All Episodes

April 8, 2025 48 mins
Welcome to the "Show Me The Way" podcast with David Seitter

In this episode of "Show Me the Way," Dave delves deep into the world of business succession planning and tax strategies with Stuart Sorkin, founder of Business and Legal Advisors. Stuart shares invaluable insights on how business owners can make informed decisions that not only protect their legacy but also maximize the financial potential of their enterprises.

Ep. 66 — From S to C: A Surprising Business Strategy for Massive Savings

Stuart Sorkin brings a unique blend of expertise to the table with his vast experience in tax law, business consulting, and succession planning. Educated at renowned institutions like the University of Miami and boasting a career that includes significant time at major firms like Arthur Anderson and Coopers, he has helped countless businesses navigate complex tax landscapes and achieve optimal exits.

Understanding the Importance of Business Succession Planning

Business succession is more than just passing the baton; it's about ensuring continued success and financial stability. Stuart emphasizes the concept of aligning personal and business goals. He believes that succession planning should focus not only on financial aspects but also on preserving family harmony and establishing a clear future for the business.

The Shift from S Corporations to C Corporations

A major topic Stuart covers is the potential financial benefits of converting from an S corporation to a C corporation, especially post the 2017 Tax Act. While many fear the perceived "double taxation" of C corporations, Stuart explains how strategic planning can lead to significant tax savings and enhanced business flexibility. He also highlights the advantages of the C corporation structure for attracting investors, thanks to its ability to offer liquidation preferences and reduced phantom income risk.

Planning for Successful Transitions

Stuart shares insights on designing a business model that supports all of an owner's long-term goals. He advocates for thorough estate planning, particularly for clients approaching significant tax limitations. Utilizing strategic tools like dynasty planning and trusts can ensure that businesses are not just handed down but are set up for future success.

The Buying and Selling of Businesses: Key Considerations

For those considering buying or selling businesses, Stuart offers invaluable advice. He underlines the importance of due diligence, integration planning, and having a clear exit strategy. Sellers should prepare their due diligence archive well in advance, while buyers should focus on integration and back their acquisition with a solid working capital line. Both should remain prepared to adapt and make the experience as smooth and beneficial as possible.

A Passion for Helping Businesses Thrive

Stuart's passion for helping others is evident, as he dedicates his career to educating business owners and facilitating successful transitions. He continues to provide consultations to potential clients and partners, reinforcing his commitment to sharing knowledge and fostering growth in the business community.

For those interested in pursuing further guidance, Stuart is open to consultations, offering a hands-on approach to learning about your unique business needs and how to best address them.

 

For further inquiries and consultations, reach out to Stuart Sorkin at stuart@businessandlegaladvisors.com or visit his website to ensure a productive session tailored to your business needs.

 

 

 

To reach out to Dave for advice or consultation, please visit www.davidseitter.com or email him at dseitter4@gmail.com

 

Disclosure

This podc

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Dave (00:00):
Show me the way episode 66, the tax master.
In this episode, we talk with Stuart Sorkin.
He's an attorney.
He's a business consultant.
He happens to be a tax attorney and he'salso the owner of business and legal advisors
about his life and assisting business owners.
And his gift today to all of you as towhy you should convert your business

(00:22):
from an S entity to a C entity.
Come to show me the way a podcastabout business succession planning,

(00:42):
the merger in acquisition experience.
And successful exits.
I am your host, Dave Sider.
I want to thank you forchecking out my podcast series.
Show me the way.
If you are seeking assistance with yourbusiness dreams, please consider checking
out the resources that I've made availableto you at Either my LinkedIn website or

(01:03):
my podcast, again, Show Me The Way, oryou can check out my book Quiet Plans
and Exciting Results available on Amazonin either written or audible format.
And as well, my website, davidsider.
com, where I have quite a bit ofcontent for you to consider and
information on how you can, for a verynominal price, access an assessment

(01:27):
that you and I can review together.
To discuss where you're at and where you wantto go as far as your dreams are concerned.
And I would look forward totalking to you about your future.
Ladies and gentlemen, boys and girlsjoining me on today's show is Stuart Sorkin.

(01:48):
He is an attorney.
He is a CPA.
He is a business consultant.
He is a tax attorney.
This guy has more degrees than anybodyI've talked to on this podcast.
It's going to be exciting becausehe has a wide range of knowledge.
And experience.
And he's going to tell this story ofhow he's been helping businesses and
why you should consider shifting atthe right time, at the right time and

(02:10):
place from an S entity to a C entity.
Stuart, welcome to the show.
Hello there.
Thank you for having me.

Stuart Sorkin (02:20):
Come on down.
Let's play The Feud.
Let's go.
Okay.
Thank you.
I was born and raised in Chicago, fiveblocks from Wrigley Field, which probably me
explains why I'm such an eternal optimist.
I was very lucky that I had a fatherwho was an entrepreneur, businessman,

(02:41):
and he allowed me to sit in to work.
I worked for him in high school and incollege and got to understand, learn
the art of the deal from someone.
It was really good at it.
But the other thing thataffected my career was my father.
I started a clerk for the lawfirm, which represented my father.

