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.

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. We dive into some powerful tactics, such as setting an extreme anchor and staying silent before discussing the importance of listening and keeping emotions at bay. Bill also highlights the value of showing understanding, being cautious of artificial deadlines, and always getting everything in writing! You don't want to miss this one!

Key Points From This Episode:

• Welcoming Bill Luce to this episode of Transaction Talk.
• What negotiation is and why it's so important to understand it.
• The importance of preparing for a negotiation and how to do it.
• Why setting an extreme anchor is a good negotiation tactic.
• The worst thing that can happen in a negotiation: getting emotional.
• Why you need to (really) listen to the other person when negotiating.
• The power of showing understanding towards the other party.
• A reminder to be wary of artificial deadlines set in negotiations.
• Bill outlines the most common mistakes people make when negotiating.
• Key takeaways: thinking outside the box and making sure everything's in writing!

Tip of the Day: Negotiating a deal? Get it in writing! A handshake won't hold up in court, but a clear, written agreement protects your time, money, and peace of mind.

Links Mentioned in Today's Episode:

Bill Luce on LinkedIn

Bill Luce Email Address

Transworld Business Advisors

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.

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, and the challenges of business valuation amid separation, Cindy shares essential strategies to help you protect your business interests, navigate financial and legal hurdles, maintain operational stability, and communicate effectively during this difficult time. We also discuss extreme scenarios like court-ordered sales and the protective role of operating agreements, offering practical tips to help business owners navigate this intersection with clarity and strategic planning. Tune in to gain invaluable insights and learn how proactive collaboration between legal and business experts can safeguard your interests when personal and professional worlds collide!

Key Points From This Episode:

• Why selling a business during divorce is uniquely challenging.
• How marital estates impact business valuation.
• The importance and role of prenups and postnups (and how they differ).
• Navigating business valuation during separation.
• Court-ordered sales and extreme divorce cases.
• How operating agreements can protect business interests.
• Balancing emotional and legal considerations in negotiations.
• Common mistakes people make when going through a divorce.
• The importance of collaborating with legal and business professionals.
• Key takeaways: how to protect both your business and yourself!

Tip of the Day: Getting divorced? Slow down and stay in control. Work with a mediator or collaborative attorney to help you protect your wallet, your business, and your sanity.

Links Mentioned in Today's Episode:

Cynthia Runge

Peridot Family Law

Cynthia Runge 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.

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 attorney for business succession planning, probate administration, and complex and simple estates, and he begins our conversation by defining estate planning and explaining why it's essential for all businesses. Then, we explore the differences between a will and a trust, what it means to avoid probate, why setting up a will or trust should be your top priority, and how estate planning informs succession planning. We also uncover the consequences of not having a will or trust when incapacitated during a sale as a business owner, why many procrastinate on their estate planning, why a healthcare proxy matters, and where spouses fit into the various components of estate planning. To end, Neil shares the Tip of the Day and we learn how to connect with him and his work.

Key Points From This Episode:

• Neil Cohen defines estate planning and explains its importance for businesses.
• Why Massachusetts leans heavily on irrevocable trusts.
• The difference between a will and a trust, and what it means to avoid probate.
• Why setting up a trust should be one of your non-negotiables.
• Protecting business owners: How estate planning informs succession planning.
• The consequences of an owner being incapacitated during a sale without a will or trust.
• When business owners should start their estate planning and tips for keeping it updated.
• Why procrastination reigns: Common obstacles that prevent estate planning.
• Understanding how often you should review your estate plan.
• The ins and outs of the healthcare proxy and its importance and where spouses fit in.
• How to connect with Neil Cohen.

Tip of the Day: Start Early! Estate planning can start even before you have kids or own a business. The only way to falter is by not starting at all, and because none of us can predict the next moment, the best time to start is now.

Links Mentioned in Today's Episode:

Neil Cohen on LinkedIn

Neil Cohen Email

Neil Cohen Phone Number: 781-246-2525 ext. 241

RS Law LLP (Regnante Sterio LLP)

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.