Every M&A story eventually gets told the same way: two companies, one transaction, a number that made headlines. We wanted this edition to resist that. Behind every acquisition sits a person who decided, at some point, that the risk was worth taking — and that decision rarely starts in a boardroom. It usually starts somewhere much smaller, much earlier, and far less polished than the press release that follows it.
That’s the thread running through this year’s M&A Leaders of the Year edition. We didn’t set out to celebrate deal size or headline value. We set out to find the people whose judgment, instinct, and refusal to quit shaped outcomes that looked inevitable only in hindsight. None of them started there. All of them had a moment where the easier path was to walk away, and didn’t.
Our cover story is the clearest version of that idea we could find. It’s built around Craig Geisler, President of Cherrywood Enterprises, and it starts in a place you wouldn’t expect from a company that now decides which multimillion-dollar debt portfolios are worth the risk — rolling loose change across a gas station counter, hoping there was enough left for groceries. That was 2007. The mortgage market had just collapsed, Craig had two daughters to feed, and there was no backup plan waiting in the wings.
What came out of that year wasn’t a pivot into an industry that looked glamorous. It was a decision shaped by necessity, and it left a mark on how Craig has run every deal since. Cherrywood was built on a premise most of the debt acquisition industry treats as soft: that empathy is good business, that people who owe money are still people, and that treating them accordingly tends to produce better numbers than treating them as line items. It’s not the industry’s reputation. It’s the opposite of it, on purpose.
We sat down with Craig to understand how that lesson from 2007 still runs through every portfolio his team picks apart today, and how a “team first” mindset survived in an industry built around the opposite instinct. It’s a conversation about what actually holds up when the stakes are personal, not just financial.
Alongside it, this edition carries a handful of other success stories — leaders who’ve made their mark on the M&A landscape in ways worth paying attention to, each in their own register, each worth the read.
Deals close on numbers. They get built on something else entirely. This edition is about that something else.
