging with tax advisors and legal professionals well before the planned sale can significantly enhance the value and smoothness of a transition.
  • Asset vs. Stock Sale: Asset sales are generally preferred for liability reasons, but specific business conditions may necessitate stock sales.
  • Seller Financing: Offering seller financing can spread the capital gain tax burden over time, making it an attractive option for sellers who don’t need immediate cash.
  • Determining Enterprise Value: Goodwill and the ability to generate earnings are crucial to establishing a business’s enterprise value.
  • Post-Sale Involvement: Structuring deals with earnouts and consulting roles can help ease the transition and ensure continued business success.


Episode Sponsor:
Legacy Lock (www.teachingtaxflow.com/legacy)
DISCOUNT CODE: Magic1495

  • (00:00) - Chapter 1
  • (00:04) - Tax and Legal Considerations When Selling a Business
  • (04:23) - Strategies for Business Transition and Asset Sales
  • (14:14) - Asset Versus Stock Sales in Business Transactions
  • (21:39) - Legal and Financial Tips for Selling or Buying a Business
  • (31:05) - Building Your Personal Board of Directors for Business Success
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Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Intro (00:04):
Welcome to the Teaching Tax Flow podcast, where the goal
is to empower and educate you tolegally and ethically minimize
taxes paid over your lifetime.

John Tripolsky (00:16):
Welcome back to the show, everybody. Episode 87.
Today, we are gonna look intowhat happens behind the scenes,
or I should say when planning tosell a business. More to come
with our great guest.
But as always, let's take abrief moment and thank our
episode sponsor.

Ad Read (00:34):
This podcast is brought to you by Legacy Lock. If you
are new to estate planning orsimply need to review your
current plan, Legacy Lock makesit as easy as pie. Legacy Lock
is a unique platform thatenables you to easily complete
your attorney drafted documentsconveniently from the comfort of
your home or office. Your firststep to this peace of mind is
simply visiting teaching taxflow.com/legacy.

John Tripolsky (00:58):
Welcome back to the teaching tax flow podcast,
everybody. As you read as I liketo say in all of them,
hopefully, you read the title ofthe episode, the show
description, and everything elsethat came with it. As mentioned,
today, we're gonna look at thosetax and legal considerations
when selling a business. So aswe like to say, it's not as easy
maybe as selling a house. Right?

(01:19):
You just don't pop up a sign inthe front yard and, you know,
people come look at yourbusiness and say, Hey, you know
what? Yes, I want it making anoffer. There's obviously more
detail that goes into that aswell as some implications on the
tax and legal side, obviously.So, Chris Bucchero, welcome
back, sir. How are you doingtoday?

Chris Picciurro (01:38):
I am amazing, John. How are you doing?

John Tripolsky (01:40):
I am doing great, man. And this is a topic
I know you know, we say we getget excited about all of them.
This one, I've been lookingforward to because I know we get
questions around this, and Iknow for a fact that a lot of
people just have questionsaround this. And they probably
you know, it's not it's not aseasy as doing a doing a Google
search and finding all thecorrect answers because I'm sure

(02:00):
every situation is verydifferent, as well as states and
really just the type ofindustry. So I look forward to
this one.

Chris Picciurro (02:08):
Yes. I'm really excited about this episode
because we we run-in thesituations where people are
transitioning a businesseverywhere from just super small
business, almost an unsaleablebusiness, to, to a very
elaborate business. I had adiscovery meeting with a

(02:29):
potential client that sold hisbusiness to an ESOP for about
$40,000,000 this this week. Soor the week of this recording.
So you just never know whatyou're gonna run into, but very
excited.
I have a long time friend ofactually, a gentleman I went to
high school with. So that'sonly, what, 10 years ago? I
don't know. Something like that.That's as bad as

John Tripolsky (02:51):
my wife saying she's turning 22 this week.
That's a lie.

Chris Picciurro (02:54):
Oh, John. There hey. There you go, John.

