If there’s one topic that consistently surfaces in almost every exit discussion — whether I’m on the acquirer side, advising founders at Legacy Advisors, or sharing deal stories on the Legacy Advisors Podcast — it’s …
In the M&A conversations we have week after week — whether on the Legacy Advisors Podcast, inside Button Holdings, or advising founders one-on-one — one topic keeps rising to the top: How do I position …
In every M&A deal I’ve been involved in — whether on the buyer or seller side — one factor consistently separates the smooth integrations from the trainwrecks: culture fit. We spend countless hours talking about …
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 …
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 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 …
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 …
One of the biggest myths in entrepreneurship is that exits happen overnight. A great offer shows up, a handshake is made, and just like that—the business is sold. But those of us who’ve lived through …
If you ask any M&A advisor to name the most overlooked variable in a successful business exit, they’ll likely tell you the same thing: timing. Not just timing the market—but timing your business, your personal …
At Legacy Advisors, we often emphasize that M&A readiness isn’t a one-size-fits-all concept. Your company’s stage in its lifecycle profoundly influences how you should prepare for a merger or acquisition. Whether you’re in the startup …