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 …
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 …