John Tripolsky (02:56):
Yeah. We know she doesn't listen to the show,
like we always say, so I couldsay anything I want to wives.
Said it's true. They neverlisten to

Chris Picciurro (03:02):
the show, so we could just throw them under the
bus pretty much every episode.But, but, no, I'm very honored
to be joined by Jim Cunningham.And, like like I said, Jim and I
have known each other for many,many years. I absolutely love
the way he does business. He isan attorney.
He is a partner at DickinsonWright, which is a large law

(03:22):
firm with a ton of capabilities.He works with clients all over
the country. He's been, I knowhe's got a big client based in
the Detroit area, here in theNashville area, and I think he's
based in Atlanta area now. Andhe works with businesses,
specifically in the merger andacquisition area and other he
does other things with withbusiness clients, but we, we

(03:45):
twisted his arm and got him onthe podcast. So, Jim, welcome to
the Teaching Tax Slow podcast.

James Cunningham (03:52):
Thank you, Chris. It's it's a pleasure to
be here. We were just reflectjust just met John here for the
first time, and we werereflecting on, our our
friendship and how long it'sbeen. It's really hard to
believe that it's been 35 years.So it's a it's a pleasure to
join you here, and, we'regetting older, man.
It's, it's good stuff. So, happyto be here. This is a, this is a

(04:15):
topic that has been near anddear to me in my practice for
for over 23 years now, buyingand selling. Basically, my
practice centers around buyingand selling assets, businesses,
real estate, and then thefinancing options that go with
that. So, I've seen a lot.

(04:37):
I've I've I've I've, beenblessed with opportunities to
represent many great clientswho, like you, some have very
large sophisticated businesses,some are smaller family
businesses, but either way,these are important transactions
And, and you go through the lifecycle of a deal, it's it's

(04:58):
really an amazing thing. And, soI'm happy to be here. I look
forward to to covering thistopic and, contributing

Chris Picciurro (05:05):
a little bit. Absolutely. Well, we're gonna I
mean, the transition of abusiness, you know, can be can
be very well thought out and itcan be involuntary. And,
obviously, from a taxperspective, timing could be is
very, very important in how sowe're gonna talk today, about
the difference between an assetsale and a stock sale in

(05:26):
general. We're also gonna talkabout a couple of different ways
to structure the the thebusiness transition, either
internally or externally, Iguess you could say, and then
financing also.
You know, obviously, the morethought out the transition plan
is, and and just in myexperience, the more internal it

(05:46):
is, the smoother it is versusyou know, like, my experience
most of it comes within thewithin the tax and accounting
world, and, personally, we'vepurchased 6 books of businesses
and we sold all of them. I wouldnot buy a book of business
anymore in the tax andaccounting world just with the
landscape, but that's a that's adifferent podcast, John. It

(06:06):
actually is. It's a differentpodcast we do for specifically
for tax professionals. But, thatbeing said, a couple times we
acquired a business from someonethat was deceased unexpectedly.
We acquired a book of businessfrom someone that was terminally
ill. We've acquired a book ofbusiness that someone stayed on
and transitioned with us. So,really, it you know, how it's

(06:30):
structured can play a role inthe success and retention of of
the clients. So, Jim, we let meask this question. At what point
in a perfect world we're nottalking about owner got hit by a
beer truck or something likethat.
At what point should a businessowner, regardless of size, start
thinking about a transition?

James Cunningham (06:53):
Well, good question. And and and that's how
we how we naturally lead it off.I think, you know, the answer
varies depending on thebusiness, the individuals
involved, where the business isin a particular life cycle. As
you know, Chris, there arecertain family owned businesses
where, you know, you know,generation 1 or generation 2,

(07:16):
whoever's actively managing andcontrolling the business, where
those generations are looking topass the business on to, you
know, the next generation. Andso, you know, those situations
are kinda natural, family ownedbusinesses, and you have the the
benefit and the ability to say,you know, when you're you're

(07:37):
working with a family ownedbusiness, you're working with,
let's call it, generation 1, andyou represent that business,
there's always the naturaldiscussion when generation 2
becomes actively involved in thebusiness, whether it's a a son
or a daughter.
They're becoming active, andthat's you know, you know,

(08:04):
generation 2 is gonna take overand run this very successful
business. So you have theability then to kinda plan
around, the transition there ina in a smaller family owned
business.

