Promotional Contest Insurance Brokerage, 9-Year Florida B2B Risk Firm

Full Editorial Writeup

This is a nine-year-old, B2B specialty insurance brokerage that underwrites and places coverage for high-value promotional contests. Think hole-in-one challenges, million-dollar shootouts, and other prize-indemnity events where a sponsor needs a financial backstop if a contestant actually wins. The firm serves over 1,000 active national clients, heavily weighted toward auto dealerships, plus corporate marketing directors and charity tournament coordinators. Revenue comes from commissions brokered through multi-billion-dollar international carriers, plus a self-underwriting book where the business keeps more of the economics.

The operation is fully digital and asset-light. There is no storefront, no inventory, no warehouse, and no commercial lease. Everything runs on cloud-based CRM and policy-binding software, which means the business can be owned and operated from anywhere in the US. On $888k of revenue it throws off $572k in cash flow, a 64 percent margin that reflects the low overhead and commission-driven model.

The retiring founders are selling and have committed to a full handoff including database transfer and warm client introductions. At $2.6M the deal is priced at 4.55x cash flow, which is a full multiple for a sub-$1M revenue specialty broker and is justified only if the commission pipeline and carrier relationships prove to be durable and transferable.