Monthly Bookkeeping · Your First Year of Ownership

You inherited the books. Now make them yours.

Monthly bookkeeping built for first-time owners of just-acquired businesses. We turn a decade of someone else’s habits into clean, current numbers, so you learn your new business from reports you can actually trust.

Stage 1
Before buying
Stage 2
During the deal
Stage 3
After closing
Stage 4
The first year
Stage 5
And beyond

Bookkeeping is the monthly rhythm of your first year, and every year after.

Why it's different for buyers

Stop wondering where the cash went in a business you just met.

In year one you’re learning the business, servicing acquisition debt, and proving out the model you bought, all at once. Guessing at the numbers isn’t an option. Clean monthly books are how a new owner catches problems while they’re still small.

What you get

Bookkeeping that knows you just closed a deal

01

Monthly reconciliations & classifications

Transactions categorized, accounts reconciled, books closed on schedule every month. No guessing which of the seller's old categories things belong in; we've already rebuilt them.

02

Reports tuned to your industry

Service business, inventory, construction, e-commerce: your statements reflect how the business you bought actually works, not a generic template.

03

Lender-ready financials, always

SBA covenant checks, annual reviews, a refinance, or the next deal's proof of performance. Your books stay current so a lender request is never a fire drill.

04

A team that knows your deal

Real people who know what you paid, how it's financed, and what diligence found. When something looks off, we explain it in plain language.

How it works

From inherited mess to monthly rhythm

01

Cleanup & catch-up

If the seller's books are behind or were never organized right, we fix what's broken and rebuild the structure first. Most buyers are current within one to two weeks.

02

Accounts sync automatically

Bank and card accounts connect straight to QuickBooks. Rules handle recurring transactions; your bookkeeper's time goes to review, not data entry.

03

We close your books monthly

Categorize, reconcile, close, and flag anything odd. You're notified when everything's ready, not chased for receipts.

04

You get reports you'll use

P&L, balance sheet, and what changed vs last month, explained. In year one, that walkthrough is how you learn your own business.

Just closed?
Bookkeeping works best on a proper foundation.

If you're inside your first 90 days, start with our post-close accounting setup: opening balance sheet, PPA, and a rebuilt chart of accounts. Bookkeeping picks up from there.

Meet the founder of Ashford Sky

Built by a CPA who has actually been the buyer.

Former Ernst & Young
Licensed CPA
Bought, operated & sold a business
10+ years in deal & tax advisory
Founder-led
Darin Pierson, CPA
Founder, Ashford Sky

I’ve been the buyer. I combed through the CIMs, submitted the LOI, ran the QoE, and closed on the business. Then I operated it, and sold it. Now I help other buyers navigate the accounting and tax issues through that same arc.

I’m a CPA who spent over a decade across Big 4 and boutique firms before founding Ashford Sky, where our team of seven specializes in acquisition entrepreneurs. Our job at every step is the same: save you money, take the headaches off your plate, and free you up to operate.

“In year one you’re learning the business from its numbers. If the books are wrong, you’re learning the wrong business.”

FAQs

Bookkeeping questions from new owners

The seller's books are a mess. Can you fix them?

Yes, that’s the normal starting point, not the exception. We clean up miscategorized history, reconcile what was never reconciled, and rebuild the chart of accounts before moving to monthly support.

Yes. Everything is categorized with tax reporting in mind and kept current, so filing season, covenant checks, and lender reviews draw from the same clean set of numbers.

Monthly for most owners. Higher transaction volume or tight cash management in the first year sometimes calls for more frequent updates; we’ll recommend a cadence based on how you use the numbers.

Yes. You work with a team that knows your business and your deal. Questions get answers, not ticket numbers.

Get started

Make the numbers make sense in year one.

Book a free consult. If the books you inherited are behind, we’ll scope the catch-up on the call.