Nightmare On Enrollment Street | Insurance 360 Ep. 34 - HALLOWEEN SPECIAL

In this second annual Halloween spooktacular episode of Insurance 360, hosts Bob and Rob are replaced by Ted Lasso and the Milburn Pennybags (better known as the "Monopoly Man"), who add a Halloween twist to the show.

This episode tackles the challenges and opportunities present during the Annual Enrollment Period (AEP) for insurance agents. Packed with some spooky special guests who come to share tips on overcoming tech troubles, embracing new business practices, and the importance of compliance. 

Bob and Rob also dive into the history of Monopoly, its unexpected ties to World War II, and the importance of adaptability in both board games and the insurance industry. The episode concludes with encouragement to seize new opportunities and to keep moving forward, even when facing disruptions.

#AEP2026 #HalloweenSpecial #Insurance360 #PinnacleFinancialServices #PFSInsurance #InsuranceMarketing #MedSupp #MedicareSupplement #FMOTraining #Insurance #InsuranceBroker #InsuranceAgents #InsuranceAgent #MedicareInsurance #Annuities #Annuity

Transcript

Bob: [00:00:00] All right, well good morning everybody on this Halloween Eve. We've got a great show today. Our second annual Halloween Spectacular here at Insurance 360, and I'm really happy to be sitting in for Bob and Rob. If now I'll introduce myself in real quick. I am Ted Lasso.

I am, uh, rich 

Rob: Uncle. We, we'll call him nickel bags to exactly [00:01:00] say that.

We don't get in trouble 

Bob: exactly Mr. 

Mr. Mon, Mr. Monopoly guy. Mr. Monopoly. I can see the monocle there. 

Rob: Yeah. So, 

Bob: so something 

Rob: did, did you know this, that actually the monocle, I don't know. Apparently he doesn't have a monocle. It, it's like a, uh, Mandela effect. 

Bob: That's the Mandela effect?. 

Rob: I always thought that he had one, but he does not.

Bob: Interesting. Now, something I always find thinking about the monocle. Is that you gotta feel like if you needed one eye to be fixed, both eyes probably needed to be adjusted. So in essence, one eye was blind while you're looking with the other. 

Rob: Yeah. You know, I never understood the mechanics of a monocle, but then again, I have a big bag of money.

So I guess I don't really need to worry 

about it. 

Bob: And now since you're telling me that Mr. Monopoly actually didn't use the monocle. The only person I can ever think of that actually had a monocle Colonel Clink from Hogan's Heroes 

Rob: Oh yeah. 

Bob: Is [00:02:00] probably the only one that's got, that's for you young folks.

You know, you probably probably don't remember Hogan's Heroes Classic, you know, but, uh, that, 

Rob: yeah. God, I haven't seen that show in a long time. 

Bob: . It's been quite a bit there. But, you know, we wanted to start today I think as we're in the midst of some of the things going on, we'll say this is sort of the, nightmare on enrollment street.

If you, if you would, would hear, some words of wisdom. I, I think some encouragement is needed for all of us as we go through all the trials and tribulations of the AEP season so. You know, we know AEP can be scary. Right. You know, it's almost like a haunted house on midnight sometimes, right?

Oh, yeah. It, it's, it's a situation where, you've got spooky deadlines, you've got some new plans coming out. Tech trouble. Who doesn't have trouble? 

Rob: Who doesn't have tech trouble 

Bob: these days? But, I think we have to just not fear. We have to look at them as like the ghosts, then we're not gonna fear them, and we're gonna just trust in our training.[00:03:00] 

We're gonna lean on the PFS support team and we're gonna turn all those tricks into treats here. This AEP, and that's the way we gotta go about looking at it. And we gotta remember one important thing, right? You gotta believe Rob. 

Rob: Gotta believe. 

Bob: You gotta believe 

Rob: Ted Lasso with this one-liners. I love it there.

Bob: There you go. So when we talk about training, I thought it would be really appropriate to be the head of our support team to come and give us. Some insights and some words to calm us during this. So we do have Theresa here that's gonna jump in and give us a little bit about what she's seeing here in the tech world and with all the training going on this year.

