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Proactive Bookkeeping Strategies Every Entrepreneur Needs to Know
Episode 140 • 23rd September 2026 • Empowering Entrepreneurs • Glenn Harper
00:00:00 00:11:56

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Learn how effective bookkeeping, accounting, and proactive financial strategies can transform your small business from the inside out.

Ever wondered if bookkeepers are just folks with pocket protectors and stacks of green paper? Julie Smith and Glenn Harper bust that myth wide open, talking through how bookkeepers do way more than just punch numbers. They’re the ones making sure your money is in the right places, your expenses actually make sense, and no one’s accidentally (or not-so-accidentally) shopping for themselves on the company card.

They also dig into what happens when business owners wait till the last minute to figure out their finances (hint: it’s not good). And why getting proactive with your bookkeeping and working with accountants all year can help you actually grow instead of just stressing every tax season. Glenn Harper shares insider tips on turning those “write-offs” into real savings. No weird “girl math” or sitcom-level confusion required.

Whether you’re googling bookkeeping for the first time or trying to level up your systems, this episode breaks everything down in a way that’s easy to get, with plenty of laughs along the way.

This episode is brought to you by PureTax, LLC. Tax preparation services without the pressure. When all you need is to get your tax return done, take the stress out of tax season by working with a firm that has simplified the process and the pricing. Find out more about how we started.

In this episode, you’ll learn:

  • The core functions of a bookkeeper versus an accountant, and when you need each
  • Why internal controls are essential for protecting your business from errors and fraud
  • The real story behind business write-offs and how to maximize legitimate tax deductions
  • The pitfalls of once-a-year bookkeeping and how monthly financial statements empower better decisions
  • How investing in professional advice can dramatically improve your company’s financial health

Moments

00:00 Delegating financial tasks in a company

05:21 Maximizing tax write-offs in business

08:27 Importance of proactive bookkeeping

10:34 Understanding the value of feedback

Running a business doesn’t have to run your life.

Without a business partner who holds you accountable, it’s easy to be so busy ‘doing’ business that you don’t have the right strategy to grow your business.

Stop letting your business run you. At Harper & Co CPA Plus, we know that you want to be empowered to build the lifestyle you envision. In order to do that you need a clear path to follow for success

Our clients enjoy a proactive partnership with us. Schedule a consultation with us today.

Download our free guide - Entrepreneurial Success Formula: How to Avoid Managing Your Business From Your Bank Account.

Glenn Harper, CPA, is the Owner and Managing Partner of Harper & Company CPAs Plus, a top 10 Managing Partner in the country (Accounting Today's 2022 MP Elite). His firm won the 2021 Luca Award for Firm of the Year. 

An entrepreneur and speaker, Glenn transformed his firm into an advisory-focused practice, doubling revenue and profit in two years. He teaches entrepreneurs to build financial and operational excellence, speaks nationwide to CPA firm owners about running their businesses like entrepreneurs, and consults with firms across the country. Glenn enjoys golfing, fishing, hiking, cooking, and spending time with his family.

Julie Smith, MBA, is a serial entrepreneur in the public accounting space. She is the Founder of EmpowerCPA™, Founder of PureTax, LLC, COO for Harper & Company CPAs Plus, and Co-host of the Empowering Entrepreneurs podcast. 

Named CPA.com's 2021 Innovative Practitioner of Year, Julie led Harper & Company's transition to an advisory-focused firm, doubling revenue and profit in two years. She now empowers other CPA firm owners nationwide through consulting and speaking, teaching them how to run their businesses like entrepreneurs. Julie lives in Columbus, OH with her family and enjoys travel, coaching basketball, sporting events, and the occasional shopping spree.

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Copyright 2026 Glenn Harper

Mentioned in this episode:

Brought to you by Harper & Company CPAs Plus

Running a business takes vision, grit… and the right financial partner. At Harper & Company CPAs Plus, we don’t just crunch numbers—we empower entrepreneurs. From proactive tax strategy and accounting to business advisory services, our team helps you keep more of what you earn and scale with confidence. Whether you’re launching, growing, or preparing for exit, Harper & Company is in your corner with expert guidance built for business owners like you. Visit www.harpercpaplus.com to book a complimentary discovery call today - or call us at 614-456-7222.

