Author: Kristopher Jones
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Exit Planning During Economic Uncertainty: Best Practices
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Economic uncertainty can make even the most confident founders second-guess their timing. Do I sell now?Should I wait for the market to rebound?Will buyers pull back entirely? These questions are natural. I had them myself when I exited Pepperjam in 2009 — right after the financial collapse. And yet, the…
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How Market Positioning Changes During Different Deal Cycles
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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…
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Strategic Timing: Should You Exit Before or After a Major Product Launch?
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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…
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How Economic Cycles Impact Exit Strategy
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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…
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Riding Industry Trends to Boost M&A Appeal
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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…
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What to Do if You Miss the Peak of the Market
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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…
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Identifying the Optimal Window for Selling Your Business
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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…
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Optimizing Your Balance Sheet for a Future Exit
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When most founders think about getting acquired, they focus on top-line growth, brand value, or customer acquisition. But sophisticated buyers care just as much — sometimes more — about what’s underneath that growth. Your balance sheet is where buyers go to find truth. It reveals your financial maturity, your risk…
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Leveraging Forecasting to Support Your Exit Narrative
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When it comes time to sell your company, buyers don’t just care about what you’ve done — they care about what’s next. They’re asking: “Can this company perform in the future the way it says it can?” And the only way to answer that question credibly is with a well-built…
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Planning Your Capital Structure to Maximize Exit Outcomes
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You’ve probably heard this line before: “It’s not what you sell your company for — it’s what you keep.” And it’s absolutely true. At Legacy Advisors, we’ve helped dozens of founders navigate exit planning, and one of the most overlooked — but incredibly impactful — aspects of a successful deal…