So, Theresa, take it away 

Rob: Let's hear it 

Teresa: Crow-ella here for some technology can be terrified, but not when you have pinnacle by your side. Our training and support teams turn those eerie [00:04:00] enrollments platforms and quoting tools into trusted allies. With just a little guidance, you'll conquer your digital fears and discover a world of efficiency and confidence.

So don't run from the tech. Embrace it. With Pinnacle's help, you'll master every tool like a true agent of the future.

Bob: There you go, Rob. You have to have words to live by, you know? Tech always gonna be trouble support. You're always gonna need it. There's always gonna be things that don't actually work the way they should. Right. Murphy's Law, they, if it can go wrong, it will go wrong. And it, and, and it's always gonna be the time you need it the most.

Rob: Yeah. 

Bob: You know, that's where the tech comes in mostly during the AEP season. So I think it's really important that we all lean on the Pinnacle team. Right. And Mr. Monopoly guy. You're always running all the [00:05:00] training here. Yeah. Does everybody not know at this point that we have live trainings going on 

Rob: every day?

Basically 

Bob: probably every day at this point. Taking advantage of those can be critical, right? All these little things that you probably didn't, know about. Little nuances. And then we can also run them trainings anytime you need them. So you just kind of have to ask. You gotta kind of speak up a little bit, you know, kind of put yourself out there.

And I think that goes a long way for having a successful AEP season. 

Rob: Yeah, and I, I keep telling people too, I think the key phrase for me is it's never too late. We're seeing people still take their AHIPs, do certain trainings. There might be a carrier that you didn't certify for that now you surprised you and is actually competitive in your market, so you need to certify.

So. If you need tidbits and help, we have a vast amount of knowledge here between not my, not just myself and our support staff, but obviously all of our sales team as well. 

Bob: Yeah, absolutely. 

Absolutely. 

[00:06:00] And 

some other thought I had about Halloween, which, I think Halloween's like second to Christmas now, it's really becoming , pretty popular.

If anybody hasn't seen the 40 foot skeleton, you can now buy from Home Depot and put it on your lawn. 

Rob: The wifey 

keeps trying to get me to do that, and I told her there's no way. 

Bob: So what's, 

what's the obvious question about buying a 40 foot skeleton? 

Rob: Well, one, how do you put it up and two, how do you take it down?

Bob: Where? Where, where do you put it? The rest of the year. 

Rob: Yeah, that's true. 

Bob: It's not going in the garage. It's not going in your attic. So it's gonna be put up in your backyard, or I guess you buy a storage unit for the year.

Rob: Just for it. 

Yeah. 

Bob: You see some of the houses up there right now and they've got more Halloween stuff than you have 

Christmas stuff.

Rob: I pass a house, I literally pass a house on my way home from work. And they have not a 40 foot, they have like the 12 foot balance. 

Bob: Oh, only 12. Okay. And, 

Rob: and they have eight of them on their front lawn. Oh my gosh. And I don't know where they put them all. There's, there's gotta be some sort of trick to it.

Maybe they like disconnect or something. Who [00:07:00] knows. 

Bob: Oh, that's, that's 

good. So another thing that's nice about it is you get to relive all these things that we don't want to get forgotten. 

Rob: Yeah. 

Bob: Like board games. Board games are making a big comeback. You know, 

Rob: they 

are, 

Bob: is everybody here before, before video games or the, the big video game systems of today used to play board games until all hours of the night with your friends.

That was all the different games that were out there. That would kind of be your video games? 

Rob: Yeah. 

Bob: Back in the day. 

Rob: Yeah. I mean that 

and, and card games. Right. Uno 

Bob: and card the card games out there. 

Rob: Card games, and I mean, it was really kind of the way people entertained themselves. 

Bob: Exactly. Exactly. And as far as monopoly goes, that's.

Got a ton of history on it. 

Rob: Yeah. Yeah. I, you know, I did wanna talk a little bit since, obviously, let me put on my monocle first, because that's the only way you can

Bob: Make sure you're reading out of that eye. 

