Author: Jason Black

The Coordination Series · Part 1 of 5

Most business owners call an M&A advisor the same month they decide to sell, which makes sense. They’re busy building a business, wearing (too) many hats and making sure their employees and customers are taken care of. But by the time they make that call, the biggest levers for preparation have already been pulled — or missed.

Two very different processes:

In one, an owner reaches out unprepared. A buyer has approached them or a competitor just sold to a PE firm doing a roll-up. But their CPA still needs to clean up the financials, and the tax structure was never designed with a sale in mind. Their wealth advisor oversees some retirement accounts but isn’t brought inside the tent to look at the business. No one ever sat down with them to model what life looks like after the sale. The owner wants to move forward quickly. Everything happens under pressure, on the buyer’s timeline, with real value left on the table because there wasn’t time to address what diligence would find.

In the other, the owner’s CPA, estate-planning attorney, tax & wealth advisor, and M&A counsel have been building toward this for years. Their CPA has ensured the financials are ready for a buy-side Quality of Earnings (QoE) review. Their estate-planning attorney restructured ownership while there was time to review options, and their tax & wealth advisor modeled an efficient deal structure alongside what “enough” actually looks like for their family. And before they executed the letter of intent (LOI), they brought in their M&A counsel to help negotiate the key deal points, rather than wait for final documentation. That process tends to move faster, holds up better under diligence, and gives the owner more leverage on price and terms.

The difference doesn’t have anything to do with who’s a better owner-operator. It’s which owner brought the right advisors into the room, and how early they got there. We’ve watched both versions play out enough times to know which an owner would choose, if anyone had told them they had the choice.

The Right Team

While many business owners have built a very capable team, they’re often under a false assumption. Job titles that work fine for running the business don’t map cleanly onto an M&A transaction. Their controller or outsourced bookkeeper capably prepares financials on a cash basis. A CPA with an eye toward the future is different. They make sure years of accrual and revenue-recognition policies will hold up once a buyer’s QoE team starts testing them.

Their CPA files tax returns for the family and the business, while their wealth advisor is kept separate, focused on investing their annual distributions. But the best tax outcomes require structures put in place years in advance, and those windows close quietly, without warning. Tax structures and the question only a wealth advisor can answer, “is this enough”, are really one conversation, not two.

Attorneys aren’t interchangeable either. Their corporate attorney set up the initial corporate structure and helps with regulatory issues and key customer contracts. But estate planning and M&A counsel are different roles. An estate-planning attorney’s best moves work well before a deal is in motion. M&A counsel has a completely different job, one that begins with the LOI negotiation and runs through closing, with the goal of mitigating the owner’s post-closing risk.

Over the next four posts, we’ll go through each of these in turn. What transaction specialists see that no one else does, and why timing matters. We’ll also discuss the specific ways we work alongside each of them throughout the sale process. As the fifth advisor on the team, BPCA’s job goes beyond marketing to buyers and negotiating valuation. We also ensure the other four advisors are coordinated and working towards a single timeline to close.

When does it make sense to talk to an M&A advisor? Earlier than most owners assume. A conversation about realistic valuation ranges, what buyers are actually paying right now, and where a business has gaps a buyer would flag. That’s information every other advisor on this list can put to use immediately, whether a sale happens next year or in five. Having that conversation early costs an owner nothing, and it usually makes every other conversation with their advisors more productive.

Next: The Numbers Have to Hold Up Long Before a Buyer Looks at Them.

The Coordination Series · Part 2 of 5

Once the letter of intent (LOI) is signed, a buyer’s diligence team doesn’t start by diving into the projections. They start by confirming that the historic numbers presented can be trusted. Their quality-of-earnings (QoE) team will analyze every line item in the P&L and balance sheet, and test every accrual and revenue recognition policy. The owner wants the buyer to honor the price they agreed to in the LOI, and the QoE report is often the most important hurdle to achieving that goal.

Two Kinds of Problems:

Gradual margin erosion. Customer concentration. A sales pipeline that lacks consistency. Most buyers have seen these issues before, and they don’t walk away from the deal. They’ve been made aware of them during the pre-LOI process, and they price it accordingly. It may have resulted in an earnout or a lower multiple, but the deal survives because the problem is understood and the numbers describing it can be trusted.

Multi-year contracts recognized as revenue in a single period. Accrual policies that misalign project costs with revenues. Gross margins that aren’t fully burdened and overstate operating leverage. This is why deals that looked settled weeks earlier come apart in diligence. Once a buyer stops trusting one number, they stop trusting all of them. An owner who waits until an LOI is on the table to think about any of this has already lost the window of opportunity to address these issues. By the time a quality-of-earnings team finds them, there’s no way to fix them, only a slower and more expensive path to potentially restructuring the deal.

The difference between these two scenarios comes down to whether a CPA was in the room early enough to shape how these numbers were recorded in the first place.

