Transaction Talk

Jennifer Fox and Eric Sigman
  • 5.0 (6)
  • ENTREPRENEURSHIP
  • UPDATED BIMONTHLY

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.

  1. 2D AGO

    When Is the Right Time to Sell

    s 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.

    21 min

  2. MAR 12

    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.

    17 min

  3. FEB 24

    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.

    29 min

  4. FEB 4

    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.

    33 min

  5. JAN 15

    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.

    16 min

  6. JAN 5

    Breaking Down the LOI: What Business Owners Need to Know

    A Letter of Intent may not be legally binding, but it can determine whether a deal moves forward or falls apart. In this episode of Transaction Talk, hosts Jennifer Fox and Eric Sigman break down the role an LOI plays in buying and selling a business, and why it deserves serious attention from both buyers and sellers. They explain what an LOI is, what it typically includes, and how it sets expectations around price, structure, timing, contingencies, and exclusivity. The conversation covers how LOIs provide a framework for due diligence and financing, how exclusivity protects buyers during the process, and why clear timelines help prevent deals from stalling. The episode also explores working capital, financing terms, and how sellers evaluate competing offers. Eric closes with a practical reminder that even when it is nonbinding, an LOI carries weight and should be approached thoughtfully. Listen in for a clear, practical breakdown of how LOIs guide successful transactions!   Key Points From This Episode: What a Letter of Intent (LOI) is and why it starts most business transactions. How LOIs, term sheets, and offers are commonly used interchangeably. Why buyers use LOIs to show seriousness and begin due diligence. Laying out a purchase price structure and why it matters more than a single number. Why written terms carry more weight than verbal agreements. How LOIs create a working framework before diligence costs begin. The importance of timelines and target dates in preventing delays. What exclusivity means and how it protects buyers during due diligence. Common contingencies like financing, diligence, and approvals. The difference between binding and nonbinding LOI terms. Why working capital expectations surface early in deals. A reminder to take LOIs seriously, even when they are nonbinding.   Tip of the Day: Take Letters of Intent seriously, because even when they are not binding, they set the framework and structure of the deal.   Links Mentioned in Today's Episode: Jennifer Fox on LinkedIn Eric Sigman on LinkedIn Ruberto, Israel, & Weiner 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.

    21 min

  7. 12/16/2025

    Deal Challenges and How to Solve Them - Steven Hanson - Part 2

    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.

    23 min

  8. 11/29/2025

    Deal Challenges and How to Solve Them with Steven Hanson - Part 1

    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.

    30 min
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out of 5
6 Ratings

About

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.

Information

  • Creator
    Jennifer Fox and Eric Sigman
  • Years Active
    2023 - 2026
  • Episodes
    48
  • Rating
    Clean
  • Copyright
    © Transaction Talk 2023
  • Show Website
    Transaction Talk