Rob: It's actually so cloudy that you can't see out of it. But I did wanna talk about the origin story monopoly, which lot of people [00:08:00] don't know.

Uh, it was actually mass produced by Parker, right? Par, uh, the Parker Brothers. They did in 1935, which, do you know what time that was? 

Bob: Depression era. 

Rob: The Great Depression. 

Bob: There you go. 

Rob: They built a game about buying property and wealth during the time, which nobody had property or wealth. 

Bob: Makes sense. Okay.

Rob: Uh, and uh, I thought that that was, uh, kind of an interesting topic because, you know, we're talking about disparity now and a lot of things that we do, and I think compared to the origin story of monopoly. We're not like that now. I think the disparity is, is a lot thinner. You have a lot more tools at your disposal.

Bob: Oh, yeah. 

Rob: Including us here. I mean, look at all the things that we offer agents as well as not, I mean, all the AI you have available as well. 

Bob: Oh yeah, for sure. For sure. 

Rob: Can't, can't 

not mention AI in any episode that we do. 

Bob: Yeah, yeah. Well, that's sort of a perfect segue here because what I think when we think about all this, the moving parts that are going on, I think we, we think about.

[00:09:00] You know, the fear of compliance roles. Right. And we gotta just remember compliance, they're not the monsters out there. Right? Yeah. You know, take a sports analogy on it, the compliance is really the lines in the field, and we gotta stay within the lines. Right? 

Rob: Agreed. 

Bob: We're playing, within the rules of the game and we don't wanna get flagged.

Right. Yeah. Nobody wants to get flagged, do it while they're playing. And our marketing design compliance team here at Pinnacle has a ton of stuff. Guidance. You know, you don't want to go down the dark path. 

Rob: No, no, no, no. 

Bob: You, you wanna make sure you're running stuff past us. So I actually have a couple of the compliance and marketing team.

Who wants to talk a little bit about best practices and how you can just lean on us here and make sure you're doing things the right way. 

Rob: Yeah, yeah. And they're great and they do a lot of stuff and uh, I think their stuff continuously gets better. 

Bob: Exactly. Exactly. So [00:10:00] get ready some more words of wisdom from the Pinnacle team, and this is gonna be from our marketing support team.

I'm excited for this. Here we go.

Kate: Beware the AI slop. It can just drain the life out of your business. Nonsense logos, crazy creations, and just so many fingers. It can all just be so terrifying. 

Scott: But at Pinnacle, our marketing team brews up creative and original content that captivates your audience 

Cristina: from hauntingly good logos to flyers for every need.

We'll make sure you don't 

get caught in AI's spell, 

Nikki: so go ahead and try that bold new idea, you're safe under the protection of the pinnacle creative coven. No spooky AI slop here. We promise. 

Bob: There you go. All you gotta do is reach out to us and we're here to support [00:11:00] you. We're here to make sure that you're doing things the right way.

You're staying within the lines of the field, within the rules of the game. And if you do that, you're gonna come out with a winning, hand. That's just the way it is. 

Rob: It's 

important. It's important, I think, when we talk compliance, you see a lot of the, you know, stay away from me, type like they're vampires.

But, I think it's important. And at the end of the day when you have a compliant piece and, and you know that it's compliant, you're not just winging it, which, okay, we get, I mean, you know, we all wing it a little bit here and there, right? Uh, but I didn't get this bag of money by just winging it back. 

Bob: No, you got, you gotta 

Rob: make sure a lot of compliance 

in here.

Bob: Yeah. Abs. Absolutely. Make sure you're doing things the right way. Always, always important to do that. And we know when we're dealing with AEP, and especially this year, there's so much turmoil, so much disruption. At the end of the day, we wanna make sure we are treating our clients, not tricking.

Rob: Yeah. Right. 

Bob: And I think a big part of that is, what kind of trick is it when a client goes to the doctor, goes to a [00:12:00] hospital, and all of a sudden they're like, where did these bills come from? Right? Yeah. Where are these out of pocket costs coming from, my insurance agent, maybe they should have talked to me about some of these things out there, right?

