Ray Delany: How I turned a failing business into a 5x + exit
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Ray Delany: How I turned a failing business into a 5x + exit
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About this listen
He bought 51% of a business that was already going down the gurgler… then the GFC hit.
In this episode of 2 Commas, Ray Delany shares the full story behind turning a struggling technology services company into a 5X+ exit. What followed the acquisition wasn’t momentum. It was cash bleed, lost customers, leadership doubt, a global financial crisis, and significant personal upheaval.
Ray walks through what actually changed the trajectory. Shifting from chasing growth to building profitability. Taking full ownership rather than leaning on inherited thinking. Rebuilding credibility with customers. Attracting the right people. Moving early to cloud infrastructure. And learning that selling well often matters more than building something exceptional.
We also explore the original MailMarshall exit, the realities of services multiples, structuring an earn-out, and why values alignment mattered more than squeezing the last dollar from the deal.
This is a grounded conversation about responsibility, resilience, and earning an outcome over a decade.