Transaction Talk

Hosted by Jennifer Fox and Eric Sigman

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Jun 2026

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About the show

Business broker Jennifer Fox and attorney Eric Sigman team up to provide a 360-degree view of the current Boston Business for-sale market. From buying and selling to franchising and everything in between, Transaction Talk breaks down the deal process from a business, brokerage, and legal perspective. A resource for business owners, buyers and entrepreneurs, Transaction Talk offers interviews and real-life deal experiences from industry experts and key transaction players.

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53 recent

June 12, 202621 min

Understanding Reps, Warranties & Deal Risk

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 provisions. They discuss why these provisions remain important after a transaction closes, how buyers can seek compensation when a warranty is breached, and how escrow funds, seller notes, and survival periods provide financial protection. They also explore common claims involving inaccurate financials, how sellers can reduce their exposure, representations and warranties insurance, the different risks involved in asset and stock sales, and why due diligence cannot uncover every possible problem. Tune in to learn how buyers and sellers can negotiate a fair allocation of risk and protect themselves throughout the transaction process. Key Points From This Episode: Discover what representations and warranties mean in an M&A agreement. Learn why risk can continue after closing a deal and how to mitigate it. Explore how escrow funds protect buyers and how survival periods can limit claims. Understand how long buyers can bring claims after closing. Hear about the most common causes of financial losses after closing. Uncover why precise drafting matters for financial and asset-related claims. Find out when representations and warranties insurance may be worthwhile. Unpack how disclosure schedules protect sellers from known liabilities. Compare how asset and stock sales differ in their exposure to liability. Advice on how sellers can limit indemnification risk through caps and baskets. Tip of the Day: Buyers should protect their recourse, while sellers should limit their exposure. Links Mentioned in Today's Episode: Ruberto, Israel & Weiner 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.

May 27, 2026Episode 5119 min

Why Small Businesses Matter to Our Communities with Gregory Giacopelli

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 relationships with small businesses matter so much. We delve into the biggest mistakes Gregory sees business owners make before discussing the role the bank plays in succession planning, growth, sales, and acquisitions of businesses, as well as how successful transactions benefit employees and the community as a whole. Our guest even shares some words of wisdom for any business owner looking to build sustainable value. Finally, we touch on how listeners can support small businesses during Small Business Month (May). Thanks for listening! Key Points From This Episode: Welcoming today's guest, Gregory Giacopelli. Why small businesses are so important to communities. What a small business actually is, according to Gregory. Why banking relationships are imperative for small businesses. The biggest financial mistakes Gregory sees business owners make. Gregory explains the role a bank plays in sales, acquisitions, growth, etc. How successful ownership transactions help employees and the community. Advice for business owners who want to build long-term value. What makes Gregory optimistic about small businesses today. How to support small businesses during Small Business Month. Tip of the Day: The relationship between a small business and their bank is crucial. Banks are a long-term partner in a small business's success. They are there to lend, advocate, connect, and invest in communities because when small businesses do well, the community as a whole does well too. Links Mentioned in Today's Episode: Gregory Giacopelli on LinkedIn Gregory Giacopelli Email: g.giacopelli@easternbank.com Gregory Giacopelli Cell: 617-866-9671 Gregory Giacopelli Phone: 781-231-4897 Eastern Bank 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. The opinions expressed herein are those of the authors and do not necessarily reflect those of Eastern Bankshares, Inc., Eastern Bank, or any affiliated entities. Views and opinions expressed are current as of the date appearing on this material; all views and opinions herein are subject to change without notice. These views and opinions should not be construed as any specific recommendation. This material is for your private information, and we are not soliciting any action based on it. The information in this content has been obtained from sources believed to be reliable, but its accuracy is not guaranteed. There is neither representation nor warranty as to the accuracy of, nor liability for any decisions made based on such information.

May 12, 2026Episode 5027 min

What is My Business Worth - How Valuations are Made

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 brokerage, mergers and acquisitions, and valuation work, Louis explains the financial metrics buyers focus on, including EBITDA (Earnings Before Interest, Taxes, Depreciation, and Amortization), seller's discretionary earnings (SDE), cash flow, and valuation multiples. The conversation also explores why similar businesses can sell for very different prices, the common mistakes owners make when estimating value, and why some buyers are willing to pay more than others. Along the way, Louis shares practical advice on clean financials, long-term planning, and positioning a business for a stronger sale. Tune in for a practical discussion on what really drives value in today's market! Key Points From This Episode: Introducing today's guest, Louis Pereira of Merrimack Business Appraisers. Discover why business valuations matter to both buyers and sellers. Learn why owners should prepare years in advance before selling a business. Explore why many owners overestimate what their business is worth. What buyers focus on: breaking down EBITDA, SDE, and cash flow metrics. Find out how valuation multiples and earnings are determined. How appraisers use sales data from similar businesses to determine value. Why similar businesses can sell for very different prices. Common value killers that reduce the sale price and buyer confidence. Understanding value as an opinion shaped by multiple factors. Discover how preparation and the right advisors can increase value. Tip of the Day: A valuation sets the baseline for what your business is worth, but the right advisor can uncover buyers who see greater strategic value in it. Understanding your market and positioning your business for the right buyer can make all the difference in the final outcome. Links Mentioned in Today's Episode: Louis Pereira on LinkedIn Louis Pereira email: Lou@MBAppraisers.com Louis Pereira phone number: 1-978-975-7600 Merrimack Business Appraisers 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.

