All Episodes

August 30, 2023 22 mins
Jeff Lipsey, CPA, EA - Founder & CEO
Jeff graduated from the University of Illinois in 2006 with a dual bachelor’s degree in Accounting and Finance. He was a professional poker player for a few years before switching careers to become a manager at a local popular restaurant in Alexandria, VA.

After a few years of working outside of the accounting field, Jeff opened the doors to Lipsey and Associates in at the end of 2013. Since then, he has become an Enrolled Agent (EA) as well as a Certified Public Accountant (CPA). Through the years of business, he has successfully built his team up from a single person with a laptop to a full team and explosive growth.

Outside of his business, he enjoys the outdoors and has a very impressive garden at his house. He also spends a lot of time with his family and cooking in the kitchen. If you’d like to talk with Jeff directly, please give the office a call to schedule a meeting. If he can’t meet with you, he’ll make sure you’re taken care of by one of his many qualified staff.
Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
M and T Bank presian CEOs youshould know powered by Iheartmadia. Let's meet
Jeff Lipsey. He is the ownerof Lipsey and Associates, based out of
Falls Church, Virginia, but alsoworking with small businesses in the DMV Illinois
North Carolina. Jeff, in thistwelve member team worked with small businesses and
their taxes and we'll talk a lotmore about that, but before we do,

(00:22):
I first asked Jeff to talk alittle bit about himself, where he's
from, and his origin story.You know, I started this business about
ten years ago and I'm turning fortythis year, but I've actually been doing
this line of work for about twentytwo years. So it goes back.
I went to high school Western andsuburb of Chicago, Aurora, Illinois.

(00:42):
I went to West or Our HighSchool and I took two years of accounting
there, and that those still thosetwo years, there's still work that we're
doing today, and so it's hardfor me to say that I've got twenty
two years experience at the age ofthirty nine, but there is a little
bit of truth to that. Iback in high school, I took competitive

(01:03):
courses in accounting. I placed atthe age of seventeen, I was number
one in the city, number twoin the state, and then we went
to California and placed number ten inthe country in the in the role of
accounting. I graduated and went toUniversity of Illinois. At that point it
was the top accounting program in theUnited States. I was very fortunate that

(01:27):
it was in my state, soI could go to could I could be
in state and go to the topprogram, and I got degrees in accounting
and finance. Really to acounting hasalways been my strength, but I got
a degree in finance because I reallyreally enjoy it, and I did not

(01:47):
know at that point that I'd beable to use both of them in my
current role. But up until thenit was always like you'd have to choose
one or the other. So beforewe talk about the business, this is
my first time in this series oftalking to CEOs and owners and leaders that
you played a lot of poker,which I found very cool and interesting because
I watched it on TV. I'mfascinated by it. I'm not a good

(02:07):
card player, but it makes sensethat somebody the crunches numbers would be a
poker player, not that your accountcard counter. But that just that you
know, you're dealing in numbers allthe time and odds and all those kind
of things. So tell us aboutyour interest in that before you started your
business, about being a poker player. It's pretty cool. Yeah. So,

(02:28):
I mean I back in the midtwo thousands, I had the online
poker boom. Was was really happening, And just like you, I watched
poker on TV, you know moneymaker, I got really involved online poker,
and I quit my accounting internship toplay poker full time. I was going
into my senior year in college.It was right before Congress passed the legislation,

(02:51):
which which really hurt my future pokercareer. But what it's done as
a poker players, it's treated howI view risk and how I view money
differently than anybody else. And mywife would agree that's probably not necessarily always
a good thing on how I viewit. But if anything about playing poker,

(03:14):
like as a job, because I'veplayed it for about five years,
that most jobs, you won't gohome at the end of the day with
the potential of with having less moneythan when you go in at the beginning
of the day after working a fullday. Now that said, he don't
typically have too many losing days,maybe like one or two days a month,

(03:34):
but it definitely influences my view ofrisk and reward and much more beyond
the math in terms of like youknow, odds and you know, if
you want any counting cards, Ican count a card. I can keep
the count in blackjack. I can'ttell you what the proper plays are,
but dang, and I can keepa good account for you. That's great.