So we wanna make sure we get that stuff covered. And how do we do that? 

Rob: Ancillary. 

Bob: Ancillary, right? 

Rob: I mean, that's the key word. Dental, vision, hearing, hospital indemnity, cancer, heart attack, stroke. I could probably go all day about it, but if you're not layering in ancillary products to anything that you do, not, not even just Medicare, right?

Even if you're a life insurance agent, annuity. You gotta be layering these products in. There's a ton of gaps, especially in all the turmoil with Medicare these days. You just gotta do it.

Bob: Yeah, 

no, you gotta plan, , you gotta adjust, you gotta adapt to new things. One of the things for this year is we really wanna look at the fact that disruption is an opportunity.

Yeah. So we know that if things are changing, but our clients aren't going to know, hey. I better ask about a [00:13:00] hospital indemnity plan. 

Rob: Yeah. 

Bob: That, that's not something that's going to happen. So I, I think we have to embrace this as an opportunity to really bring about some additional products into our bag. Look at what's going on with, with commissions out there.

We're looking what's going on with the SAR areas. 

Rob: Yeah. 

Bob: People losing coverage left and right. I mean, these are the scary things, the tricks that are happening this year. But really it's us as the agents and we're gonna bring it around to where our clients still have what they need.

And it might be adding ancillary. 

Rob: Yeah. And look, I don't wanna say, , hide it into your presentation 'cause that sounds, that's non-compliant. Right. But you can layer it into your conversation and just make it part of the sale. Like even if you are just talking about it, you're gonna get people that are interested.

Now. This isn't necessarily layering, but I did wanna talk about a story. I mean, monopoly guy, right? Let's continue with the history and the lore. But [00:14:00] there was actually a World War II spy story about Monopoly, 

Bob: really. 

Rob: Now, during World War ii, the British Secret Service would hide real money to help POWs escape.

So they would put real money, they would put maps, they would put compasses in monopoly board games along with pool. And they would put that inside and under the board to help them escape. 

Bob: That's genius. , So who would've known that we could give Monopoly in board games to the POW games? 

Rob: Yeah. I guess they had to keep 'em busy somehow, right?

Bob: Yeah. But I, I guess so. No, that, 

Rob: I mean, that you wanna talk about adapting. 

Bob: Yeah. You definitely know that that's just a, a big change. So listen, we all have a plan when we go into it. We're all adapting to what's going on right now. And I know here in our office, we've got sales goals.

Rob: Yeah. 

Bob: I mean, and I know you , as, , business people, you put that plan out there. You've got goals to grow your business, not just, sustain your business. So I think, let's not be [00:15:00] scared of the sales goals 

Rob: and the goals are never less, right? 

Bob: Are never less. 

Rob: The goals are always a little bit more at least.

Bob: And really those goals only haunt the people that stop marketing and aren't willing to adapt. 

Rob: Yeah. 

Bob: So if you're out there. You're working with our team, you're adapting to the, real life situation that's on the ground, and I thought nobody better to talk a little bit about what's going on as far as adapting to the ever changing environment.

We see. I've got, I've dubbed her, our Chief Halloween officer this year because she's, she always does it right when it comes to Halloween. Angela. To talk a little bit about how you can really adapt to the changing landscape, embrace the change that we're seeing right now. So, Angela, coming into this year, we knew there was gonna be change and we're seeing it worse than even we thought it was going to be.

So again, what can we do to make sure we're embracing those changes? 

Angela: They say change can be frightening, [00:16:00] but not for those who dare to grow. In the mysterious world of AEP, new ways of doing business are the secret passages to your success. Those who venture into fresh markets and unexplored territories often find gold where others only see a shadow.

So don't fear what's new. Embrace it. The brave agents, we evolve with the times. Are the ones that'll write the next great tale from AEP. So grab your bet, take a swing at it.

