Author: Kristopher Jones
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KPIs That Signal You’re Ready to Exit
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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 the time.”“I’m getting tired, maybe I should sell.” Emotion plays a role — but smart…
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How Customer Concentration Affects M&A Outcomes
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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 deals, and now weekly as we advise founders at Legacy Advisors. Customer concentration is one…
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How Strategic Partnerships Attract Acquirers
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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 started as what most people would call a strategic partnership. GSI opened the door for…
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Using Strategic Planning Tools (SWOT, OKRs) to Guide Exit Prep
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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 (Objectives and Key Results) come into play. In my journey building and exiting multiple businesses…
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Aligning Product Roadmaps with Exit Strategy
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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…
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The Role of Brand Equity in Exit Strategy Planning
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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,…
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Thinking Like a Buyer: The Ultimate Advantage for Sellers
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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…
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Key Metrics That Make Your Business Attractive to Buyers
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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…
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Creating Predictable Revenue Streams Before an Exit
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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…
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Strategic Positioning in a Crowded Market: Stand Out to Exit
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In today’s M&A landscape, being great isn’t enough. There are thousands of profitable, well-run businesses out there—and many of them are for sale. But only a handful are positioned in a way that makes buyers stop, lean in, and say, “We want that one.” I’ve seen it firsthand in my…