For many business owners in Boston, selling a company is the culmination of decades of work. It’s the moment they finally let go of something they built from the ground up; something that’s defined their identity, their schedule, and often their family life.

That was the case for Scott Giles, founder of ScoreBuilders, who, after 34 years, decided it was time for his next chapter. “After 34 years, it just came to the point where there was more regulation, more documentation, more HR,” Scott shared on the Transaction Talk podcast, hosted by Jennifer Fox of Transworld Business Advisors of Boston and Eric Sigman of the law firm Ruberto Israel & Weiner. “So, randomly out of the blue, I said, let’s sell the business.”

It sounds simple, but as Scott quickly learned, the hardest part of selling a business often begins after the offer is accepted. The due diligence phase can feel like running a marathon after crossing the finish line, and without the right team, it’s easy to feel overwhelmed.

When Scott partnered with Jennifer of Transworld, he discovered just how vital an experienced brokerage team can be, especially when navigating the complex, detail-heavy process of due diligence.

The Buyer’s Deep Dive — When Due Diligence Gets Real

After months of marketing, meetings, and negotiations, Scott reached what every seller dreams of: an accepted offer for his business. But as he soon found out, that’s when things get real.

During the due diligence phase of selling his business, the buyer wanted to understand every layer of ScoreBuilders, from revenue trends and staffing to inventory and post-pandemic performance. “The requests didn’t stop,” Scott recalled. “Every time we thought we were done, it was, ‘Can you produce this document? Can you explain why your inventory has these levels, and why it was different pre-pandemic?’”

It wasn’t that the buyer was difficult; this level of scrutiny is actually quite standard during due diligence. Buyers investing in an established business are verifying what they’re purchasing. But for sellers, it can be exhausting. Every question feels personal, every delay feels consequential.

In Boston’s competitive M&A landscape, where Jen and her team of business brokers at Transworld routinely handles both Main Street and lower-middle market deals, due diligence can stretch for weeks or even months at a time, depending on the complexity of the transaction. And as Scott experienced, the volume of requests can feel endless without a structured process in place.

That’s where Transworld Boston’s team approach makes a difference. Rather than leaving sellers to fend for themselves, brokers like Jennifer Fox provide support to sellers during this stressful time. They help clients stay grounded when the process feels invasive or uncertain.

Takeaway # 1: Preparation Is the Key to Due Diligence

Scott’s story highlights a simple truth: preparation is everything. The more organized a seller is before listing, the smoother the process will be once an offer comes through.

Business owners considering a sale in the next year or two should:

• Gather documentation early. Have your financial statements, tax returns, lease agreements, and employee information ready. Buyers will ask for them.
   
• Anticipate buyer questions. Think about how your business evolved, especially during major events like COVID-19, and be ready to explain shifts in performance or expenses.
   
• Work with experienced advisors. A qualified business broker can provide support while you prepare the necessary documents and information.
   

In short, the due diligence phase doesn’t have to be painful—it just needs to be planned.

Takeaway # 2: Having the Right Team in Boston is Critical

Scott attributes much of the successful sale of his business to one thing: his team. He had Jennifer from Transworld Boston and a trusted CPA handling financial documentation. But as due diligence intensified, he realized his general attorney wasn’t equipped for the workload of a business transaction.

“At one point,” Scott explained, “I went back to Eric and Jennifer to ask if they could recommend an attorney who specialized in transactions. The best thing about this process was the team we had around us: the brokers, the accountant, and the attorney. If any one of those three people couldn’t pull their weight or were slow to engage, it would have impacted the deal.”

That reflection captures one of the most overlooked lessons for sellers: experience matters. An attorney who “does a few closings” a year may not be ready for the speed and precision required in an M&A transaction. The same goes for accountants and advisors.

At Transworld of Boston, every sale benefits from a built-in network of specialists, including CPAs, lenders, attorneys, and financial advisors. That means sellers have access to experts who understand Boston’s unique market conditions, tax implications, and local regulations. It’s this integrated support system that allows Transworld to consistently close big, complex deals throughout Middlesex, Essex, Norfolk, and Suffolk Counties.

If He Had to Sell His Business Again, What Would Scott Do Differently?

Looking back, Scott admits he might have done a few things differently. “Had I known a year or two earlier that I was going to sell, I would have timed out some business activities differently,” he said. “I may not have done all the projects we did, because we didn’t have time to make that help our EBITDA. Our books could have looked better had I been able to strategically think about the sale for a couple of years.”

It’s advice every business owner should hear. Strategic planning, not just for growth, but for eventual exit, can significantly influence valuation and buyer confidence. Sellers who plan ahead are better positioned to highlight their business’s strengths, address potential red flags, and navigate negotiations from a place of confidence.

Scott’s honesty also underscores the importance of having partners who know how to adapt when timing isn’t perfect. Even though he made the decision quickly, Transworld of Boston helped him prepare, present, and ultimately sell his business successfully.

Listen to the full episode:What Business Owners Don’t Expect During Due Diligence — Lessons from a Real Seller.

About Transaction Talk

Transaction Talk is a podcast hosted by the Transworld Business Advisors team, featuring real stories from entrepreneurs who’ve bought or sold a business. Each episode breaks down the human side of business transactions, such as what worked, what didn’t, and what future sellers can learn. From exit planning to negotiations and due diligence, Transaction Talk offers practical insights for anyone considering a sale. Explore more episodes ontheir website.

About Transworld Business Advisors of Boston

Transworld Business Advisors of Boston helps business owners across Massachusetts buy, sell, and grow small to mid-sized companies. Backed by the global Transworld network, the Boston office brings together a powerful team of brokers, CPAs, and attorneys who guide clients from valuation to closing with integrity and confidentiality.

With a proven track record across industries like manufacturing, education, logistics, and healthcare, Transworld Boston has become one of the area’s largest and most trusted brokerage firms. Their innovative approach, local expertise, and hands-on support make even the most complex transactions feel seamless, whether you’re selling a Main Street business in Essex County or a multi-million-dollar company in The Seaport.

Transworld’s commitment is simple: help Boston business owners get maximum value, simplify the process, and create a stress-free transition to the next chapter.

Helpful Links: Sell A Business in Boston

• Find Out What Your Business Is Worth
• FAQs About Selling a Business in Boston
• Talk to Jen Fox About Selling Your Business

Related Reading: Selling A Business in Boston

• Navigating a Business Sale with a Commercial Lease in Massachusetts
• Do You Need an Attorney to Sell Your Business in Boston?
• Understanding Capital Gains on a Business Sale