Category: M&A Strategy and Planning
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How to Strategically Delay an Exit Without Losing Value
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In a perfect world, you’d go to market when your revenue’s surging, your metrics are clean, and your buyer interest is peaking. But reality often throws curveballs — market conditions shift, a product launch runs late, a key exec leaves, or your personal timeline changes. So what happens if you…
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Building an Internal Exit War Room: Planning for All Scenarios
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You wouldn’t go to war without a strategy room.Why would you enter the high-stakes world of mergers and acquisitions without one? When a buyer shows interest — or when you decide to pursue an exit — the speed of decisions, intensity of diligence, and magnitude of risk all spike. The…
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When and Why to Hire an M&A Advisor Pre-Deal
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A lot of founders wait until they get a term sheet to bring in an M&A advisor. By then?It’s too late to shape the outcome. If you want to maximize valuation, control the narrative, and avoid costly mistakes, you don’t wait until the buyer is at the door — you…
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Strategic Partnerships as Stepping Stones to Acquisition
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Introduction Not every acquisition starts with a banker and a formal offer.Some of the most lucrative deals begin with a handshake, a pilot program, or a strategic integration that seems, at first, purely collaborative. I’ve lived it. Before I sold Pepperjam to GSI Commerce (which was later acquired by eBay),…
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Exit Planning During Economic Uncertainty: Best Practices
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If you’re a founder thinking about selling your business, economic uncertainty can feel like the worst possible time to do it. Volatile markets. Inflation spikes. Interest rate swings. Geopolitical instability. It’s enough to make any entrepreneur press pause. But here’s the truth:Some of the best exits happen in uncertain environments.They’re…
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When and Why to Hire an M&A Advisor Pre-Deal
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Introduction When is the right time to hire an M&A advisor? Ask ten founders and you’ll get ten different answers — usually based on hindsight. Some bring in help too late, when deal terms are already on the table. Others never bring in help at all, thinking they can manage…
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Planning for a Partial Exit: Selling a Stake, Not the Whole Business
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Introduction When most founders hear “exit,” they think of walking away. But not every deal has to be a full departure. Sometimes, the best move is a partial exit — where you sell a stake in the company, unlock personal liquidity, and keep building. This kind of transaction—often structured as…
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Creating Strategic Flexibility in Your Go-to-Market Plan
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Introduction One of the most overlooked drivers of M&A success is go-to-market (GTM) flexibility. When I built and exited Pepperjam, we didn’t lock ourselves into a single rigid growth model. We were constantly iterating on our approach to customer acquisition, pricing, vertical focus, and delivery — and it’s that adaptability…
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Planning an Exit Around a Key Executive’s Retirement
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Introduction A well-timed exit can be a masterpiece of strategy. But what happens when one of your key executives — the CFO, COO, or even a co-founder — is planning to retire right around the time you’re planning to sell? In my career as a founder and advisor, I’ve seen…
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Pivoting Business Models to Align with M&A Trends
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Introduction Not all exits follow a straight line. In fact, many of the most successful M&A outcomes I’ve witnessed — both in my own career and through advising founders at Legacy Advisors — came after a pivotal change in business model. When I sold Pepperjam, we had evolved significantly from…