Tailored Insurance. Trusted Guidance.
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Tap To Call: 866-812-4777
866-812-4777

info@protectwiththeo.com

Mon - Sat 9am-8pm

Sunday Closed

St. Augustine, FL

Multi-State Offices

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Testimonials

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WHAT CLIENT SAY?

Satisfied Clients

See what our clients are saying about the peace of mind, personalized service, and expert guidance they’ve received working with Greg O’Rourke

Greg O'Rourke and his team provided clear, unbiased guidance on Medigap plans. They took the time to explain my options without any pressure and helped me find the best supplemental coverage. He made it make sense and made a tough choice simple. No pressure, Highly recommend!

Rick F Radio Personality

Greg saved me from a bad insurance plan! He showed me my health coverage wasn’t real major medical—despite what the other company claimed—and found me the right plan. He also got me better life insurance at a lower price than anyone else. Truly the best—Thank you so much!

Tammy M Paralegal

Truly puts clients first! I was set on switching plans, but he showed me my current plan was actually the best choice. Another company tried to push a bad plan on me, and Greg made sure I didn’t fall for it. He spent tons of time helping—never any pressure. Honest, knowledgeable

Marilyn O Medical Business

Better Coverage, Smarter Savings

Protect What Matters – At the Right Price.  Affordable Coverage, Trusted Protection

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We believe buying insurance should be simple, stress-free, and affordable. That’s our commitment to you!

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Contact Info

  • Main Office St. Augustine, FL
  • 866-812-4777
  • info@protectwiththeo.com
  • Mon - Sat 9am-8pm

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© 2025 Gregory O’Rourke. All rights reserved.
Protection-first strategies for life, health, and retirement — focused on fixed annuities and insurance solutions designed to protect income, preserve wealth, and provide long-term security.

Independent. No fees for insurance guidance. No pressure. 100% client-focused approach.

Gregory Scot O’Rourke (“Greg”), Licensed Insurance Agent
FL License #G166831 | NPN #21340769 | Multi-State Licensed Agent

Greg is not a registered investment adviser or securities broker-dealer and does not provide investment, tax, or legal advice. This website is for informational purposes only.
Product features and availability may vary by state and carrier. All guarantees are based on the claims-paying ability of the issuing insurer. Coverage is subject to underwriting approval and policy terms. Not affiliated with or endorsed by the U.S. government, Medicare, or the Federal Marketplace.