Turning 65? Let Us Help You Navigate Medicare.

Medicare can feel confusing, but you don’t have to figure it out alone. The Sholar Agency provides clear, personalized guidance to help you understand your options and choose coverage that fits your needs.

Let's Plan Together

Explore Solutions

3+

Decades of Expertise

4

Core Solutions

Local

Virginia

Free Guidance for Your Medicare Journey

Dan Sholar's background as a former pilot shaped an approach built on preparation, clear communication, and a calm, steady hand. Whether you're launching a business, turning 65, or planning retirement, we chart the course and fly alongside you with honest advice and clear answers at every waypoint.

Trusted Benefit Solutions, Personalized for You

We deliver knowledgeable guidance, personalized services, and innovative solutions that protect, support, and empower.

Employee Benefits

Comprehensive benefits strategies to help businesses attract, retain, and support their most valuable asset — the people.

Medicare Resource Center

Personalized guidance to help you understand your options and choose Medicare coverage with confidence.

Retirement Planning

Strategic solutions to help you build, protect, and enjoy the retirement you envision.

Individual Insurance

Solutions to protect what matters most, with coverage designed for every stage of life.

Turning 65? Here's Your Medicare Flight Plan.

Don't let Medicare confusion cloud your journey. We'll guide you through each step with clear information and steady support.

Know Your Timeline

Understand your Initial Enrollment Period and the important dates surrounding your 65th birthday.

Learn Your Options

Get plain-language guidance on Original Medicare, Medicare Advantage, Part D, and supplements.

Compare Your Needs

Consider your doctors, prescriptions, budget, travel, and personal healthcare priorities.

Enroll Confidently

Move forward with personalized support and answers before, during, and after enrollment.

Our Mission

To be your trusted benefit resource and solutions provider delivering knowledgeable guidance, personalized services, and innovative solutions that protect, support, and empower individuals, families, and businesses.

Trusted by Virginia Beach Businesses for Over 30+ Years

For over 30+ years, The Sholar Agency has helped Virginia businesses simplify employee benefits, business insurance, HR, and compliance with honest guidance and personalized solutions. Founded on the belief that business owners deserve straightforward advice instead of sales pitches, we focus on building trust through practical strategies that support long-term success.

Let's Plan a Brighter Tomorrow, Together.

Get clear information, personalized solutions, and ongoing service through every stage of life

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