Chris Picciurro (08:15):
Yeah. I agree. I think that, you know, tax and
legal considerations are veryimportant. But most importantly,
the transition has to work wellor else you have nothing to
transition. You know, if it'stransitioning to the wrong
people, especially as a lot oftimes, g two people or gen
second generation people, ifthey're not actively involved in
the business already, they mightstruggle to be good operators.

(08:37):
So depending on that, you know,there's different strategies as
far as you can use gifting attimes of of some of the assets.
You can you depending on thefamily structure, you could have
a sale, you could have whereyou're selling the assets and
and then versus selling thestock. I wanna start real quick
before we start diving into morecomplicated things. From a

(08:59):
practical standpoint, Jim, whathappens let's say you have a
literally a mom and pop shop.Let's say the let's say the the
the the the husband or the male,is owns a small engine machine
shop engine repair shop out oftheir garage, and he passes away

(09:20):
unexpectedly.
He doesn't have anyone tosucceed. At that point, you
know, you really don't have asellable asset most likely. Does
the spouse kinda just try tosell the the equipment? I mean,
what what makes, I guess, whatmakes in your mind a business an
actual have some type ofenterprise value versus just a
job? Yeah.

(09:42):
Yeah.

James Cunningham (09:42):
I think, you you know, businesses, of course,
come in all shapes and sizes. Imean, the the value the
business, of course, ownsassets. Right? So you have the
asset value of a a business. Butas as many of you know, if you
have a a business, you built areputation, you know, you have
some what's commonly known asgoodwill, That's really where

(10:05):
you have a a a business goingconcern that has the ability to
kinda continue to to grow, youknow, and generate income.
And so I the the issue ofgoodwill, I think, is probably
the best. I mean, if you have acouple contracts here and there
and and, you know, and someassets, that's all fine and

(10:28):
good. But the real the realenterprise value of a business,
I think, is is the goodwill andthe ability to generate
earnings. And so and and sothat's how I would would, I
guess, phrase it.

Chris Picciurro (10:41):
Right. And it's how sticky the business is. I
mean, if if this general ifsomeone's running a small engine
repair shop and they have acouple contracts with local
power sports sports companies,or dealerships, and and then in
2 weeks they could be replaced,you really have no goodwill.
You've got some equipment.

James Cunningham (10:57):
That's right. That's right. That's right. And
I I think one one thing that I Iwanna mention as as part of this
discussion, you know, myinitial, remarks were focused on
kind of the family ownedbusiness where you have multiple
generations. The other salesthat you see, of that's a
transition of the business,right, within the family, so to

(11:19):
speak.
The other sales that you morecommonly see are, you know, so
and so has a family business,and they they're gonna sell it
to a third party. The questionis, how does that come about? In
in in my experience, we've seenit really one of 2 ways. Either
the business owner is approachedby a competitor, someone who's

(11:42):
strategically in the market andis looking to scale up, if you
will, like you mentioned, thatyou you bought books of
business. And so as part ofthat, you may have approached
some of those firms and and, youknow, started a dialogue about,
hey.
Would you like to sell yourbusiness? I mean, that and and
that kinda happens naturally andorganically. And oftentimes,

(12:04):
that may may not necessarilycome as a surprise, but it may
be somewhat unexpected for thatbusiness owner. So, you know,
you're always then, if if youhave a client who is interested
in selling their business andhas been approached by a
competitor, then you kinda haveto really start from scratch,
Right? Because it was kind of anunexpected sale proposal.

(12:26):
The other the other situation isone where the business is, you
know, you have a business ownerwho's established a business.
Their earnings are, you know, ata at a they've grown their
earnings substantially. Theyknow that they can have an exit,
and they wanna monetize on thatexit. So they're planning to

(12:47):
move forward with the saleprocess. And and many times,
clients will come to you in thatsituation and and because
they're anticipating an exit,they have an opportunity to
plan, get their legal docscleaned up, you know, make sure
that earnings look as good as asthey can look, perhaps engage an

(13:09):
investment banker to help go outand market, the business, to
sell the business.
And so, you know, in thosesituations as a lawyer, you have
an opportunity. And as a taxadviser, we would work together
to say, okay. You know, client awants to exit this business next
year. Let's get our house inorder. Let's clean everything up

(13:32):
so that when we go to market, wecan maximize, the value of this
business.
So I'm sure you've seen that inyour press.