(03:03):
And I saw the relationship that my fatherhad with his tax attorney and how the two
of them would, the yin and yang that wasbuilt between the businessman and the tax
attorney and how a deal was put together.
And I said, this is what I want to do.

Dave (03:22):
Lucky man, lucky man, you figured it out so early on.
Let's talk about, I think, next.

Stuart Sorkin (03:30):
Where'd you go to school?
I spent two years having a wonderfultime at the University of Wisconsin.
And after that two year period of time,even though I said I wanted to be a
lawyer, I said, if that's what I want,I gotta take school more seriously.
And to find that out, I took a gapyear, started as a messenger with a law

(03:50):
firm, worked my way up to a paralegal,went from there to American University
in Washington, D. C., where I got mydegree in accounting and finance, sat for
and passed the CPA exam while I was inlaw school at the University of Miami.
Crazy.
And I went to the Universityof Miami for one major reason.
It was the only school in thecountry that allowed to take

(04:13):
courses in the master's program.
Now that was incredibly good until Itried to go for my master's degree.
And I was at George Washington universityand they had to permissibly allow me to
transfer to Georgetown because I didn't haveenough courses that I didn't already have.
Oh, well, so I got a very broad base.

(04:34):
I did the, I did the LLM while Iwas, while I was working full time.

Dave (04:39):
Good gravy.
That's just, I don't want to say impressivebecause that might undersell what
you're doing, but that's significant.
You're able to do that with all thoseadditional challenges of essentially being
in school full time or working full time.
So after you get out of school, what

Stuart Sorkin (04:54):
did you do?
I started working for Arthur Anderson.
And it was 1981, and I started workingaround with the early incarnations of PCs.
And I had my first experience of becomingan expert in something that was repealed as
quickly if you remember Safe Harbor Leasing.
I became an expert in Safe HarborLeasing, but what I figured out was it

(05:20):
was a perfect place to do spreadsheets.

Dave (05:22):
Because

Stuart Sorkin (05:23):
you could track.
Across how the benefits worked, whothey went to and everything else.
And I was then approached byCoopers and Library to start their
tax application software division.
And I feel I gained an incredibleknowledge of the internal revenue code,
because if you can put the internalrevenue code into four into mathematical

(05:44):
formulas, they prove out all times.
You can create amazing planning tools.
And in, I spent four years with Coopersand in that period of time, I built
the department of 14 people and mysoftware was used by the House Ways and
Means Committee and the Senate FinanceCommittee to analyze the 1986 Tax Act.

(06:05):
And because of that, I was quoted at32, I was quoted to be a bleeding tax
expert in USA Today and Time Magazine.
I had reached my firstmajor life goal, to be an

Dave (06:15):
expert.
Good for you.
And by the way, ladies and gentlemen,he lives outside of Washington, D.
C., so I'm asking him to be in chargeof watching those people inside
the Beltway, but please continue.

Stuart Sorkin (06:26):
I don't know if that'll, that'll work.
I left Cooper's and went to a large Lawfirm and ended up having a client that
was set up a mutual fund to buy failingSNLs and banks under the Southwest plan.
Oh, wow.
And I then created spreadsheets to analyzethe Oreo, the back that experience.

(06:52):
And sitting in meetings with myclient, OCC, FDIC, they'd always try
to jam me with extra bad debt money.
Right.
And I could put the number in andsay, if it's more than this, we walk.
Because they had proved out my formula.
So, fairly successful negotiating technique.
Large firm, Louisville based, didn't knowhow to run a Washington based office.

(07:16):
Washington based partnerpassed away unexpectedly.
Firm went through a Saturday night massacre.
I had an offer the day, the day it wasannounced cause I saw the writing on the wall
and I went to work for a boutique securitiesfirm where I read, wrote business plans and
read the offerings for one of the significantangel financiers in the, in the area under

(07:40):
learning how no good deed goes unpunished.
The securities partner at the formerfirm was looking for a place and I
brought him to the firm I was at.
And within six months, he andthe manager partner got in a
major fight and bloped the firm.

Dave (07:56):
Jeez.
Well, that was not you, but that happens.
And I, I understand,

Stuart Sorkin (08:01):
but I ended up going back with the real estate and business arm of that
firm and did mergers and acquisitions, estateplanning, general corporate, and probably
one of the other reasons why I'm good atwhat I do is I'm a dinosaur and I think.

(08:22):
You're smiling because you know what I mean.
I know what you mean.
And that is, I love that thelaw has become specialized.

Dave (08:30):
Yeah.

Stuart Sorkin (08:30):
But the problem is that specialization means the estate planner
doesn't know the effects of an M& A deal.
On the estate plan.
And having that broader understanding ofhow it all goes together is, is important.
So now we're 1992 and there is, asyou remember, a major real estate.

(08:55):
recession.
In fact, the joke around Washingtonwas, you know, the difference between
a pigeon and a real estate developer?
No, sir. That one didn't come.
At least, at least, at least the pigeoncan make a deposit on a Mercedes.

