One of the biggest mistakes founders make when thinking about selling their company is assuming exit timing is purely emotional or market-driven. “We’ve grown a lot, I think we’re ready.”“The market is hot, maybe now’s …
If you talk to founders who’ve been through M&A — or listen to almost any episode of the Legacy Advisors Podcast — one phrase comes up more and more often during diligence discussions: Quality of …
When you get deep into an M&A deal, there’s a universal truth that becomes crystal clear: Deals don’t fall apart because buyers can’t read spreadsheets. They fall apart because they don’t trust the financial story. …
In the world of M&A, most founders obsess over EBITDA, revenue growth, and margin expansion. And they should — those financial metrics absolutely matter. But the founders who consistently command premium exit multiples — the …
If you’re a founder thinking about your exit — especially in today’s evolving M&A market — there’s one phrase that’s showing up in diligence conversations more often than ever: ESG. For years, Environmental, Social, and …
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 …
Ask any seasoned M&A advisor what keeps buyers up at night during diligence, and you’ll hear it quickly: customer concentration. I’ve seen it repeatedly — as a founder selling Pepperjam, as an acquirer through multiple …
If you study enough M&A transactions — especially founder-led exits — a surprising pattern emerges: many acquisitions begin as partnerships. I’ve lived it personally. Before Pepperjam sold to GSI Commerce (and ultimately eBay), our relationship …
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 …