Brought to you by Harper & Company CPAs Plus

Transcripts

Julie Smith:

So Glenn, what is the function of a bookkeeper? Oh,

Glenn Harper:

that's a great question. It can vary depending on— Do they wear a pocket

Julie Smith:

protector? I'm just curious. You can if you want to be really good at it.

Glenn Harper:

You would wear that. With the green paper. Very important. The

Glenn Harper:

multi-ledger paper and a 10-key is imperative. And if you don't have those things, you're

Glenn Harper:

probably not serious about your job. Let's just be honest. If you want to see

Glenn Harper:

your doctor and they don't have the stethoscope, they're probably not doing their job,

Glenn Harper:

right? Correct. Guarantee it. So what ends up happening is in a company,

Glenn Harper:

the owner generally is the person in charge of, hey,

Glenn Harper:

this is what we're going to bill this customer. This bill is okay to pay,

Glenn Harper:

and they're going to pay those bills. So the owner is the

Glenn Harper:

person in authority to supervise or to approve

Glenn Harper:

the money leaving the company and the money coming in. The

Glenn Harper:

bookkeeper's job then is to account for that money and put it where it needs

Glenn Harper:

to to be in the right categories. Like we talked a little bit earlier on,

Glenn Harper:

the function of a bookkeeper is to put it in the right accounts and do

Glenn Harper:

that. At some point, the owner is going to be too

Glenn Harper:

busy to approve all these expenses. Like,

Glenn Harper:

how can they do this, right? There's just so many things an owner's doing. Like,

Glenn Harper:

they're not going to want to be bothered if we got to go to buy

Glenn Harper:

postage for $50, right? So usually they'll give the

Glenn Harper:

credit card to the bookkeeper. or to the office manager to say, hey, these

Glenn Harper:

are further expenses for the company. Try to keep them under a certain amount. You

Glenn Harper:

can go pay for those expenses. So the authority then changed

Glenn Harper:

to the office manager or to the internal bookkeeper or to

Glenn Harper:

whoever to go buy these things. Well, now the owner doesn't really see what

Glenn Harper:

happened. It's now incumbent on the bookkeeper to make sure they account for it in

Glenn Harper:

the right place. Okay? And so there's this

Glenn Harper:

disconnect then. Well, somebody's stealing my money. Like, I'm not— I gave somebody authority,

Glenn Harper:

but I can't see what they're doing. So you always worry about that. So you

Glenn Harper:

put in these things called internal controls about who is authorized to do

Glenn Harper:

what for how much money. And it makes it very nice to make you sleep

Glenn Harper:

well at night because people are always trying to steal from everybody and that's just

Glenn Harper:

the nature of it. But you put in these controls and those odds of somebody

Glenn Harper:

stealing from you are way minimized. And so

Glenn Harper:

the bookkeeping's role is to kind of maybe pay for some things, check something

Glenn Harper:

down. We would say, hey, what's this check to ABC Company? They put it in

Glenn Harper:

office expense. We don't recognize that as the external account at Harpo. We're like, what

Glenn Harper:

is ABC Company? They would though go track down, oh, ABC

Glenn Harper:

Company was actually something, a vendor for

Glenn Harper:

our cost of goods sold account for our production facility. Okay, great. We'd move

Glenn Harper:

that from office expense back up to this other account. So

Glenn Harper:

they are the boots on the ground finding what these things are for. Or

Glenn Harper:

the owner writes a check somewhere, writes a credit card. We don't like, What is

Glenn Harper:

this company out of California? Oh, that was something personal for me. I

Glenn Harper:

bought it for my wife and I just used the company card by mistake.

Glenn Harper:

Great. So the bookkeeper's job is to try to find out where

Glenn Harper:

these transactions were to and from so they can put 'em in the right category.

Glenn Harper:

And then as the accountant's job over here, we want to just kind of confirm

Glenn Harper:

that that's probably what that is. So that's the first step of a bookkeeper. So

Glenn Harper:

from— I know you're probably going to ask this, but what is Harper's role in

Glenn Harper:

this? Well, our role then is to kind of double-check and confirm

Glenn Harper:

that these places where the bookkeeper and maybe the owner put these

Glenn Harper:

transactions, that's where they really belong, okay? And if we see

Glenn Harper:

something weird, we've done bagajillions of

Glenn Harper:

transactions, we kind of know where things are supposed to go and what it should

Glenn Harper:

probably look like. And we can sense pretty good, see something that looks kind of

Glenn Harper:

funny, what could that be? Is there any strategy to that? Of

Glenn Harper:

us being able to sniff it out? That's just experience. No, no, no, I mean

Julie Smith:

strategy in regards to, you know, I feel like maybe a bookkeeper

Julie Smith:

sees it very black and white, Does Harper ever see the gray in that?

