Some deals die for good reasons, but too many die unnecessarily. In this episode of Napkin Numbers, Scott Lundt and Rahsaan Freeman unpack the most common and avoidable pitfalls that derail M&A transactions. From financing issues and unclear legal communication to operational surprises and bad timing, they share real stories and strategies to help you navigate the deal process with clarity and confidence.
Why Good Deals Die: Top Mistakes That Can Kill a Transaction
You’ll learn why transparency with your team matters, how to avoid holiday slowdowns, and why the right deal team makes all the difference. Whether you’re a buyer, seller, or advisor, this episode is packed with insights to help you keep your deal alive and get it across the finish line.
Napkin Numbers Talking Points
[0:00] Deals that Die Unnecessarily
- Scott and Rahsaan discuss common reasons why M&A deals fail, including financing, legal issues, and operational changes.
- They explain how many of these deal-breakers are avoidable with better preparation and communication.
[0:51] Financing Challenges
- Scott shares an example of a deal that unraveled due to a lender’s job change, which led to weeks of delays.
- He underscores the importance of vetting lenders, securing written term sheets, and understanding the financing process early.
[3:17] Timely Action and Legal Matters
- Rahsaan highlights the importance of responding quickly to requests in today’s fast-changing banking and SBA environment.
- He emphasizes how clear communication and collaboration between legal teams can minimize friction and keep deals on track.
[5:58] Operational Changes and Transparency
- Scott explains how late-stage disclosures—such as compensation tied to revenue for key employees—can threaten deals.
- He stresses that transparency and open conversations between buyers and sellers help resolve issues faster and with less friction.
[8:08] Timing and Deal Team
- Rahsaan points out how poor timing, especially around holidays, can stall or kill deals.
- He encourages assembling an experienced deal team that can anticipate obstacles, ask the right questions, and keep momentum strong.
Thanks for listening to this episode of Napkin Numbers.
Deals fall apart for all kinds of reasons, but many of those reasons are preventable. Whether it’s financing delays, late-stage surprises, or holiday timing, what matters most is communication, preparation, and having the right team in your corner.
Talk to your advisors. Ask the hard questions early. And don’t try to carry it all on your own.
If you’re looking for guidance on keeping your deal moving or getting one back on track reach out to us at Freeman Lundt. We’ll see you on the next episode
