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Recent Episodes
Restrictive Covenants 101: Protecting Buyers from Bad-Faith Sellers
Eric Pacifici and Kevin Henderson examine restrictive covenants in small business acquisitions on Main Street Deals. The discussion clarifies how business sale non-competes differ from employment…
First 90 Days of Owning a Business: Why You Can't Avoid the J Curve
Sam Rosati and Kevin Henderson are joined by Kevin's wife Tara Henderson to discuss the realities of buying and operating a business as a married couple. Tara recently stepped into the full-time…
Exploring the Most Common Mistakes First-Time SMB Buyers Make
Sam Rosati and Kevin Henderson explore common mistakes first-time small business buyers make during the search and acquisition process on this episode of Main Street Deals. Drawing from their work…
Lessons Learned from ETA and Building SMB Law Group
Eric Pacifici and Kevin Henderson reflect on four years of building SMB Law Group from scratch, using the anniversary as a lens to examine the realities of entrepreneurship through acquisition, lower…
Quality of Earnings and the Hidden Risks in Acquisitions
In this episode of Main Street Deals, Sam Rosati and Kevin Henderson break down the role of Quality of Earnings reports in small business acquisitions and why financial diligence can make or break a…
Deep Diving Legal Due Diligence
Kevin Henderson and Eric Pacifici break down the realities of legal due diligence in small business acquisitions, clarifying one of the most misunderstood parts of the deal process. Drawing on…
How to Negotiate Working Capital in Acquisitions
Sam Rosati and Kevin Henderson break down one of the most misunderstood and critical concepts in small business acquisitions: working capital. Prompted by listener requests, they walk through why…
Small Business Acquisition Strategies That Actually Win
Sam Rosati and Kevin Henderson break down what it actually takes to win a small business acquisition without being the highest bidder. Drawing from real deal experience and active transaction volume,…
How to Prepare a SMB for Sale
Sam Rosati and Eric Pacifici break down the realities of sell-side M&A in the lower middle market, drawing from their experience advising both buyers and sellers. They share practical insights on…
The SMB Acquisition Process Explained - Main Street Deals #10
Eric Pacifici and Kevin Henderson walk through the full lifecycle of acquiring a small business, breaking down each stage from sourcing deals to post-close integration. They provide a practical,…
The Most Overlooked Legal Risks in Acquisitions - Main Street Deals #9
Kevin Henderson is joined by Evan Thomson to break down one of the most overlooked yet critical parts of any acquisition: legal due diligence. Drawing from Evan’s experience as fractional general…
Planning for Acquisition Costs - Main Street Deals #8
Kevin Henderson and Sam Rosati break down one of the most overlooked aspects of buying a small business: how to properly plan and structure the full capital stack. Using a practical sources and uses…
How to Structure Your Deal: What are you Actually Buying? - Main Street Deals #7
Sam Rosati and Eric Pacifici break down one of the most important structural decisions in any small business acquisition: whether to buy a company through an asset purchase or a stock purchase.…
Post-Acquisition Disasters Buyers Face - Main Street Deals #6
Eric Pacifici and Kevin Henderson draw on their experience closing hundreds of lower middle market transactions to break down real problems that can surface after buying a business. Rather than…
How to Protect Yourself in an LOI - Main Street Deals #5
In this episode of Main Street Deals, Kevin Henderson and Sam Rosati continue their deep dive into letters of intent, picking up where the prior conversation left off. They move beyond headline…
How to Structure a Winning LOI for Small Business Acquisitions
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…
From Big Law to Small Business M&A - Main Street Deals #3
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…
What Really Kills Small Business Acquisitions - Main Street Deals Episode #2
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…
#1: What Buyers Get Wrong in Acquisitions - Welcome to Main Street Deals
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,…
Main Street Deals Trailer
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…
Frequently Asked Questions
Main Street Deals has published 20 episodes since January 2026, covering topics in Business, Entrepreneurship.
Main Street Deals is currently highly active with new episodes weekly. Average episode length is 44m.
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