If you want to understand what’s happening in M&A, follow the money. And few forces shape the cost — and availability — of money more than interest rates. Over the past two decades, I’ve watched deals surge and stall based on one key lever: the cost of capital. When rates…

There’s no such thing as “static” market positioning. Especially not in the world of M&A. One of the biggest mistakes founders make when preparing for an exit is assuming that what worked last quarter — or last year — will work again. But buyer psychology doesn’t sit still. It moves…

Timing your exit is hard enough. Add a major product launch into the mix, and it becomes even more complex. As founders, we’re wired to believe that the next big release — that feature set, integration, or new vertical — will unlock exponential value. But in M&A? Timing isn’t just…

You’ve built something real. Revenue is up, your team is humming, and your customers are locked in. But then… headlines start to shift. Inflation rises. Interest rates follow. Capital markets tighten. Whispered warnings of a coming recession turn into front-page forecasts. What now? Do you hit the gas and take…

If you’re building toward a successful exit, one thing is certain: The economy won’t wait for you to be ready. Markets expand. Markets contract. Buyer sentiment shifts. Capital availability changes. And all of it directly affects how — and when — you should sell your business. Having been through multiple…

Buyers don’t just invest in your numbers — they invest in your story. And one of the most compelling story arcs in M&A? “We’re riding a massive trend — and we’ve figured out how to win.” When I sold Pepperjam, affiliate marketing was on the rise. Major retailers were waking…

Let’s face it — not every founder gets to exit at the top. You blink, and the peak is in the rearview mirror. The market softens. Buyers pull back. Valuations dip. And that perfect deal you were counting on? Gone. At Legacy Advisors, we’ve worked with dozens of founders who…

Timing isn’t everything in M&A — but it’s damn close. One of the most common questions I get from founders is: “When is the right time to sell?” It’s not an easy answer. But after selling my company Pepperjam to GSI Commerce (which was later acquired by eBay), building and…