Dave (09:09):
I'm going to save that one.
It may come back around again.
I hope not.
It's so, it's so funny you say that becauseof the 85, 86 time period, the 91 to 93
time period and looking at the bubbleof 2001 and 2008, we've been blessed
the last however many, what, almost15 years other than even with COVID.

(09:30):
We've just been dumb lucky.
Yeah.

Stuart Sorkin (09:32):
Anyway, please continue.
And so, and the firm is having issues.
They owe me money.
I have just gone through a divorce withmy, and my two children who at the time
were nine and seven wanted to live with me.
And so I became a, I, the money theywere giving me over a couple of months

(09:54):
and I became a stay at home dad.
But I was working with as many as 13 lawfirms during that period because all of
my partners had spread to various places.
They appreciated my expertise.
They appreciated having.
My credentials on their letterhead, butthese were the days before the internet.

(10:15):
So I would get a disc FedEx to me at 8am inthe morning and I had to finish work by seven
so I could get to the local FedEx officeso it could be delivered the next morning.
Oh, well.
But, it helped me in a major way becausein what we do, Dave, exit planning and

(10:37):
succession planning is a team sport.
Yes.
And if you don't and can't playwell with multiple others who also
have egos, you're going to have a,you're not going to succeed at it.
So my ability to work with 13 different lawfirms who had 13 and some were really easy

(10:57):
to work with some not, but I sure as hecklearned how to get things done on that level.
And they're all special, ladiesand gentlemen, just ask them.
And so, 2005, I'm standing on the sidelineswith my son, who's my middle child, who was
the last one who was living with me, and Isaid, okay, what are you going to do now?

(11:18):
And I first, which, if you are abusiness, if you are looking, And you
need, don't know how to market, network.
BNI is one of the greatest placesto learn basic networking skills.
I am still working with people 20years later that I met in B, in BNI.

(11:38):
So

Dave (11:38):
please explain to people what BNI is all about so they know.

Stuart Sorkin (11:42):
BNI is a, basically a networking organization that you commit.
To come to once a week with the goalof helping being there effectively
being the sales arm for the othervarious members in that group.
And their slogan is givers game.
And that is how I look atlife also, is giver's gain.

(12:08):
I then did a workshop, a men's communicationsworkshop, and I ran, met a businessman
who named Dick Stiglitz, who I helpedsell his government contracting business.
And we decided as a give back to writemy book, our book called expensive

(12:29):
mistakes when buying, selling businessesand how to avoid them in your deal.
And it came out in January of 2010, thefirst year, the baby boomers hit 65.
And it was written as a give back.
And I guess it's gratifying that 12years, 14 years later, it's still got
four to four and a half stars on Amazon.

(12:50):
So, and that was the goal.
It was a give back on general knowledge.
But I also learned things in workingwith Dick about putting M& A deals
together of how an entrepreneurwho's ran this business for 20 years.
And so it gave me a philosophy oflooking at how we look at the business.

(13:13):
How do we look at the business?
What is the purpose of the business?
And decided to concentrateon succession planning 2010.
2018, I formed a business legal advisorswith its tagline being Aligning your personal
and business goals for a successful future.

(13:36):
The number of deals theywill can probably tell you.
Uh, unhappy sellers, unhappy buyers,sellers who ran out of money, sellers,
kids who wasted all the money.
I decided that there was a, there's ahole and that I was uniquely qualified

(13:56):
to help business owners fill that hole.

Dave (14:00):
Well, let's get into it.
That is a critical part ofwhat I want to cover today.
So let's, let's talk about what isthe business model, if you would.
The business

Stuart Sorkin (14:12):
model is one between now and 2042, the value of the transition
market is between 35 and 70 trillion.
If you consider that the entiregross national product is 26

(14:32):
trillion, this is a massive area.
It is an area.
And the reason of the differences.
It's how successful that transition is.
And I'm dedicating myself to try tomake it as successful as possible
for as many people as possible.
Ladies

Dave (14:49):
and gentlemen, I have, it's interesting because I have quoted
somewhat of the same numbers, not quitethe same, but I know it's in that range.
But here's the first guy that I have met whosaid, I'm dedicating my, basically the rest
of your career to this commitment to make.
The transition with all of this money, butreally more the heartache, the anxiety, the

(15:12):
emotion that comes with this, that you wantto get out in front of it and help people.
I don't, I don't hear anythingin here about money either.
That's the funny part.
It's the passion.
It's the commitment as a human being.

Stuart Sorkin (15:23):
And it's the idea that it's not what you leave your kids.
Yeah.
It's how you left it to them.
Very good.
Are you, the other one is.
You want Christmas dinner to beas pleasant after you take that
long dirt nap as it was before.
Do not do, there are so many mistakesI have witnessed in family transitions

(15:44):
that have broke fractured families.
And so the concept of making sure thatone, that the fit that you've done
everything you can to protect the familyto that we have partners who are all
rowing the boat in the same direction.
And three.
We are designing a business that, if weare successful, will fulfill all of the

(16:10):
owner's desires financially for the restof their lives and any legacy they want.
And as I've said to you, Dave,when we first talked, I can't
believe people pay me to do this.
Mm hmm.
Because if I'm doing it right, I'mhelping people achieve their dreams.
And as John Grisham said, tax lawis the highest form of legalized

(16:31):
gambling with other people's money.
Yeah.
Yeah.
And if I can help, if I can help clientspreserve assets, preserve family harmony
and get them a better value for theirbusiness, that's a great way to live.
Absolutely.