Rob: Lot of good stuff, 

Bob: lot of good stuff. And just remember, it could be something you're not thinking of. You gotta get on the training. It could be products you're not aware of that you have access to. It could be, just a way to do things a little bit different, to make you more effective, more efficient in your business.

So don't fear the change. That's our business and we know this every single [00:17:00] year. 

Rob: Yeah. I mean, I don't think there's any other industry outside of technology that makes as many changes as our world. And, now they're starting to come together, which is, it's fun to see, I've been around not as long as you, , sir, but I've seen enough change to know that, this, this world that we're in here with Medicare and insurance, it's just an ever changing landscape, but.

There's always opportunity to pivot, I think is a, is a good word. Pivot and, stay afloat. 

Bob: And remember just thinking about AEP we're talking about now, but this is really all of 2026. 

Rob: Yeah. 

Bob: This is going to be, what we're dealing with on an ongoing basis. We're already seeing some of the carriers mid AEP, pull commissions, pull products, make changes.

We knew it was gonna happen, but it, it's, it's going on and it'll probably happen continuing to happen through 2026. So this isn't just a couple of months thing. This is like all year. 

Rob: Yeah. Yeah. 

I think hopefully it's just some cloudy days, [00:18:00] right? Cloud may be a cloudy year and hopefully as things progress, we'll see some sunshine peek through.

Bob: We all have to make sure that. Just like another sports analogy, we all have to be like the goldfish, Rob, you know why the goldfish is the happiest animal on the planet? 

Rob: Why is that 

Bob: ten second memory? Forget about the bad stuff and just keep moving on and adapting. Right? I think that's gotta put, you gotta put it behind you.

You can't dwell on it. 'cause if you dwell on it, 

how can you move forward? 

Rob: I mean, that's a great mindset to have, especially in, in what we're doing. And I think if you go into this. Forget. And a lot of the, the best athletes in the world have a ten second memory. Right. You miss that big shot.

You lose that game. They don't think about it. 

Bob: Yeah. That's exactly how you have to do it. So we're talking about World War II a little bit there, and obviously Monopoly's been around, a long time. Even longer than Medicare. . At 

this point. 

Rob: Yeah. Well, did you know that my real name, Mr.

Nickel bags here is actually Millburn penny [00:19:00] bags. And I don't know where they got Millburn, 'cause I've never seen it before. I don't know if I've ever seen that name in my entire lifetime, but he's actually modeled after, JP Morgan. 

Bob: Interesting. 

Rob: Yeah. 

Bob: There you go. , 

Rob: I didn't know that going into this, which I thought was pretty interesting.

I've never, also never, I don't know if I've ever seen a picture of JP Morgan. Is he still alive? I probably shoulda have looked at. 

Bob: I I haven't . I 

haven't as well. No, absolutely. Absolutely. I got one more guess that I lined up for us here today. Some final words.

I think that are important when we talk about all the disruption out there. But when we talk about Medicare, one of the things that we all know is we have to become very adept in acronyms. 

Rob: Yep. 

Bob: So if you're not familiar with Heidi.

Moop, AEP troop, SEP, and then 

Rob: I mean, then the alphabet, A, B, C, 

D, E, F, GH, blah, blah, blah. 

Bob: It 

is a world of acronyms that we [00:20:00] all live in when it comes to this year. So we're talking about disruption. You've gotta changes. I actually have our resident acronym, Medicare expert, our VP of Sales, Jeff Palo, and I asked Jeff to to hop on with us because.

Everybody needs some final thoughts on how they're going to continue to push forward and have that best AEP. So Jeff, what are your thoughts on this disruption and everything we're seeing going on around us? 

Jeff: The landscape is shifting. Benefits transforming before your eyes. Some agents flee from product changes.

The wise ones know disruption is merely the opportunity in disguise. Each new plan, each update twist in the Medicare maze, opens the door to something bigger. Don't hide from the storm. Keep your eye on the ball because in the state of chaos, true opportunity arises from the mist. [00:21:00] 

Bob: There you go. 

Rob: Man the myth the legend.

