Eric Pacifici and Sam Rosati break down one of the most important documents in any small business acquisition: the Letter of Intent. In this episode, they walk line by line through their LOI template and explain why every sentence matters, from structuring purchase price to protecting exclusivity. Drawing on real transaction experience and common deal failures, they highlight the practical decisions buyers must make before signing and the risks that often surface after financial diligence.

They discuss:

Why the LOI exists and how exclusivity protects buyers before spending on diligence

Structuring purchase price including cash, SBA debt, and seller notes

The importance of debt free, cash free language and buying assets free and clear

How seller notes should be modeled thoughtfully to protect post close cash flow

Why clarity in acquisition structure and assumed liabilities prevents future disputes

This episode is essential listening for buyers, sellers, and advisors who want to understand how a well drafted LOI can either set up a smooth closing or quietly create problems down the road.

Links:

SMB Law Group - https://smblaw.group/

Eric on LinkedIn - https://www.linkedin.com/in/eric-b-pacifici/

Kevin on LinkedIn - https://www.linkedin.com/in/khendersonco/

Sam on LinkedIn - https://www.linkedin.com/in/sam-rosati-68787a8/

(00:00:00) - Intro
(00:01:10) - Introduction to LOIs
(00:04:06) - Why LOIs Exist
(00:08:02) - LOI vs. IOI + What’s Actually Binding
(00:10:26) - How to introduce yourself in the LOI
(00:15:37) - Who signs the LOI? Using an entity, affiliates, and liability shield
(00:18:26) - Setting the closing date: 60 vs 90 days and managing expectations
(00:21:35) - Asset purchase language
(00:24:04) - Asset list pitfalls
(00:25:11) - Debt-free, cash-free deals explained
(00:28:09) - Buying assets free & clear: Liens, lenders, and “immaterial encumbrances”
(00:31:32) - Assumed liabilities in asset purchases
(00:33:28) - Purchase price section: Why deals die after QoE (and how LOIs foreshadow re-trades)
(00:36:00) - Sources & uses 101
(00:38:44) - Seller notes deep dive
(00:44:44) - Wrap-up & what’s next

In this episode of Main Street Deals, Sam Rosati and Kevin Henderson step back from deal breakdowns to share the origin story behind their partnership and the law firm they built to serve the small business acquisition community. Kevin walks through his path from growing up in California to Michigan Law and the highest levels of big law, navigating the 2008 financial crisis, burnout, and ultimately walking away from the corporate grind. From there, the conversation shifts to how a connection through the emerging ETA community led to the launch of their firm and why they saw a massive gap in legal services for small business buyers.

They also unpack what today’s searchers and independent sponsors actually look like, how deals are being financed, and the industries attracting the most activity. Drawing from hundreds of transactions, they share perspective on who is buying businesses, how those deals are structured, and what makes this ecosystem different from traditional private equity.

They discuss:

Links:

SMB Law Group - https://smblaw.group/

Eric on LinkedIn - https://www.linkedin.com/in/eric-b-pacifici/

Kevin on LinkedIn - https://www.linkedin.com/in/khendersonco/

Sam on LinkedIn - https://www.linkedin.com/in/sam-rosati-68787a8/

Topics:

(00:00:00) - Intro

In this episode of Main Street Deals, Kevin Henderson and Sam Rosati break down the most common reasons small business acquisitions fall apart and what buyers can do to spot red flags early. Drawing from real transaction data and firsthand deal experience, they walk through the financial, psychological, and external factors that derail deals long before closing. The conversation offers a candid look at how quality of earnings, seller behavior, financing challenges, and even buyer readiness can determine whether a deal survives.

They discuss:

• Why financial reality gaps are the leading cause of busted deals

• How quality of earnings findings often force renegotiation or termination

• The role seller psychology and trust play throughout the deal process

• Common financing and SBA-related issues that can unexpectedly kill transactions

• How to identify warning signs early and protect yourself in the LOI stage

This episode is a practical guide for buyers who want to understand what actually kills deals and how to improve their odds of getting to the closing table.

Links:

SMB Law Group - https://smblaw.group/

Eric on LinkedIn - https://www.linkedin.com/in/eric-b-pacifici/

Kevin on LinkedIn - https://www.linkedin.com/in/khendersonco/

Sam on LinkedIn - https://www.linkedin.com/in/sam-rosati-68787a8/

Topics:

(00:00:00) - Intro
(00:02:05) - Understanding deal killers
(00:03:26) - The importance of data and LOI
(00:05:32) - Breaking down deal killers
(00:06:12) - Financial reality gaps
(00:09:05) - Seller psychology and trust issues
(00:09:24) - External factors and financing
(00:11:03) - Recognizing deal signals
(00:16:09) - Addressing financial reality in LOI
(00:25:14) - Pressure testing assumptions in quality of earnings
(00:25:39) - Negotiation strategies for buyers
(00:28:13) - The human element in LOI negotiations
(00:29:40) - Building trust and addressing psychological factors
(00:36:00) - External factors impacting deals
(00:40:29) - Legal matters and deal killers
(00:46:37) - Personal reflections and final thoughts

In the inaugural episode of Main Street Deals, co-hosts Sam Rosati, Eric Pacifici, and Kevin Henderson lay out why small and medium-sized business acquisitions deserve a more honest, experience-driven conversation. Drawing from hundreds of closed and broken transactions, they explain why M&A at the Main Street level is harder, messier, and more consequential than most people expect. The discussion sets the tone for the show by focusing on real-world deal execution, common failure points, and the responsibility that comes with advising buyers and sellers navigating life-changing transactions.

We discuss:

Links:

SMB Law Group - https://smblaw.group/

Eric on LinkedIn - https://www.linkedin.com/in/eric-b-pacifici/

Kevin on LinkedIn - https://www.linkedin.com/in/khendersonco/

Sam on LinkedIn - https://www.linkedin.com/in/sam-rosati-68787a8/

Topics:

(00:00:00) - Intro

Main Street Deals is a practical podcast for entrepreneurs buying, selling, and operating small businesses. Hosted by experienced M&A attorneys, the show breaks down what actually matters in real-world acquisitions—from LOIs and diligence to closing and the first 90 days of ownership.

Each episode combines deal education, war stories, and conversations with buyers, operators, and industry experts to give listeners a clear-eyed view of how small business deals really work. The focus isn’t theory or hype—it’s judgment, structure, and lessons learned inside hundreds of transactions.

Main Street Deals is hosted by Eric Pacifici, Kevin Henderson, and Sam Rosati. The three are former Big Law M&A attorneys, active dealmakers, and operators who have sat on both sides of the table. Together, they bring pattern recognition earned from hundreds of transactions and the empathy that only comes from ownership.