Recognized for its energy and diversity, Boston's M&A market stands out as one of the most active in the world. Joining Eric and Jennifer on the show today is senior broker Jonathan Zsittnik from Transworld Boston. With over 15 years of experience completing successful transactions, from small business sales to large mergers and acquisitions, Jonathan brings a wealth of insight to the table. Today, he'll walk us through a real-life business sale: a 30-year-old asbestos company in the Boston area. From preparing the retiring owners to closing the deal, he breaks down the entire process and shares how he helped them achieve their goals. Be sure to start listening now to learn more from Johnathan Zsittnik today on Transaction Talk!

Key Points From This Episode:

• An introduction to what listeners can expect from today's episode.
• Who is Johnathan Zsittnik?
• How Johnathan approaches initial conversations and goal setting with clients.
• A real-life example of conversations with the sellers of the asbestos business.
• Diving into the details about how he valued the business.
• What he means by the quality of earnings and the factors that can influence it.
• How the sellers navigated the process of sorting through the multiple buyer options.
• Next steps and what they discovered in the due diligence.
• Contracts in place and what that means: asset versus stock sale.
• Johnathan's thoughts on what made the process smooth from beginning to end.
• Aftermath of the sale and what it currently looks like for the seller.
• Johnathan shares his tip of the day.

Tip of the Day: Enter a deal in good faith, align early on what matters most to both sides, and save the finer details for when you draft the purchase agreement.

Links Mentioned in Today's Episode:

Johnathan Zsittnik

Johnathan Zsittnik Phone Number: +1 978-472-4385

Johnathan Zsittnik on Email

Johnathan Zsittnik on LinkedIn

Johnathan Zsittnik on X
Jennifer Fox on LinkedIn

Eric Sigman on LinkedIn

Transaction Talk

Disclaimer:

The material on this site may be considered advertising under the rules of the Supreme Judicial Court of Massachusetts. This site is solely for informational purposes and provides general information only. Nothing on this site should be construed as legal advice or consultation either generally or in a particular case. Neither the receipt nor the distribution of materials constitutes the formation of an attorney-client relationship.

Smart tax planning starts when you form your business! Today, we are joined by Caleb Powers to discuss one of the best-kept secrets in the tax code, Section 1202. Tuning in, you'll hear about our guest's impressive career, what 1202 stock is, why it's important to consider it when planning to sell a business, who qualifies, and so much more. We delve into the drawbacks of being a C-Corp business before Caleb tells us how the Big Beautiful Bill has enhanced Section 1202. We also discuss common mistakes he sees businesses make that cause them to lose their Section 1202 status, and Caleb reminds listeners of the importance of having a good team when planning an exit. Finally, Caleb ends with his invaluable tip of the day. If you want to save a fortune in exit taxes, this episode is for you, so be sure to press play now!

Key Points From This Episode:

• Introducing Caleb Powers and a brief overview of his career.
• What 1202 stock is and why it should be considered when selling a business.
• Caleb walks us through who qualifies and who doesn't for Section 1202.
• The drawbacks of being a C-Corp and what to consider when converting.
• How the Big Beautiful Bill has enhanced Section 1202 and why it's for small businesses.
• Some potential burdens that may come with having a Section 1202 business.
• Common mistakes Caleb has seen that have caused businesses to lose their 1202 status.
• The importance of having the right team in place when considering your exit options.
• Caleb tells us a story about an entrepreneur who saved massively using Section 1202.

Tip of the Day: Surround yourself with people who understand Section 1202! It can make an enormous difference to the wealth you're trying to build!

Links Mentioned in Today's Episode:

Caleb Powers on LinkedIn

Caleb Powers Email Address
Jennifer Fox on LinkedIn

Eric Sigman on LinkedIn

Transaction Talk

Disclaimer:

The material on this site may be considered advertising under the rules of the Supreme Judicial Court of Massachusetts. This site is solely for informational purposes and provides general information only. Nothing on this site should be construed as legal advice or consultation either generally or in a particular case. Neither the receipt nor the distribution of materials constitutes the formation of an attorney-client relationship.

All businesses experience some seasonality, but what sets the sale of a seasonal business apart from a typical transaction? Joining the podcast is Aaron Fox, Managing Director of Transworld Boston, and partner to host Jennifer Fox, to break down "The Seasonal Sale" and what makes these deals unique. They walk through a real-life seasonal sale, explain why annual financials are critical for valuation, and explore how to manage transition periods effectively. He shares thoughts on what it might look like to buy or sell during a busy season and unpacks one of the highest strategic acquisitions they see. The conversation also covers how lenders approach seasonal businesses and why the type of buyer can significantly influence the outcome. For more insights—and Aaron's tip of the day—tune in now.

Key Points From This Episode:

• An introduction to our guest today, Aaron Fox.
• What makes the process of selling a seasonal business different from a regular business.
• He unpacks what a seasonal business is and shares an example of a transaction where a seasonal business was part of the deal.
• Annual pictures for the valuation of seasonal business.
• How to handle seasonal business transition periods.
• His thoughts on selling (or buying) a business in the middle of the busy season.
• How lenders view seasonal businesses and why they look at the annual picture.
• Whether the type of buyer affects the outcome of a seasonal business sale.
• A level of seasonality and seasonal implications is present in almost all businesses.
• He unpacks one of the highest strategic acquisitions that they see.
• Dealing with the potential uncertainty and unpredictability of seasonal businesses.
• Why buyers and sellers need to know they're buying the future but paying on the past.
• How to contact Aaron Fox.
• A recap of the episode on buying and selling seasonal businesses.

Tip of the Day: Cash flow is king—keep clean books, prepare monthly financials, and be ready to clearly show and document your cash flow!

Links Mentioned in Today's Episode:

Aaron Fox Transworld Boston

Aaron Fox Phone Number — +1 (781) 773-8922

Aaron Fox on Email
Jennifer Fox on LinkedIn

Eric Sigman on LinkedIn

Transaction Talk

Disclaimer:

The material on this site may be considered advertising under the rules of the Supreme Judicial Court of Massachusetts. This site is solely for informational purposes and provides general information only. Nothing on this site should be construed as legal advice or consultation either generally or in a particular case. Neither the receipt nor the distribution of materials constitutes the formation of an attorney-client relationship.