Chris Picciurro (13:39):
Absolutely. You've got I mean, you've in in
having as clean of books as youcan have, the larger the
business, the more due diligencethat's gonna occur, and that
that's, you know, that's humannature. So let me let me so I so
let's do this. Let's assume Jimand I are at first advising a

(14:00):
seller of a business, and thatseller is considering selling
his or her book of businesseither as an asset sale or a
stock sale. They're alsoconsidering, carrying the note,
which we could chat about.
Jim, I'll start with you. From alegal 30,000 foot legal
consideration, seller sellersaying what what are my again,

(14:21):
every situation is different,but what are my pluses and
minuses of of either carryingthe note 1 and then designing as
an asset versus stock sale?Yeah. So if we have

James Cunningham (14:34):
a client, Chris, you and I are working
with a client and we're we'redetermining structure, the asset
versus stock sale, I would say 9out of 10 times you see asset
deals from a legal perspective.As you know, the tax strategy,
of course, often drives, thestructuring of the transaction.
But from a legal perspective,nearly all buyers will prefer

(15:00):
and, again, just from a purelylegal perspective, nearly all
buyers will prefer to do anasset sale for liability
reasons. Because when you youknow, just to think about it
very simply, when you buy thestock of a business, you are
taking on that business as itis. And with all of its warts,

(15:22):
if you will, whateverliabilities are out there on the
books, you're taking thatbusiness over as a as a stock,
buyer.
Whereas if the deal isstructured as an asset sale, as
a buyer, you are forming oftenforming a new entity, and you
are acquiring the assets fromthe selling entity. And because

(15:45):
of that, from a legalperspective, as a buyer, you
generally are more you're you'rebetter off because you let's say
they're unexpected liabilitiesthat this business, has. As a
buyer of assets, you don'tnecessarily assume those
liabilities. You only assume theliabilities that you
specifically agree to assume. Soso oftentimes, Chris, the deals

(16:09):
are are asset deals.
Now there are times when we dostock sales. I don't see it as
much, but it it certainly doeshappen, if there are reasons. I
I actually had a deal, that weclosed last year, a flooring
company, and it's a family ownedbusiness. And for a variety of
reasons, it was better to do astock sale and so we structured

(16:33):
it that way. And as you know,and I know you're gonna chime in
on the tax, implications, butthe tax issues in a stock versus
asset are are like I said, theydrive the train often.

Chris Picciurro (16:44):
Right. From the so from the seller perspective,
typically, it's a it doesn'tmatter too much between asset
and stock. A lot of it dependson how you allocate the purchase
price of the assets and ifthere's depreciation recapture.
In general, a stock sale isgonna be better for a seller,
but it's not terrible to be anasset sale. I've seen I would
say 9 out of 10 are gonna beasset sales.

(17:07):
The the stock sales I've seenare due to due to potentially
licensing and contracts. I'vebeen in the m and a space,
especially with, like, insurancebrokerages. They're appointed
with certain carriers and or ormedical professionals where
they're just they have theserelationships set up that are
not very easily transferrable.That's where a lot of times and
that drives that enterprisevalue. From the seller

(17:28):
perspective, you know, theadvantage of carrying the note
is that you get to spread thegain over time, which is really
attractive.
But if the seller deeds thatcash immediately, that's where,
you know, you're gonna be ingeneral paying tax on whatever
the the capital gain is based onthe cash you receive. If you
have a seller that doesn't needthe cash immediately, then a

(17:48):
seller finance note ispotentially an option for the
seller, although the seller istaking some risk on financing
this. They do not wanna take thebusiness back. Or you can get
you can, you can engage in a amore complicated transaction
called the deferred sales trust,where the where you basically
create the create a trust thatsell that the, the seller sells

