About Richard Cummings

President / CEO

CLEARWATER, FL • SERVING TAMPA BAY

Based in Clearwater, Florida, serving clients throughout Tampa, St. Petersburg, Largo, Palm Harbor, and surrounding Pinellas County communities.

Richard Cummings has been working with individuals and couples preparing for retirement for over 35 years.

His work focuses on helping people understand how retirement decisions are made—especially when it comes to Social Security, retirement income, and how savings are used over time.



Many people first meet Richard through a class or seminar, where he explains these topics in a clear, step-by-step format before any decisions are made.

Background & Experience

Richard Cummings is the founder of Cummings Insurance, Inc., a Clearwater-based firm that was incorporated in 1984. A longtime Florida resident and graduate of the University of Tampa, Richard has worked with individuals and couples across the Tampa Bay area for many years, focusing on retirement planning, Social Security timing, and income strategies.

Richard works with his wife, Laura Cummings, who has been an integral part of Cummings Insurance and the firm’s success serving the Tampa Bay community for more than 35 years.

His approach centers on education—helping people understand how different parts of retirement planning work together before taking action.

This includes explaining how Social Security, retirement accounts such as IRAs, 401(k)s, 403(b)s, pensions, and other retirement accounts, along with income strategies, are structured and how they may affect long-term financial outcomes.

In the News & Community Education

Richard has been involved in retirement education through local seminars and community-based programs for many years. He participates in educational workshops that cover topics such as Social Security timing, retirement income planning, and how financial decisions can affect long-term outcomes.

Through his work with the Council of Financial Educators (COFE), Richard helps provide structured, classroom-style education designed to make complex retirement topics easier to understand. These classes are held throughout Clearwater and the Tampa Bay area and are often the first step for individuals and couples looking to better understand their retirement options before making important financial decisions.

Why Clients Refer Richard

Many clients are introduced through referrals from others who have attended classes or worked with Richard directly.

Common reasons people refer others include:

A Local Approach to Retirement Planning

Cummings Insurance, Inc., a financial services company is a Clearwater-based financial services and education center serving Tampa Bay, including Pinellas County communities like Largo and Palm Harbor, as well as St. Petersburg and Tampa. Richard continues to work with individuals and couples who want to better understand how retirement planning works before making important financial decisions. Whether attending a class or starting with a conversation, the goal is to provide clarity around Social Security, income planning, and retirement decisions.