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 offices in the network, Steven has been a business owner and broker for almost 12 years. Together, we dive into in-depth examples of what can happen once due diligence is complete, but a deal continues to drag on, and a buyer repeatedly pushes for additional concessions. Steven unpacks how to navigate these moments, manage expectations, and protect the integrity of the transaction. Along the way, we touch on key considerations around leases, asset sales versus stock sales, contractual nuances, and the often-overlooked power of simply knowing when and how to say no. This episode is a practical look at preparing for challenges in advance, so you can operate your business and approach transactions with more confidence and control. Thanks for listening!

Key Points From This Episode:

• Introducing Part 2 of our conversation on deal challenges with expert Steven Hanson.
• Challenges associated with the deal that Steven is currently working on.
• The supportive role of a broker in navigating concessions between buyers and sellers.
• Considerations to help determine whether or not to extend a lease as a business owner.
• An example of resolving a recent issue between landlord and tenant.
• Managing expectations and making informed choices as a renter.
• What changes when a transaction goes from an asset sale to a stock sale.
• Understanding the contractual implications of changing a transaction type.
• The tax implications of changing from one transaction type to another.
• Preparing for deal challenges and operating your business with this in mind.

Tip of the Day: Sometimes you just have to be prepared to say no. That's it. Hold your ground, say no, and then keep your mouth shut. It can be very effective when you put it back on the other person. Sometimes you just have to be ready to say no.

Links Mentioned in Today's Episode:

Steven Hanson
Steven Hanson Phone Number
Steven Hanson 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.

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 experienced business intermediary with more than a decade at Transworld, where he and his team help business owners navigate confidential sales, franchise growth, and mergers and acquisitions. In our conversation, Steven explains why every transaction has ups and downs, how brokers end up acting as both quarterback and coach for all the moving parts, and why you should never consider a deal done until the money is in the bank. Together they explore the impact of key employees on a sale, the pros and cons of when to loop staff into the process, what to do when valuations or lender decisions change late in the game, and how to manage the emotional toll of "deal fatigue." Steven also shares creative solutions he's used to keep deals alive and his simple but powerful tip for staying calm when tensions run high. To learn how preparation, flexibility, and a deep breath can help get more deals across the finish line, tune in now!

Key Points From This Episode:

• Hear about the typical challenges and hurdles in almost every deal.
• Find out how every deal has good days and bad days and why.
• Learn ways to reduce risk and why employees are the major source of risk.
• Why the real business value is in people and relationships, not just the hard assets.
• What point in the transaction the buyer should be able to meet the employee/s.
• How Steven pivots with sellers when bank feedback or valuation issues require changes.
• Explore the concept of "deal fatigue" and learn how to overcome it.

Tip of the Day: When a deal gets tense, pause to take a slow, deep breath before you respond.

Links Mentioned in Today's Episode:

Steven Hanson

Steven Hanson on LinkedIn

Call Steven Hanson: 858-699-3346

Transworld Business Advisors | San Diego
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.

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.

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 value. He is also the founder of iBridge Global Partners, the only firm in the US that integrates family, business, and transition into a comprehensive strategy. In our conversation, he explains the difference between a family business and a family enterprise, why starting early is essential, and how aligning family members is just as important as growing the company. He also delves into navigating family dynamics when transitioning a business, the pitfalls of poor planning, how families can prepare both relationships and business strategies for a smooth transition, and more. Join us to hear how fixing the family and the business can set the stage for a smoother, more valuable transition with Jeremy Stevenson!

Key Points From This Episode:

• Jeremy's background and how he became known as the family business guy.
• Learn about the difference between a family business and a family enterprise.
• Why starting early matters and assuming the kids will take over is a mistake.
• Understand how unclear expectations can lead to conflict and failed transitions.
• How Jeremy helps families align expectations and his idea of family governance.
• Unpack the common mistakes owners make and how to avoid them.
• How Jeremy navigates conflict and why the controlling owner's buy-in is critical.
• Find out when selling is the right decision versus succession or scaling.
• Final advice from Jeremy on how to unlock the full potential of your business.

Tip of the Day: Start now, involve advisers early, and think beyond just tax and legal considerations.

Links Mentioned in Today's Episode:

Jeremy Stevenson on LinkedIn

Jeremy Stevenson Email

iBridge Global Partners
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.

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 expertise to the conversation. Join us to learn what an ESOP is and why a business might choose one over other options. We'll explore how ESOPs function as retirement plans, unpack the concept of beneficial ownership, and break down vesting components. Mary also discusses the advantages of being ESOP-owned, the various legal areas associated with these transactions, the importance of a strong management team, and other crucial considerations for business owners. This episode is an insightful guide to understanding all things ESOPs. Don't miss out—start listening now!

Key Points From This Episode:

• We introduce today's guest, Mary McCooe.
• What is an ESOP anyway?
• Why businesses would choose to sell to an ESOP rather than a private buyer.
• How ESOPs work as a retirement plan for employees.
• A small distinction: selling to the ESOP for the benefit of the employees.
• Beneficial ownership of a company and what that means.
• Mary breaks down the vesting component of ESOPs.
• What happens when employees leave an ESOP-owned company.
• The advantages of a company being ESOP-owned.
• Her thoughts on why every company isn't already an ESOP-owned company.
• The various areas of law associated with ESOP transactions.
• Why having the right team is essential.
• We dive further into the advantages of being ESOP-owned.
• Why it's beneficial for business owners: the succession plan.
• The importance of having management teams in place.
• Mary describes her role on the ESOP team.
• Other ESOP considerations for business owners.
• How these transactions are financed.
• The ideal size for ESOP company success.

Tip of the Day: If you are considering selling your business, learn about what an ESOP is. Spend some time talking to somebody who is knowledgeable about ESOPs and consider whether it's the right option for you.

Links Mentioned in Today's Episode:

Mary McCooe on LinkedIn

Mary McCooe at Maselan & Jones

Mary McCooe on Email

Mary McCooe Phone Number: +1 617 310 6567

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.

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 businesses, and so much more! We delve into the timeline involved in these kinds of loans before discussing the importance of selecting a good attorney for this process. Jennifer even shares what causes SBA deals to fall apart. Finally, our guest shares her tip of the day with listeners. Be sure to press play now!

Key Points From This Episode:

• A warm welcome to today's guest, Jennifer McKay.
• Jennifer tells us what an SBA loan is and how it differs from other loans.
• What loan approvers are looking for in buyers and sellers.
• Why SBA transactions mostly move quite quickly.
• The importance of having the right attorney to represent you.
• Jennifer shares some common reasons SBA loans fall apart.
• One key takeaway from this conversation: surround yourself with trusted advisors!

Tip of the Day: If you're navigating an SBA loan, you need to surround yourself with trusted advisors. A solid team can save you from costly missteps and set you up for success!

Links Mentioned in Today's Episode:

Jennifer McKay on LinkedIn

Jennifer McKay Email Address

Jennifer McKay Phone Number: 508 244 2309

Live Oak Bank

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.