(18:11):
their assets to a trust, andthen the trust ultimately sells
it to the to the buyer. So thatcreates the advantage of that is
that the seller now gets capitalinstallment sale treatment and
even if the buyer is paying cashor getting bank financing.
If the seller carries the noteand the buyer refinances, then
the seller doesn't control whenthey pay the tax on it. And

(18:33):
right now, as we know, we are ina low capital gain rate
environment. We have an electioncoming up here that could
president Biden has proposedgreatly increasing the capital
gain rates, which woulddefinitely deflate the values of
businesses because of the taxburden. You know, that's that so
that's that's how I see it fromthe seller perspective. Now from
the buyer perspective, I'll jumpin and go first just on the tax

(18:56):
side.
If I'm representing the buyer, Iwould pay a premium to get the,
to get it to be an asset sale.Now Jim could Jim mentioned the
liability issue. Right? Why whydo you wanna bring on someone
someone else's liabilities? Ofcourse, they can be I've seen
their money set aside forpotential lawsuits or hold
harmless agreements in place,but if I'm ever if I'm advising

(19:17):
the buyer, the reason you wantan asset sale is that the assets
you purchase are depreciableassets or you can amortize them.
So, like, goodwill, that's a 15year asset that you're gonna
write off straight line over 15years. But if I'm buying real
estate, if I'm buying equipment,a lot of those assets can are

(19:39):
are eligible for bonusdepreciation, which we've talked
about on the show, and you canget a significant downstroke as
far as a immediate depreciationdeduction. Sometimes that
depreciation deduction is morethan the cash you even layout if
you're doing seller financing orusing an SBA loan. So in general
for the buyer, I'm gonna wantthem to, you know, to to push

(20:01):
towards the asset sale. Jim,what are your thoughts on
advising the buyer?

James Cunningham (20:06):
Yeah. Yeah. So, again, from from a legal
perspective, agreedwholeheartedly, you know, as a
from as a buyer in order toinsulate liability, an asset
sale is typically the best wayto go. You would hit the nail on
the head. In certain businesses,you end up doing a stock deal

(20:26):
for reasons like issuestransferring license, license,
requirements, etcetera.
So I I would say, really, 9 outof 10 times, you're gonna see an
asset sale structure that way.Did wanna mention something
about the seller note financingpiece. From a legal perspective,

(20:52):
you know, of course, there's thefinancial consideration, whether
you need the cash now or whetheryou're okay with carrying the
note. I think, from ourperspective, on the seller side,
if you are going to operate witha seller note, the important
thing you would want from alegal perspective would be
security for that note. So ifyou are gonna if you're gonna

(21:13):
finance the the the deal, it maymake sense and it may make
financial sense.
You wanna protect yourself andyou would wanna have a pledge of
really all anything you sell. Soif you're selling assets, you
would wanna have a pledge ofthose assets, and you would want
you would also wanna have apledge of the equity of that new

(21:34):
company so that if there is adefault that's the obvious risk.
There's a default here. And youwould want the ability not that
it's a great answer becauseyou're selling your business for
a reason. You don't necessarilywant it back.
But if there's a default, youwant the ability to take it back
and protect yourself.

Chris Picciurro (21:52):
And, I mean, and do you see you know,
sometimes on some of these, Iwouldn't even say larger deals.
I mean, when you're selling abusiness with 200 employees,
sometimes the risk is less thanin a business with 2 employees.
Right? Because one, you know,one employee isn't as is,
integral in every piece of thebusiness, I would say, in
general. But especially for maymaybe, like, a smaller, like, a
4 or 5 employee business.

(22:14):
Do you see it ever when there'sa seller note, do you do you
ever see it collateralized bymaybe life insurance or or
assignment of some lifeinsurance proceeds?

