July 28, 2025
From tax surprises and deal delays to value erosion and legal missteps, the hidden costs of selling your business can quietly chip away at your final payday. Fortunately, many of these hidden costs are avoidable — especially with the right planning and the guidance of a seasoned mergers and acquisitions (M&A) advisor.
Here’s what to watch out for — and how to avoid leaving money on the table.
Taxes can have a significant impact on your final outcome, yet many business owners underestimate how the structure of a deal affects their take-home amount.
Many sellers focus on the sale price, but the number that really matters is what you keep after taxes. A lack of early tax planning can result in:
Bring a tax advisor into the process early — ideally before the business goes to market. Based on your tax practitioner’s expert advice, you may want to consider:
Pro Tip: A good M&A advisor works hand-in-hand with your tax practitioner to build a tax-efficient deal structure from the outset. For example, Woodbridge offers professional and seamless tax planning to all clients via our parent company Mariner Wealth.
Selling a business is time-sensitive, and momentum matters. The longer a deal takes, the more variables — and stakeholders — come into play.
Every additional week of due diligence increases legal fees, operational distractions, and the risk of buyers walking away. Delays often come from unpreparedness, such as not having financials in order, unclear contracts, or disorganized data rooms.
Pro Tip: From Woodbridge’s 30-plus years of experience selling mid-sized businesses in North America, we know that “time kills deals”. That’s why we stick to a strict 150-day deal timeline for all M&A deals. Book an obligation-free appointment with one of our M&A experts today to find out more.
Even the simplest deals require legal oversight. But as complexity increases, so does the time and cost involved in navigating the transaction.
Legal expenses can quickly exceed expectations, especially if the deal involves complex earnouts, licensing/IP issues, or multiple jurisdictions. Remember, too, that if negotiations get adversarial, costs can balloon.
Pro Tip: Seasoned M&A advisors, like Woodbridge, work hand-in-hand with trusted M&A legal specialists who offer cost-effective, deal-savvy support to business sellers throughout the sales process.
The sale may be complete, but certain obligations can extend well beyond closing if sellers remain accountable for specific terms in the agreement.
Even after the deal closes, certain liabilities can come back to bite you — especially if warranties, indemnities, or earnout targets are poorly negotiated.
Pro Tip: A seasoned M&A advisor knows where buyers try to shift risk post-close — and how to build safeguards into the deal structure and/or push back.
Perception plays a critical role in how buyers assess your business. The way your company is presented can influence both interest and valuation.
Your business may be worth more than you think — but only if it’s positioned correctly. Without a compelling story, buyer fit, or competitive process, you risk accepting a lower offer than the market would actually bear.
Pro Tip: Seasoned M&A advisors create a tailored “deal thesis” and run targeted buyer outreach to attract the right suitors — not just whoever happens to knock on your door. For example, Woodbridge creates detailed pitch books for each seller, along with bespoke marketing videos that tell a compelling story about your business to appeal to specific buyers.
Preparing for a sale is demanding — often more than expected. For many owners, it becomes a second full-time job alongside running the business.
Running a sale process while managing daily operations is like flying a plane while building the runway. Business performance can dip during the process, hurting valuation and putting your deal at risk.
Pro Tip: A full-service M&A advisor handles coordination, buyer communication, and due diligence — freeing you up to keep the business thriving.
Selling your business is one of the biggest financial transactions of your life. Doing it right means more than just negotiating a good number — it’s about preserving value through every stage of the deal.
Avoiding hidden costs broadly requires:
A trusted M&A advisor doesn’t just save you time and stress — they help you walk away with more money, more certainty, and fewer regrets.
Thinking of selling in the next 6–24 months? Start planning now. Book a free appointment with one of our M&A experts now (only for companies with an annual revenue of $5M-plus).