Dave (16:46):
Along those lines, that's a lot to take on.
Is this something you do all by yourself?

Stuart Sorkin (16:51):
No, because I think I just said to you earlier,
this is a team sport, right?
To do what I do, I come inat a 50, 000 foot level.
And bring it down to the 10, 000 foot level.
When I then can bring the airplanein full of the consultants to fill
the pieces that need to be done.

(17:13):
But you have to get by it.
You have to make sure thatthe partners are all good.
You have to make sure that you're built.
If you're building a managementteam that you're going to have,
you put the plan in to keep them.
Yes.
So these are things.
And as I said, I have a passion forit because also with the BEI, I take

(17:35):
probably at least one to three calls aweek from someone at BEI or some other
strategic partner saying, Hey, yougot an, I got this tricky situation.
Can you help me?
Can you got an idea?
Now probably 60 percent of the time, 70percent of the time I give them, I help them.
It's not going to be billboardfor me, but I'm helping.

(17:56):
It's the same thing in myview of working with a client.
I don't, I do complimentary meetings, butI don't do a complimentary meeting until
the client fills out a questionnaire.
I want to know what I'm walking intoand so I can make the most of it.
I provide white papers that summarizethe things that we've covered in that

(18:17):
thing and then says, if you thinkthis is a value, contact me and then
we can talk about it and engage.
So,

Dave (18:26):
let's start at the very beginning.
Let's start with, I think mostrecently, we remember, uh, former
President Trump and the 2017 Tax Act.
Let's start from that pointforward in dealing with the issues
of S entities and C entities.

Stuart Sorkin (18:43):
Well, what I have told, tell every client at this point in
time is if you have not Evaluated the Sthe flow through, because there's also
LLCs flow through entities versus theC corp since the 2017 act, you may be
leaving millions of dollars on the table.

(19:05):
And I will also tell you that you willprobably find a lot of your CPAs will
tell you, no, you don't want to do that.
There's double tax.
Well, there is some double tax, and we'lltalk about that in a minute, but it's really
the issue is that they have to do some realwork when it comes to year end planning,

(19:30):
because it's one thing if you're an S ownerand they say to you, oh, well, you know, you
got a little more income, you're reporting onyour tax return because we missed something.
That you're okay with.
But if they miss and you end up witha significant amount sitting in your
corporation that you're going to haveto take out and pay double tax on,
you're not going to be very happy.

(19:51):
So therefore, that is somethingthat you have to understand is you
will run some resistance from CPAs.
But some, some do understand how this,the, the, the advantages and so on.
But I will say you will get somepotentially some resistance, but here's

(20:11):
the real, let me give you a couple ofthings to think that what, where this
would be really important to think about.
The reason people don't like Ccorporations is quote double taxation.
Well, it is not really double taxation, theeffective tax rate on money that goes into a

(20:35):
corporation and then comes out as a dividend.
Is either 32 percent or 37.
85%, depending on if you're inthe maximum tax bracket or not.
Considering that the 21 percent tax rate isthe only permanent change in the 2017 act.

(20:57):
And that effective one, one26, you're going to have 39.
6 percent individual rates.
So a couple of comments I'm going to make is.
I would say, in my experience,The vast majority of S corporation

(21:17):
stockholders, a significant amountof cash in their business and don't
take out all of the S distributions.

Dave (21:27):
By definition, sometimes whether it be a lender or a bonding company,
in particular with constructioncompanies, I'm on your page.

Stuart Sorkin (21:33):
So if you have to keep money in the company.
Would you rather do that with aneffective 25 percent tax rate?
Cause you do get deductible state incometaxes on the corporate side versus 39.
6 and for the next two years, nondeductible state income taxes.

(21:54):
Now, so that's one side of the investment,but here's a couple other points.
If you have heavy debt, becauseyou've done some acquisitions.
Or major financing.
Would you rather pay off that debtwith 75 cent after tax dollars
or 60 cent after tax dollars?
Also, I have some clients here thatmake million, million and a half a year.

(22:20):
They're living on half a million after tax.
Why would you take thatmoney into your own name?
Why not keep it in the company?
You have to show reasoning whyyou're doing that, but the point
is you keep it in the company.
And you reinvest it in publicly tradedstock because the corporation gets a 50

(22:44):
percent dividend exclusion on the investmentof stock, which means the effective tax
rate on growing your reinvestment income.
Is 10 and a half percent right now comparethat to the 39 and probably it's actually 43
because anything you're doing in investmentincome is also going to trigger the 3.

(23:05):
8 Medicare tax.