James Cunningham (22:22):
I have seen that. I have seen that.
Absolutely. Yeah. I mean, in abusiness, if there is a key key
man or or woman situation, thenyou would see that.
The the the key as as theseller, the key is, look. You
are you're effectivelyfinancing, at least in part,

(22:42):
this this acquisition for thebuyer. You know, putting the
financial terms aside, if thereis any you wanna get paid first,
but if you're not getting paid,you wanna be able to take that
business back, and then whoknows? I mean, down the road,
sell it again or or grow it, youknow, moving moving forward. I
mean, you know, there arecountless stories in that.
And, you know, for example, theDan Gilbert's business, I mean,

(23:08):
he famously sold that businessway back in the day when it was
Quicken Loans, and then he endedup it wasn't through a default
situation, but he ended upbuying that business back and
then growing it into, you know,what it what it is is today. So
you see situations where thereis a take back on

Chris Picciurro (23:26):
Mhmm.

James Cunningham (23:26):
On a on a business. And and so that's the
legal point. If you're gonna dothe no, make sure you get
collateral.

Chris Picciurro (23:32):
Final thing I wanna bring up today, which is
and and this is anotherdependent situation on the or
depends on the situation. But,you know, I have someone that
owns a business, and I'vetransitioned some of mine. It's
scary because of that controlfactor. Like, you you really
deeply care about yourcustomers, your clients, your
your team members, and thenthere's some people that are

(23:55):
that are kinda, like, at its endand just wanna sprint away. So
one of the things that and Iwant, you know, get your opinion
on the legal side of it.
I you know, depending if I'm repif I'm working with a seller or
buyer, I might have a differentopinion. But there's also that
human element, the transition.Does the owner stay on in in a
consulting role for x amount oftime? Is does the owner get

(24:17):
paid? Is the sale price variablebased on some type of
performance?
We see that a lot with insuranceagencies. Can you take us
through some of the just thelegal considerations? Because,
you know, I know and, Jim, youknow, I mean, you're at a large
firm, but, I mean, there's therein the tax world, there's a lot
of people that do we all, ingeneral, do things the right
way, but we do things differentways. And what I'm the way I

(24:39):
might show something on abalance sheet might not be or
the way I classify somethingmight not be some a way someone
else would. So what are some ofthe thing you know, to wrap it
up, I guess, is theconsiderations from a transition
standpoint.
If you're how would you talk toa business owner that's kind of
a control freak that wants stayinvolved, assuming the seller's
okay with it, versus someonethat wants to hand over the keys

(25:02):
and run far away, go down to thego down to the beach and have,
pina coladas all day. Yeah. No.It's a it's a great point. And
you see it you see it on in manytransactions.

James Cunningham (25:12):
You what what you're touching on is the issue
of control post closing. That'sright. We and you have you often
have and I've seen this manytimes. You often have businesses
where, the the selling owners,it's been a family business for
years years years. And so theydeeply care about where that

(25:36):
company is gonna go after thesale.
They've worked with theiremployees for years years years.
And so it's a difficult thingbecause a buyer is coming in and
paying, you know, top dollar fora business. They wanna be able
to control that business on agoing forward basis. But, often,
the seller wants to stayinvolved. So you have to kinda
juggle that.
Usually, the issue of theemployees are that that comes up

(25:59):
in many, many family owned typebusinesses where it's, hey. I
wanna sell this business, but,you know, Mary has been working
with me for 50 years, and Iwanna make sure she's taken care
of. And that makes all the sensein the world. So always
something that's negotiated andand a little bit delicate and
tricky. Chris, you mentionedanother thing, post closing

(26:21):
consideration.
So what what we see more thanever, sales often have earn out
provisions. So, you know,there's a purchase price for the
business, whatever it might be.And then on a going forward
basis, whether it's a year or 2years, if that company achieves
certain milestones and issuccessful, there's more payment

(26:43):
that the owner gets. So it's,you know, it's incentive. And
oftentimes, you know, the therelated issue that you mentioned
is you have a a selling ownerwho does stay with the business
for a period of time.
They wanna make sure there's asmooth transition. And,
oftentimes, yes, they are paidas consultants, but they're

(27:03):
they're they have a veryimportant stake in the the earn
out provisions. So they it's ineverybody's best interest for
that company to be successfulpost sale. You see that often,
you know, Chris, you run intotransactions where you have
private equity or what we'llcall financial buyers. Right?

