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 PartnersJennifer 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.

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 alongside real estate, the implications of a business not paying rent, and why business owners should engage a broker sooner rather than later. Dave also breaks down the nuances of 1031 exchanges, the importance of due diligence in real estate and business deals, and how LandVest’s sophisticated marketing network helps connect sellers with the right buyers, even when the ideal buyer isn’t obvious. Don’t miss this insightful conversation packed with expert advice on navigating the complexities of commercial real estate!

Key Points From This Episode:

• The different types of valuations that Dave does for commercial real estate.
• How to determine the value of a business when it owns the property.
• Interesting properties that Dave has worked on with LandVest.
• The difference between real estate and commercial real estate brokers.
• How Dave finds buyers for unique properties and developments.
• The typical timeframe for commercial property valuation and sales.
• When business owners should contact a commercial real estate broker.
• How to do a 1031 exchange (and how to know if it’s right for you).
• Conducting due diligence for business and commercial real estate transactions.

Tip of the Day: Price your property realistically. In today’s market, deals that are priced appropriately will move, while overpriced listings are likely to stall. The period of aspirational pricing is behind us, so sellers should focus on setting a fair market value from the start!

Links Mentioned in Today’s Episode: Dave Killen

Dave Killen on LinkedIn

Call Dave Killen on 508-451-0020

LandVest 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.

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 language models (LLMs), are being used in business and the legal risks they pose. From the dangers of AI-generated misinformation to increasingly convincing phishing scams, he shares examples of AI misuse and how companies can protect themselves. We also discuss why every business should have an AI policy in place and how leaders can ensure their employees use AI responsibly. Whether you’re excited by AI’s potential or wary of its risks, this episode will equip you with the knowledge you need to navigate AI with confidence!

Key Points From This Episode:

• An overview of how we use AI every day, from autocorrect to ChatGPT.
• Why AI's output depends on the quality of the data it is trained on.
• How to instruct Large Language Models (LLMs) like ChatGPT for optimal results.
• The risks of using AI without proper oversight.
• Suggestions on how to responsibly use AI as a tool for efficiency.
• What companies can do to safely navigate the AI landscape.
• Why businesses should seriously consider hiring a Chief Technology Officer (CTO).
• How a CTO and AI policy can help protect you against potential harm.
• Adam’s predictions for the future of AI and how to set your business up for success.

Tip of the Day: AI is a powerful tool, but like any tool, it works best when you understand how to use it. Don’t be afraid to ask questions and admit what you don’t know. Taking the time to learn first will save you from costly mistakes down the road!

Links Mentioned in Today’s Episode: Adam G. Gutbezahl, Esq. on LinkedInFind Adam at 255 State Street, 7th Floor | Boston, MA 02109

Call Adam direct at 617-570-3502 or on his cell at 508-649-4216

Contact his office at 617-742-4200 or fax him at 617-742-2355

Email Adam at [email protected]

Ruberto Israel & WeinerSign up for the CHATAdamG Newsletter

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.

How would you run your business differently today if you knew exactly how you would leave it tomorrow? A business exit strategy is not something you plan when you are ready to sell. It is something you build from day one. Without the right preparation, you could leave money on the table or even struggle to sell your business. In this episode of Transaction Talk, we welcome Megan Kearney, entrepreneur, franchisee, and Partner at Exit Factor Lexington, to discuss why every business owner needs an exit plan. Exit Factor is a business coaching and consulting firm that helps entrepreneurs increase profits, free up their time, and unlock their business’s true value. In our conversation, we delve into Megan’s transition from corporate life to entrepreneurship, how she identified a major gap in exit planning, and why many business owners fail to prepare for their eventual exit. We also unpack how Megan helps make businesses more sellable, explore generational differences in approaches to entrepreneurship, learn about common exit planning mistakes, and more. Tune in to learn why starting a business with the end in mind is key to long-term success with Megan Kearney!

Key Points From This Episode:

• Megan's journey into entrepreneurship and why she chose exit planning as a specialty.
• What Exit Factor does and how Megan helps owners build sellable businesses.
• Common pitfalls and why many businesses are not set up for successful exits.
• Why an exit strategy does not always involve selling the business.
• The differences between millennial and baby boomer entrepreneurs.
• A real-world case study of a flower shop that struggled to sell due to poor exit planning.
• How owners can shift their mindset to focus on long-term value.
• Reasons that building a business with an exit strategy in mind is crucial.
• Insights into what buyers look for in a business and how to foster a long-term plan.
• Why you should think about your business as an investment.

Tip of the Day: Think about your business not just as a venture to run, but as an investment to grow. Start with the end in mind to build a scalable and valuable company!

Links Mentioned in Today’s Episode:

Megan Kearney on LinkedIn

Megan Kearney Email

Call Megan Kearney

Exit Factor

Good Sports

Big Brothers Big Sisters 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.

Welcome back to Transaction Talk! Today, we’re joined by a very special guest, Brook Hartnett, one of our top brokers from the Transworld Boston office. A U.S. veteran and seasoned entrepreneur with a strong background in the fitness industry, Brook has seamlessly transitioned his expertise into the world of business brokerage. Now, he’s helping business owners confidently navigate the buying and selling process with insight and precision. Join the conversation as they delve into his story and journey to becoming a business broker, what he would have done differently with his first deal, and what it was like to work on that deal with his mom. We share on the importance of allowing the donning of different hats throughout different phases of a process, and Brook reflects on factors that have impacted his success as a broker and entrepreneur. To hear more from Brook, including his tip of the day, be sure to tune in now.

Key Points From This Episode:

• We introduce today’s special guest, Brooke Hartnett.
• Brook shares his story, from a US veteran to the fitness industry, to a business broker.
• What he would have done differently in his first transaction process.
• He unpacks his experience working on the deal with his mom.
• The importance of allowing the donning of different “hats” during the process.
• Thoughts on what has impacted his success as a broker and entrepreneur.
• How his personal understanding influences his approach to helping sellers position themselves for success.
• Setting appropriate expectations for the sales process: why it can be crucial to get right.
• One of the worst things they see during the selling and transition process.

Tip of the Day: It’s never too early to start planning your exit. Engaging in conversations with your trusted advisors—your attorney, your accountant—can make a huge difference. Even if you’re a few years away from selling, let them know your intentions. Chances are, one of them has valuable connections that can help you take the right steps now to prepare your business for a successful sale

Links Mentioned in Today’s Episode: Brook Hartnett on LinkedIn

Brook Hartnett

Brook Hartnett Email

Brook Hartnett Phone Number — +1 631 965 9073

Coach Brook Inside Sales

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.