The Greatest Wealth Transfer in History is Happening...

Welcome back to the Mid Market Insider!

Today, we’re discussing the greatest wealth transfer in history… and what you need to focus on to be prepared for it.

The greatest wealth transfer in history is already happening... and most owners aren’t ready for it.

Over half of all privately owned U.S. businesses (roughly 3 million companies worth $10 trillion) are owned by the generation of Baby Boomers.

Most founders are in their late 60s to 70s, and over the next decade, they’ll face a choice: exit or plan for succession.

Here’s the problem:

83% have no transition plan. Nearly half haven’t done any planning. And 98% of M&A professionals say unrealistic valuation expectations are the biggest obstacle to a successful sale.

The reality? Selling your business isn’t just about timing or numbers. It’s about preparation.

Boomers need a quarterback: a trusted advisor who can assemble the right team, clarify goals, assess readiness, and build both an exit plan and a life-after plan.

That means cleaning up operations, diversifying customers, creating investor-grade financials, and planning for what comes next, whether that’s retirement, philanthropy, or passive investing.

The “Bad Ds” (death, divorce, disagreement, disability) will happen to some, forcing premature exits. But thoughtful planning turns that pressure into opportunity.

This decade’s $10 trillion transition is a generational handoff.

For Boomers, it’s the last great business challenge: leaving well, with clarity, confidence, and legacy intact.

Reader Question of The Week

For context, this is a recent section I’ve decided to add. After receiving many questions in my day-to-day as the co-founder of Four Pillars, I wanted to share the most common ones in my newsletter in hopes that it’s valuable to you in some way.

If you have a question you want answered in a future newsletter, please reply directly to this email and I’ll do my best to answer it. Now, onto this week’s question:👇

Q: “What kind of reporting do buyers actually care about?”

First, buyers need to see enough detail trends can be identified. Lumping all COGS into one category would make that hard.

Additionally, buyers want you to be able to make sense of what is going on. If COGS are going up, do the analysis to uncover why, how much of an impact it is having, and how to mitigate it.

That’s all for today’s newsletter! Thanks for reading!

📅 Next Week:

Next week, I’ll be diving into why adaptability in the negotiation process is better than trying to come off as “flawless.”

Keep building,
Nick

P.S. If you’re serious about preparing your business for a future sale, I’ve built a free community to help you do exactly that.

It’s called Pre-Sale Prep and inside, I share the same frameworks we use when buying and growing companies.