(03:55):
Well, listen, I want totalk to you about the business because
I know it's almost ten years inthe making and having a decade of investment
of business, especially a small businessin today's climate, is epic to do
and to continue that sustainability and possiblegrowth. I know you have twelve one
year staff right now, but youstarted as a one person band. So
tell me about the origin story aboutgetting kind of segueing out of poker to

(04:18):
starting your own business, and thentell everybody about exactly what you do.
Yeah, so you know, playingonline poker buy yourself mostly in your living
room or at your desk, right, it's very lonely. It's almost like
the og of remote working, right, and so you know you see that

(04:39):
happening now with remote working people beingdepressed or not being not being social,
right, Like that was me andI and that's particularly what happened. That's
why I got out of it.And you know, I decided maybe I
wanted to open a restaurant. SoI worked at a restaurant for a while,
and you know, and then theywant you to work sixty hours a
week, and I was like,well, I'm not going to work sixty
hours a week doing If I'm gonnawork sixty hours a week, I'm gonna

(05:00):
go back into accounting because at leastthen i'll make some I'll make some good
money around the Around the same time, I was also taught myself how to
code htmail. I'm not saying I'mvery good at it, but I had
like a very small, very smallwebsite design like affiliate marketing business going on.
And again all those skills also helpedme today. But through that line

(05:27):
of work, I got connected toother another CPA who introduced me to another
CPA who later became my partner,who later, like I, later purchases
firm off of him. And it'sjust slowly grown. I was a one
man band, as you said,like I remember sitting on my couch staring
at my like laptop, hoping fora new client to email me. That

(05:50):
was, you know, thirteen twentyfourteen, staring and just and then you
remember, all of a sudden,they just came out of nowhere and grown
to the twelve today after after tenyears. And I would say, it's
been ten years of of almost completestruggle of you know, transitioning from what

(06:14):
I was, you know, bookkeeperwhen I started and then enrolled agent taking
the CPA exam while my daughter wasyou know, one years old. Like
I would study at night after workingfor two hours a night for a whole
year to get to pass that exam. It's just been Meanwhile, there's there's

(06:35):
growing pains, right, Like I'veonly ever invested a thousand dollars in my
business, Like I started that witha with a laptop and my own website,
and I bought some like some trainingwith QuickBooks. That was it.
Like I've got zero prior like industryexperience. Like I've had to teach myself

(06:59):
everything from every single tax lot tohow to use every software. And it's
better real challenge. But at thesame time, like that has given me
the opportunity when you have to goand learn every single thing and then you
have to go and explain that toa client. You almost have to learn

(07:19):
every in and out about it,which then you become an expert in the
field. And then that's just kindof like you expand your circle and you
become an expert and you move onto something else. Well, I'm glad
you explained all that because I thinkit can skip all the leadership of questions
that we'd like to ask our leadersbecause you answered a lot with your explanation.

(07:41):
Yourself made You taught yourself quite afew things. You had a lot
of intestinal fortitude, passion, andyou put yourself into areas that you probably
weren't comfortable with at the time,but you made sure that you learn and
you taught yourself how to get intothese areas so you could have a lot
on your resume that you can builttogether to start this business. So,
with that said, starting back aboutten years ago, tell us about what

(08:03):
it's like as a business owner whenyou're a one person ban and you want
to do tax strategy and you're aCPA and you're working on people's taxes for
small businesses, what is that likein that first couple of years to try
and build a business, get theword of mouth out there that hey,
I can help you save money.What was that like? Well, honestly,
the first couple of years, you'rereally just figuring it out and getting

(08:26):
your getting your I wouldn't even saygetting your processes right. You're literally just
figuring it out and making sure thatyou can pay the bills at night and
help that. But as I transitionand you learn more about it, you
know, fortunately, as a asa CPA, you've got to take your
continue education and the education that youchoose. And I see this so as

(08:48):
CPAs we have to take forty credithours a year and education, and you
get the choice of what credit hoursyou want to take. There are discounts
education providers out there. Okay,take your get your forty hours for one
hundred dollars, right, and I'mexaggerating there that might have probably exists.
Don't get me wrong, that probablyexists. Or you could choose to spend

(09:09):
your forty hour, take your fortyhours and spend you know, a thousand
or two thousand dollars on the investin yourself. It's the same forty hours,
right, so why not take thoseforty hours and use them for your
benefit and really learn how to howto use the how how to do what

(09:30):
it is that you need to doto get better at your job. And
woulda the biggest challenge is transitioning fromaccount the CPA the CEO, because your
your clients still think of you asa CPA, but my staff think of
me as a boss. I wasnever trained as a boss. I was

(09:50):
trained as a CPA. So ifyou ask any one of those people if
they care, they're going to sayno, I don't don't. I don't
care, like they want what's bestfor them. And that's probably the biggest
challenges. And it's thinking of myself, right, like going from thinking of
yourself as as a trained accountant tonow like I do I run the business

(10:16):
more than I do anything else.I do some client work, but it's
it's mostly like how do you makesure that the work is being done on
time, being done correctly, gettingit you know well, also trying to
make a profit. Is that's themost challenging part. Yeah, I understood,
And as we tell all our futureleaders out there, it's windy iss
at the top when you're running acompany. There is a lot to do,

