What can 231 business acquisitions teach you about buying, scaling, and selling companies? In this video, I break down the most powerful lessons I’ve learned from real-world experience in business acquisitions, from identifying red flags to building post-close growth strategies. If you’re an entrepreneur, business buyer, or M&A professional, you’ll gain actionable insights into deal sourcing, due diligence, and integration.

Whether you're just getting started or looking to scale through acquisition, these proven tips will help you avoid costly mistakes and close smarter deals. Learn what sets a successful business acquisition strategy apart, and how to create long-term value in every transaction.

Watch now and take your business buying journey to the next level with lessons from 231 company acquisitions.

We break down:
What makes a business truly durable and sellable
The $15 trillion transfer of private business ownership
Private equity vs. family office deal dynamics
How to avoid slimy deals and structure smart exits
Why most founders regret selling (and how to prepare better)

00:00 – Meet James Thompson: From Montana to 231 Business Acquisitions
01:00 – His Path: CFO, CEO, VC, and Back to M&A
02:45 – Why Durability is the #1 Trait of a Sellable Business
04:50 – Signs You’re Ready (or Not) to Exit
07:00 – What Buyers Really Want in a Business
09:00 – The $15 Trillion Opportunity Explained
11:30 – Private Equity vs. Family Offices vs. Debt Funds
15:00 – Anatomy of a Great Deal (Cold Call to Close)
21:00 – Emotional Rollercoaster of Selling a Business
23:00 – Red Flags That Kill Deals (Revenue, Working Capital, Trust)
27:00 – Deal Structures: Cash, Seller Notes, Equity Rolls
31:00 – Choosing the Right Buyer (Culture Fit & Track Record)
35:00 – Best Sectors for Roll-Ups Right Now
38:00 – B2B, Home Services, IT, and Under-Managed Assets
42:00 – Individual Buyers: Capital Risk & Track Record
44:00 – James’ Full Sell-Side M&A Process (Step by Step)
50:00 – Final Thoughts: Boards, Advisors, and What Most Founders Miss

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