To incentivize Clapp's founders, part of the deal included convertible bonds in Lemlist's parent company. This structure avoids the complex process of setting a formal valuation for Lemlist today, instead granting the founders the right to buy shares at a 20-30% discount during a future liquidity event.

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Successful founders prioritize cash upfront over potentially larger payouts from complex earnouts. Earnouts often underperform because founders lose control of the business's future performance, leading to dissatisfaction despite a higher on-paper valuation.

Instead of a large upfront equity investment, strategic partners can use warrants. This gives the corporation the option to earn equity later if the startup achieves specific milestones, often through their joint partnership. This approach de-risks the initial investment and directly rewards successful collaboration.

Serial acquirer Lifco improves post-acquisition performance by having sellers retain an ownership stake in their business. This goes beyond typical earn-outs, keeping the founder's expertise and incentives aligned with the parent company for long-term growth, rather than just hitting short-term targets.

Granting stock options is only half the battle. To make equity a powerful motivator, leaders must constantly communicate a clear and believable narrative for a future liquidity event, such as an acquisition. This vision is what transforms paper ownership into a tangible and valuable incentive in the minds of employees.

Alex Bouaziz's core M&A principle, learned from his father, is to optimize for long-term satisfaction over short-term leverage. Even when holding the upper hand in negotiations, he structures deals to be fair for both sides. The goal is for both the acquirer and the acquired founder to look back in five years and feel the deal was a great outcome, ensuring better integration and alignment.

Lemlist's M&A thesis focuses on acquiring companies like Clapp, which had a superior product built by just seven people but lacked market reach. They believe Clapp is a '$20M ARR product' trapped at $2M ARR, creating an opportunity to plug strong tech into their own powerful distribution engine for rapid growth.

The acquisition of Clapp wasn't driven by market analysis but by the Lemlist team becoming passionate users first. The CEO fell in love with the product, leading to company-wide adoption. This bottom-up conviction in the product's quality was the starting point for the M&A conversation.

To minimize upfront cash, Lemlist structured the deal with only $5M cash, a $5M 'vendor loan' (the seller finances part of their own sale), convertible bonds for founder alignment, and a $15M performance earn-out tied to growing revenue from $2M to $10M ARR in three years.

The Clapp acquisition began when Lemlist's CEO sent a random cold email to the founder. Despite competing against larger companies who bid more, Lemlist won the deal by focusing on product synergies and team fit, proving that a strong relationship and shared vision can be more valuable than the highest offer.

To retain founders who've already cashed out, use a dual incentive. Offer rollover equity in the new parent company for long-term alignment ('a second bite at the apple'), and a cash earn-out tied to short-term growth targets. This financial structure is crucial when managing wealthy, independent operators who don't need the job.

Lemlist Uses Convertible Bonds in Acquisitions to Align Founders Without Setting a Valuation | RiffOn