Julie Smith:

I love the gray, obviously. Great question, Julie. And I meant this

Glenn Harper:

perfect. So what ends up happening is everybody comes,

Glenn Harper:

when you start a business, it's the greatest Seinfeld episode. Well, Jerry, it's a write-off.

Glenn Harper:

Well, it's, what is a write-off? Like, I don't even know what a write-off— I

Julie Smith:

trust Jerry. Yeah, exactly. Well, it's Kramer. Kramer wants to write off and Jerry. But

Glenn Harper:

what ends up happening is people think when they own a business, everything's a write-off.

Glenn Harper:

They get to expense it off, meaning you deduct it from your company's

Glenn Harper:

profit. So you bring in $100 and you go get yourself a

Glenn Harper:

write-off. That means you spent money and it makes your $100

Glenn Harper:

get smaller. Your profit gets less and less and less because you're ultimately

Glenn Harper:

taxed on your profit. So everybody says, I want write-offs.

Glenn Harper:

Well, I mean, we all would like to have a write-off, but I don't want

Glenn Harper:

to spend money to get a write-off if I don't need it. That's

Julie Smith:

what I think we call— what did we discuss yesterday? Girl math?

Glenn Harper:

Am I getting a headache? This was a big dinner discussion last night is

Julie Smith:

girl math. No, no. So it's sort of like the goal is to make

Glenn Harper:

as much money as possible. Generally, if you're going to put effort and time into

Glenn Harper:

something, you want to make money at it. So the goal is to spend the

Glenn Harper:

least amount of money, quote, write-offs, to make the

Glenn Harper:

most amount of profit. That's the goal. If I'm lucky

Glenn Harper:

enough where I just literally call on my cell phone,

Glenn Harper:

make a sales deal, and make $1 million, my only expense is my

Glenn Harper:

cell phone. I just made $1 million minus my

Glenn Harper:

$30 cell phone bill. That's a pretty good deal. We gotta find some of those.

Glenn Harper:

But if I got a company where I gotta go make $1 million, but I

Glenn Harper:

gotta pay 20 employees, I gotta pay building

Glenn Harper:

expenses, I got machinery, and I go bring in $1 million. And by the time

Glenn Harper:

I get done with my write-offs, I made $50. Which company

Glenn Harper:

would you rather have? The one that made you $50 or the one that made

Glenn Harper:

you $1 million? So having a write-off doesn't mean

Glenn Harper:

that you are good or bad at your job. It just means you want to

Glenn Harper:

have as least of them as possible because you want to be as profitable as

Glenn Harper:

possible. The key we do at Harper is

Glenn Harper:

if you're going to spend money, how can we make it a write-off?

Glenn Harper:

Right? That's the key. It's not, hey, I'm just going to spend some

Glenn Harper:

money over here business-wise and it's probably all write-off. Then I'm going to go over

Glenn Harper:

here and spend money personally. Well, did you know that if

Glenn Harper:

you were to do this in a certain way, this money you're spending personally, if

Glenn Harper:

you do it a certain way to make that related to the business,

Glenn Harper:

that's money you spent that's now a write-off? Okay.

Glenn Harper:

It's important to know the difference between the two. And that's our job is to

Glenn Harper:

help coach and teach people that, hey, something you would

Glenn Harper:

think would be a personal expense because you don't know how to do it and

Glenn Harper:

how the test you have to have to make sure that it becomes a write-off.

Glenn Harper:

People don't know that. We help teach them that. There's nobody's supposed to pay any

Glenn Harper:

more tax than they're supposed to pay. And you don't even, there's no cheating involved.