April 29, 2026Episode 4925 min

Top 5 Deal Killers With Aaron Fox

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 through the most common deal killers, including poor books and records, inconsistent financials, and a lack of supporting documentation. He also explains why lease issues can create major risk for buyers, how working with only one buyer can weaken a seller's negotiating position, and why due diligence surprises often create unnecessary friction in a sale. They also explore unrealistic expectations around valuation, deal terms, post-closing payments, and changes that may arise before closing, as well as the importance of staying prepared. Tune in to learn how sellers can avoid preventable mistakes, protect buyer confidence, and keep business sales on track from offer to closing with Aaron Fox! Key Points From This Episode: Learn why poor books and records remain a major deal killer. Hear how sellers can prepare cleaner financials before going to market. Find out how many years of financial records buyers usually request. What makes business books reliable, consistent, and useful to buyers. Tips for dealing with inconsistent bookkeeping and financial records. Understand why personal and one-time expenses need clear documentation. Discover why leases and landlords can create major transaction risk. Practical steps to prevent lease issues before selling your business. Unpack why sellers should avoid working with only one buyer. Explore how changes during a transaction can affect buyer confidence. Why sellers should always disclose risks and how to align expectations. Unpack why major changes may require renegotiation before closing. Tip of the Day: Run your business every day like it's not for sale! Links Mentioned in Today's Episode: Aaron Fox Email Aaron Fox Call Aaron Fox Transworld Business Advisors 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.

April 13, 2026Episode 4823 min

Inside the Buyer's Mind: Who's Buying & What Industries

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 growth potential and scalability to long-term alignment. The conversation also explores shifting industry trends, key risks shaping buyer behavior, and what can make or break a deal during the process. Throughout, Steven emphasizes a central theme: success in today's market comes down to fit, not just chasing the hottest industries. Tune in to hear the full scope of our conversation and what today's buyers are really looking for! Key Points From This Episode: Welcoming returning guest, Steven Smith of Business Transfers & Strategies. Types of buyers: individuals, private equity groups, strategics, and family offices. What each type of buyer is looking for, from scalability to long-term fit. Key risks buyers assess: employees, customers, and industry factors. Industries that are gaining traction, like home services and electrical contracting. Why buyers must differentiate themselves in a crowded, competitive market. How tariffs and supply chain disruptions are impacting manufacturing deals. AI and automation as emerging factors in buyer decision-making. The importance of fit over chasing "hot" industries. How buyer background, skills, and experience shape what makes a "good fit." Common seller mistakes: poor financials, delays, and lack of transparency. Why communication and preparation can make or break a deal. Tip of the Day: Don't chase industry, chase fit. The long-term value of a deal depends on how well you align with the business and your ability to improve it over time. Links Mentioned in Today's Episode: Steven Smith on LinkedIn Business Transfers & Strategies 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.

March 30, 2026Episode 4720 min

When Is the Right Time to Sell

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 perfect time to sell can be risky, why selling when your business is in a stable financial state offers the best leverage and valuation, and the typical signs that it is time to sell. He shares why buyers should prioritize recent revenue and profit trends, why market conditions and supply chain stability can swing deals, and how a dependable staff makes a business more attractive. Jonathan also breaks down a clear approach to timing your retirement, how to plan effectively to avoid last-minute pressure-driven sales, and how to ensure that you sell on your own terms. Tune in to learn how to prepare for a successful and stress‑free business sale with Johnathan Zsittnik. Key Points From This Episode: Introduction to Johnathan Zsittnik, Senior Manager and Business Broker at Transworld Boston. Why there is rarely a perfect time to sell a business, and why you should not wait. Learn how strong and growing financial performance attracts better offers. Discover why selling from a position of strength gives owners better leverage. Find out how earnouts can help bridge gaps in valuation when revenue has declined. Explore how supply chain stability can impact timing and valuation when selling. The importance of having experienced, reliable staff to share the workload. Uncover the common reasons why most owners decide to sell. What to take into account to ensure a smooth and effective transition. Johnathan highlights mistakes that owners should avoid when selling. Advice for owners who are considering selling and how to contact Johnathan. Tip of the Day: Start early, talk to a broker or exit planner, and create a plan that allows you to sell by choice, not necessity. Links Mentioned in Today's Episode: Johnathan Zsittnik Transworld Business Advisors Boston Inside the Deal: How One Business Sale Really Happens with Boston Broker, Johnathan Zsittnik 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.

