From Captive to Independent: Dan Kitajima’s Journey to Insurance Agency Freedom

Welcome to another episode of The Insurance Dudes! In this powerful conversation, hosts Jason Feltman and Craig Pretzinger sit down with Dan Kitajima to unpack a truly wild journey from building a $17 million captive insurance agency to making the bold leap into the independent world.

Dan shares the highs and lows of his experience—from signing a jaw-dropping $20,000/month office lease just before his carrier pulled the rug out by non-renewing $6 million in policies, to learning how to pivot, retain clients, and ultimately rebuild—this time with even greater focus, flexibility, and profitability. The trio dives into the nuances of switching from captive to independent, breaking down differences in closing ratios, broker fees, marketing strategies, and what it really takes to survive (and thrive) through massive industry disruption.

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