Glenn Harper:

This is black and white stuff. I know you like the gray, but black and

Glenn Harper:

white stuff, low-hanging fruit that just people just don't know when you have a business,

Glenn Harper:

'cause nobody's ever taught 'em. So our job is to work with the owner, work

Glenn Harper:

with the bookkeeper to say, hey, if you're going to spend these things,

Glenn Harper:

this is how you should do it. And then before you go buy something, if

Glenn Harper:

you're unsure about it, Call us and we'll say,

Glenn Harper:

oh, you know, if you do it this way, I can't write it off. But

Glenn Harper:

if you do it like this, we can take the write-off. Ooh, I just heard

Julie Smith:

something really important. Good. So it sounds like

Julie Smith:

I shouldn't bring you a box of bank statements to

Julie Smith:

look over my bookkeeping. I'm going to join you. On

Julie Smith:

March 12th, when my tax return's due March 15th. Does that

Julie Smith:

seem like a great idea to you? No. And this is the

Glenn Harper:

curse of the small business owner that

Glenn Harper:

doesn't understand the value of getting their

Glenn Harper:

bookkeeping, accounting, financial statements complete timely,

Glenn Harper:

and somebody advising you proactively as you go.

Glenn Harper:

You come to me in March and give me everything that you did for last

Glenn Harper:

year, we're dead in the water. We're just typing in data and there's nothing I

Glenn Harper:

can really do for you but in a category. You bring that to me every

Glenn Harper:

month, we can do some cool stuff. So you as a

Glenn Harper:

business owner, if you are doing this once a year, you know, that's on you,

Glenn Harper:

but you don't know any better, right? 'Cause that's what you've been told or that's

Glenn Harper:

what you do. But I'm telling you now, don't do that. Do your books,

Glenn Harper:

close out your books and your financial statements every month. Get yourself a good bookkeeper,

Glenn Harper:

get yourself a bookkeeper and an accountant, or just an accountant and not the

Glenn Harper:

bookkeeper. You may or may not need one. We'll help you evaluate that. and have

Glenn Harper:

somebody like ourselves advise you through that process, you get the best result.

Julie Smith:

So I feel like I asked this question at one point, but I'm going to

Julie Smith:

go back and ask it and maybe answer it for you. If

Julie Smith:

someone's Googling bookkeeping, bookkeeping services, bookkeeping

Julie Smith:

and accounting, what's the one thing you'd want them to know? Me as an

Julie Smith:

entrepreneur, I want to know, I need to know that

Julie Smith:

I cannot wait till March 12th to bring you I joke about

Julie Smith:

a box, but things aren't quite like that. It's very digital now, but I can't

Julie Smith:

wait to give you all my information on March 12th and expect the best outcome.

Julie Smith:

I need to be engaging with someone like yourself a

Julie Smith:

year prior. I need to make sure that I'm staying in my lane and getting

Julie Smith:

those things done so that you can, you

Julie Smith:

meaning Harper CPAs, can use their strategy and not

Julie Smith:

just be data in and data out is kind of what it sounds like.

Julie Smith:

It sounds like we've got to have somewhat of a proactive approach in our

Julie Smith:

foundation of our bookkeeping to get the best result for the best health of the

Julie Smith:

company. I'm hearing what you're saying. You're saying

Glenn Harper:

I'm awesome at what I do. Is that what you're hearing? You're okay. No,

Glenn Harper:

what I'm, what I'm hearing you say is, as whatever

Glenn Harper:

business you're in as an entrepreneur, you're selling widgets, you're doing whatever,

Glenn Harper:

The pride and passion you take in selling your product or

Glenn Harper:

service, and you know it's going to help your customer

Glenn Harper:

so much. That's what they're paying you for, to do these things. And you know

Glenn Harper:

that you do that so well. If you can put that same

Glenn Harper:

mentality to getting your

Glenn Harper:

bookkeeping, accounting, taxes, if you put that same passion to

Glenn Harper:

that and hire the same professional that you're selling to, hire somebody to do that

Glenn Harper:

for you like us. That will solve

Glenn Harper:

probably 90% of your money problems that you're having at your business.

Glenn Harper:

It is monumental change, exponential change. So

Glenn Harper:

hire that professional like ourselves to come in and help you set that up,

Glenn Harper:

the accounting system, work with your bookkeeper, augment your bookkeeper, come in and

Glenn Harper:

do the accounting, do the advising side. That money you

Glenn Harper:

invest in that, not spend, you're going to invest in it. You're going to get

Glenn Harper:

a bajillion return on that. And you're going to have a really nice looking

Glenn Harper:

company to know what you're doing, what you're doing right, what you're doing wrong. Just

Glenn Harper:

like when you go help your customers and they hire you to do something, you

Glenn Harper:

know, you're making an impact for them. That's why you're selling them what you're selling

Glenn Harper:

them for. So you want to look at this piece as something that's

Glenn Harper:

critical to your business. Sounds great. It does.

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