The Wiser Financial Advisor Podcast

Get Real. Get Honest. Get Clear.

Guest Dannette Riddle – Medicare Specialist

Josh Nelson interviews Dannette Riddle on setting up a Medicare plan that suits your needs. Addressing the most basic need anyone about to sign up for Medicare needs to be aware of. Plus, how Dannette’s entrepreneurial spirit helped lead her into a career as a Medicare specialist.


Hi, Everyone. Welcome to the Wiser Financial Advisor with Josh Nelson, where we get real, we get honest, and we get clear about the financial world and your money.

This is Josh Nelson, Certified Financial Planner and founder and CEO of Keystone Financial Services. We love feedback and we’d love it if you would pass it on to me directly at . Also, please stay plugged in with us and get updates on episodes and help us promote the podcast. You can subscribe to us at Apple podcasts, Google, Spotify, or your favorite podcast service. Let the financial fun begin!

Josh Nelson: Today we’ve got a special guest, Dannette Riddle, who is a great friend and business associate that a lot of our clients have worked with over the years. She’s a Medicare specialist and owns a Medicare consulting business that actually spans multiple states. The interesting part today will be a couple of items. One of those is Medicare. I think it’s a topic that a lot of people find confusing and important, so we’re going to tackle that a bit. Also, we’ll talk about business and life stuff. She’s got a breadth of experience that she can bring to the table. Welcome, Dannette.

Dannette Riddle: Thank you, Josh. I’m really happy to be with you today.

Josh: Glad you could make it today. Medicare business is what you’re doing right now. It’s a niche a lot of people find really important and confusing. So how did you get into that business? What do you enjoy about it?

Dannette: For me, it just kind of flowed because previously I had been involved with Aflac for 13 plus years and enjoyed that very much. I enjoy working with people, helping them, doing some good, making new friends, and so after I retired from Aflac, I moved from Durango to the Denver area where my daughter was. She had just started working with a Medicare broker and he offered me a position. I took him up on the offer, and I was already on Medicare myself. I knew a lot about the confusion that exists. I myself made a mistake that I hope people don’t do. I let it come down to the bottom line. It was time to enroll and I put it off and put it off because I thought I was too busy with other things. It was Aflac mainly, so I called my claims assistant who was six or seven years older than me. I knew she was on Medicare and very happy with it. So, I called her and said, “Ruth, I need Medicare. I want to have what you have.” And that’s how I fell into it. I was lucky. It could have been a big mistake not to educate myself and take the time to find out my options. So anyway, it was kind of a natural flow, being able to educate people about the possibilities of helping themselves while doing something that I enjoyed –something very important because there is a lot of confusion around Medicare.

Josh: Yeah, there sure is, and a lot of our clients have reported back that it was so helpful to talk to you, and once they had that conversation, they got some clarity. Also, you’ve been involved in other businesses back into the 80s, right? So this was not your first business. You’d actually run a number of businesses over the years.

Dannette: Yes, there were a variety of things I already knew that I liked, such as meeting new people.

Josh: Just from speaking with a lot of clients over the years, I know Medicare is an area that people are not only very confused about, but they also realize how important it is because it’s their healthcare, absolutely. So, speaking specifically about Medicare, what are some of the biggest misconceptions that you hear from people about how Medicare works?

Dannette: Well, I can tell you one thing that surprised me when I started on Medicare: Most of us have had experiences with insurance companies who deny claims, and typically create some frustration. So I was pleasantly surprised with how Medicare works in a positive way for people with their healthcare and how simple and straightforward it can be once you get through that network and that crazy confusing maze of what it is and what it isn’t. Once you’re there it’s refreshingly comfortable.

Josh: You mentioned you made a mistake before—what would you say are some of the biggest mistakes you see people make with regard to Medicare?

Dannette: Probably one of the biggest mistakes is to do what I did. To say, “I have a friend who’s on a specific plan,” and decide that your friend’s plan is going to work for you. I was lucky in that although I did that very thing, it proved to be a plan that was satisfying to me. But the biggest mistake is to let life run away with you so you don’t take the time to educate yourself about all the aspects of Medicare. There are many options to Medicare. You want to understand what Medicare is, what it offers you, and the different options that you have.

I have clients call me all the time and say, “I saw this ad on TV the other day and it was talking about this, this, and this. Would that be something I should have instead of what I currently have? So, we go through the process and remind them of what they have and compare it to what they saw. Then they’re satisfied.