What a CPA’s Job Actually Becomes

A controller or outsourced bookkeeper keeps the business running day to day: payroll, monthly closes, a cash-based P&L an owner can read at a glance. None of that is wrong, but none of it was built for an M&A process. A CPA with an eye on an eventual transaction is doing something else. They’re making sure years of revenue-recognition and accrual policies will hold up once someone outside the company starts testing them line by line, under no obligation to give the business the benefit of the doubt. That’s a different skill set than closing the books every month, and it’s worth knowing which one an owner’s CPA actually has before a buyer is the one asking.

As an M&A advisor, our role at BPCA isn’t to sit inside the CPA’s books. But with our years of deal experience, we can flag the accounting issues likely to come up during the process. This only works if we’re brought in early, while there’s still time to address them. We can work directly with an owner’s existing CPA regarding deal timing, what’s realistic to fix in-house, and where outside help may be needed before we start a process.

We’ve worked with businesses where the numbers are cash-based or accruals are hit and miss. Sometimes it doesn’t make sense, either because of timing or cost, to clean up the books before going to market. And we’ve successfully closed those transactions by being transparent with buyers from the start. But the benefit of clean numbers is that they tend to protect the valuation in the LOI. It’s worth it to start thinking about that years before selling.

Next: The Attorney Conversation With the Shortest Shelf Life.

The Coordination Series · Part 3 of 5

Estate-planning moves, such as gifting shares into a trust or restructuring ownership between generations, are most efficient at today’s valuation. Every year of growth without pre-sale planning raises their tax cost, and once a sale is under negotiation, the window may close altogether.

This is arithmetic, not preference. Whether it’s a discounted gift of minority interests into a trust, a grantor retained annuity trust (GRAT), or a family limited partnership, these structures are valued as of the transfer date, so some or all of the growth after the transfer happens outside the owner’s taxable estate. Funding a structure earlier, at a lower valuation, allows more future appreciation to pass to the owner’s family and other beneficiaries. If an owner waits until a buyer is circling, and the valuation is documented in a letter of intent (LOI), the same structure may remove far less from the estate, or may no longer make sense at all.

Two Owners, Two Timelines:

Consider two owners. One owner starts thinking about estate planning once a buyer is at the table. By then, the valuation is likely to be anchored to whatever the buyer has said the business is worth, with a deal in motion to prove it. The window to use a lower number has largely closed. Whatever pre-sale estate planning gets done at this point is more expensive, more rushed, and in some cases not available at all.

The other owner had this conversation years earlier, back when the business was worth a fraction of what a buyer will eventually pay. Shares moved into a trust at that lower value, the growth happened outside the estate, and by the time a sale is real, the most time-sensitive planning is already behind them.

The difference between these two owners isn’t how much estate planning they eventually did. It’s whether they did any of it before a number existed for anyone to negotiate over.

What an Estate Attorney Is Actually Racing

An estate-planning attorney’s best moves are most effective before a deal is in motion. The M&A advisor and M&A counsel are working to protect the valuation in the LOI and racing against the exclusivity clock. The estate attorney is racing against the rising valuation itself, and that clock starts running the moment a business starts growing, not the moment the owner decides to sell.

As an M&A advisor, BPCA can offer a market-based view of what the business is worth today and where that value may be headed over the next several years, based on the owner’s growth plans. While that’s not a qualified independent appraisal that meets IRS requirements, it’s a great starting point to for the owner to talk with an estate attorney and valuation firm. Sometimes an owner’s existing CPA offers the appraisal service, and when they don’t, we can introduce a firm that does.

For owners whose estates may exceed the federal or state exemption, pre-sale estate planning can protect future growth from being taxed in the owner’s estate, and doing it early is usually the most efficient move. But it isn’t the only estate planning lever, and for some owners it won’t happen. Family dynamics are unsettled, the timing never feels right, or rapid growth in a steady business consumes their attention. When that’s the case, there is still real value to preserve by structuring the deal with tax efficiency in mind and by using post-close estate planning vehicles. Either way, tax and wealth planning shouldn’t be siloed. That’s the topic of our next piece.

Next: Tax and Wealth Planning Are One Conversation, Not Two.

The Coordination Series · Part 4 of 5

It’s common for business owners to treat “tax planning” and “wealth planning” as two separate conversations with two separate people: one who structures the deal, and one who manages what’s left afterward. We usually recommend the opposite. They’re really one conversation, because the two inform each other. That conversation can happen with one integrated advisor, or with an owner’s CPA and wealth advisor working from the same set of numbers. What matters is that it happens together.

Two Advisors, Two Blind Spots:

A tax advisor optimizing purely for the deal will chase the structure that minimizes tax on the sale: asset versus stock, purchase price allocation, installment payments, rollover equity into the buyer’s new entity. These decisions matter, but in a vacuum they fail to answer a critical question: are the proceeds remaining after the transaction enough for the owner to move on to the next phase of their life? That phase could be retirement, with enough to maintain their lifestyle or provide for future generations. Or it could be capital to provide some security while they plan their next business venture.

