Before the LOI. After the Close.
Built for Acquisition Entrepreneurs.

Specialist accounting, tax, and CFO support for the people who actually buy businesses. Tax structuring and Quality of Earnings before the deal closes. Financial architecture and operating support from day one after.

At Ashford Sky, we help every stage from LOI to tax strategy execution

Most CPAs come in for a piece of the deal and then disappear. We don’t work that way. We’ve been the buyer ourselves, so we know how much falls apart in the gap between closing and your first month of operations. Our job is to make sure nothing falls into that gap. Here’s what working with us looks like at every stage.

step 1

Looking for a business

step 2

LOI financial review & strategy

We pressure-test the numbers and help you build an LOI that protects you on price, structure, and contingencies.

step 3

Get a “ Quality of Earnings Lite”

Our QoE Lite gives you the same core protection at a fraction of the cost so you walk into the next negotiation knowing exactly what you’re buying.

step 4

Tax structuring of the acquisition

Asset deal or stock deal, LLC or S-Corp, F-reorg or rollover equity. How the deal is structured can swing your tax bill by six figures, and these decisions get locked in at signing.

step 5

Close 

step 6

Financial architecture setup (QBO, Payroll, Billpay)

Most sellers hand you a chart of accounts that hasn’t been touched in a decade and a payroll system you can’t log into. We rebuild it from the ground up so you have a real operating system instead of a hand-me-down.

step 7

Purchase price accounting

The first 90 days set the tone for everything that follows. We handle the technical work of allocating the purchase price, opening balance sheets, and recording the deal so depreciation and amortization flow right for years.

step 8

Monthly accounting & bookkeeping work

Clean bookkeeping every month, AP and AR moving on schedule, and reports that tell you what’s actually happening. 

step 9

CFO & Advisory (Cash flow forecasting, budgeting, etc.)

We build a forward-looking cash flow forecast so you can see what’s coming twelve weeks out, plus a CFO in your corner for the bigger calls on pricing, hiring, and growth bets.

step 10

Ongoing tax advisory for new businesses

Tax planning isn’t something you do in April. We do it every quarter, looking at entity moves, depreciation strategy, retirement contributions, owner comp, and credits you probably don’t know exist so you keep more of what the business earns.

step 11

Tax compliance (Inc. Transaction tax reporting)

Federal, state, local, sales and use, payroll, 1099s, K-1s, and transaction tax reporting tied back to the deal itself. All of it filed cleanly and on time, with the planning we’ve already done baked in so the return reflects the strategy.

Traditional accounting firms aren't built for this

Most accounting firms are set up for ongoing businesses with clean books and stable operations. That’s not what you’re dealing with. You’re stepping into a business with inherited numbers, unclear margins, and a lot of unknowns. You need help understanding what’s real, fixing what isn’t, and setting things up properly going forward.

Traditional CPA firms

With Ashford Sky

Trusted by Buyers Making High-Stakes Decisions

Whether you’re making your first acquisition or your tenth, we’ve been there. Let’s talk.

Built by an Acquisition Entrepreneur

Darin Pierson, CPA

Founder

Acquisition Calendly BookingDarin has sat on both sides of the closing table, as the CPA structuring the deal and as the buyer who had to operate the business the morning after.
He started at Ernst & Young, then spent a decade at Big 4 and boutique firms working with clients in a range of industries before founding Ashford Sky. Along the way, he bought an e-commerce business, ran it for three years, and sold it. So he knows the full arc firsthand: messy diligence, the post-close scramble to clean up books and stand up a tech stack, and what it actually takes to exit cleanly.

That’s the experience he built Ashford Sky around. At every step of a deal, the firm has the same job: save you money, take headaches off your plate, and free you up to operate. During diligence, that’s catching QofE adjustments. At close, it’s structuring the deal so tax doesn’t eat what you negotiated. After close, it’s keeping the books clean, the tax planning continuous, the tech stack working, and a CFO in your corner so you can run on data, not gut feel.

Whether you’re leaving a W2 to buy your first business, or you’re three deals deep and need a CPA team that actually speaks the language, that’s the seat Ashford Sky fills.

Outsourced SaaS Tax Director

Get a “ Quality of Earnings Lite” Without Overpaying

Set it up Right From Day One

Understand Why Cash Feels Tight

Know Which Jobs are Actually Profitable

Turn Inherited Numbers Into Something Usable

Reporting icon

Use the Right Financials Tools

Don’t Figure this Out Alone

Make Better Decisions as You Grow

Free Download

The 7 Red Flags We See When Buying a Business

After years of helping buyers close, run, and exit businesses, the same warning signs keep showing up in diligence. This free guide walks through the seven red flags we’ve seen kill more deals (and ruin more first years of ownership) than anything else, plus what to ask before you sign.
Red Flag Financials When Buying a Business

Need a Financial Partner Before & After Buying a Business?

We’ve seen what works and what doesn’t. Book a free consultation and we’ll help you understand exactly what you’re getting into before you sign, and exactly what to do after you do.