Educating yourself is probably the number one thing that you do not want to make a mistake about. You want to get all the information and knowledge that you can.

Josh: Yeah, I think people get overwhelmed because at age 63 to 64 you start getting deluged by insurance companies with Medicare information, because of course they want you to sign up with their company. People get overwhelmed and sometimes just want to hit the easy button. They’ll say “Alright, what did you do? What did my friend do? What did my brother do?” But their situation is not the same. They might be on different medications. They might be in a different Health Network. What’s best could be very different based on the individual.

Dannette: Absolutely, that’s one of the things I do: find out all about this person that I’m speaking with and learn what they’re looking for, learn their lifestyle and understand their current health situation so I can educate them about the options they have and tell them, “If you go in this direction, this is what you’ll have. There are some good things about it and there are maybe some things that you may not feel comfortable with, based on what you’re looking for.” Then I’ll show them another direction and do the same thing. “These are things that likely will feel good to you, but these may not feel as good. But let’s talk about everything, so you will feel good about the decisions that you make.”

Josh: What are some bad recommendations that you’ve heard?

Dannette: Something I might hear a lot is just what we’ve talked about: Making a decision based on a friend or on if you’ve had insurance in the past with a specific company you’ve been happy with. It could be Humana, United Healthcare, Cigna, Aetna. So you assume it would be comfortable for you to call that particular company now that you’re ready to do Medicare. And of course, that company is going to be happy you called, but then they’re going to present to you the plans that they have available. They’re not going to educate you completely about the possibilities. It’s a mistake to go into Medicare with blinders on and not really open up your view to everything that’s available.

I think it’s important to speak with a broker such as myself, who doesn’t have an agenda for my employees. I want my clients to be able to understand all the possibilities. And because I’m licensed with multiple insurance companies, I’m not going to lead anyone down a specific path that would benefit me by them purchasing that plan. I can offer lots of possibilities because of multiple licenses. That potential client has lots of choices and we can feel confident that once they’ve settled in on a decision, that person feels confident and I feel comfortable that I have helped them understand the possibilities.

Josh: That’s pretty important in a lot of areas of financial planning—whether investments or , insurance. If you are getting advice and you’re not doing your own research, find somebody that doesn’t have an agenda. I can speak for you, Dannette, that you’ve worked with a number of our clients that have had a retiree medical plans through their old employer, and you’ve been honest with them and said, “We should go with that,” even though you don’t get paid for it. People are always looking for somebody who is going to look out for their best interests regardless of if that person is being compensated more or compensated less.

Dannette: It makes a difference. You know, this is probably one of those corny sounding things, but I like myself and I want to like myself, so I feel good when I am straightforward and honest with people. It’s more important that I help them and direct them in the right direction. It’s more important to me to do that with them rather than earn a commission. And I get compensated appropriately either way.

Josh: You mentioned before you’ve been in a number of different businesses over the years. Where did you get that entrepreneurial spirit? How did that get sparked in you?

Dannette: I guess maybe growing up with a kind of restricted outlook on life. I came from a very religious family and you were expected to accept things the way they were. For some reason or other, I was one of those people who wanted to look beyond everything and not just look at the same function within the same box. I like to learn new things, so I think it’s just about curiosity and a feeling of, you know, “That sounds exciting.” If I get a chance to come back in another lifetime, I’m going to put in a plug for hopefully being a paleontologist next time. I just love the variety of options and learning.

Josh: Certainly this last year during the pandemic, it was a terrible economy, at least for a while. Things are getting better, showing signs of life now, but a lot of people have had to pivot. They’ve had to make some big changes and one thing I was going to ask you is what advice would you give somebody that is looking at making a big change, whether they’re just out of college or whether they’ve been working for somebody else, but they’re in a position where they need to pivot and go do something different.

Dannette: It would be to take those blinders off. You’re right, I have truly pivoted a number of times, jumping from one thing to another in ways I never would have expected. Just take those blinders off and be openminded and willing to look around. If you have some possibilities of interest to you, I think the bottom line is to listen to your heart and go with something that feels good to you deep inside, even though you may not completely understand what it is, what the opportunity might be, but you feel good about it. Be open minded and willing to explore. Always maintain your standards, to feel good about yourself.

Josh: I’d certainly agree, and you’re a great example of somebody who has retired, but still, you know, has a business and is enjoying it. I think you’re passionate about it. You get up in the morning and you’re excited about what you’re going to be doing and who you’re going to be working with. That’s one of the keys to the happy retirees that I interact with. They are people that never stop learning, never stop growing. They’re very curious. They are people that aren’t satisfied with being done—and you are a great example. So, on the other end of the spectrum, what advice would you give a smart, driven college student about to enter the real world, especially the world that we’re in right now where we’re just coming out of this terrible recession?