(27:25):
They're buying a, I'll use theflooring company as an example,
they're buying the flooringcompany, but they don't know
anything about flooring, really.They know it's a really
successful business, and theywanna operate it moving forward.
So, oftentimes, it's importantto those financial buyers to
have, you know, continuity ofbusiness and that owner stick
around for a while. So, yes,it's it's important, and we see

(27:46):
it a lot.

Chris Picciurro (27:47):
5 live. Final question. This will be can you
give give everyone 1, 2, maybe 3tips? Because we're talking
about transactions. You know,this this is about tax planning
and strategy and and reducingthe tax of paying your lifetime
in this podcast.
So what tips, just rule ofthumb, easy tips, can you give

(28:08):
someone thinking about sellingtheir business in the future
that wants to actually add tothe enterprise value? And then a
couple tips for people that areconsidering buying a business
that that have never gonethrough due diligence. Any red
flags that they should look outfor?

James Cunningham (28:24):
Yeah. So I think on the sell on the sell
side, if if you are someone thathas a an operating business and
you're thinking that you may beinterested in selling it, you
know, it's it doesn't have tonecessarily be tomorrow, but
maybe within the next, I don'tknow, 3 to 5 years, something
along those lines. I don't thinkit's ever too early to meet

(28:47):
with, you know, someone like youon the financial side, just to
talk a little bit about, hey.I'm thinking of selling this
business. You know, whetherwhether you think that your
business would be attractive toa competitor or whether you'd
like to go and and have aninvestment banker, you know,
market and try to sell thebusiness, I think it would be

(29:07):
good to talk to a financialadvisor to help understand, you
know, the the issues around, youknow, how how will my how will
my business be valued?
As you know, Chris, oftentimes,it comes down to your earnings
and what multiple Mhmm. Will beapplied in a transaction. But a
lot of people don't know thatnaturally. And so I I think
talking to a a financial adviseron the sell side, it it's also

(29:30):
never too early to talk to thethe attorney, that you may use,
or if you don't have one, reachout and say, hey. Thinking about
selling my business.
Are there things that I shouldthink about? Of course, on the
on the diligence side, you youmentioned look. A lot of
businesses kinda get going, andthen they run. And sometimes the
paperwork isn't necessarilywhere it needs to be. On the

(29:52):
legal side, you know, we couldcome in and help a company get
prepared for a potential sale.
So talk to your tax person, talkto your attorney, and just have
a casual conversation on thesell side. On the buy side, I
think that, you know, oftentimesthe issue is finding,

(30:12):
identifying these businessopportunities where you want to,
invest. And so, you know, on thebuy side, if you're looking, I
think that, oftentimes the bestcourse of action would be to try
to get in touch with investmentbankers, other people in that
network that, you know, dealwith businesses that, you know,

(30:35):
come up for sale often. I andand so I would I would suggest
that would probably be the firstplace to start. I mean, you
could certainly start with anattorney.
I I'm not terribly helpful untilyou've identified a business and
you say, Hey, I like thisbusiness. I've been working with
my financial advisor, and Ithink we're gonna offer x. At

(30:55):
that point, that's when youwould wanna, you know, come talk
to me. We could help you get theLOI together and start that
that, that that acquisitionprocess.

John Tripolsky (31:05):
Awesome. Awesome. Well, you you guys
finally I mean, very rarely do Iever shut up for an entire show,
but I I filled up about 2, 2notepads full of random comments
here. And, Jim, before weforget, if anybody has any
specific questions about this,what's the best way that they
can go about maybe contactingyou or or contacting your firm

(31:26):
directly?

James Cunningham (31:27):
Yeah. Our our firm's Dickinson. Right? You
know, quick quick search. You'llfind us there.
And, we have, don't quote me onthis, but probably close to 600
lawyers now. We're a growingfirm. We're in we're in a number
of states. Don't quote me on it,but it's 13 or 14 different
states, and and we are a fullservice firm and and, you know,

(31:49):
cover all practice areas. Youyou should be able to find me
there, and then, yeah, Chris, Iunderstand that we're gonna put
some information out so that ifif people do have questions,
please feel free to reach out.
Always happy to, you know, talkabout this topic. And like I
said, it's an important one andand, one that, that I'm pretty
passionate about.