Dave (23:07):
I'm going to ask people when they get here.
Uh, these are big numbers.
I want you to understand the numbers.
You're gonna have to run thepodcast back and listen to it.
I think to get the full effect,but let's, let's do this.
Let's quantify The use of this device byasking you who would be the best candidates.

Stuart Sorkin (23:28):
Okay.
Best candidate.
There are a couple of different candidates.
First, I want to say that if you arecreating a product and it's going to
take you at least five years to get it towhere you're going to hit a liquidation
of that, you are absolutely missingthe greatest thing in the world almost.

(23:50):
With regard to not being able to electsection 1202, 1202 qualified small business
stock allows each stockholder, it's not alimit on the company, it's each stockholder,
10 million of excluded gain, or 10 timesyour 11 times your investment now, obviously.

(24:14):
That helps you a great deal with the conceptof if you need to raise investment capital.
Also, I don't know many investors whoreally like to invest in S corporation.
I'm sorry.
I agree.
But yeah, go ahead.
Because one They're scared they mayget phantom income from you because
they may not make the tax distribution.

(24:35):
And on the other side of the coin isthey really don't want you to make
the tax distribution because you'restripping out 40 percent of the profit.
So the idea of having a C corporationwhere your investors only get dividends
also with a C corporation, youcan give a liquidation preference.
Most investors like the concept of saying,Hey, I don't mind investing in this

(24:59):
business, but if this goes to hell in ahandbasket, I want my money out before you.
You can't do that with an S. But I thinkanother issue that has come into play in the
technology in certain companies is the recentrulings on, on non competition agreements.
Whether the FTC rule is establishedor is thrown out or not on a federal

(25:22):
level, there are enough states outthere who have adopted it in some form.
So in most cases, you probably don'tneed a non compete, a non solicitation
agreement of employees, et cetera, or work.
But in those cases where you needa covenant not to compete, the best
and only way to do it today is tocreate an employee class of equity.

(25:46):
The employee class of equity can mirror anoption in the sense of vesting valuation.
Example is that if someone gets their stockand it's a five year vest, they leave at
the end of two years, they get the higherup 40 percent of the fair market value or
what they actually paid for the equity.
Secondly, though, 20 percent of anymoney that goes in that they get

(26:12):
goes into a covenant not to compete.
That is paid out on a monthly basis.
If you compete, it's paid intoescrow can't be a funding vehicle and
prevailing parties gets their fees paid.
You have a liquidating damageclause, but the next level is.
If I've done this right, I'veconverted what would have been

(26:34):
100 percent ordinary income to Mr.
Key Executive to 80 percent capital gains.
Okay, so now I can ask something of the,I can ask something of that key employee
because I just saved him a ton of money.
You're getting 20 percent of closing,you're getting 60 percent at the earlier
of one year after acquisition or 30days after constructive termination.

(26:58):
Change your job title, moveyou, cut your pay, et cetera.
The balance in the fundedcovenant not to compete.
I believe that most companies would payyou significantly more for a company where
they had your management team locked up fora year and a covenant for a second year.
You've also done something else.

(27:19):
You've funded the severance package ifthey want to get rid of the executive.
You've also increased thelikelihood you will actually close.
From LOI to definitive documents becausethe percentage I think currently is about
63% Of those deals that are, you haveassigned LOI, 63 percent do not close.

(27:43):
One of the bigger reasons isthe key employee who green nails

Dave (27:46):
you.
And to your point too, if you put themin a position that they have an equity or
potential equity stake, they're now an ownerand courts treat owners differently than
employees across the board on not competing.
Exactly.

Stuart Sorkin (28:00):
So you nailed it.
Well, not only that.
You've aligned your goals.
You have aligned your goals.
They have as much desireto grow the business.
And, you know, now the, the big problemthat most people have is how do you
get them the equity, because there's alittle code section known as code section

(28:21):
83, which says, if you give stock toan employee, they have phantom income
to the extent of the fair market value.
Okay, the position that I take is,well, I think everyone understand,
well, I'm going to assume that if I saythat concept of valuation discounts.

(28:43):
For lack of marketability, lack of control.
I would believe that I have an even ahigher percentage when I have someone
who is signed on to a vesting valuationand a 20 percent haircut for covenant,
not to compete and a stable, right?
So I can go to Mr. Key employee and say.
I got a deal for you.

(29:03):
I'm going to sell you equity in my companyat 60 percent of its fair market value.
And I'm going to let you, and I'm goingto, you're going to pay for it out of a
note that's going to be paid for out of thediscretionary bonuses I'm going to declare
for you over the next couple of years.
Some of my clients are very, arevery generous and they say only the

(29:27):
after tax that they take the tax out.
Some say, I want to paysome skin, pay half the tax.
So now for Mr. Founder, let's,now I'm going to give you a real
good numeric example here, Dave.
Mr. Founder has 100, 000 ofdiscretionary income in the company.
He takes it.

(29:47):
He nets 55, let's say.
Reasonable, 55, 60.
Instead, he pays to Mr. Key employee.
Mr. Key employee is still in asignificantly lower tax bracket.
So let's say that his burden is 30%.
70 percent rolls into thecompany, which now Mr. Founder
can take out as a dividend at 15%.

