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 to be different on purpose. Raising capital is the question I get asked more than almost any other, and it’s also the question founders answer […]

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 everything that made it worth building in the first place, and flip it to the next buyer before the ink is dry. I’d rather sell […]

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 worn out a bit. Everything quiets for a second, and the words come out like an unplanned confession. And they say it the way you’d […]

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 quietly decides whether a business gets a real offer or a polite pass. It’s never phrased the same way twice, and it never gets written […]

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 saved thirty thousand dollars on his M&A fee. He then negotiated the rate down from two percent to one and a half. He felt like […]

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 a process, model a deal, push back on the seller’s numbers, and maintain their nerve through a tense Investment Committee. The people who do it […]

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 thirty seconds, and made three decisions that the rest of us had been circling for the better part of a week. Then he picked up […]

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 financial engineering. Not the value creation plan. Conversations. The ones the founder had been putting off. Sometimes for months. Usually for years. The VP of […]

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 exit day, you’re not making one decision. You’re making two. The first is whether to sell at all. Most founders understand that one. The second […]