John Tripolsky (32:08):
Awesome. Awesome. Well, thanks, Jim, for
joining us on this. And, youknow, it is as mentioned, I
believe, you know, we spokebriefly before we started
recording this as it's nice tonice to see somebody that's
known Chris even longer than Ihave. So as much as me and him
banter back and forth, maybeI'll ping you one day and we can
get some skeletons in thiscloset out in the Yeah.

(32:28):
On the public.

James Cunningham (32:29):
I'm down for the Oh, lord. I'm down for that
for sure. Just let me know.That's great stuff. It's great
stuff.
But, yeah, thanks for theinvite. It it it, this was fun.
Pleasure. Chris, I know you dothis a lot. This is my first go
at it, so, audience, pleaseforgive me.
I enjoyed it, and, thank you,Bill.

Chris Picciurro (32:45):
You did amazing, and you could see why
we wanted Jim on the podcast.You know, whenever you hear
about attorney, your accountscome with a certain stigma,
CPAs. Right? Like, oh, yeah. I'mgonna smell like a sandwich from
yesterday or a carton ofcigarettes, and I'm gonna have a
coffee stain on my shirt and apack of protector, and be
unkempt.
But in attorneys sometimes and Idon't find this with the ones we

(33:06):
work with, but, you know, theythey come with a certain kind of
a stiff stigma, but I thinkyou're extremely practical, and,
that's among other greatattributes, but that's one of
the things I really knew thatyou'd connect with our audience
with. So thank you.

John Tripolsky (33:21):
Well, thanks, Chris. Thanks. I appreciate it.
You mean, Chris, you're talkingabout you're talking about
accountants with pocketprotectors and coffee stains and
that it's, what was it? I can'tthink of the the movie, but oh,
Ron Burgundy.
Right? He goes attorneys. Hereminds me of the leather bound
books and rich mahogany. Butanyways, on on that note,

(33:42):
gentlemen, both thank you somuch for this. I know our
audience is gonna absolutelylove this topic again.
It's as we mentioned as wekinda, you know, treaded water a
little bit here at the beginningis that we we know it's
something a lot of people havethose questions on and, you
know, even going way back intobusiness school, I think we
probably all heard at some pointin time, you know, you build to
sell, you know, when you go intobusiness. So it's I think we I

(34:03):
wouldn't say we exposed. Wediscussed a lot of the little
topics. I think that, you know,some people don't think about
maybe. Right?
So just going through thatprocess. But I think the
important thing to leave on thisnote is that this probably is
not the best thing to take on onyour own. Right? Seek out some
professional advice. Reallygoing back to something that I

(34:24):
know teaching tax flow, Chrisand myself and even various
guests have always talked aboutis building your personal board
of directors for yourself, foryour business.
Not we're not talking to aformalized board necessarily
like you hear in a lot ofnonprofits and organizations and
businesses. But just havingthose individuals that you could
call on, you can lean on forthat information. So, Jim would

(34:45):
probably make a good one ofthose individuals as well as as
Chris yourself. So thank youboth again. I know I said a
couple of times as we close outhere as I always like to end
every show with, we will see youback here next week.
Same time, different date, butdifferent topic here on the
Teaching Tax Hello Podcast.Thank you, Jim and Chris, for

(35:10):
diving into this one with us. Iknow we, we tend to get a little
lengthy on some of these topicsbecause they are so interesting.
I really do like it how ourfirst episodes way back when,
you know, episode maybe, like, 1through 15, we really tried to
stay about 15 minutes and kindaprided ourselves with that for a
while, but then these topicsjust keep getting so good. The
guests are so great.

(35:32):
You know, honestly, we don'teven keep track of the time
anymore. We just let it rollwith minimal editing, believe it
or not. So we love doing these.As always, keep the topic
interest coming our way. We lovethem.
That's what drives us here atTeaching Tax Flow, and we look
forward to seeing or I shouldsay you guys hearing everyone
again next week. Thank you asalways.

Disclaimer (35:57):
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

(36:18):
securities. Offerings can onlybe made through an offering
memorandum, and you shouldcarefully examine the risk
factors and other informationcontained in the memorandum.
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