Get to know Lindsey

Lindsey brings a distinctive combination of legal training, business experience, and nearly a decade in the insurance industry to his work as an independent agent with Premier Benefit Consultants. He is committed to helping individuals and families understand their health insurance options and navigate Medicare with clarity and confidence.

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Lindsey assists individuals who are becoming eligible for Medicare, current beneficiaries who want help understanding or reviewing their existing coverage, and those preparing to retire and transition from employer-sponsored insurance to individual coverage. He also welcomes questions from family members, guardians, caregivers, employers, physicians, and anyone seeking a clearer understanding of Medicare.

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Recognizing that Medicare can feel complicated, Lindsey takes the time to listen, clearly explain the available options, and help each client make an informed decision based on their individual healthcare needs and circumstances. Complimentary consultations are available by appointment over the phone or through video conference.

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Lindsey’s commitment continues after enrollment. He remains available to answer questions, address concerns, and provide ongoing assistance as his clients’ healthcare needs or circumstances change. His goal is to provide every client with knowledgeable guidance and the confidence of knowing they have someone dependable to turn to.

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A graduate of Punahou School, Lindsey earned his Juris Doctor from the William S. Richardson School of Law in 1989. He is a third-generation attorney whose family has a distinguished history of public service in Hawaiʻi. His grandfather, Michiro Watanabe, became the first appointed Attorney General of Japanese ancestry in the Territory of Hawaiʻi, serving from 1952 to 1953. His father, Wilfred Watanabe, served as a District and Circuit Court judge from 1981 to 2003.

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Lindsey practiced law for six and a half years, working as a litigator in the areas of medical malpractice and real estate. He is also a published author and has an extensive background in business and sales. His legal education and diverse professional experience strengthened his ability to analyze detailed information, communicate clearly, and guide people through important decisions.

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Lindsey has worked in the insurance profession since 2016 as an independent agent affiliated with Premier Benefit Consultants and Hoku Legacy Solutions LLC. His broad experience allows him to approach each client’s situation thoughtfully, carefully explain available options, and provide attentive ongoing service.

 

Lindsey is a highly valued member of the PBC family. His intelligence, professionalism, extensive experience, and commitment to serving others make him a trusted resource for Medicare beneficiaries and their families. PBC appreciates the knowledge and integrity he brings to his work and has complete confidence in the thoughtful, dependable service he provides.

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Lindsey has been happily married to his wife, Karen, since 1992, and they are the proud parents of two daughters, Kailey and Cassidy. Lindsey and Karen attend New Hope Hawaiʻi Kai, where they assist with premarital counseling ministry. Outside of work, he enjoys traveling, gourmet cooking, golfing, and spending time with his family. He continues to pursue that elusive round of golf in the 60s!

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