Do You Actually Need to Raise Capital? Most of what I write starts somewhere inside an idea and lets you find the structure as you go. This one is going...

Why I Left Private Equity. And Why I’m Going Back. “Private equity? No thanks. I’ve seen what they do. They come in, dress it up, load it with debt, cut...

Leadership Is Lonely Because You Built It That Way “Leadership is lonely.” You’ve heard it hundreds of times. Usually late in a conversation, when the polished version of things has...

Strategy is what you refuse to do. There’s a question that gets asked in every serious deal committee, usually about twenty minutes into the discussion, and it’s the question that...

How Different Buyers Structure Deals—and How to Protect Yourself​

The Most Expensive Cheap Decision You’ll Ever Make Nobody ever lost four million dollars by overpaying their advisor. However, I do know a founder who built a twenty-million-dollar business and...

Most Acquirers Can’t Run What They Buy Most acquirers shouldn’t be allowed to operate the businesses they buy. They’re good at buying them, often brilliant at it. They can run...

You’re Not Busy. You’re Scared. In 2003, a CEO walked into his own board meeting forty minutes late. No apology. No explanation. He sat down, read the room in about...

The Conversations You’re Not Having Are Costing You Millions Every PE-backed business I walked into as an operating partner had the same first job waiting for me. Not strategy. Not...

Two Checks, Not One: How Founders Actually Build Wealth Through PE Let me teach you something almost nobody tells founders before they sell. When you get to the table on...

The Danger of Already Knowing There’s a version of your business that only exists in your head. I know because I had one. Several, actually, across four different businesses. And...

Not All Revenue Is Real Let me teach you something that took me several scale up journeys to fully understand. Not because it wasn’t explained to me. Because the first...

The Room Where Your Deal Lives or Dies I want to take you somewhere most founders never get to go. Not because it’s exclusive. Because nobody thinks to tell you...

Due Diligence Starts Two Years Before You Think It Does I’ve sat in enough sell-side processes to know, within the first hour of a management presentation, whether a founder prepared...

The Acquisition Sequence There’s a question I used to ask in every deal committee when a buy-and-build thesis landed on the table. Not “What are we buying?” … and not...

The Board You Build Before You Need One The first board meeting after a PE acquisition is always revealing. Seven people around a table. Two fund partners. An operating partner....

The Hire That Changes Everything (And Why You Almost Always Get It Wrong) Most founders and CEOs think that hiring key senior leadership is the solution. Bring in an experienced...

The Five Assumptions That Will Cost You Your Earnout The wire hits. The lawyers shake hands. The champagne gets opened – metaphorically, at least, because your new PE partners don’t...

Prize vs Prey: The Mindset That Determines Your Multiple The acquisition banker called me at 7:43am on a Tuesday. “We have a problem.” The founder he represented – let’s call...

What PE Firms Actually Look For Most people think PE firms evaluate businesses purely based on financials. Revenue growth. EBITDA margins. Customer retention. Clean books. And yes, those matter. But...

The Acquisition Game This week I want to talk about why buying a competitor is often smarter than grinding through organic growth, how to actually structure your first acquisition without...

What Changes When You Go From Founder to CEO (And Why Most Resist It) This week I want to share my thoughts on what being a real CEO actually means,...