(10:39):
you know, your staff and keepingclients happy, building your clientele,
paying the bills and all that goeswith running a small business. So let's
talk about that. I love toknow again because I had I touched on
it just a little bit, butlet's hear it from you what your speciality
is and what kind of businesses doyou work with. So we serve small
business owners and their families, andwe come in right at where the large

(11:05):
national tax firms discount based or youknow, the free tax filers. I
don't want to name any names,but typically where they can no longer process
your work. We come in rightat that level. Whether you're too complicated
for those for that, for that, for that business, or you're just

(11:26):
not happy anymore with the quality ofwork that they're giving you that we can
take you from from that level allthe way up to you know, a
multimillion dollar company. We can serviceat that whole window, and we take
dose ball business owners whether they're consultants, whether they're doctors, they're physicians,
the contractors and our goal and thisis what we do, is we save

(11:52):
them money on taxes like plain andsimple, and you know how do we
do that? Right? Like,I think that's everybody's goal. Okay,
we want to pay less money intax, So how do you do that?
DA? And we create tax strategiesthat maximize deductions that it incorporates proper
tax planning into their overall financial plan. So we we typically recommend them working

(12:13):
with a financial advisor because you know, I can't give investment advice, and
tax is just a small proponent oftheir overall financial plan. And you know,
it's a it's a big important it'sa big component. But like if
the client comes, I mean asksto me, joh, how can I
say money on taxes? I'm goingto make sure that my answer is representative

(12:35):
of their overall financial picture and notjust like, well, I can save
you five thousands on taxes, butthen it'll cost you ten thousand dollars down
the road. That's not that's notproper tax planning. And so we look,
we take a holistic view of ourof our client's financial picture, work
with their financial planners, and atthe end of the day, save them
money on taxes. I know thatyou're based on a false church, but

(12:58):
how far does your net when it'sworking with small businesses in the DMV.
We service clients Virginia, DC,Maryland, North Carolina. I've got a
strong presence. I actually opened upan office this year at Illinois back home
congratulations. And I've got a coupleof remote staff already there. I mean,
it's we're I wouldn't say bootstrapping itas the right word, because we're

(13:20):
you know, we've got we've gota fully funded office. But I'm I'm
expanding to the point where it's likeit's I'm there enough that you know,
I can grow into that market.I've got staff who are experts in that
market. It would be you know, it would be rather unfortunate of myself
to not take advantage of that whileI have it understood, Jeff. When

(13:41):
I talked to a lot of leadersout there and ask them about challenges,
sometimes they welcome them because it keepsthem frosty and to make sure they stand
top with their game. But Iknow there are always are challenges no matter
whatever type of business you run.And we're hearing taxes and news a lot,
especially in the last five to tenyears. It's at the forefront of
the news all the time. Debtsylinks into trades, we go on and

(14:01):
on about what it's for a personalperson or running a business. So what
that said, what kind of challengesare you facing today? How to be
what everybody wants me to be?Right at the same time, you can
serve a client at the same time, while you're serving that client, you're
hurting a staff, right. Youcan help your staff at the same while

(14:26):
at the same time like hurting yourfamily. So how do you how do
you check all those boxes right?And it starts with one making sure that
you have the right clients, right, That's probably the easiest thing that we
do. It's it's begin and thenyou make sure you have the right staff.

(14:46):
And you know, right now,I've got to I've got a very
great team. I can't I can'texplain to you I've had. I have
the best team now that I've everhad in my entire life. And I
can't like thank them enough for howthey help me. And then you've always
got to be grounded with what's themost important thing in your life, right,
and that is like you and yourfamily. Like I didn't start this

(15:09):
business to work sixty hours a week, I hate to say it, like
it and I have empathy for mystaff that like they don't want to work
sixty hours a week, right,we barely want to work forty hours a
week like we want to. Wewant we work because we want to enjoy
our life. And it's not likeour life is not our work. But
at the same time, we enjoywhat we do, so we that kind

(15:31):
of provides us a quality of Wehave high quality of life in the in
the business, but also outside becausewe enjoy what we do. And that's
the biggest challenge is you can't makeeverybody happy, so you limit who your
clients are, and you limit whoyou're who you're helping to those that are

(15:52):
mutually beneficial to everybody. Jeff,when you get a chance to take breath
from work in your family and itcomes to philanthropic or ney charity work,
what do you like to be apart of well, I mean, I
would say that the organization that wesupport the most right now is National Forest
Foundation. And this is because accountantsare known for what like paper pushers,

(16:15):
right, Like you go through somany paper and you know, back when
I bought my first firm five yearsago, I remember going into their local
office and I swear they had theirwhole office was just wall to wall filing
cabinets full of printed copies of taxreturns, and I was like mortified,

