Letting Go: The Emotional Side of Selling Your Business

Every entrepreneur understands what it takes to build a business. The focus, resilience and countless decisions made along the way. Yet few are truly prepared for what it feels like to step away. 

When DLI advised on the recent Cobra–Alterra transaction, the financial and strategic dimensions were clear. But like many founder-led deals, it also carried an emotional layer. The reality of seeing a business continue under new ownership after years of personal investment and leadership. 

For this founder, the sale represented both a professional milestone and a personal transition. After decades of driving growth and steering through change, handing over a majority stake meant adjusting to a new role outside the company’s day-to-day operations. 

From our perspective, it was a meaningful transaction, not only because of the strategic outcome, but because it reflected the trust and understanding that make these moments successful. 

At DLI, we often see how the sale of a business can blend pride, anticipation and uncertainty. A company is rarely just an asset; it’s the product of years of purpose and persistence. Recognising that helps owners approach the process with clarity and confidence. 

The most successful exits combine sound deal structure with thoughtful preparation, both financial and personal. Selling a business changes what comes next: your focus, your relationships, even your sense of pace. Preparing for that transition is as important as preparing the numbers. 

For advisors, it reinforces the need to guide, not just transact. At DLI, we create space for open conversation, helping founders define their next chapter and approach it with confidence. 

Behind every transaction are people. The Cobra–Alterra deal reminded us that while M&A is built on analysis and strategy, it’s also shaped by human experience. 

At DLI, our goal is always to help business owners achieve not just the right deal, but the right transition – one that protects what they’ve built and positions them for what’s next. 

About Deal Leaders International

Deal Leaders International (DLI) is a boutique sell-side M&A advisory firm specialising in helping business owners and executives, with a business EBITDA between R20 million and R300 million per year, engineer their growth-to-exit journey.  

We go beyond traditional advisory services, partnering with our clients to design, execute and optimise strategies that achieve maximum value when selling their businesses.  

Our mission is to empower our clients to achieve outcomes that align with their financial, professional and personal goals while positioning their businesses as highly attractive to the right buyers.  

As the Africa representative of the Pandea Global M&A Network, we offer our clients both local and international expertise and experience. With 69 offices in 34 countries, and over 2500 successfully completed transactions with a combined deal value over €30 billion, DLI offers deep market insights, practical expertise and a results-driven approach to prepare and successfully execute on business growth and exit strategies.