About Us

Darr Schackow Insurance: Serving Florida Since 1992

Licensed in 32 states, Darr Schackow has offices in Gainesville, Jacksonville, Milton, Perry, Fleming Island, and Okeechobee, offering home, auto, life, flood, watercraft, business, annuity, health insurance, workers’ comp, and employee benefits options for all.

Leveraging extensive relationships across the insurance industry, DSI offers insurance solutions that meet your specific needs in every situation.

Our Mission

“At DSI, we work diligently to reduce stress, provide the best options, and offer affordable pricing for all clients.”


What Our Clients Are Saying


What We Do

Darr Schackow Insurance is an Insurance Broker with relationships with the nation’s top-rated insurance carriers, which means we help our clients find coverage that matches their described needs.

Explore Coverage

Outline of the state of Florida

Our History

John Darr, Sr. and Ray Schackow enter the insurance world

John Darr, Sr. and Ray Schackow entered the insurance business in 1992 as Nationwide agents in the Gainesville regional office. They were at separate agencies but always shared a common space.

John Jr. Joins His Father

John’s son John, Jr. (Johnny) joined his father. The father-son agents were committed to creating lifetime relationships with their customers and providing quality customer service. As a result, the agency grew significantly.

John Darr, Sr. Retires

John Darr, Sr. retired and sold the agency to his son, Johnny, and son-in-law Richard Rowell.

Darr and Schackow Merge

The landscape of the Florida insurance market changed dramatically when, after sharing space for 16 years, Darr and Schackow officially merged.

DSI Partners With The Liberty Company

In 2020, DSI joined The Liberty Company Insurance Brokers, expanding its reach and service offerings.

Our Managing Partners

Profile photo of John Darr, Chief Executive Officer/Owner at Grove Financial & Associates

John Darr

Chief Executive Officer/Owner

Profile photo of Ray Schackow, Chief Operations Officer/Owner at Grove Financial & Associates

Ray Schackow

Chief Operations Officer/Owner

Profile photo of Richard Rowell, Chief Financial Officer/Owner at Grove Financial & Associates

Richard Rowell

Chief Financial Officer/Owner

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