Client Reviews

Helping Tampa Bay Retirees Make Confident Decisions

For more than 35 years, Richard Cummings has helped individuals and couples throughout Clearwater, Tampa, St. Petersburg, and surrounding communities better understand their retirement options. From Social Security timing and retirement income planning to annuities, Medicare supplements, and long-term care insurance, our focus is on providing education, clarity, and personalized guidance.

Hear What Our Clients Have to Say

We're proud of the relationships we've built and the trust our clients place in us. Read reviews from individuals and couples who have worked with Cummings Insurance and learn about their experiences.

Excellent service. Entire staff is professional as well as polite and very helpful.

Pandora S.

Excellent service. Entire staff is professional as well as polite and very helpful.
I trust Richard Cummings 100% with my investments. I have been with him about seven years.

Monica U.

I trust Richard Cummings 100% with my investments. I have been with him about seven years.
If you are looking for a

Nancy P.

If you are looking for a "safe" financial advisor (versus a "risk" advisor) I highly recommend Richard Cummings. He's been in this business for over 40 years and is extremely knowledgeable and personable. You won't be sorry!
Richard Cummings truly cares about our financial picture and takes the time to explain details about the wonderful advice and strategies he proposes to us. We have been with him for 10 years.

Mary E.

Richard Cummings truly cares about our financial picture and takes the time to explain details about the wonderful advice and strategies he proposes to us. We have been with him for 10 years.
We have been with Richard about 10 years and are very pleased that he really takes what we need for our retirement needs to heart. We would highly recommend him.

Deb W.

We have been with Richard about 10 years and are very pleased that he really takes what we need for our retirement needs to heart. We would highly recommend him.
Richard Cummings truly cares about our financial picture and takes the time to explain details. We have been with him for 10 years. I am impressed how well an insurance company can grow our investments. Richard really knows what he is doing and how to handle our situations. I trust him very much.

Dan E.

Richard Cummings truly cares about our financial picture and takes the time to explain details. We have been with him for 10 years. I am impressed how well an insurance company can grow our investments. Richard really knows what he is doing and how to handle our situations. I trust him very much.
We have been working with Cummings Insurance for over 8 years. Richard has always been professional and guided us through the process and helped us make the best decision for our needs.

Judy T.

We have been working with Cummings Insurance for over 8 years. Richard has always been professional and guided us through the process and helped us make the best decision for our needs.
Richard has been extremely helpful with regards to annuities, how they work, Pros, things to consider, Etc especially for someone like myself who really knew very little about annuities! He spent quite a bit of time going over all of the information in detail making sure we understood prior to moving forward. Have been very happy with Richard's service and would recommend him without any reservation.

Teri S.

Richard has been extremely helpful with regards to annuities, how they work, Pros, things to consider, Etc especially for someone like myself who really knew very little about annuities! He spent quite a bit of time going over all of the information in detail making sure we understood prior to moving forward. Have been very happy with Richard's service and would recommend him without any reservation.
We have had Richard take care of our money security for years now. He has ALWAYS done right by us and we make money using . We will NEVER stop using Cummings Ins.

Francis W.

We have had Richard take care of our money security for years now. He has ALWAYS done right by us and we make money using . We will NEVER stop using Cummings Ins.
Richard makes things easy to understand and can help you make informed decisions about retirement income plans.

Peter D.

Richard makes things easy to understand and can help you make informed decisions about retirement income plans.
Richard has worked many years with me. Always been very helpful choosing what works best for my situation. Has always been upfront and never pressured me to buy.

Dean S.

Richard has worked many years with me. Always been very helpful choosing what works best for my situation. Has always been upfront and never pressured me to buy.
Attended a seminar that Richard was hosting. Sure glad I did. I've been with him ever since. Richard takes the time to understand your financial needs. Based on these needs, he sets up your investments accordingly. My wife and I could not be happier. Thank You Richard!!

Steve S.

Attended a seminar that Richard was hosting. Sure glad I did. I've been with him ever since. Richard takes the time to understand your financial needs. Based on these needs, he sets up your investments accordingly. My wife and I could not be happier. Thank You Richard!!
We met Richard seven years ago at one of his Social Security Seminars. At that time, we were having some issues with the SSA. Richard stepped in and resolved our issue. We also have a portion of our retirement funds with Richard. He set us up in an annuity program that not only takes care of my RMD but also provides us with lifetime annual income. We have been extremely pleased with the service he has provided to us and if you are looking for a financial advisor with impeccable integrity, he's your guy.

Craig B.

We met Richard seven years ago at one of his Social Security Seminars. At that time, we were having some issues with the SSA. Richard stepped in and resolved our issue. We also have a portion of our retirement funds with Richard. He set us up in an annuity program that not only takes care of my RMD but also provides us with lifetime annual income. We have been extremely pleased with the service he has provided to us and if you are looking for a financial advisor with impeccable integrity, he's your guy.
I have been doing business with Cummings Ins. for many years. Richard has invested my money as he would his own. I have total assurance that this company is doing right by me.