Dannette: Of all the questions you’ve asked me, that’s probably the trickiest one. But I would say to be positive, don’t be discouraged, understand that we all make mistakes and those mistakes are something to learn from, not to be beaten down by. Take the positives of any situation and ask yourself what can I do to learn from that? And to have that attitude of positivity and determination, knowing that you can count on yourself, you have the capacity. Today we’re all capable of far more than we realize.

Josh: And what advice should they ignore?

Dannette: I guess anything that doesn’t resonate, anything that makes them feel that it’s just not part of who they are. Like when you choose your friends, you want to hang out with people who uplift you, make you feel good, make you laugh, people who accept you for what you are. You should not try to conform or be someone you’re not.

Josh: One question along those same lines: if you imagine yourself back in say, your 20s, as you’re just getting going with your career, when you feel overwhelmed or unfocused or let’s say you’ve lost your focus temporarily, what do you do? What advice would you give that 20 something year old?

Dannette: Gosh. I started having a family when I was young. I was only 20 and so that gave me a great deal of determination to stick to my guns. I had a lot of responsibility. But if someone is not yet in that position of having other persons dependent upon them, then they have to think of themselves and what they want to accomplish in life, how they want to feel about themselves five years down the road, 10 years down the road. Know that they can pull through. I always told my daughters when they were feeling down, and I applied this to myself: Tomorrow is another day. Today might look pretty bleak, but tomorrow is a brand new day and we don’t know what it’s going to bring. Things will not stay the way they are at this moment. If they are on the blink side, it always changes. There’s always opportunity.

Josh: Yep, every day above ground is a good day, right?

Dannette: Absolutely.

Josh: You’ve got kids and you’ve got some grandkids too, right?

Dannette: I do, yes. I have a couple of grandsons who are actually grown themselves now. They are 26 and amazing young men.

Josh: You’re great role model to them as well, with the stories you’re able to tell and the experience you’ve gotten.

Dannette: Thank you, I hope so.

Jsoh: Yeah, absolutely. Well, again, Dannette is a Medicare specialist and her business is Ever Sure strategies. You can reach her by going to the website .

I know just from working with her and working with her other clients that if you ever have questions about Medicare or maybe you have a family member, (we often find that the kids or grandkids are helping their parents or grandparents figure out how to navigate Medicare). And one thing to throw out there as well is that the traditional age for applying for Medicare benefits is age 65. But there’s an open enrollment every year, right?

Dannette: Well, open enrollment applies to those people who are already on a part C Advantage plan or prescription drug plan. An individual open enrollment is whenever someone is turning 65 like you just stated, or when someone is going into Medicare for the first time, whether they are 65 or older. But the normal concept of open enrollment typically does not apply to someone entering Medicare for the first time because it’s based on their birth date.

Josh: Even if you’ve already made some Medicare decisions, or maybe you’re questioning, “Gosh, did I do the right thing?” there’s value in talking to somebody that knows what they’re doing and making sure that you’re navigating your own healthcare because nobody is going to rescue you, that’s for sure. We’ve got to take responsibility for our own decisions, even if we’re using people to help us. Sometimes it’s just a matter of raising a hand and saying, “Hey, I need help, and certainly Dannette is a great example of somebody who can do that.

We definitely appreciate the conversation today, not only about Medicare, but about life too. You have a breadth of wisdom to be able to bring to the table, and I’m sure you’re sharing that with your family as well.

Dannette: Thank you, thank you.

Josh: Again, Dannette Riddle and her business is at And you know, we will continue to work with her doing webinars every year or so on the Medicare topic. Thanks Danette, thanks for your time and have a wonderful day.

Dannette: Thank you so much, Josh.

Josh: Okay, thank you for listening. I want to wish you the very best. I hope this was helpful for you. Please like our podcast and if you’ve got coworkers, friends, family that would benefit from this please subscribe and pass it on to them. Anything you can do to help us promote the show would be great. A lot more people are finding out about us, so thank you.

I hope all is well, and God bless.

The opinions voiced in this episode of the Wiser Financial Advisor with host Josh Nelson are for general information only and not intended to provide specific advice or recommendations for any individual. Investment advisory services offered through Keystone Financial Services, an SEC Registered Investment Advisor.