Five things I learned closing $300M of mid-market M&A

At o3 Capital I worked on more than five sell-side and buy-side mandates in IT services, totalling over $300M — including the sale of a cloud services provider to an international buyer for close to $100M. A few patterns repeated across every one of them.

First, valuation is agreed early and justified late. Buyers anchor in the first two weeks; the rest of the process is either defending that anchor or watching it erode. Everything in deal preparation — the quality of the data room, the consistency of the story, the cleanliness of the numbers — exists to protect the anchor, not to set it.

Second, deals die in diligence, not negotiation. The transactions that failed didn't fail on price. They failed when revenue recognition didn't reconcile, when a key customer contract couldn't be assigned, or when founder answers drifted between meetings. Sellers who audit themselves before going to market close faster and at better terms.

Third, process is leverage. A well-run process with two or three credible buyers outperforms a single enthusiastic buyer at a higher headline number. Competitive tension is the only discount-insurance a seller has.

Fourth, the founder's calendar is a deal risk. Mandates stall when the promoter is also running the company at full tilt. The best outcomes I saw had a second line of management who could hold the business while the founder held the deal.

Fifth, the best deals feel boring at close. If the final weeks are dramatic, something was left unprepared. These lessons now shape how I advise founders directly — get your house in order a year before you think you need to.