Get a Bookkeeper or DIY? The Pros and Cons of Hiring Bookkeeping Services

Small business life is a whirlwind—customers, deadlines, and that one lightbulb you keep meaning to fix. Somewhere in there, you’ve got to keep your books straight, and the big question hits: Should you DIY or start hiring bookkeeping services? It’s a fork-in-the-road moment—handle it yourself with grit and Google, or hand it off to a pro? As a public accounting firm that’s worked with small businesses for years, we’ve seen both paths play out. Let’s break down the pros and cons of hiring bookkeeping services versus going it alone, so you can pick what fits your hustle.

Why Bookkeeping’s a Big Deal

Before we dive into DIY versus hiring bookkeeping services, let’s get why bookkeeping even matters.

Cash Flow Reality

A client once said, “I thought I was fine—then I couldn’t pay my vendor.” Books show you the real money picture.

Tax Traps

Messy numbers mean missed deductions or fines. Good bookkeeping keeps the IRS off your back.

Growth Fuel

Need a loan? Investors? Clean financials are your proof. A business we helped stalled until their books shaped up.

DIY Bookkeeping: The Lowdown

First up—doing it yourself. No hiring bookkeeping services here—just you, some software, and a can-do vibe.

How It Works

Apps like QuickBooks Online or Wave—$20-$50/month—plus your time. A client called it “me versus the numbers.”

Who It’s For

Solo owners or tiny startups with simple setups—few transactions, no payroll headaches.

Hiring Bookkeeping Services: The Basics

Now, hiring bookkeeping services—bringing in pros to take the wheel, from freelancers to agencies.

What You Get

They log transactions, reconcile accounts, spit out reports—$100-$1,000/month depending. A business owner said, “It’s like outsourcing my stress.”

Who Needs It

Growing businesses, complex needs—think payroll, multi-state taxes, or investor pitches.

DIY Pros: Why It’s Tempting

DIY’s got appeal—here’s why skipping hiring bookkeeping services might work.

Cost Control

Software’s cheap—$30/month beats $300. A client said, “I saved cash and felt like a boss doing it.”

Hands-On Power

You know every penny. A founder loved tweaking their books—total control freak (in a good way).

Learning Curve Pays Off

Mastering it builds skills. A client learned their numbers inside out—helped them strategize.

DIY Cons: The Rough Side

But DIY isn’t all sunshine—here’s why hiring bookkeeping services might start looking good.

Time Drain

Hours on books steal from your hustle. A business owner said, “I lost weekends—sales dipped.”

Error City

No training? Mistakes happen. A client’s DIY mess cost $2,000 in tax penalties—ouch.

Growth Limits

Simple tools don’t scale. A startup outgrew their app fast—DIY couldn’t keep up.

Hiring Bookkeeping Services: The Wins

Now, the perks of hiring bookkeeping services—why it’s a game-changer for some.

Time Back

A client told us, “I handed it off and got my life back—worth every penny.” Focus on growth, not numbers.

Pro Precision

Experts catch what you miss—tax breaks, errors. A business saved $1,500 with a pro’s eagle eye.

Scales with You

From $200 freelancer to $800 agency—grows as you do. A client scaled up seamlessly with help.

Hiring Bookkeeping Services: The Downsides

But hiring bookkeeping services isn’t perfect—here’s the flip side.

Cost Jump

$20 DIY vs. $400 pro? It stings. A client balked at the price—tight budgets feel it.

Less Control

You’re not in the driver’s seat. A business owner missed tweaking things themselves—felt detached.

Trust Factor

Picking the wrong help? Risky. A client’s cheap hire flaked—left them scrambling.

DIY vs. Hiring Bookkeeping Services: Head-to-Head

Let’s stack DIY against hiring bookkeeping services—here’s the showdown.

Cost

DIY wins short-term—$30/month vs. $300. But long-term? Pros save you from costly slip-ups.

Time

Hiring frees you—hours back. DIY eats them— a client said, “I traded sales for spreadsheets—dumb move.”

Expertise

Pros bring know-how; DIY’s a gamble. A business swapped to hiring when their taxes got tricky.

How to Decide What’s Right

DIY or hiring bookkeeping services—which fits? Here’s your cheat sheet.

Your Time

Got hours to spare? DIY’s fine. Swamped? A client said, “Hiring was my lifeline—should’ve done it sooner.”

Your Budget

Cash-tight? Start DIY—$50 max. Room to spend? $200-$500 on hiring bookkeeping services pays off.