(30:09):
So it's a virtual, if there's a bigenough difference in the salary, Uncle
Sam is effectively paying your, it'sall coming out of Uncle Sam's taxes
because the founder is paying less taxesbecause he shifted that income to the
employee and then he gets the income backat favorable capital gains treatment.

Dave (30:27):
It's just fascinating to listen to you.
So thank you.
I know the audience feels the same way.
Again, I think you're going to want to goback and listen to this very carefully.
So roll back the podcast when youhave a chance and listen to it.
But let's talk now about generalbenefits of this conversion.
I love the process on succession plan,but now the day in day out player.

(30:49):
Well, let me add

Stuart Sorkin (30:51):
one other point about succession planning.
And that is most of my clients.
If they're selling their business aregoing to be pushing against the new estate
tax limitation when it changes in 2026.
Correct.
You cannot do dynasty planning withthat, with, with flow through entities.
Correct.
Because a trust reaches the highesttax bracket on ordinary income at

(31:14):
13, 000 versus a trust does getfavorable capital gains treatment.
So all it's going to receive is C income is,is Capital gains, income and sales proceeds.
So you now can build up that dynasty.
Well, the other point is using this trust is.

(31:35):
A lot of my clients say, yeah, but Idon't know that I want to give it away
where I can never access it again.
How about naming the surviving spouse as theprimary lifetime beneficiary during her life?
Then you've given it away, but youcould effectively strip it all back.
Not a good idea from a tax standpoint,because you've now wasted part of
your unified credit, but you can,you can handle the disaster scenario.

(32:00):
What we do Dave, is risk management.
Yes, sir. This is how you can manage therisk of, I've got one client now that we're
looking, he's, he's right at 14, he's 70years old, and we're going to probably
strip out 2 million before he gets an LOI.
And that point, he should probably,he'll probably be, won't have

(32:23):
enough growth to probably push himback over the inflation number.

Dave (32:27):
Ladies and gentlemen, this is advice you're not going to
see off the street, so to speak.
Very insightful.
Let's talk about John Q., public businessowner, and how he should look at it as he's
running his business day in and day out.
Okay.

Stuart Sorkin (32:44):
Here's another point.
If you are an owner and an employee of an Scorporation, you can't take, you have to pick
up his income, all of your benefits, right?
No longer true if you're a C corp, butthe better piece is you can also establish
a medical reimbursement plan and cover.
If you don't have a lot of employees,you can cover a lot of them.

(33:09):
You can give three, five, 10, 000.
And free medical effectivelyto your employees.
Great benefit for employee retention.
Cause that is the major issueis your most valuable assets and
most businesses, your employees.
So you need to figure out how you'regoing to treat them better, but I'll

(33:29):
give you one, I had one client, weconverted them to see for only one reason.
He had a daughter that hada substance abuse problem.
She was under 25.
We could cover her and he wasable to put through two rehabs at
50, 000 a piece above the line.
Wonderful.
Wonderful.
So, also.

(33:49):
One, one other thing, individual, not havinga 1231 year in the idea that if you have
a September 30th year at each year, you,as the founder have the ability to decide
how much dividends you want in or howmuch income you want in which year, right?
Absolutely those benefits, but it's theidea also that if you're a family business.

(34:16):
This is the one area where you haveto, is family businesses manage
transfers, C Stock is, is, works well.
You have to do some real planning.

Dave (34:26):
You hit the nail on the head, planning, planning, planning.
You're not going to do this one daybefore you sell your company, obviously.
Well, here's the

Stuart Sorkin (34:34):
point.
You need, as an example, since the corp,if the corporation is sold, if you're
selling, if you end up in an asset sale.
And you will have a C corp. That'sgoing to be absolutely terrible.
If you have a whole bunch of depreciableequipment, you have to recapture, right?
So the idea I'm telling to a lot ofmy clients that are heavily equipment

(34:55):
oriented is to set up a lease, drop alltheir equipment into a leasing company.
So they will have only a singlelevel tax on the worst asset.
You also, people don't realize thatyou can't have personal goodwill.
So personal goodwill isanother way to shave at it.
But so there are ways there, but you need to,you need to plan for these things in advance.

(35:21):
This doesn't happen overnight.

Dave (35:23):
Let's go into a little bit of my favorite area of code,
which is mergers and acquisitions.
What would be your What would be youradvice to a seller of a business?
What would be your top three,four things that you would mention
to them in any transaction?

Stuart Sorkin (35:41):
First, take due diligence seriously.
If you do not, one of the areas whereI've had more complaints from clients
post acquisition is they did not do enoughwork during due diligence on how they
were going to integrate the acquisition.
If your integration plan isn't at least50 percent done by the time you do due

(36:04):
diligence, you're behind the eight ball.
Because if you, the longer that you wait onintegration, The more chance you're going
to have a problem, or you're not going toreceive the benefits that you should receive.
So now I'm also going to tell yousomething else that I think you are.