(16:37):
mortified, and I was like,what are you guys doing here? This
is just you guys, and thisis it's a systemic of every TPA from
all over the country like that goesthrough un necessarily paper. It was like,
we all deal with PDFs and digitaldocuments. Why are you printing that
stuff out? No one, You'renever gonna look that ever. Again,
we don't need to do it.Why are you doing it? So we

(17:02):
created a policy several years back whereevery ream of paper that we use the
office, I don't need one hundreddollars through the actual Horse Foundation and using
that like environmental friendly mantra. Youknow, I'm not perfect at it right,
like, but we tried to usethat as a guide like, Okay,

(17:22):
what should we be doing? Right? Should do we really need to
print this out through this bank reconciliationor can we figure out a way to
do it on a computer? Dowe can we convince our clients that they
really don't need that tax to turnprinted? Help for them, because what
are you gonna do with it?You're gonna stick it in an envelope.
You're gonna stick it in a drawerand it's gonna collect dust for seven years.

(17:45):
How about this, how about Igive you seven years access to digital
files online and I won't even chargeyou for it, because like we have
that anyway, right. But it'sit's a challenge because you know, we're
dealing with clients, and clients wantto have that printed copy of their return.
Those returns gonna be like hundreds ofpages, Like every return could be

(18:06):
half a rem of paper easily,and we we do we do very well.
We can't paper file, we can'tdefile everything, but like we do
very well. We print a veryfew number of returns and we you know,
we try at least to have thatgoal of like, all right,

(18:26):
what's the most environmentally finally option thatwe can do here? And I would
say that's that's been very helpful.Well, I appreciate you sharing that,
and what you're doing is you're justsaving your little part of the world.
And that's all we can do andask for. And I feel the same
way when it comes to things thatI'm involved into. So as we put
them on our conversation, Jeff,and we have a lot of people that
listen to the series, and alsoa lot of companies and small businesses.

(18:48):
If you were to leave your companyand one takeaway with everybody that's listening,
what would it be? I reallyI enjoy what I do and it's unfortunate
that there aren't as many accountants asthere needs to be in the field.
They're off doing probably things that aremore money, right, computer science or

(19:11):
coding. I would when when Iwas seventeen years old that my accounting my
accounting teacher, mister Gilmour said thathave any accounted agree, you'll always have
a job your entire life, becauseyou could do a thousand different jobs that
one agree, and it's absolutely truein that regard. I also want to

(19:36):
say thank you Dennis for having meon. I want to say, you
know, thank you to Kasaki Fukuhori, who's my marketing individual who helped me
connect this, my high quality staffas I said, and the clients who
believe in me, and most ofall my wife who's put up with me
for these ten years because it's beenvery hard to grow, to get to

(20:00):
scale to the point where I cango out and have meetings and have interviews
like this to continue growing and Ihope all of them for my success,
and it's very little on my shoulders, and a lot of it is just
making sure that having my quality staffand believing that I've got a really good

(20:22):
staff. Well, Jeff Wilson andyou're quite welcome. And as we finish
out, if anybody would like topartner with you and maybe take a look
at some tech strategy that you dofor small businesses, what's your website that
they can check out and also reachout to you? Sure, So my
website is Lipsy and Associates dot com. It's all spelled out and you go
there. You can submit, youcan spend a web form. You could

(20:44):
also just give us a call.I phone hammers on the website. I've
got multiple people on them like waitingto answer phones because we're here for here
every day and I feel like backwhen I was first starting out, one
thing that motivated me was that whenI try to reach out to account counting
firms to help me with my business, only one person out of six or

(21:08):
more ever got back to me.And so has always talk with me.
Is that like we'll get back toyou. We might not be a good
fit for you, but we're herewe're here every day. We're working,
and we're working at the benefit ofour clients communication and also customer service.
And that's a lot to count on, which is really cool. Hey,
Jeff, listen, continue you need, yeah, continue, all you need,

(21:32):
it's all you need, like youdon't have to do anything else is
answer your phone and you'll be successful. I agree, Hey, continued success
man. Thank you so much,and we really appreciate you joining us on
CEO as you should know. Thankyou, Dennis. Our community partner,
M ANDT Bank supports CEOs you shouldknow as part of their ongoing commitment to
building strong communities, and that startsby backing the businesses within them. As

(21:52):
a bank for communities, M ANDTbelieves in dedicating time, talent, and
resources to help local businessesses thrived,because when businesses succeed, our communities succeed.
Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Special Summer Offer: Exclusively on Apple Podcasts, try our Dateline Premium subscription completely free for one month! With Dateline Premium, you get every episode ad-free plus exclusive bonus content.

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

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

Connect

© 2025 iHeartMedia, Inc.