A wealth advisor working from the other direction often builds a retirement plan primarily around a valuation provided by the owner, with no view into either the corporate structure or the contemplated tax structure for the sale. With only half the story, they may not know which pre-sale estate planning vehicles, which can meaningfully reduce estate tax, could be applied to this deal. And if an owner waits until a buyer is at the table, it may be too late for the advisor to put them to work. The retirement plan built with only half the story can start to come up short.

Neither advisor is wrong. They’re just answering half the question. A deal structure that minimizes tax but leaves an owner short of “enough” isn’t a good outcome. Neither is the reverse: a retirement plan built around a sale price that was never achievable, or around a tax treatment that could never be applied.

What Integrated Planning Actually Looks Like

An advisor or team that sees both sides at once models deal-specific tax structuring against the owner’s personal financial picture. That’s the best way to know whether a given structure actually gets an owner to “enough,” rather than just minimizing a tax bill in isolation. Some of the most valuable moves benefit from years of lead time, no matter who is advising: transferring ownership interests to family trusts, contributing business interests to charitable vehicles well before a sale is legally binding, or changing the business’s entity type where it makes sense. Which moves make sense depends on how the business is organized, which is one more reason to start the conversation early.

BPCA encourages owners to surround themselves with professionals who can support them along the entire continuum, from pre-sale estate planning through post-sale retirement. Working alongside an owner’s wealth advisor, we can provide a market-based view of value to model against, before a letter of intent (LOI) exists. That can happen before any estate planning has taken place (alongside a formal independent appraisal), or as an annual check-in to see how the market has moved and whether the plan needs adjusting.

Even the best planning depends on a well-run process. The next post is about the advisor who protects the deal from the LOI negotiation through closing: M&A counsel.

Next: Spend the Ten Weeks on What Matters.

The Coordination Series · Part 5 of 5

Most of the advisors in this series do their best work years before the letter of intent (LOI) is signed. M&A counsel is the exception. They usually come in for the LOI negotiation and stay through closing, a stretch of roughly ten weeks when the deal gets documented and confirmatory diligence wraps up. An owner who has spent years assembling a CPA, an estate attorney, and a tax and wealth advisor can’t treat the legal side of closing as a formality. It isn’t, and the wrong attorney at this stage can stall a deal that took years to set up.

Two Attorneys, Ten Weeks:

Consider two attorneys. The first may be an excellent corporate counsel, advising the owner on regulatory compliance or subsidiary formations, but doesn’t do enough M&A deals to know which terms are market and which carry real risk. So on the indemnification cap, the escrow period, and the working capital methodology, the attorney settles for “market-standard” language in the LOI. Then the buyer’s first draft of the purchase agreement defines “market” differently than the attorney assumed, and those same points come back marked up and flagged as deal-breakers. The buyer’s counsel starts to wonder what else will be contested. Weeks are lost arguing over points that should have been settled in the LOI, a deal that should have closed cleanly starts to feel harder than it needs to be, and every unnecessary negotiating point adds to the legal bill.

The second attorney has seen the same indemnification cap, escrow period, and working capital methodology dozens of times. In this deal, they made sure the key points were addressed in the LOI. “Market standard” wasn’t left to guesswork. They know which terms matter most to the owner and push hard on those, while conceding the ones that don’t. They’re problem solvers, not problem spotters. When something unexpected comes up, they come ready with solutions. This attorney keeps the deal on schedule, mitigates post-closing risk for the owner, and avoids unnecessary legal fees.

The Real Value of M&A Counsel

The job isn’t knowing the owner’s business for years. It’s having the foresight and confidence to tell an owner it’s worth taking the time to pin down key deal points in the LOI before signing it. When the first draft of the purchase agreement arrives, it’s knowing the difference between a deal term that’s an overreach by the buyer and one that only looks that way. It’s taking the time to read critical customer contracts and recognizing that, with this specific deal structure, the assignment language the buyer is requesting may only require notification. That judgment comes from years of M&A experience, ideally in the owner’s industry.

As an M&A advisor, BPCA has worked with many attorneys, and the best ones know which points are worth fighting for. We’ve also learned that personality fit and communication style can be just as important as industry experience, if not more so. If the role of M&A counsel is unfilled going into a transaction, we can make introductions so the owner can get comfortable with an attorney months before offers are on the table. From the LOI stage through closing, we work with the owner and counsel to stay aligned on the deal points that matter most. Our goal during that final stretch is to protect what the CPA, the estate attorney, and the tax and wealth advisor spent years getting right.

That’s the whole team: the CPA, the estate attorney, the tax & wealth advisor, and M&A counsel, with BPCA working alongside them. Owners get the best results when their advisors are talking to each other before a buyer ever appears. Whether a sale is years or months away, the clock on getting ready is already running, and we’ll join that conversation whenever the owner is ready.