(36:26):
We're all aware of not all mergers work out.
So I have successfully done a conceptwith several clients of do clients
say, yeah, we want to get together.
We think we have great economies of scale.
We think we can work together, et cetera.
Great.
Prove it to me.
We set up a management company.
The management company does allthe GNA, all of the expensing,

(36:49):
all of the central processing.
It runs at a breakevenat the end of 12 months.
If everyone plays well in the sandbox,they throw their equity into the management
company, they've completed their merger.
If someone doesn't like it, you haven'tmade tax elections that are irreversible,
you haven't combined in a way that'sgoing to come back and bite you.

(37:11):
So, the idea of living together.
Before you get married is, is reallyfrom the, what is your clear plan?
Also, what is your plan withregard to when you exit?
What are you going to do if you're a serialentrepreneur, do you want to set up some kind
of credit or protected trust for part of theassets to make sure if the next deal doesn't

(37:35):
go as well, you haven't risked everything.
Have you met with a financial plannerto find out what your number is?
Have you done a waterfall is what I call it.
Have you done a waterfall?
The question I love asking iswe want you walk out of this
meeting and you get hit by a bus.
What happens to this business?
What's your disaster strategy?

(37:55):
Cause that's going to tell me how far I haveto go creating something that has value.
And then do you have kids in thebusiness or is there management in
the business you're trying to protect?
If you have kids into the businessand out of the side of the business,
how are you going to equalize?
And I will give you one otherthing, the equalization that
I think gets missed regularly.

(38:17):
And that is a client will say, Iown the underlying real estate.
I'll let my kid, I'll let the other,the non business kids own part of
the real estate with the kid andthey want to sell the real estate.
And so the concept is putting a rightof first refusal in there hurts.
The family members, because who makes anoffer under a right of first refusal when

(38:40):
there's a stalking horse, the other side.
So every family lease should have aright, a first offer family says, you
know, it's been nice job, but we wantyou out fine buildings appraised.
Usually somewhere between a five and 10percent discount in the purchase price.
Cause there's no broker and a quick sale.

(39:00):
And if we, if the business doesn't.
Do it.
Then they're free to sellto whoever they want.
And that's a way to preserve family harmony.
Same thing you got to dowith also vacation homes.
You've got to specify what happensif someone moves out of the area.
You've got to specify how holidaysare going to be allocated.
I've seen more fights on those issues.
So these are things thatneed to be considered.

(39:23):
As I said, seller needs to consider,where's he going to be estate tax
wise when this is all said and done?
This gets into, does he needto consider a gifting program?
And if he's going to consider a giftingprogram, Is he going to gift directly,
which means he probably wants to giftnon voting stock because he doesn't
want to give his kids control, or doeshe want to gift it to a trust, get it

(39:44):
out of his estate, but still controlit because he can control the trustee?
And they also give his wife, give his wifeback, or I should say spouse, give his
spouse the right to re tap it if needed.
A number of years ago, I attendeda lecture, a seminar put on by the
head of Blackstone Acquisition.
And he went out to the audienceand posed a question, when are

(40:05):
you going to sell your business?
And of course, he got 50 different answers.
And he said, you know what?
You're all wrong.
You will sell your businesswhen someone wants to buy it.
Which means you alwayshave to be ready for sale.
I consciously tell my clients that if you'rean all would consider an offer, you need

(40:28):
to build your due diligence library day andupdate it every quarter or every six months.
More the biggest destroyer between LOI andfinal documents are blows and due diligence.
And you don't get a second chance tomake a first impression with your buyer.
You're right.
Now we can go back to where we were,but I missed that story in my notes.

(40:54):
And I think that's a very important story.

Dave (40:56):
Stories I'll tell you what stories resonate with folks.
So that's important.
All right, let's flip the switchhere and talk about now the buy side.
What would be your top hints for buyers?

Stuart Sorkin (41:10):
Closing is not success.
Integration and profitabilityis success, right?
If you don't integrate, if you do not,you will not gain the venues, the values
of the business, unless you integrate.
Second, too many acquisitions, the buyergoes out and gets acquisition funds and

(41:31):
doesn't have a working capital line.
I always tell my clients that if you'regoing to go out and make this deal
contingent on financing, you need tohave not only the acquisition financing
place, but a working capital line inplace, because the first six months, you
don't really know what's going to happen.
And even if you get a working capital.

(41:52):
reserve from them.
So it's, and also you're in your bestposition with the bank when they want to loan
you the money to give you a working capitalloan versus going to them a year later where
you have a credit history they may not like.
An agreement.
You must develop your own five year plan.
What are you doing this for?
Where, you just bought this business, whereis it going to be five years from now?

(42:13):
What's your role in?
If you don't have a plan for it, you andI have offshoots of the same, of, of, of a
similar expression, which I take, which I'lltell you is a pirate off Lewis and Carol
Nelson wonderland, which is exit strategybegins the day you start your business.
Cause if you don't know where you'regoing, how are you going to get there?