Bob: And Jeff, if you're not aware of it. Mr. Happy Gilmore himself. He's a rabid Flyers fan. So the fact that I was seeing him in the Boston jersey today,

Rob: oh, that's rough. 

Bob: Little bit roughs, little bit rough. I, I, I, I gotta say that. I'm taking it as a Halloween.

Rob: Don't let Dustin 

see him in that. 

Bob: Yeah. You know, it's tough. It's tough when you see. That, but, we'll give it a break since it is the Halloween time of year, and we're all doing a little bit of stuff outside the ordinary, right? 

Rob: Yeah. Well, something outta the ordinary that I think plays really well into this.

Right? And I didn't know this going into this. Do you know the longest game of Monopoly ever recorded? 

Bob: Longest game. Now, now I usually last until about 3:00 AM. So it it, whoever had the most money at that point kind of 

Rob: was done, right? 

Bob: You, you won. Yeah. 

Rob: Yeah. Uh, 70 straight days. 

Bob: Oh, 

Rob: I can't even imagine playing it for 10 hours, let alone [00:22:00] 70 straight days.

But much like those guys that or whoever sat down to play Monopoly for 70 straight days, perseverance. There was a, there was a winner at the end of the day, right. And I think that that bodes well into what we do here and might seem mundane. You might be doing the same thing every day, but if you stick it out, you're going to come out a winner at the end of the day.

Bob: Exactly. 

So remember 54 days of AEP, so it's not even as long as the longest monopoly. 

Rob: There you go. 

Bob: So head down, do what you gotta do, make sure you're leaning on us. You know, we have this year or so. This year, let's just say it's, again, it's the nightmare on enrollment street, right? We all knew what was coming.

So we're planning for change. We got new lead opportunities out there you gotta take a look at. 

Rob: Yep. 

Bob: Right? New ways of doing business, right? If you haven't done phone sales before, maybe this is the year, you gotta take a look at doing some phone sales because you need to work [00:23:00] into some different areas of business, maybe the area you normally do business.

The products are just not there. 

Rob: Yeah. 

Bob: The networks are just not there. So you have to take a look at some other opportunities. And then also the products, the HIPs, the cancer, the de dental vision, hearing, not as robust on the Medicare Advantage as they were in other years and in many of the areas we're doing business with.

So these are all things we have to take a look at. 

Rob: Not to mention, I mean, hip dental vision hearing, you could talk about them during your Medicare sale. So if you have an opportunity to layer in some extra products, I mean, what do they say? It's three products. , 

Bob: Turn that, , policy holder into a client.

Rob: Yeah. And 

Bob: say that's what you have to do. Get a couple of products in there, and it really cements them, and you're gonna have a happy client again. We don't, they don't want the tricks coming and those bills come down the road, right? Hey, three days in a hospital, how come I got a $700? 

Rob: Yeah, I, I don't want that 

call.

I do not 

Bob: want that call. We do not want that call. And you look at the hospital indemnity, it's just cash. It is just cash paid. To the individual [00:24:00] directly. 

Rob: Yeah. 

Bob: They can use that money, 

Rob: pay their bills, they take vacation, whatever they wanna do. 

Bob: Well, hopefully they're not going into the doctor's or hospital enough.

Rob: Yeah. 

Bob: But if they did, it's cash paid. to them. 

Rob: And I mean, I 

don't know about you. I love cash. Cash is a beautiful thing. 

Bob: There you go. Working, working hard. So the, I hope everybody takes this. Don't fear. AEP. Don't fear Medicare. As long as you keep moving forward, you keep adapting, you keep learning new stuff, and we stay on top of it, we're all going to be okay.

There's a light at the end of the tunnel. The dark tunnel here 

Rob: always, always is. 

Bob: Yeah. So for everybody, keep your head down. Let's keep working hard. AEP, we're about halfway through at this point. It's gonna go fast, but 2026. A lot of opportunities. 

Rob: Remember. Believe people. Believe, 

Bob: believe. [00:25:00] Thank you again for joining us.

Rob: Thanks guys. 

Bob: Have a great rest of your day.