Category: M&A Strategy and Planning
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Building a Management Team That Survives Exit
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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 management team depth. In M&A, buyers don’t just acquire revenue streams, product lines, or customer…
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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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The Role of Digital Transformation in Boosting Exit Value
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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 my business for maximum valuation before an exit? Sometimes it’s product strategy. Sometimes it’s leadership…
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Why Culture Fit Matters in Strategic M&A Outcomes
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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 multiples, EBITDA, strategic synergies, and earnouts — and while those metrics absolutely matter, no spreadsheet…
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How to Plan for Strategic Acquisitions Along Your Own Path to Exit
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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 the most powerful growth levers available. In my work with Button Holdings and through the…
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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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Growth Levers That Attract Strategic Acquirers
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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 Advisors Podcast. The truth is, not every successful company is acquirable. And not every growing…
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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,…