(42:33):
Right.
And it's the white rabbit talking to themad hatter, but that, those are the ones.
And lastly.
Don't become a mile wide and aninch deep acquisition strategy
has to be thought through.
And the other point about acquisitionstrategy is this key from the seller

(42:57):
side is if you're not at your number,how are you going to get there?
Can you do it through internal growthor do you have to become a strategic?
And if you're going to become a strategicacquirer, what are you going to acquire?
Cause acquisition for the sake ofacquisition doesn't necessarily grow.

Dave (43:14):
You're not a big proponent of just top line revenue, sir. No

Stuart Sorkin (43:20):
sticking to your knitting is sticking to your knitting
within reason is, is, is my view.
And that's the other point.
All M and a deals needto be a win win, right?
If you think you're going to get ahundred percent of what you want.
You're going to have a very unhappy, you'regoing to have a very difficult getting a deal
done, and you're going to have someone veryunhappy on the other side, if they do it.

(43:44):
Another thing, last thing fora buyer, employing the seller.
You may need to keep the seller forsome transition period, but sellers.
This is their baby.
All of a sudden they're no longer aparent that does not bode well for
how they're feeling emotionally.

(44:04):
When they see you making decisions,they may be the right decision,
but they don't agree with it.
It also fosters problems with delegationbecause they will go to the seller.
If, if an employee has a problemthat he thinks is going to be tough,
he's going to go to the seller.
So he's going to cut off your, the directcommunications with some of your employees.
So that has this as they're like guests.

(44:25):
The long, like fish, the longerthey stay, the more they're going to

Dave (44:28):
stink.
100 percent of all owners orsellers are fired to me within
nine months, if not before.
I'm in total agreement.

Stuart Sorkin (44:37):
And I learned that lesson from my coauthor because my coauthor
was a former nuclear military officerand he said, I know myself, I know I
would go, it would draw, this is mybaby and I know it would drive me nuts.
And I didn't, he walked away fromprobably over a million dollars.

(44:59):
He could have gotten more forsaying, yep, but that's the smart
guy that knows their limitations.
And so that's the other pointof knowing what the seller and
buyer, what are your limitations?

Dave (45:10):
All right, so Stuart, what's next for you personally
and professionally in your life?

Stuart Sorkin (45:17):
Well, first off, I get up every morning loving what I do.
So I don't ever see unless, untilI'm unable, I envision I will do
this because I love to give back.
I love the helping people.
I love the channel.
It's playing chess.
Five chess boards at one time.

(45:38):
It's, it's also working in a collaborativefashion with other professionals and learning
every day, because in this business, yeah,I know, I know a fair amount, but I don't
think there's a day that goes by that.
I don't learn something from someoneelse and this business, this business.

(45:59):
Has to be collaborative.
So in that sense, I'm in abusiness that allows me to do it.

Dave (46:05):
Ladies and gentlemen, I don't know that anyone has ever seen this much energy,
enthusiasm, and passion from a tax attorney.
Okay, but, and to say he's a tax attorney,a CPA, and an attorney and everything
else is a self limiting statement.
Not self limiting, I'm making thestatement, but it's a limiting statement.

(46:25):
The guy brings so much to life.
I want to thank you, Stuart.
How do people find you?
How do they reach out to you?
How do they have this kind of experiencethat we're having today with you every day?

Stuart Sorkin (46:37):
Very simply, they can send me an email at Stuart Sorkin.
At Stuart at business and legaladvisors, or they can book an
appointment through my website.
I give complimentary appointment.
I give complimentary consultations tostrategic partners and potential clients.

(46:58):
You need to be comfortable with me ifyou're going to completely open your kimono.
So I'd rather we find that out.
However, I asked that I get a, Ihave a short questionnaire that I
would ask clients to fill out first.
So I will know something about the business.
And that way I also can be preparedwith some potential ideas on how to

(47:18):
work with this particular business.

Dave (47:20):
Ladies and gentlemen, I've enjoyed this.
I hope you have.
I find this to be fascinating, andquite candidly, I'm very much in this
whole space, so thank you, Stuart.
Really appreciate the input,the knowledge, the wisdom.
It is, I'm sure, a difference maker formy audience, so thank you very much.

(47:41):
You're very welcome.
I really enjoy it.
I really enjoyed speaking.
Hey, thank you so much forlistening to my podcast.
If you're seeking assistance with yourbusiness dreams, please consider checking
out the resources that I can make availableto you at either my LinkedIn page,
obviously my podcast, my book, Quiet Plans,exciting results available on Amazon.

(48:03):
Either in a written or verbal format andas well, check out my website, davidsider.
com.
A lot of content, a lot of information there.
And there's also a way for you to access anassessment, a quick 16 question survey that
would allow us to get together and discusswhere you're at and where you seek to go.
I'm here to help you with yourdreams until then be safe.

(48:34):
By the way, this podcast isprovided for educational purposes.
It does not constitute legal adviceand it's not intended to establish
an attorney client relationship.
The recommendations contained in thepodcast are not necessarily appropriate
for every individual or business indetermining the best course of action.
Business owners should consult with anattorney on their distinct circumstances.
Advertise With Us

Popular Podcasts

24/7 News: The Latest
Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.