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 strategy with their exit strategy consistently outperform those that don’t. Too often, product development is…

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: brand equity. As a serial entrepreneur who built and sold multiple companies — including Pepperjam,…

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 metaphor — it’s a critical business feature that impacts valuation, risk tolerance, and long-term growth.…

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 scalability. In my 27 years as a founder, investor, and M&A advisor—across exits like Pepperjam…

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, and a bright future. But if the metrics don’t back it up, your company will…

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 buyers perceive your company. Revenue isn’t just revenue. In the eyes of a buyer, it’s…

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 biggest drivers of valuation in M&A. Why? Because predictability equals reduced risk. And reduced risk…

Let’s cut through the noise. If you’re a founder thinking about exiting your company, you’ve probably heard the standard advice: grow revenue, boost profit, keep your books clean. Important? Absolutely. But here’s the truth I’ve learned after nearly three decades as a founder, operator, and dealmaker: Buyers don’t just want…

When it comes to selling a business, the cold truth is this: most companies look the same on paper. Buyers see spreadsheets, forecasts, KPIs, and EBITDA margins—and most businesses blend into the noise. The companies that stand out, the ones that get competitive bids, strategic suitors, and above-market multiples? Those…