March 12, 2026Episode 4617 min

Don't Go It Alone: Building the Right Team to Sell Your Business

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 profitable transition. From a business broker who guides the sale, to a CPA who helps navigate tax implications, to a skilled transaction attorney who protects your interests in the contracts, they outline the key roles every seller should have in place. In their discussion, they also highlight other important experts who can help safeguard your financial future and point out common mistakes owners make when assembling their advisory teams. Tune in to learn why deals are far less likely to fall apart when experienced M&A professionals are involved, and why starting to build your team early can make all the difference when it's time to sell. Key Points From This Episode: Today's topic of conversation: building the right team. Jennifer unpacks who should be on your team, and why it matters. Why a business broker is an important member of your team. Working with your CPA, and how that makes the broker's job easier. The role of a transaction attorney (and why the right one is key!) How a financial advisor can support your transaction: understanding your financial situation. Other key players who have a role to play on your team. Jenn shares common mistakes made when compiling teams. A key takeaway from today's topic. Tip of the Day: When selling your business, don't go it alone—build a team of experienced professionals to ensure you do it right and maximize the value of your deal. Links Mentioned in Today's Episode: 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.

February 24, 2026Episode 4528 min

Building Businesses Together: What Makes Couples Successful

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. Jennifer married into Ryan's multi-generational family egg farm, where they learned firsthand the complexities of working with extended family. Their unstructured exit from that business became a defining lesson and now fuels their passion for helping owners plan thoughtful, value-driven exits. They discuss dividing roles based on their strengths, navigating communication challenges unique to married partners, balancing parenting with entrepreneurship, and building a strong team culture together. Tune in to hear the full scope of our conversation on communication, commitment, and navigating business ownership as a couple! Key Points From This Episode: Introducing 20-year partners in business and marriage, Jennifer and Ryan Armstrong. Jennifer and Ryan's experiences growing up with family businesses. How they first worked together on Ryan's family egg farm, and expanded the business. Their family business's unstructured exit and how it inspired their work with Transworld. Insights on organizing your workspace as a couple and assigning roles and tasks. Unique communication and co-working challenges that come with marriage and co-parenting. Building a strong office team by modeling teamwork and commitment as a couple. Key strengths of running a business as a couple, like authenticity and commitment. How their experiences have helped them support other sellers through emotional transitions. Final reflections on how communication, commitment, and family values shape lasting success. Tip of the Day: Success in business starts with commitment. Stay focused through the hard times, communicate clearly with your partners, and aim to improve a little every day. Links Mentioned in Today's Episode: Jennifer Armstrong Jennifer Armstrong on LinkedIn Call Jennifer — 602-551-6604 Ryan Armstrong Ryan Armstrong on LinkedIn Call Ryan — 480-447-3504 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.

February 4, 2026Episode 4433 min

What Makes a Seller Credible to a Business Buyer

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 the perspective of a buy-side broker. He discusses how buyers evaluate trust through transparency, consistent information, and professional preparation. He offers practical tips, including maintaining an open tone, responding promptly to inquiries, and disclosing business shortcomings early to avoid surprises. Emphasizing honesty and mutual respect, Steven explains how these practices build buyer confidence, facilitate financing, and help ensure a successful transaction. To learn more about the buyer's perspective on judging a seller's credibility, including Steven's tip of the day, don't miss this episode of Transaction Talk! Key Points From This Episode: Introduction to today's guest, Steven Smith of Business Transfers & Strategies. How buyers evaluate seller credibility early in the sales process. Building credibility from first contact through closing. The importance of responsiveness and communication during the courting stage. How deal dynamics change when a broker is involved. An anecdote on navigating a transaction with a litigator as a representative. The complexities of transaction financials. Why clean, reliable financials matter to buyers. Understanding and validating business operations from the buyer's perspective. Why buyers value clear access to documentation, information, and processes. The importance of disclosing deficiencies early to ensure long-term deal success. Tip of the Day: Disclose business deficiencies early—transparency builds trust, guides diligence, and protects both parties from deal-breaking surprises later. Links Mentioned in Today's Episode: Steven Smith on LinkedIn Business Transfers & Strategies 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.

January 15, 2026Episode 4315 min

What Business Owners Should Consider if Planning To Sell Their Business This Year

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 can't treat it like listing a house, and how confidentiality, timing, and emotions all factor into the process. Jennifer and Eric discuss why it is essential to understand your numbers and tax implications, as well as document processes and clean up books and records, before due diligence begins. They also delve into why buyers pay for proof rather than potential, and how to find the right team of professionals to make the deal go smoothly. To hear the steps for navigating an exit and a practical roadmap for selling on your timeline and not the buyer's, tune in now! Key Points From This Episode: What most people get wrong about how long selling and exiting a business takes. Hear why you should start early to avoid rushing to market or reacting under pressure. Learn how the emotions of many sellers makes the selling process more intense. Explore how confidence and control can positively influence buyer perception. Discover how clean documentation, books, and records build buyer confidence. Why it is critical to talk with your CPA about the tax implications of selling, before selling. Uncover how proper due diligence before selling can maximize value and reduce friction. The distinction between "proof" and "potential" and why buyers pay for what's documented. Understand why establishing your full team of professionals early is essential. Find out how preparing early for a sale helps you take control of the timeline. Tip of the Day: If you're thinking about selling your business, start preparing now and talk to your CPA and financial advisor early so you can sell on your timeline, with fewer surprises and better leverage at the negotiating table. Links Mentioned in Today's Episode: 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.