Bud L.

I have been doing business with Cummings Ins. for many years. Richard has invested my money as he would his own. I have total assurance that this company is doing right by me.
I have an annuity to help toward retirement. Richard has been very helpful with strategy for savings and having it grow.

Bill S.

I have an annuity to help toward retirement. Richard has been very helpful with strategy for savings and having it grow.
I have been a Client of Richard Cummings since 2012, fourteen years now. I have a couple of policies through him. He keeps in touch with me for annual

Susan V.

I have been a Client of Richard Cummings since 2012, fourteen years now. I have a couple of policies through him. He keeps in touch with me for annual "check-ups" to inform me of other possible things I may want to change to. He's very easy to talk to, & I trust him.
Since the first day we met Richard we were impressed with his professionalism and sincere concern for our retirement needs. Cummings Insurance is always very welcoming and worked with our schedules with no problem at all. I truly recommend Cummings Insurance for any of your retirement or financial needs that you may have. Richard and his office will take care of you!

Joe B.

Since the first day we met Richard we were impressed with his professionalism and sincere concern for our retirement needs. Cummings Insurance is always very welcoming and worked with our schedules with no problem at all. I truly recommend Cummings Insurance for any of your retirement or financial needs that you may have. Richard and his office will take care of you!
We highly recommend Cummings Insurance, Inc. for all your retirement or financial needs.  My husband and I met Richard at an educational seminar a few years ago and we were immediately impressed.  Richard is very down-to-earth, explains everything in terms that are easy to understand, and always makes sure we are comfortable before proceeding with any investments or changes we need to make.  It is comforting to know we are in such good hands.  It is very rare to find someone who always has OUR best interests at heart!

Csolarski G.

We highly recommend Cummings Insurance, Inc. for all your retirement or financial needs.  My husband and I met Richard at an educational seminar a few years ago and we were immediately impressed.  Richard is very down-to-earth, explains everything in terms that are easy to understand, and always makes sure we are comfortable before proceeding with any investments or changes we need to make.  It is comforting to know we are in such good hands.  It is very rare to find someone who always has OUR best interests at heart!
Richard always provides the best advice tailored to your specific situation, giving you options and clearly explaining everything. He and his staff are the best!

Clare L.

Richard always provides the best advice tailored to your specific situation, giving you options and clearly explaining everything. He and his staff are the best!
Professional and informative

Catherine D.

Professional and informative
I had a great experience with Cummings insurance company . They are excellent—friendly, responsive, and very helpful throughout the entire process. They made everything easy to understand and were always available to answer my questions. I would definitely recommend them to anyone looking for reliable financial services.

Maryann C.

I had a great experience with Cummings insurance company . They are excellent—friendly, responsive, and very helpful throughout the entire process. They made everything easy to understand and were always available to answer my questions. I would definitely recommend them to anyone looking for reliable financial services.
I’ve been with Richard Cummings for years now. He’s always answered my questions. I’ve never had any issues with him or the Agency. I would highly recommend him.

Jacalyn G.

I’ve been with Richard Cummings for years now. He’s always answered my questions. I’ve never had any issues with him or the Agency. I would highly recommend him.
It's a pleasure working with Mr. Cummings. He is very patient, thorough and willing to answer any questions I have. I highly recommend his services/business.

Rishika K.

It's a pleasure working with Mr. Cummings. He is very patient, thorough and willing to answer any questions I have. I highly recommend his services/business.
As retirement approached, we were looking for someone who was closer and could provide us with more direct access to our investment accounts. Cummings Insurance was a great call. We meet with Richard on a regular basis. He understandings our financial position and provides the most helpful consul for investing. For two people who need help for retirement planning. Cummings insurance was a great call.

Alan M.

As retirement approached, we were looking for someone who was closer and could provide us with more direct access to our investment accounts. Cummings Insurance was a great call. We meet with Richard on a regular basis. He understandings our financial position and provides the most helpful consul for investing. For two people who need help for retirement planning. Cummings insurance was a great call.
I have been working with Richard Cummings since 2019. He has done an excellent job on handling my retirement funds. He is very knowledgeable and explains well.

Marilyn S.

I have been working with Richard Cummings since 2019. He has done an excellent job on handling my retirement funds. He is very knowledgeable and explains well.
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Mike and Luz Meyer

"Richard has proven to be knowledgeable,& trustworthy, highly experienced and qualified to help us navigate our financial future.  Richard is very professional and has shown to be an invaluable Friend.vThank you Richard."

Ready to Start the Conversation?

Whether you're exploring Social Security timing, reviewing your retirement income strategy, or looking for answers about Medicare or long-term care planning, we're here to help.