For many founders, the idea of making acquisitions feels like a distant milestone reserved for large corporations or private equity funds. But for smart operators preparing for exit, small, targeted acquisitions can become one of …
Exit planning isn’t just a financial or legal exercise — it’s a strategic one. And like any strategy, it benefits from structure, reflection, and intentional goal-setting. That’s where planning frameworks like SWOT analysis and OKRs …
There’s a difference between building a profitable business and building a strategically attractive business. I’ve seen both — as an operator, investor, and now as a partner at Button Holdings and cohost of the Legacy …
In my years working on both sides of the table — as an operator, acquirer, and now as cohost of the Legacy Advisors Podcast — one pattern has stood out: companies that integrate their product …
When it comes to exit strategy planning, many founders obsess over revenue, margins, and growth rates. While those metrics are undeniably important, there’s another intangible that often punches well above its weight in M&A negotiations: …
In the world of M&A, one question frequently guides the decision-making of sophisticated buyers: “What protects this company from competitors?” That’s where the idea of a competitive moat comes into play. It’s not just a …
When most founders think about what makes their business attractive to buyers, they default to the obvious: revenue, profit, and growth. And yes—those matter. But there’s a fourth lever that too many sellers overlook: operational …
Let me start with something I’ve said often on the Legacy Advisors Podcast and in rooms filled with founders: buyers don’t buy potential—they buy proof. You can have a world-class product, an inspiring origin story, …
If you’re planning to sell your business in the next 1–3 years—or even if you’re just beginning to think about the future—how you structure your revenue could be the single most important factor in how …
If you’re a founder thinking about selling your business in the next few years, let me share something that most owners learn too late: Predictable revenue isn’t just nice to have—it’s one of the single …