Selling a business tends to get talked about like it is one big event. In reality, the better outcomes usually start much earlier. Long before a company ever goes to market, owners can make decisions that affect value, taxes, diligence, deal structure, and what they actually keep at the end of the process.
Brian Andreosky, Managing Director at Aldrich Capital Advisors, and Mike Whitmore, Partner and leader of Aldrich CPAs + Advisors’ Transaction Advisory Services practice, discuss why planning early matters, what owners should be paying attention to, and where they often leave value on the table by waiting too long.
Brian Andreosky: What is transaction advisory really about, and why should business owners care about it?
Mike Whitmore: One thing I tell regularly tell clients is that every business is going to transition somehow. You are either going to sell it, pass it on, or eventually shut it down. So the real question is not whether a transition is going to happen. It is whether you are planning for it in a way that gives you options.
Brian: So does transaction advisory really help an owner?
Mike: It’s about helping an owner move the business from one stage of ownership to another in a way that makes sense financially and strategically. That could mean a sale to a third party. It could mean transferring ownership to family, a key employee, or another internal group. It could be another succession path entirely.
And that is really the bigger point. Good planning is not just about getting a deal done. It is about protecting value, reducing surprises, and helping owners think through what they want for themselves and the people around them.
Brian: What types of businesses benefit most from that kind of planning?
Mike: It is usually less about industry or type and more about where the company is in its life cycle, how complex things are, and what kind of transition is most likely.
For a smaller company, a full process may not always make economic sense if the cost outweighs the potential benefit. But as the business gets larger, more mature, or more valuable, the planning opportunities usually become more meaningful, too.
And complexity tends to creep in faster than people expect. Maybe there are multiple shareholders. Maybe there is an internal succession plan. Maybe ownership is starting to shift and people have not fully thought through what that means yet. That is where planning earlier can make a big difference.
Brian: When should an owner actually start thinking about this?
Mike: Unfortunately, too many owners are reactive instead of being strategic.
A pretty common situation is that an owner already has a signed Letter of Intent or is deep into a purchase agreement before they ask for help. At that point, there is still plenty that can impact the deal, but a lot of the bigger opportunities have already passed.
The better time to start is well before the transaction is active. Sometimes that means years in advance. The reason is simple. Preparation takes time, and it tends to pay off. Owners have more room to improve reporting, think through tax structure, address issues that could come up in diligence, and get clear on what they actually want out of the deal.
Brian: How does early planning actually improve value before a transaction?
Mike: A big part of it is just having time to get the business ready.
Most privately held companies do not have reviewed or audited GAAP-based financial statements because their bank never required them. That may not be a problem while they are operating normally, but it often becomes an issue during a sale. Buyers want to understand the numbers, the accounting policies behind them, and whether there are any areas that need more explanation.
If that work has not been done in advance, the process gets more complicated. There are more questions. There is more friction. Diligence takes longer.
There is also the very practical side of organizing the business for a transaction. I sometimes call that building a deal book. It means getting financial statements, tax records, major contracts, accounting methods, and other important documents organized ahead of time. If that work is already done, the owner is not scrambling once the process starts. The business can move through the transaction more efficiently, and the story tends to come across more clearly.
Brian: Once an owner starts thinking seriously about a transaction, what matters most beyond just the sale price?
Mike: Price matters, obviously, but it is only one part of the deal.
Owners also need to look at structure, taxes, payment timing, working capital expectations, lease arrangements, retention bonuses, and how much of the purchase price they are likely to keep once everything is factored in. Sometimes a deal looks great at the headline price level and feels very different once those details are worked through.
Then, there is the personal side of it. Owners need to ask what life looks like after the transaction. What do they actually need from the sale to support their goals? Are they staying involved in any way? How does their personal balance sheet change after closing? Are there estate planning, gifting, or wealth-transfer issues they should be thinking about before the process gets too far along?
Those are important questions. They are not secondary.
Brian: Why is it important for owners to think about a transaction as more than just a sale process?
Mike: Because there is a lot more happening than simply finding a buyer.
A transaction puts a spotlight on the entire business. Financial statements, accounting processes, tax planning, documentation, and internal controls all matter. And in a lot of cases, the owner’s personal planning matters too. Buyers are usually looking at more than historical earnings. They want a fuller picture of value and risk.
That means issues that have been sitting in the business quietly for years can suddenly become very relevant. The earlier an owner identifies those issues, the more options they usually have to address them thoughtfully instead of under pressure.
Brian: What is one piece of advice you would give an owner who thinks they may sell within the next three to five years?
Mike: Get the accounting in order and start sooner than feels necessary.
Good financial records do more than make diligence easier by creating confidence. They help buyers understand the business, and they make it easier for the owner to support value.
Start organizing the financial statements, contracts, tax records, accounting methods, and other key documents now instead of waiting until negotiations are already underway. I have seen deals slow down because buyers found accounting issues that could have been addressed years earlier. Most of the time those issues can be fixed, but when that happens in the middle of a transaction, it usually costs more time, more money, and sometimes more leverage than it should.
The businesses that tend to have the best outcomes are usually the ones that were preparing long before the market ever saw them.
About Mike Whitmore
Mike Whitmore, CPA, is a partner at Aldrich CPAs + Advisors with extensive experience serving clients in real estate, healthcare, private equity, manufacturing, and other complex industries. He specializes in mergers and acquisitions, consulting and, advising, multi-state and multinational businesses.
Prior to joining Aldrich through its acquisition of HMA CPA, Mike served as a managing director at an international accounting firm.
About Brian Andreosky
Brian Andreosky is the President of Aldrich Capital Advisors, and is dedicated to helping business owners transition their companies. In this role, he provides exit planning services to help business owners find the right solution to transition and maximize the value of their business. Brian is a member of the Exit Planning Institute (EPI).
Prior to joining Aldrich, Brian held roles in investment management, management consulting, and private equity.
About Aldrich Capital
Aldrich Capital LP provides advisory services for business transactions, including succession planning, acquisitions, or mergers. We help business owners navigate challenges and unlock growth opportunities with actionable insights. Our innovative team is dedicated to your success.