Your Goals

Just surviving? DIY works. Scaling or pitching? Pros prep you better.

Tips to Make It Work

Whatever you pick—DIY or hiring bookkeeping services—here’s how to nail it.

Start Small

DIY with $20 software or a $150 freelancer—test it. A client tried both, found their groove.

Vet the Help

Hiring? Check skills—taxes, tech. A business got burned by a “pro” who didn’t know squat.

Keep Tabs

Even with pros, peek monthly. A client caught a glitch their hire missed—stayed in the loop.

The Payoff of Choosing Smart

Get this right—DIY or hiring bookkeeping services—and here’s what you score.

Stress Slashed

A client said, “No more book nightmares—I’m chill now.” That’s the vibe.

Cash Saved

DIY’s cheap; hiring catches big wins. A business saved $3,000 in taxes with a pro—net gain.

Growth Ready

Clean books open doors—loans, deals. A client landed funding with hired help—DIY wouldn’t cut it.

Wrapping It Up

DIY or hiring bookkeeping services? It’s your call—and it hinges on your time, budget, and dreams. DIY’s cheap and hands-on—great if you’ve got the hours and a simple setup. Hiring bookkeeping services costs more but saves you time, stress, and cash down the road—perfect for growth or complexity. Weigh the pros and cons—$30 DIY today might cost you $1,000 tomorrow, or $400 hiring might unlock $5,000 in wins. Start where you’re at, test what works, and keep your books from owning you. Your business deserves it—ready to choose?

Beth Calderon

Advanced Planning & Succession Team Coordinator

Beth joined our advanced planning team as a seasoned administrative professional with over 16 years of experience supporting C-suite executives in the financial services industry. A master of organization and efficiency, Beth is committed to fostering seamless collaboration and serving as a resourceful and entrepreneurial-minded administrative leader who thrives on wearing many hats. Additionally, Beth enjoys and is very much dedicated to serving as a client concierge, providing best-in-class service to all advanced planning clients.

Ben Lepinski CPA

Ben Lepinski is a Certified Public Accountant in the state of Minnesota. He graduated Summa Cum Laude from Saint John’s University in Collegeville, Minnesota with a BA in Accounting & Finance with a Public Accounting Concentration. After spending 2.5 years in the Big 4, Ben decided to pursue his passion of working with small business owners to help them navigate complex tax situations for clients who may be overlooked by larger firms. Growing up in rural Minnesota, Ben takes extreme pride in helping his community and those around him. For Ben, accounting is a way to benefit those around him and provide trusted advisory services as well as obtaining financial stability and helping clients understand the importance of accurate financial reporting. Outside of work, Ben enjoys spending time with his fiancée, Rachel, and his Sheepadoodle, Kai. His other interests include cars, trivia, and woodworking. Ben is also very active in local cornhole and cribbage leagues. He currently resides in Dayton, Minnesota, about 30 minutes North of the Minneapolis/St. Paul metropolitan area.

Lisa Good

Tax Preparer

I started my professional tax career in 1999, at a large retail tax chain. I took advantage of every tax class that I was offered, worked my way up to Senior Tax Advisor and Assistant Manager at my office. I was doing close to 400 personal returns each year and had the highest rate of returning clients. Eventually I became an instructor there. I also took college courses and earned my associate degree in accounting. In 2017 I left there and started my own tax business, in addition to working full time outside my home. I doubled my clients each year, solely from word of mouth. I understand every aspect of the tax return, the beginning, the middle, and the end, which includes the filing of the tax return, federal, state and city. In December of 2022, I was fortunate to be hired here to do taxes full time, which had always been my dream, and now it’s my reality. I continue to learn every day; my colleagues are tremendously knowledgeable. I am in the Canfield, Ohio office, where I handle the local clients and businesses, as well as our clients all over the county. I address all IRS/State notices, meet with clients and electronically file/paper mail all returns that are complete. I do plan to take the Enrolled Agent Exam this fall, after tax season slows down. I love helping people, it is very rewarding for me. I love learning, and I love my work, I am grateful to be here and to know that I am an asset to this company.

Chad Reineke

Advanced Planning & Succession Team Lead

Chad is an experienced investment and advanced planning professional specializing in capital gains, estate tax, investment strategies, business succession, and post business sale planning. After retiring from professional baseball in 2014, Chad completed his MBA and joined a regional financial planning firm to begin his career in financial services. Within a few years in the business, he realized that his passion was working with entrepreneurs and helping them solve their biggest challenges. With that in mind, he began developing a team of strategic partners around him that specialize in all the areas of planning that business owners require. Chad's role is to help our clients identify current and future planning "blind spots" and to coordinate the appropriate resources to appropriately address those needs.

