Transaction Talk

Most owners focus on valuation, buyers, and negotiation, but a confidentiality breach can really derail a deal before it ever reaches the closing table. During this episode, Transworld Boston Business Broker Greg Young makes his debut on Transaction Talk to explore why confidentiality is so important to business transactions. Join us as we unpack the harm that can happen to employee, buyer, seller...

A strong purchase price does not mean much if the agreement leaves one party exposed to unexpected liability after closing. In this episode of Transaction Talk, hosts Jennifer Fox and Eric Sigman break down representations, warranties, and indemnification provisions in mergers and acquisitions. Eric explains the difference between representations and warranties, what they cover, and the associated...

Welcome back to Transaction Talk! Today, we are joined by VP and Business Banking Relationship Manager (RM) at Eastern Bank, Gregory Giacopelli, to discuss small businesses and their impact on communities. Tuning in, you'll hear all about why Gregory believes small businesses are important to communities from a banker's perspective, how Gregory defines a small business, and why banking relationshi...

What is a business really worth, and why do buyers and sellers so often see that number differently? In this episode of Transaction Talk, Jennifer Fox and Eric Sigman sit down with Louis Pereira of Merrimack Business Appraisers to unpack how business valuations are actually determined and why preparation plays such a major role in maximizing value. Drawing on decades of experience in business brok...

What causes a business sale to fall apart before it reaches the closing table? In this episode of Transaction Talk, hosts Jennifer Fox and Eric Sigman welcome back Aaron Fox, Managing Director of Transworld Business Advisors Boston, to discuss why deals often break down, what warning signs owners should watch for, and how better preparation can keep a transaction moving forward. Aaron walks throug...

What are buyers really looking for in today's deal market? In this episode of Transaction Talk, Jennifer Fox and Eric Sigman are joined by Steven Smith of Business Transfers & Strategies, a buy-side advisor who works closely with individual buyers, private equity groups, and strategic acquirers. He breaks down how each type of buyer approaches acquisitions and what drives their decisions, from gro...

Is there ever really a perfect time to sell your business, or does the best exit come down to preparation, performance, and knowing when  not to wait? In this episode, Jennifer Fox and Eric Sigman welcome back Johnathan Zsittnik, Senior Manager and Business Broker at Transworld Boston, to discuss how to know when it is the best time to sell your business. Jonathan explains why waiting for the perf...

Selling your business is likely the largest financial event of your life, yet many owners try to go it alone or wait until the last minute to prepare. In this episode, Jennifer Fox and Eric Sigman explain why a successful exit starts with building the right professional team. They break down how the right advisors can turn what might feel like a stressful, complex process into a smooth and profita...

Building a successful business isn ' t all that different from building a strong marriage. Both require communication, trust, and long-term commitment, even when things get tough. In this episode of Transaction Talk, we welcome Jennifer and Ryan Armstrong of Transworld Business Advisors Phoenix to discuss how their business partnership has evolved over the course of their 20-year marriage. Jennife...

Is getting answers from a seller like pulling teeth—or an open, transparent conversation? Buy-side expert Steve Smith says deal success often hinges on one critical factor: tone. Today, your hosts, Jennifer Fox and Eric Sigman, are joined by Steven Smith from Business Transfers & Strategies. Steven shares insights on how business owners can establish credibility when selling their company, from th...

What should business owners be doing now if they ' re thinking about selling in 2026 or beyond? In this episode of Transaction Talk, Jennifer Fox and attorney Eric Sigman break down the key steps sellers can take to prepare for a smoother, more successful exit. Drawing on years of experience, they explain why a business sale typically takes around nine months from preparation to closing, why you c...

A Letter of Intent may not be legally binding, but it can determine whether a deal moves forward or falls apart. In this episode of Transaction Talk, hosts Jennifer Fox and Eric Sigman break down the role an LOI plays in buying and selling a business, and why it deserves serious attention from both buyers and sellers. They explain what an LOI is, what it typically includes, and how it sets expecta...

Overcoming challenges is important, but what if you could prepare for them before they ever surface? In this conversation, Steven Hanson joins us again to share from his wealth of hard-earned experience and practical knowledge around transactions, deal challenges, and how to resolve them before they become deal-breakers. As Partner of the San Diego Transworld office, one of the top-performing offi...

What happens when your "straightforward" business sale suddenly runs into nervous employees, bank surprises, shifting valuations, or a seller who is just exhausted by the process? In this episode of Transaction Talk, Jennifer and Eric are joined by Steven Hanson, Transworld Business Advisors owner and partner, to dig into real-world deal challenges and practical ways to solve them. Steven is an ex...

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. Tod...

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 b...

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 valuat...

For many family businesses, the biggest obstacle to a successful exit is not the market; it ' s family dynamics. In this episode of Transaction Talk, we welcome Jeremy Stevenson to discuss how he helps owners " fix the family and the business" during the transition process. Jeremy is an entrepreneur, consultant, and adviser who has helped over 150 family businesses unlock more than $5 billion in v...

Are you a business owner considering a sale but want to explore all your options? Then this episode of Transaction Talk is for you! Today, we dive into the world of Employee Stock Ownership Plans (ESOPs) with Mary McCooe, a Corporate and Benefits Lawyer from Maselan & Jones. As a specialist in ESOPs, financing transactions, and a wide range of employee benefits issues, Mary brings a wealth of expe...

SBA loans can be a powerful tool for business buyers and sellers once you understand how they work and what approvers are really looking for. Today, we are joined by Jennifer McKay, senior loan officer at Live Oak Bank, to discuss all things SBA loans. Tuning in, you'll hear all about what an SBA loan is, why it's a unique kind of loan, what loan approvers are looking for in buyers, sellers, and b...

Negotiation isn't just a skill; it's a strategy that can make or break your next big deal! Today on Transaction Talk, we are joined by senior business advisor at Transworld Business Advisors, Bill Luce, to discuss the art of negotiation. From defining what negotiation really is to explaining why preparation is key, Bill walks us through the negotiation methods every business owner should master. W...

Selling a business is challenging on its own, but when paired with the emotional and legal complexities of a divorce, it can feel overwhelming! In this episode, we're joined by family law attorney Cindy Runge, who draws on her extensive experience to unpack the critical legal and financial factors involved. From understanding how marital estates are valued to the impact of prenups and postnups, an...

Estate planning is a vital component for all business owners, and today, we unpack everything you need to know about estate planning for your business. We are joined by Neil Cohen from RS Law LLP (previously Regnante Sterio LLP), an AV-rated firm bringing a collaborative approach to legal representation in order to provide comprehensive and efficient legal services. Neil is an estate planning atto...

On this episode of Transaction Talk, hosts Jennifer Fox and Eric Sigman sit down with Dave Killen, a commercial real estate broker at LandVest, a firm specializing in customized commercial real estate solutions. Dave shares his expertise on everything from complex property valuations to identifying the right buyers for unique properties. Tune in to learn about the challenges of valuing businesses...

Artificial intelligence is changing the way businesses operate, but do you know how to use it responsibly? Today on Transaction Talk, we ' re joined by Adam G. Gutbezahl, an AI thought leader in the legal field, litigation attorney, and author of the CHATAdamG newsletter, a monthly digest of AI trends shaping the legal landscape. In our conversation, Adam breaks down how AI tools, especially large...