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.

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.

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.