Jamila Mansour, CPA

Sr Tax Preparer

Jamila Mansour is a Certified Public accountant licensed In Ohio. With over 7 years of professional experience, she has developed a deep understanding of tax regulations and practices. In previous positions, her expertise allowed her to to work with high net worth individuals, trusts, corporations, and partnerships, providing them with comprehensive tax planning and compliance services. She enjoys building strong client relationships and providing personal guidance to help achieve goals.Jamila is a Cum Laude graduate from Cleveland State University where she was involved with many organizations including Beta Alpha Psi. Outside of her career, she enjoys spending time with her husband Mohammad and two sons Zach and Noah.

Emery Rich

Sr Tax Preparer

I grew up in South Texas, I started my journey at H&R Block, I fell in love with tax compliance with individuals and small businesses specializing in working in tax research. I graduated Summa Cum Laude from A&M Corpus Christi in 2022. Moved to Minnesota that summer and I worked at a local mid-size regional firm in Minneapolis where I furthered my knowledge working with a large team of CPAs and gaining more experience in organizing small businesses (S-Corp & Partnership financials), quarterly estimates, and K2/K3 preparation. I'm currently working on obtaining my CPA license here in Minnesota. I look forward to building on the experience I've obtained, my desire to learn and improve is one of my strongest characteristics.

Mark Walker CPA

Director of Tax

Mark is a Certified Public Accountant with over 40 years of tax and investment experience, primarily with HNW clients. While still a student at Pace University, he was recruited into a HNW tax pilot program at Coopers and Lybrand (now Price Waterhouse Coopers LLP). Subsequently, he worked in various HNW tax programs including Rockefeller and Company, the current Rockefeller Capital Management, before he was recruited to financial services. Mark was a Managing Director at Citigroup Global Markets Inc for 19 years, moving to Morgan Stanley where he worked in discretionary and non-discretionary advisory programs before making an intra-firm move to Graystone, the institutional arm of the firm. He currently holds Series 27 and Series 66 licenses. Mark has a BBA in Public Accounting from Pace University and an MBA in Finance from Fordham University. He is married 35 years to his wife Eileen, has four adult children, and currently lives in Pearl River, NY.

Jackie Kwasinski

Accounting Manager

Jackie has over 22 years of experience in the accounting industry. She spent most of her career at a mid-size accounting firm in the Chicagoland area, where she started right out of college and served as their Controller for almost 15 years. As a Certified QuickBooks ProAdvisor, Jackie leverages her expertise to help small businesses streamline their financial processes. Making the switch from being on the corporate side of accounting to helping small businesses has not only been rewarding for her, but seeing the impact it makes on small businesses has driven her to go above and beyond. Jackie’s personable attitude and attention to detail enable her to tailor each project to the specific needs of her clients. She is strongly committed to providing efficient results and creating solid relationships with her clients. Jackie graduated magna cum laude from Elmhurst University and was a member of the Phi Theta Kappa Honor Society.

Brenda Weingardt

Office Manager

Brenda Weingart, Certified Advanced QuickBooks ProAdvisor Office Manager, Canfield Office Over 20+ years of bookkeeping, office, and QuickBooks experience (both Desktop and now Online versions).

Responsible for local and non-local customer relations (via in person/phone/email), general office tasks, co-managing TaxDome portal, client accounts, compiling final tax return invoices and tax return access to clients.

Outside of work, I love to participate in Revolutionary War Re-enacting and camping. I have 2 grown children, 4 cats, 1 dog, and my daughter (still at home) has 3 indoor rabbits.He’s been fortunate to mentor under a couple of well known and highly regarded tax and financial advisors, becoming practiced at coordinating the financial, legal, and accounting teams needed to solve the multitude of tax exposures faced by the SME community.

Ian Grove

Founder

Ian came into professional services in 1999 via the banking industry and moved into regional mortgage operations management. He remained active in the banking sector as an operations manager through 2011. After a 3 year sabbatical, he decided to pursue a career within the financial service space with a focus on HNW families and their business interests.

He’s been fortunate to mentor under a couple of well known and highly regarded tax and financial advisors, becoming practiced at coordinating the financial, legal, and accounting teams needed to solve the multitude of tax exposures faced by the SME community.