Meet John Mason: A Visionary, a Rebel, and the President of Chenango Brokers LLC

John Mason isn’t your cookie-cutter insurance magnate. Born without a silver spoon and hailing from a humble town in upstate New York, John embodies the audacity of the American dream. Over the last three decades, this ingenious trailblazer has defied the odds, marching right into the heart of the financial capital, New York City, and acquiring a staggering five brokerages. Today, his empire stretches across 25 states, right from his tropical base in the Caribbean.

Don’t let John’s laid-back island vibe fool you; he’s a businessman first, a dynamo of creativity and strategic thinking. His early realization, 25 years ago, set the pace for his career: to truly make it in the insurance business, one must be more than just an agent. So, in 1988, he purchased a struggling small-town agency and supercharged it with high-impact marketing strategies. The result? Rapid growth, followed by further acquisitions and exponential expansion.

John’s vision is colossal yet crystal clear: make all of Chenango’s core products available for broker quoting 24/7 and streamline the submission process. He is hell-bent on eradicating inefficiencies and driving the team toward operational excellence. From Commercial Auto and Workers Comp to Cyber and Umbrellas, John offers an expansive product portfolio targeted to a variety of sectors including restaurants, contractors, and tech companies.

While John thrives on working ON the business, he’s no stranger to the trenches. Whenever his team is overwhelmed, he rolls up his sleeves and dives in. Not only does this keep him grounded in the daily operations, but it offers him invaluable insights into areas that need improvement, be it a process, technology, or personnel change.

When he isn’t steering Chenango’s ship, you’ll find John soaking up the sun either by the pool, on his boat, or at his island retreat. Family and friends are his anchor, and his passion for exploring new places, dining out, and non-business related travel shows that he lives his life just as he runs his empire—on his own terms.

To John, insurance is more than policies and premiums; it’s about empowering independent and semi-captive agents with quality, competitive products from financially robust markets. John Mason is not just a businessman; he’s a vision-caster, a team-builder, and the unshakeable pillar upon which Chenango Brokers stands tall.

Here’s to John Mason—our fearless leader, guiding star, and the indomitable spirit keeping Chenango Brokers on the cutting edge of the insurance industry!