The Hiring Headache That Led Jake to Rethink His Bookkeeping (And What He Did Instead)

Let me tell you about Jake. Like Gary before him, Jake is fictional—but his story is a blend of very real experiences I’ve seen over and over again from small business owners trying to do it all.

Jake runs a residential painting company in Bozeman, Montana. He started with just a van, a couple of ladders, and enough grit to turn weekend gigs into a full-time business. Within a couple of years, Jake had a team of five, a steady stream of referrals, and a phone that wouldn’t stop ringing. Business was booming.

But Jake had a problem that many business owners face when growth kicks in: he needed to hire more people—but couldn’t figure out if he could actually afford it.

Hiring Based on Gut (Not Numbers)

Jake’s calendar was booked solid for the next two months. He was turning down work because he didn’t have enough crew members. “I need to hire,” he told himself. “How hard can it be?”

He brought on two new painters.

What he didn’t realize was that his cash flow was tighter than he thought. He hadn’t fully accounted for:

• Increased payroll taxes

• The cost of onboarding and uniforms

• Fuel expenses for the extra crew van

• A spike in material costs due to new contracts

Within 30 days, he felt like he was barely treading water. He was working more hours, managing more people, and—despite bringing in more revenue—he wasn’t seeing more money in his account.

That’s when he opened QuickBooks, stared at a balance sheet he didn’t understand, and realized he was flying blind.

Jake Meets the Numbers Wall

Jake had a bookkeeper—a friend of a friend who “did books on the side.” She logged hours every few weeks and gave him a quarterly report. But when Jake asked, “Can I afford to hire?” she replied, “Well, it depends.”

That was the moment Jake knew he needed something better.

He didn’t want vague advice. He didn’t want old data. He wanted answers. Clear ones.

So he started searching for a professional bookkeeping service.

The Interview Process (And a Few Red Flags)

Jake spoke with a few local options and quickly realized what he didn’t want:

• One guy promised to “figure it out as we go.”

• Another firm took three days to return his email.

• One bookkeeper suggested he just “stop hiring until things felt better.”

Then Jake met with a bookkeeping firm that specialized in service-based businesses. They spoke his language. They understood seasonal trends, materials markups, job costing, and labor load.

They even asked questions he hadn’t considered:

• “How are you estimating jobs?”

• “What’s your accounts receivable timeline?”

• “Have you set up payment reminders or a customer portal yet?”

Jake’s jaw hit the floor. He had been guessing for months—now someone was offering real data and a strategy.

What Changed After Switching

Within two weeks of onboarding, here’s what Jake had:

• Clean, reconciled books that actually matched his bank accounts

• A dashboard view of income, expenses, and projected payroll costs

• Job profitability reports that showed which services were most (and least) profitable

• Automated invoicing and payment reminders

• A synced online payment portal that reduced customer payment delays

He also had a bookkeeper who could say, “Yes, you can afford another hire next month—but only if you trim costs in X and collect Y on time.”

Jake wasn’t just reacting anymore—he was planning.

Clarity = Confidence

Three months later, Jake had:

• Hired a new crew lead

• Streamlined his services to focus on higher-margin jobs

• Paid himself a regular salary for the first time ever

• Started saving for a second van

He went from worried and overwhelmed to calm and in control. All because he finally had clear financial visibility.

What You Can Learn from Jake

If you’re growing and thinking about hiring—but you’re not sure if your books are solid—take a cue from Jake:

• Trusting your gut is fine, but numbers don’t lie.

• Vague bookkeeping creates vague decisions.

• The right bookkeeper won’t just keep records—they’ll help you make smarter moves.

Don’t wait until you’re drowning in payroll costs or stuck chasing unpaid invoices. Good bookkeeping turns confusion into clarity.

Hire With Confidence, Not Chaos

Whether you’re a painting contractor like Jake, a landscaper, or a local cleaning company, hiring should be a strategic decision—not a leap of faith.

With a good bookkeeping team behind you, you’ll know when to hire, how much you can afford, and which parts of your business actually make you money.

📞 Call Blackfin at 406-404-8955. We’ll help you understand your numbers, prepare for growth, and make hiring a step forward—not a financial misstep.